An official website of the United States government

Eugenol

PubChem CID
3314
Structure
Eugenol_small.png
Eugenol_3D_Structure.png
Molecular Formula
Synonyms
  • eugenol
  • 97-53-0
  • 4-Allyl-2-methoxyphenol
  • 4-Allylguaiacol
  • Eugenic acid
Molecular Weight
164.20 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Eugenol appears as clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Eugenol is a phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis. It has a role as an allergen, a human blood serum metabolite, a sensitiser, a volatile oil component, a flavouring agent, an EC 1.4.3.4 (monoamine oxidase) inhibitor, a radical scavenger, an antibacterial agent, an antineoplastic agent, an apoptosis inducer, an anaesthetic, an analgesic, a voltage-gated sodium channel blocker, a NF-kappaB inhibitor and an anti-inflammatory agent. It is a phenylpropanoid, a monomethoxybenzene, a member of phenols and an alkenylbenzene. It is functionally related to a guaiacol.
Eugenol is a naturally occurring phenolic molecule found in several plants such as cinnamon, clove, and bay leaves. It has been used as a topical antiseptic as a counter-irritant and in dental preparations with zinc oxide for root canal sealing and pain control. Although not currently available in any FDA-approved products (including OTC), eugenol has been found to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties. Its exact mechanism of action is unknown, however, it has been shown to interfere with action potential conduction. There are a number of unapproved OTC products available containing eugenol that advertise its use for the treatment of toothache.
See also: Clove Oil (part of); Cinnamon (part of); Cinnamon Leaf Oil (part of) ... View More ...

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Eugenol.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-methoxy-4-prop-2-enylphenol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RRAFCDWBNXTKKO-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC1=C(C=CC(=C1)CC=C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H12O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

97-53-0

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 FEMA Number

2.3.10 HMDB ID

2.3.11 JECFA Number

1529

2.3.12 KEGG ID

2.3.13 Metabolomics Workbench ID

2.3.14 NCI Thesaurus Code

2.3.15 Nikkaji Number

2.3.16 NSC Number

2.3.17 PharmGKB ID

2.3.18 Pharos Ligand ID

2.3.19 RXCUI

2.3.20 Wikidata

2.3.21 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Eugenol
  • Phenol, 2-methoxy-4-(2-propenyl)-

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
164.20 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
164.083729621 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
164.083729621 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
29.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
145
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Eugenol appears as clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Other Solid; Liquid, Other Solid; Liquid
Colorless to pale yellow liquid with an odor of cloves; Darkened and thickened by air; [Merck Index] Colorless, light yellow, or amber liquid; [CAMEO]
Solid
Colourless to pale yellow liquid; Aroma of cloves

3.2.2 Color / Form

Colorless or pale yellow liquid
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 665
CRYSTALS FROM HEXANE
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 73rd ed. Boca Raton, FL: CRC Press Inc., 1992-1993., p. 3-244

3.2.3 Odor

Odor of cloves
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 665
Warm, spicy, floral
Schreiber WL; Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2012). New York, NY: John Wiley & Sons; Perfumes. Online Posting Date: Sept 23, 2005

3.2.4 Taste

Spicy, pungent taste
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 665

3.2.5 Boiling Point

489 °F at 760 mmHg (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
252.00 to 253.00 °C. @ 760.00 mm Hg
The Good Scents Company Information System

3.2.6 Melting Point

15.4 to 15.6 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
-9.2 to -9.1 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 665
-12.00 to -10.00 °C. @ 760.00 mm Hg
The Good Scents Company Information System

3.2.7 Flash Point

219 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
>212 °F (>100 °C) (closed cup)
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-76

3.2.8 Solubility

less than 1 mg/mL at 68 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
In water, 2460 mg/L at 25 °C
Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 687
Miscible with alcohol, chloroform, ether, oils; one mL dissolves in 2 mL 70% alcohol; soluble in glacial acetic acid, in aqueous fixed alkali hydroxide solutions
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 665
Slightly soluble in water; Soluble in ether, most fixed oils
Soluble (in ethanol)

3.2.9 Density

1.0652 at 68 °F (NTP, 1992) - Denser than water; will sink
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
1.0652 g/cu cm at 20 °C
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-12
1.064-1.070

3.2.10 Vapor Density

greater than 1.0 (NTP, 1992) (Relative to Air)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.11 Vapor Pressure

0.01 mmHg at 68 °F ; 0.03 mmHg at 77 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
0.01 [mmHg]
VP: 1 mm Hg at 78.4 °C. Percent in saturated air: approx 0.004 at 25 °C, 760 mm Hg
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5: 867
0.0221 mm Hg at 25 °C
Van Roon A et al; Chemosphere 61: 599-609 (2005)

3.2.12 LogP

log Kow = 2.49
Dias NC et al; Analyst 128(5): 427-433 (2003)
2.270
The Good Scents Company Information System

3.2.13 Stability / Shelf Life

Darkens and thickens on exposure to air.
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 680

3.2.14 Decomposition

When heated to decomposition it emits acrid smoke and irritating fumes.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1735

3.2.15 Viscosity

7.817 centipoise at 20 °C
Razdan TK et al; Parfuem Kosmet 66: 444-449 (1985)

3.2.16 Surface Tension

30.929 dynes/cm
Razdan TK et al; Parfuem Kosmet 66: 444-449 (1985)

3.2.17 Refractive Index

Index of refraction: 1.5405 at 20 °C/D
Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 3-12
1.540-1.542

3.2.18 Dissociation Constants

pKa = 10.19 at 25 °C
Kortum G et al; Pure and Applied Chemistry, Vol. 1, No 2-3 (1961)

3.2.19 Collision Cross Section

125.03 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

132.22 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

129.52 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

138.94 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.2.20 Kovats Retention Index

Standard non-polar
1337 , 1363 , 1397 , 1368 , 1385 , 1345 , 1346 , 1338 , 1327 , 1374 , 1332 , 1357 , 1335 , 1356 , 1344 , 1380 , 1320 , 1325 , 1327 , 1331 , 1325 , 1377 , 1325 , 1324 , 1333 , 1329 , 1350 , 1331 , 1344 , 1381 , 1345 , 1344 , 1330 , 1333 , 1338 , 1323.2 , 1323.8 , 1325.9 , 1327.9 , 1334.1 , 1340.6 , 1332.7 , 1335.83 , 1360 , 1364 , 1337 , 1342 , 1327 , 1337 , 1339 , 1330 , 1337 , 1340 , 1330 , 1340 , 1337 , 1354 , 1327.7 , 1325 , 1326 , 1338 , 1354 , 1347 , 1347 , 1367 , 1368 , 1347 , 1347 , 1339 , 1352 , 1355 , 1356 , 1327 , 1337 , 1330 , 1392 , 1337 , 1358 , 1333 , 1323 , 1327 , 1354 , 1326 , 1357 , 1392 , 1337 , 1392 , 1329 , 1331 , 1341 , 1334 , 1331 , 1339 , 1327 , 1332 , 1364 , 1351 , 1364 , 1335 , 1335 , 1321 , 1326 , 1326 , 1326 , 1326 , 1328 , 1332 , 1373 , 1351 , 1327 , 1327 , 1351 , 1332 , 1340 , 1333 , 1333 , 1359 , 1339 , 1356 , 1357 , 1332.8 , 1330 , 1336 , 1336 , 1345 , 1322 , 1323 , 1324 , 1327 , 1359 , 1364 , 1364 , 1327 , 1330 , 1341 , 1331 , 1324 , 1333 , 1327 , 1340 , 1342 , 1323.9 , 1319 , 1335 , 1335 , 1350 , 1337 , 1337 , 1394 , 1328 , 1327 , 1327 , 1325 , 1327 , 1329 , 1329 , 1336 , 1329 , 1320 , 1340 , 1336.5 , 1336 , 1327 , 1355 , 1334 , 1321 , 1358 , 1371 , 1327 , 1338 , 1327 , 1329 , 1341 , 1325 , 1399 , 1327 , 1351 , 1333 , 1338 , 1338 , 1343 , 1330 , 1333 , 1331.4 , 1367 , 1384.1 , 1334 , 1326 , 1330 , 1330 , 1319.7 , 1327 , 1327.5 , 1327.7 , 1332.8 , 1356 , 1356 , 1330 , 1351 , 1324 , 1325 , 1325 , 1368 , 1324 , 1344 , 1348 , 1368
Semi-standard non-polar
1356 , 1359 , 1371 , 1374 , 1358 , 1356 , 1359 , 1357 , 1365 , 1365 , 1346 , 1368 , 1358 , 1370 , 1360.5 , 1356 , 1390 , 1356 , 1359 , 1359 , 1357 , 1355 , 1370 , 1353 , 1355 , 1356 , 1358.7 , 1359 , 1356 , 1356 , 1351 , 1356 , 1356 , 1366 , 1356 , 1359 , 1353 , 1358.7 , 1362.4 , 1364.6 , 1358 , 1353 , 1359 , 1357 , 1357 , 1356 , 1366 , 1356 , 1356 , 1360 , 1358 , 1358 , 1357 , 1351 , 1358 , 1356 , 1358 , 1356 , 1370 , 1360 , 1363 , 1356 , 1356 , 1358 , 1353 , 1357 , 1351 , 1359 , 1356 , 1357 , 1358 , 1369 , 1356 , 1356 , 1365 , 1364.5 , 1355 , 1341 , 1350 , 1357 , 1354 , 1376 , 1358 , 1353 , 1380 , 1349 , 1352 , 1357 , 1355 , 1351 , 1356 , 1343 , 1357 , 1357 , 1356 , 1356 , 1362 , 1366 , 1353 , 1353 , 1352 , 1384 , 1359 , 1373 , 1368 , 1367 , 1348 , 1348 , 1342 , 1378 , 1348 , 1356 , 1358 , 1356 , 1354 , 1356 , 1356 , 1362 , 1358 , 1356 , 1359 , 1356 , 1365 , 1366 , 1332 , 1350 , 1356 , 1357 , 1360 , 1359 , 1365 , 1364 , 1363 , 1358 , 1352 , 1355 , 1356 , 1355 , 1357 , 1357 , 1357 , 1357 , 1358 , 1360 , 1336 , 1337 , 1353 , 1353 , 1362 , 1356 , 1356 , 1353 , 1361 , 1358 , 1356 , 1359 , 1355 , 1361 , 1353 , 1365 , 1356 , 1359 , 1356 , 1359 , 1361 , 1363 , 1386 , 1365 , 1359 , 1358 , 1359 , 1360 , 1353 , 1358 , 1351 , 1362 , 1358 , 1359 , 1356 , 1359 , 1367 , 1367 , 1368 , 1370 , 1371 , 1374 , 1367 , 1357 , 1360 , 1364 , 1366 , 1356 , 1357 , 1356 , 1357 , 1334 , 1366 , 1374 , 1364 , 1384 , 1356 , 1361 , 1364 , 1356 , 1356 , 1356 , 1361 , 1359 , 1361 , 1360 , 1353 , 1353 , 1360 , 1356 , 1322 , 1360 , 1359 , 1330 , 1356 , 1359 , 1361 , 1359 , 1354 , 1355 , 1359 , 1330 , 1359 , 1356 , 1322 , 1364 , 1352 , 1359 , 1373 , 1361 , 1351 , 1358 , 1354 , 1354 , 1375 , 1377 , 1358 , 1359 , 1359 , 1351 , 1359 , 1360 , 1360 , 1364 , 1355 , 1356 , 1362 , 1357 , 1353 , 1355 , 1368 , 1359 , 1371 , 1339 , 1355 , 1352 , 1355 , 1369 , 1370 , 1374 , 1374 , 1379 , 1382 , 1358 , 1358 , 1360 , 1380 , 1359 , 1361 , 1356 , 1356 , 1346 , 1356 , 1355 , 1362 , 1356 , 1353 , 1356 , 1344 , 1357 , 1356 , 1354 , 1378 , 1357 , 1355 , 1329 , 1353 , 1353 , 1353 , 1353 , 1353 , 1367 , 1356 , 1358 , 1353 , 1359 , 1356 , 1350.3 , 1357 , 1375 , 1362 , 1360 , 1336 , 1358 , 1335 , 1358 , 1356 , 1359 , 1356 , 1360 , 1356 , 1356 , 1342 , 1355 , 1356 , 1359 , 1350 , 1365 , 1361.3 , 1348 , 1351 , 1351 , 1353 , 1355 , 1354 , 1389 , 1364 , 1365 , 1365 , 1356 , 1361 , 1376 , 1369 , 1355 , 1355 , 1354.3 , 1369 , 1356 , 1369 , 1360.5 , 1348 , 1357 , 1355 , 1358 , 1358 , 1361.7 , 1352 , 1358 , 1364 , 1364 , 1365
Standard polar
2167 , 2186 , 2172 , 2156 , 2116 , 2182 , 2170 , 2177 , 2164 , 2185 , 2179 , 2172 , 2182 , 2164 , 2187 , 2171 , 2146 , 2153 , 2164 , 2164 , 2165 , 2163 , 2175 , 2151 , 2141 , 2166 , 2153 , 2135 , 2173 , 2143 , 2184 , 2154 , 2122 , 2166 , 2154 , 2172 , 2176 , 2153 , 2180 , 2200 , 2145 , 2155 , 2155 , 2162 , 2184 , 2153 , 2169 , 2180 , 2117 , 2210 , 2185 , 2186 , 2165 , 2139 , 2176 , 2177 , 2122 , 2180 , 2130 , 2131 , 2157.3 , 2159.4 , 2140 , 2192 , 2198 , 2141 , 2141 , 2175 , 2183 , 2192 , 2186 , 2167 , 2175 , 2169 , 2173 , 2186 , 2186 , 2176 , 2179 , 2166 , 2166 , 2185 , 2152 , 2186 , 2153 , 2159 , 2159 , 2179 , 2186 , 2139 , 2186 , 2157 , 2171 , 2156 , 2194 , 2136 , 2152 , 2153 , 2186 , 2151 , 2186 , 2186 , 2156 , 2155 , 2162 , 2167 , 2180 , 2171 , 2179 , 2186 , 2172 , 2174 , 2118 , 2120 , 2186 , 2186 , 2186 , 2117 , 2117 , 2172 , 2144 , 2161 , 2151 , 2205 , 2163 , 2186 , 2186 , 2158 , 2167 , 2159 , 2174 , 2192 , 2186 , 2192 , 2147 , 2162 , 2162 , 2186 , 2150 , 2151 , 2152.9 , 2186 , 2186 , 2186 , 2186 , 2164 , 2198 , 2191 , 2156 , 2154 , 2161.7 , 2122 , 2186 , 2186 , 2186 , 2193 , 2186 , 2169 , 2171 , 2172 , 2152 , 2154.5 , 2178 , 2178 , 2186 , 2186 , 2186 , 2186 , 2181 , 2157 , 2186 , 2162 , 2162 , 2186 , 2197 , 2157 , 2118 , 2156 , 2169 , 2201 , 2209 , 2162 , 2160 , 2169 , 2149 , 2152 , 2192 , 2167 , 2176 , 2140 , 2158 , 2185 , 2161 , 2179 , 2140 , 2140 , 2140 , 2198 , 2172 , 2180 , 2169 , 2192 , 2159 , 2143 , 2191 , 2213 , 2193 , 2158 , 2159 , 2145.5 , 2150 , 2167.9 , 2168

3.2.21 Other Experimental Properties

Distills between 250 °C and 255 °C
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 991
Oily; Becomes brown in air; Optically inactive.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 543
Crystals; MP: 69-70 °C; BP: 360 °C; practically insoluble in water; freely soluble in benzene, chloroform, ether, hot alcohol /Eugenol benzoate/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 665

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Biological Agents -> Plant-Derived Allergens

3.4.1 Drugs

Pharmaceuticals -> Analgesics and anti-inflammatories
S57 | GREEKPHARMA | Suspect Pharmaceuticals from the National Organization of Medicine, Greece | DOI:10.5281/zenodo.3248883
Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.4.2 Cosmetics

Cosmetics ingredient -> Base; Emulsifier; Flavor; Fragrance; Moisturizing/Humectant; Other (Specify)
Denaturant; Tonic
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.4.3 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.4.4 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.4.5 Fragrances

Fragrance Ingredient (Eugenol) -> IFRA transparency List
Fragrance
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

3.4.6 Pesticides

Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
NMR: 260 (Varian Associates NMR Spectra Catalogue)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
JEOL
Frequency
400 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
5.96:49.00, 6.84:42.00, 5.03:157.00, 3.28:185.00, 3.28:138.00, 6.84:196.00, 5.99:46.00, 6.66:302.00, 6.65:101.00, 6.67:64.00, 6.67:261.00, 5.03:155.00, 5.08:98.00, 3.80:1000.00, 6.64:60.00, 5.91:56.00, 5.05:117.00, 6.66:181.00, 6.65:71.00, 5.92:55.00, 5.08:112.00, 5.08:152.00, 5.88:53.00, 5.05:134.00, 5.73:43.00, 6.64:87.00, 3.30:184.00, 6.65:137.00, 5.97:91.00, 6.82:239.00, 5.94:126.00, 3.30:136.00, 3.29:111.00, 6.83:47.00, 5.90:112.00, 6.65:78.00, 5.93:130.00, 5.95:50.00, 5.03:135.00
Thumbnail
Thumbnail
2 of 3
View All
Instrument Name
BRUKER AC-300
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
NEVA
Frequency
15.09 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
121.26:929.00, 55.84:771.00, 137.91:567.00, 114.46:1000.00, 131.94:295.00, 111.28:857.00, 115.49:814.00, 146.60:205.00, 39.92:795.00, 144.03:305.00
Thumbnail
Thumbnail
2 of 3
View All
Source of Sample
Givaudan Corporation, Clifton, New Jersey
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 17
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

164.0 99.99

77.0 38

149.0 37

103.0 31

131.0 27

Thumbnail
Thumbnail
Notes
instrument=HITACHI RMS-4
2 of 17
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

164.0 99.99

149.0 31.14

131.0 19.23

137.0 17.53

103.0 15.22

Thumbnail
Thumbnail
Notes
instrument=HITACHI M-80

4.2.2 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

109.0284 100

124.0521 16.68

105.0449 9.96

81.0324 9.33

110.0315 8.06

Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

109.0285 100

124.0521 77.56

105.07 19.37

137.0599 11.62

103.0542 11.39

Thumbnail
Thumbnail

4.2.3 LC-MS

1 of 8
View All
Authors
Markus Kohlhoff, Natural Product Chemistry Lab (CPqRR/FIOCRUZ, Brazil)
Instrument
maXis (Bruker Daltonics)
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Waters Atlantis C18 3um 2.1x150mm
Precursor Adduct
[M+H]+
Top 5 Peaks

165.091 999

137.0596 552

124.0518 527

133.0647 506

105.0698 169

Thumbnail
Thumbnail
License
CC BY-NC
2 of 8
View All
Authors
Markus Kohlhoff, Natural Product Chemistry Lab (CPqRR/FIOCRUZ, Brazil)
Instrument
maXis (Bruker Daltonics)
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Waters Atlantis C18 3um 2.1x150mm
Precursor Adduct
[M+H]+
Top 5 Peaks

124.0518 999

137.0596 300

105.0696 290

109.0284 163

133.0646 125

Thumbnail
Thumbnail
License
CC BY-NC

4.2.4 Other MS

1 of 10
View All
Other MS
MASS: 77576 (NIST/EPA/MSDC Mass Spectral Data Base, 1990 Version)
2 of 10
View All
Authors
NAKAYAMA M, MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
HITACHI RMS-4
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 80 eV
Top 5 Peaks

164 999

77 380

149 370

103 310

131 270

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 UV Spectra

UV: log epsilon = 3.55 at 290 nm
NIST; NIST Chemistry WebBook. Eugenol (97-53-0). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of Jun 26, 2012: https://webbook.nist.gov
UV: 3-254 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V4: 4072

4.4 IR Spectra

IR Spectra
IR: 5146 (Coblentz Society Spectral Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
BETWEEN SALTS
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bio-Rad FTS
Technique
Neat (KBr)
Source of Spectrum
Forensic Spectral Research
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
PerkinElmer SpectrumTwo
Technique
ATR-IR
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
A0232
Lot Number
BLQTM-PL
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4.3 Near IR Spectra

1 of 2
Instrument Name
BRUKER IFS 88
Technique
NIR
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
BRUKER IFS 88
Technique
NIR
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.4.4 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Vapor Phase
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
E51791
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
A0232
Lot Number
BLQTM-PL
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.6 Other Spectra

SADTLER REF NUMBER: 3880 (IR, PRISM)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-303

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Eugenol is not currently available in any FDA-approved drug products. There are a number of unapproved OTC products that advertise it for the use of toothache. Eugenol is is also commonly used in combination with zinc oxide in dental procedures for the cementation of temporary prostheses and the temporary restoration of teeth and cavities.

7.2 LiverTox Summary

Eugenol, also called clove oil, is an aromatic oil extracted from cloves that is used widely as a flavoring for foods and teas and as an herbal oil used topically to treat toothache and more rarely to be taken orally to treat gastrointestinal and respiratory complaints. Eugenol in therapeutic doses has not been implicated in causing serum enzyme elevations or clinically apparent liver injury, but ingestions of high doses, as with an overdose, can cause severe liver injury.

7.3 Drug Classes

Herbal and Dietary Supplements

7.4 FDA National Drug Code Directory

7.5 Drug Labels

Drug and label
Active ingredient and drug
Homeopathic product and label

7.6 Therapeutic Uses

... Has been used as an antipyretic but it is relatively ineffective. /Eugenol/ has... been used in medicine for the study of mucous secretion /and/ gastric cytology, without gastric resection or gastroenterostomy. It has been shown to have anthelmintic properties. /SRP: Former use/
Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1691
Nonprescription medicines for toothache commonly contain eugenol, and some products for canker-sore may do so also.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 78 (1985)
Eugenol is used as a component of several dental materials (e.g., dental cements, impression pastes and surgical pastes). Such products are principally combinations of zinc oxide and eugenol in varying ratios. They are reported to be widely used in dentistry as temporary filing materials, cavity liners for pulp protection, capping materials, temporary cementation of fixed protheses, impression materials and major ingredients of endodontic sealers. In addition, eugenol has been used in dentistry for disinfecting root canals.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 77 (1985)
Analgesic (dental)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 690

8 Food Additives and Ingredients

8.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

8.2 FEMA Flavor Profile

Burnt, Clove, Spice

8.3 FDA Substances Added to Food

Substance
Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
Document Number (21 eCFR)
FEMA Number
2467
GRAS Number
3
JECFA Flavor Number
1529

8.4 Associated Foods

8.5 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

Chemical Name
4-ALLYLGUAIACOL
Evaluation Year
2005
ADI
0-2.5 mg/kg bw (1982)
Comments
The ADI established at the twenty-sixth meeting was maintained.
Tox Monograph

9 Agrochemical Information

9.1 Agrochemical Category

Pesticide active substances

9.2 EU Pesticides Data

Active Substance
eugenol
Status
Approved [Reg. (EC) No 1107/2009]
Date
Approval: 01/12/2013 Expiration: 30/04/2026
Legislation
2007/442/EC, Dossier complete 2011/266/EU, Reg. (EU) 2018/155, Reg. (EU) 2023/1757, Reg. (EU) No 546/2013
ADI
1.0 mg/kg bw/day [Reg. (EU) No 546/2013]
AOEL
1.0 mg/kg bw/day [Reg. (EU) No 546/2013]

10 Pharmacology and Biochemistry

10.1 MeSH Pharmacological Classification

Anti-Infective Agents
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)
Solvents
Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant and Hackh's Chemical Dictionary, 5th ed) (See all compounds classified as Solvents.)

10.2 FDA Pharmacological Classification

1 of 2
FDA UNII
3T8H1794QW
Active Moiety
EUGENOL
Pharmacological Classes
Established Pharmacologic Class [EPC] - Standardized Chemical Allergen
Pharmacological Classes
Physiologic Effects [PE] - Increased Histamine Release
Pharmacological Classes
Physiologic Effects [PE] - Cell-mediated Immunity
Pharmacological Classes
Chemical Structure [CS] - Allergens
FDA Pharmacology Summary
Eugenol is a Standardized Chemical Allergen. The physiologic effect of eugenol is by means of Increased Histamine Release, and Cell-mediated Immunity.
2 of 2
Non-Proprietary Name
EUGENOL
Pharmacological Classes
Allergens [CS]; Cell-mediated Immunity [PE]; Standardized Chemical Allergen [EPC]; Increased Histamine Release [PE]

10.3 Absorption, Distribution and Excretion

Intraperitoneal injection of a single 450 mg/kg dose of (14)C methoxy labelled eugenol resulted in rapid distribution to all organs. Both ether- and water soluble materials were recovered from most tissues and excretions. Only 0.2-1.0% of the dose was eliminated as expired (14)CO2. Over 70% of a lethal dose of eugenol was recovered on death, from the urine of rabbits.
WHO; Food Additive Series 17: Eugenol (1980). Available from, as of April 21, 2005: https://www.inchem.org/documents/jecfa/jecmono/v17je10.htm
No penetration of mouse skin was demonstrated after dermal application of eugenol.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 86 (1985)

10.4 Metabolism / Metabolites

Following ip injection of (14)C eugenol into rats, ... the presence of (14)CO2 in expired air indicated the demethylation of eugenol.
Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon Press, 1979., p. 376
The metabolism and toxic effects of eugenol were studied in isolated rat hepatocytes. Incubation of hepatocytes with eugenol resulted in the formation of conjugates with sulfate, glucuronic acid and glutathione. The major metabolite formed was the glucuronic acid conjugate. Covalent binding to cellular protein was observed using (3)H eugenol. Loss of intracellular glutathione and cell death were also observed in these incubations. Concentrations of 1 mM eugenol caused a loss of over 90% of intracellular glutathione and resulted in approximately 85% cell death over a 5 hr incubation period. The loss of the majority of glutathione occurred prior to the onset of cell death (2 hr). The effects of eugenol were concentration dependent. The addition of 1 mM N-acetylcysteine to incubations containing 1 mM eugenol was able to completely prevent glutathione loss and cell death as well as inhibit the covalent binding of eugenol metabolites to protein. Conversely, pretreatment of hepatocytes with diethylmaleate to deplete intracellular glutathione increased the cytotoxic effects of eugenol. These results demonstrate that eugenol is actively metabolized in hepatocytes and suggest that the cytotoxic effects of eugenol are due to the formation of a reactive intermediate, possibly a quinone methide.
Thompson DC et al; Chem Biol Interact 77 (2): 137-47 (1991)
Two metabolites of eugenol, 3-piperidyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone and 3-pyrrolidinyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone, have been isolated from rat urine.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 86 (1985)
Epoxidation of eugenol by rat liver cell cultures has been reported. The dihydrodiol metabolite of eugenol has been isolated from liver homogenates and urine of rats pretreated with eugenol.
WHO; Food Additive Series 17: Eugenol (1980). Available from, as of April 21, 2005: https://www.inchem.org/documents/jecfa/jecmono/v17je10.htm
For more Metabolism/Metabolites (Complete) data for EUGENOL (9 total), please visit the HSDB record page.
Eugenol has known human metabolites that include Hydroxychavicol and (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-(2-methoxy-4-prop-2-enylphenoxy)oxane-2-carboxylic acid.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

10.5 Mechanism of Action

The exact mechanism of action of eugenol is unknown. However, eugenol has been shown to interrupt action potentials, which may be involved in its anti-pain activity. Research has also shown eugenol to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties.
... Thymocyte suspension was irradiated by gamma-rays, and the malondialdehyde (MDA) formation was measured with the thiobarbituric acid reactive species (TBARS) method. The results showed an increase in MDA in irradiated (2 Gy) thymocytes, which was inhibited in samples treated with increasing concentrations of eugenol (10-200 uM) prior to irradiation. The concentration of eugenol required to inhibit half of the MDA formation (IC(50)) in irradiated thymocytes was 100 uM. A dose-dependent increase in the generation of ROS was observed in irradiated thymocytes (0.5-200 cGy) as measured by 2,7-dichlorodihydro fluorescein diacetate (DCH-FDA), which was inhibited by eugenol administered before irradiation.
Pandy BN, Mishra KP; J Environ Pathol Toxicol Oncol 23 (2): 117-22 (2004)
Respiratory inhibition of isolated rat liver mitochondria by eugenol was dose related and uncoupled oxidative phosphorylation from electron transfer.
Cotmore JM et al; Arch Oral Biol 24 (8): 565 (1979)
Polymorphonuclear leukocytes (PMNL) play an important role in the modulation of inflammatory conditions in humans. PMNL cells recruited at the site of inflammation, release inflammatory mediators such as leukotrienes, proteolytic enzymes and reactive oxygen species. Among these, leukotrienes are implicated in pathophysiology of allergic and inflammatory disorders like asthma, allergic rhinitis, arthritis, inflammatory bowel disease and psoriasis. 5-lipoxygenase (5-LO) is the key enzyme in biosynthetic pathway of leukotrienes. Our earlier studies showed that spice phenolic active principles significantly inhibit 5-LO enzyme in human PMNLs. In this study we have further characterized the inhibitory mechanism of eugenol, the active principle of spice-clove on 5-LO enzyme and also its effect on leukotriene C((4)) (LTC(4)). Substrate dependent enzyme kinetics showed that the inhibitory effect of eugenol on 5-LO was of a non-competitive nature. Further, eugenol was found to significantly inhibit the formation of LTC(4) in calcium ionophore A23187 and arachidonic acid (AA) stimulated PMNL cells. These data clearly suggest that eugenol inhibits 5-LO by non-competitive mechanism and also inhibits formation of LTC(4) in human PMNL cells and thus may have beneficial role in modulating 5-LO pathway in human PMNL cells.
Raghavenra H et al; Prostaglandins Leukot Essent Fatty Acids 74 (1): 23-7 (2006)
The Ca(2+)-activated Cl(-) channel TMEM16A is involved in epithelial fluid secretion, smooth muscle contraction and neurosensory signaling. We identified a Thai herbal antidiarrheal formulation that inhibited TMEM16A Cl(-) conductance. C18-reversed-phase HPLC fractionation of the herbal formulation revealed >98% of TMEM16A inhibition activity in one out of approximately 20 distinct peaks. The purified, active compound was identified as eugenol (4-allyl-2-methoxyphenol), the major component of clove oil. Eugenol fully inhibited TMEM16A Cl(-) conductance with single-site IC(50)~150 uM. Eugenol inhibition of TMEM16A in interstitial cells of Cajal produced strong inhibition of intestinal contraction in mouse ileal segments. TMEM16A Cl(-) channel inhibition adds to the list of eugenol molecular targets and may account for some of its biological activities.
Yao Z et al; PLoS One. 2012;7(5):e38030. doi: 10.1371/journal.pone.0038030. Epub 2012 May 30.
For more Mechanism of Action (Complete) data for EUGENOL (21 total), please visit the HSDB record page.

10.6 Human Metabolite Information

10.6.1 Cellular Locations

Membrane

10.7 Biochemical Reactions

10.8 Transformations

11 Use and Manufacturing

11.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
A fragrance and spice derived from the oil of cloves; used in cosmetics, over-the-counter drugs, toothpastes, and foods; [Marks, p. 172-3] From numerous natural sources and the main active ingredient in cloves; Used in perfumery, flavoring, manufacture of vanillin, medicine (germicide and in over the counter drugs), dentistry (analgesic, root canal disinfectant, and in cements and other materials); Also used as an insect attractant, chemical intermediate, and denaturant for alcohol; Has been used as fungicide in pharmaceuticals and cosmetics, as antiputrescent, and to treat flatulent colic; [HSDB] Active ingredient in consumer insecticides and Japanese beetle baits/traps; [NPIRS]
Marks - Marks JG, DeLeo VA. Contact and Occupational Dermatology, 2nd Ed. St. Louis: Mosby, 1997., p. 172-3
For eugenol (USEPA/OPP Pesticide Code: 102701) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
National Pesticide Information Retrieval System's USEPA/OPP Chemical Ingredients Database on Eugenol (97-53-0). Available from, as of June 21, 2012 https://npirspublic.ceris.purdue.edu/ppis/
Insecticide
Crop Protection Handbook Volume 98, Meister Media Worldwide, Willoughby, OH 2012, p. 416
Perfumes, essential oils, medicine (anaglesic), production of isoeugenol for the manufacture of vanillin, flavoring.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 543
Eugenol is used in perfumery in clove and carnation compositions as well as for oriental and spicy notes. It is a common component of clove and other aroma compositions. In dentistry, it is used as an antiseptic.
Fahlbusch K-G et al; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2012). NY, NY: John Wiley & Sons; Flavors and Fragrances. Online Posting Date: January 15, 2003
For more Uses (Complete) data for EUGENOL (10 total), please visit the HSDB record page.

Use (kg; approx.) in Germany (2009): >10

Consumption (g per capita; approx.) in Germany (2009): 0.000122

Calculated removal (%): 76.5

11.1.1 Use Classification

Food additives -> Flavoring Agents
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Cosmetics -> Denaturant; Tonic
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

11.1.2 Industry Uses

  • Flavoring and nutrient
  • Odor agents
  • Fragrance
  • Intermediates

11.1.3 Consumer Uses

  • Odor agents
  • Fragrance

11.1.4 Household Products

California Safe Cosmetics Program (CSCP)

Cosmetics product ingredient: Phenol, 2-methoxy-4-(2-propenyl)- (EUGENOL)

Eugenol is a fragrance allergen. Fragrance allergens are hazardous only to individuals who suffer from fragrance allergies. The Cosmetic Fragrance and Flavor Ingredient Right to Know Act of 2020 requires fragrance allergens included in Annex III of the EU Cosmetics Regulation No. 1223/2009 be reported to the California Department of Public Health. Fragrance allergens are only required to be reported if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million).

Product count: 6321

Household & Commercial/Institutional Products

Information on 424 consumer products that contain Eugenol in the following categories is provided:

• Auto Products

• Commercial / Institutional

• Inside the Home

• Personal Care

• Pesticides

• Pet Care

11.2 Methods of Manufacturing

The oil containing eugenol is treated with a 3% aqueous solution of NaOH; the nonacid components are extracted with ether; the alkaline solution is acidified to isolate the phenols and subsequently is fractionally distilled under reduced pressure; to avoid the formation of emulsions, a pretreatment of the oil with tartaric acid is preferred.
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 680
It can be extracted from clove oil with aqueous potassium hydroxide, followed by liberation with an acid, and distillation in a stream of CO2. It can be synthesized by the reaction of allyl chloride with guaiacol.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 77 (1985)
Since sufficient eugenol can be isolated from cheap essential oils, synthesis is not industrially important. Eugenol is still preferentially isolated from clove leaf and cinnamon leaf oil (e.g., by extraction with sodium hydroxide solution). Nonphenolic materials are then removed by steam distillation. After the alkaline solution is acidified at low temperature, pure eugenol is obtained by distillation.
Fahlbusch K-G et al; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2012). NY, NY: John Wiley & Sons; Flavors and Fragrances. Online Posting Date: January 15, 2003

11.3 IFRA Fragrance Standards

IFRA Substance
Eugenol
Synonyms
Eugenol; 4-Allylcatechol-2-methyl ether; 1-Allyl-4-hydroxy-3-methoxybenzene; 4-Allyl-2-methoxyphenol; Caryophyllic acid; 2-Hydroxy-5-allylanisole; 1-Hydroxy-2-methoxy-4-allylbenzene; 4-Hydroxy-3-methoxy-1-allylbenzene; 1-Hydroxy-2-methoxy-4-propenylbenzene; 2-Methoxy-4-allylphenol; 2-Methoxy-4-(2-propenyl)phenol; Phenol, 2-methoxy-4-(2-propenyl)-; Eugenic acid; Allylguaiacol; 4-Allylguaiacol
Amendment
51
IFRA Standard type
Restriction: This material should be used only in the limited quantity as stated in the Standard
Intrinsic property driving the risk management measure
DERMAL SENSITIZATION AND SYSTEMIC TOXICITY
Flavor use consideration
Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

11.3.1 Restriction Limits in the Finished Product (%)

Category 1 (%)
0.45 [Products applied to the lips]
Category 2 (%)
0.14 [Products applied to the axillae]
Category 3 (%)
1,0 [Products applied to the face/body using fingertips]
Category 4 (%)
2.5 [Products related to fine fragrances]
Category 5A (%)
0.64 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]
Category 5B (%)
0.64 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]
Category 5C (%)
0.64 [Products applied to the hands using the hands (palms), primarily leave-on (Hand cream)]
Category 5D (%)
0.21 [Products applied to babies using the hands (palms), primarily leave-on (Baby cream, oil, talc)]
Category 6 (%)
1.5 [Products with oral and lip exposure]
Category 7A (%)
2,0 [Rinse-off products applied to the hair with some hand contact]
Category 7B (%)
2,0 [Leave-on products applied to the hair with some hand contact]
Category 8 (%)
0.21 [Products with significant anogenital exposure (tampon)]
Category 9 (%)
4.9 [Products with body and hand exposure, primarily rinse off]
Category 10A (%)
4,0 [Household care products with mostly hand contact (excluding aerosol/spray products)]
Category 10B (%)
18 [Household care products with mostly hand contact (household aerosol/spray products)]
Category 11A (%)
0.21 [Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure]
Category 11B (%)
0.21 [Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure]
Category 12 (%)
No restriction [Other air care products not intended for direct skin contact, minimal or insignificant transfer to skin]

11.4 Formulations / Preparations

Technical product contains 95-100% eugenol.
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 3rd Edition, Volumes 1-2. Boca Raton, FL: CRC Press 1994-1995., p. 274
Grades: Technical, USP, FCC.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 543

11.5 Consumption Patterns

Eugenol is used primarily as a fragrance and flavoring agent, as an analgesic in dental materials and nonprescription drug products, as an insect attractant, and as a chemical intermediate. Several other applications have been reported, the commercial status of which is unknown. (1985)
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 77 (1985)

11.6 U.S. Production

Aggregated Product Volume

2019: 500,000 - <1,000,000 lb

2018: 500,000 - <1,000,000 lb

2017: 100,000 - <500,000 lb

2016: 100,000 - <500,000 lb

(1972) 2.15X10+8 g
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 77 (1985)
(1975) 1.45X10+8 g
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 77 (1985)
(1984) 1.63X10+8 g
USITC. SYN ORG CHEM-U.S. PROD/SALES 1984 p.119
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
1986
Production Range (pounds)
10 thousand - 500 thousand
Year
1990
Production Range (pounds)
10 thousand - 500 thousand
Year
1994
Production Range (pounds)
10 thousand - 500 thousand
Year
1998
Production Range (pounds)
10 thousand - 500 thousand
Year
2002
Production Range (pounds)
10 thousand - 500 thousand
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Phenol, 2-methoxy-4-(2-propenyl)- (97-53-0). Available from, as of June 12, 2012: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Phenol, 2-methoxy-4-(2-propen-1-yl)-. Aggregated National Production Volume: < 500,000 lbs.
US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. Phenol, 2-methoxy-4-(2-propen-1-yl)- (97-53-0). Available from, as of June 20, 2012: https://cfpub.epa.gov/iursearch/index.cfm?s=chem&err=t

11.7 U.S. Imports

Rubifacient
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-257
In perfumery instead of oil of cloves; manufacture of vanillin.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 690
Insect attractant derived essentially from clove oil.
Crop Protection Handbook 2004. (Formerly Farm and Chemicals Handbook) Willoughby, OH: Meister Publishing Co., 2004., p. C-220
Clove oil substitute in foods; germicide used in medicine; flavor chemical; intermediate for 4-allylveratrole & isoeugenol (perfume)
For more U.S. Imports (Complete) data for EUGENOL (8 total), please visit the HSDB record page.

11.8 U.S. Exports

(1984) 1.51X10+9 g /Citronellal, Eugenol, Geraniol, Heliotropin, Hydroxycitronellal and Isoeugenol/
BUREAU OF THE CENSUS. U.S. EXPORTS, SCHEDULE E, 1984 p.2-83

11.9 General Manufacturing Information

Industry Processing Sectors
  • Wholesale and Retail Trade
  • Food, beverage, and tobacco product manufacturing
  • Other (requires additional information)
  • All Other Basic Organic Chemical Manufacturing
  • Soap, Cleaning Compound, and Toilet Preparation Manufacturing
  • Plastics Material and Resin Manufacturing
  • All Other Chemical Product and Preparation Manufacturing
EPA TSCA Commercial Activity Status
Phenol, 2-methoxy-4-(2-propen-1-yl)-: ACTIVE
Eugenol ... is the main component of several essential oils, clove leaf oil and cinnamon leaf oil may contain greater than 90%.
Fahlbusch K-G et al; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2012). NY, NY: John Wiley & Sons; Flavors and Fragrances. Online Posting Date: January 15, 2003

12 Identification

12.1 Analytic Laboratory Methods

This paper reports the development and validation of an HPLC-diode array detection (DAD) method for the determination of eugenol in clove. HPLC separation was accomplished on an XTerra RP18 column (250 x 4.6 mm id, 5 microm) with an isocratic mobile phase of 60% methanol and DAD at 280 nm. Calibration graphs were linear with very good correlation coefficients (r2 > 0.9999) from 12.5 to 1000 ng/mL. The LOD was 0.81 and the LOQ was 2.47 ng/mL. The method showed good intraday precision (%RSD 0.08-0.27%) and interday precision (%RSD 0.32-1.19%). The method was applied to the analysis of eugenol from clove cultivated in various countries (Indonesia, Singapore, and China). Quantitative analysis of the 15 clove samples showed that the content of eugenol varied significantly, ranging from 163 to 1049 ppb.
Yun SM et al; J AOAC Int 93 (6): 1806-10 (2010)
A method for the detection and quantitative assay of eugenol in dental materials and-filling agents was developed. Its sensitivity limit is 10 ng/ml for liquid samples and 25 mcg/g for solid ones. Metrologic characteristics of the method make it suitable for the detection of eugenol in dental fillings after their long-term contact with biological tissues.
Shabalina AE et al; Sud Med Ekspert 52 (2): 31-5 (2009)
Eugenol was determined by HPLC on Kontron RP-18 column or on nucleosil column.
Gracza L; Dtsch Apoth-Ztg 120 (40): 1859 (1980)
... UV spectrophotometry may be used to yield results accurate to concentration /in air/ as small as 0.005 mg/mL.
Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2533
For more Analytic Laboratory Methods (Complete) data for EUGENOL (6 total), please visit the HSDB record page.

12.2 Clinical Laboratory Methods

Sensitive HPLC assay used for the determination of eugenol in body fluids. Amount in the range 0.02-100 ug of eugenol/mL of body fluid were determined with intra-assay coefficients of variation <4% (1.13-3.72%).
Fischer IU, Dengler HJ; J Chromatogr 525 (2): 369-77 (1990)

13 Safety and Hazards

13.1 Hazards Identification

13.1.1 GHS Classification

1 of 3
View All
Note
Pictograms displayed are for 96.7% (2714 of 2806) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 3.3% (92 of 2806) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (17.4%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (20.7%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (96.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (77.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2806 reports by companies from 27 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 92 of 2806 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 26 notifications provided by 2714 of 2806 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

13.1.2 Hazard Classes and Categories

Acute Tox. 4 (17.4%)

Skin Irrit. 2 (20.7%)

Skin Sens. 1 (96.7%)

Eye Irrit. 2 (77.2%)

Eye irritation - category 2A

Skin sensitisation - category 1

13.1.3 NFPA Hazard Classification

NFPA 704 Diamond
2-2-0
NFPA Health Rating
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
NFPA Fire Rating
2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.
NFPA Instability Rating
0 - Materials that in themselves are normally stable, even under fire conditions.

13.1.4 Health Hazards

SYMPTOMS: This compound is a primary irritant and sensitizer and can cause contact dermatitis. Irritation of the skin, eyes and respiratory tract occurs. Ingestion of this compound may cause gastroenteritis, vomiting and gastric secretion of mucin. It may also cause abdominal burning, nausea, diarrhea and convulsions. Ingestion of large amounts can cause liver damage and gastrointestinal damage. Inhalation of this compound can lead to bronchial irritation, dizziness, and rapid and shallow breathing. Skin contact may cause an inflammatory reaction on the skin. Prolonged or repeated skin contact may cause allergic dermatitis. Eye contact may cause burns. Skin sensitization may also occur. Symptoms of exposure to this type of compound include intense irritation of all tissues, circulatory collapse, dysuria, hematuria, unconsciousness, tachycardia, pulmonary edema, bronchial pneumonia, abortion and irreversible renal damage.

ACUTE/CHRONIC HAZARDS: This compound may be harmful by ingestion or inhalation. It is a primary irritant and sensitizer. When heated to decomposition it emits acrid smoke, irritating fumes and toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

13.1.5 Fire Hazards

This chemical is combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

13.1.6 Hazards Summary

A contact skin allergen present in cosmetics and foods; [Marks, p. 172] Occupational asthma confirmed in a hairdresser; [Malo] Toxic by ingestion: metabolic acidosis, proteinuria, hepatotoxicity, CNS depression, ataxia, and convulsions; [HSDB] Generally regarded as safe (GRAS) for use in foods; [FDA] A primary irritant; May cause skin sensitization and contact dermatitis; [CAMEO] Safe when used as a flavoring agent in food; Acceptable daily intake (ADI) of 0-2.5 mg/kg; [JECFA] Mildly irritating to human skin; [RTECS]
Marks - Marks JG, DeLeo VA. Contact and Occupational Dermatology, 2nd Ed. St. Louis: Mosby, 1997., p. 172

13.2 Safety and Hazard Properties

13.2.1 Critical Temperature & Pressure

Critical temperature: 699.844 deg K; critical pressure: 30.142 atm
Razdan TK et al; Parfuem Kosmet 66: 444-449 (1985)

13.2.2 Explosive Limits and Potential

Combustible
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 543

13.3 First Aid Measures

13.3.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

13.4 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

13.5 Accidental Release Measures

13.5.1 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

13.6 Handling and Storage

13.6.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

13.7 Exposure Control and Personal Protection

13.7.1 Acceptable Daily Intakes

Joint Expert Committee on Food Additives ADI: 0 to 2.5 mg/kg bw
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 680

13.7.2 Personal Protective Equipment (PPE)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

13.8 Stability and Reactivity

13.8.1 Air and Water Reactions

Darkens and thickens on exposure to air. Also darkens with age. It may decompose on exposure to light. Insoluble in water.

13.8.2 Reactive Group

Hydrocarbons, Aliphatic Unsaturated

Phenols and Cresols

13.8.3 Reactivity Profile

EUGENOL is incompatible with strong oxidizers. This includes ferric chloride and potassium permanganate. It reacts with strong alkalis. It is incompatible with iron and zinc. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

13.8.4 Hazardous Reactivities and Incompatibilities

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 665

13.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Phenol, 2-methoxy-4-(2-propenyl)-
California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Fragrance Allergen

Authoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance Allergens

Report - if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)

Status Regulation (EC)
2007/442/EC, Dossier complete 2011/266/EU, Reg. (EU) 2018/155, Reg. (EU) 2023/1757, Reg. (EU) No 546/2013
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Eugenol: Does not have an individual approval but may be used under an appropriate group standard

13.9.1 FIFRA Requirements

Exemptions for pesticides of a character not requiring FIFRA regulation. The pesticides or classes of pesticides listed in this section have been determined to be of a character not requiring regulation under FIFRA, and are therefore exempt from all provisions of FIFRA when intended for use, and used, only in the manner specified. Eugenol is included on this list.
40 CFR 152.25 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2012: https://www.ecfr.gov
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Eugenol is found on List D. Case No: 4038; Pesticide type: insecticide; Case Status: Pesticides in the case have been exempted from regulation under FIFRA Section 25 (b).; Active ingredient (AI): eugenol; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.
United States Environmental Protection Agency/ Prevention, Pesticides and Toxic Substances; Status of Pesticides in Registration, Reregistration, and Special Review. (1998) EPA 738-R-98-002, p. 311

13.9.2 FDA Requirements

Substance added directly to human food affirmed as generally recognized as safe (GRAS).
21 CFR 184.1257 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 19, 2012: https://www.ecfr.gov
Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Eugenol is included on this list.
21 CFR 582.60 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 19, 2012: https://www.ecfr.gov
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Eugenol is included in external analgesic drug products and skin protectant drug products.
21 CFR 310.545 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 19, 2012: https://www.ecfr.gov
Zinc oxide-eugenol is a device composed of zinc oxide-eugenol intended to serve as a temporary tooth filling or as a base cement to affix a temporary tooth filling, to affix dental devices such as crowns or bridges, or to be applied to a tooth to protect the tooth pulp.
21 CFR 872.3275 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of August 1, 2012: https://www.ecfr.gov

13.10 Other Safety Information

Chemical Assessment
IMAP assessments - Phenol, 2-methoxy-4-(2-propenyl)-: Human health tier II assessment

13.10.1 Special Reports

DHHS/NTP; Toxicology & Carcinogenesis Studies of Eugenol in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 223 (1983) NIH Publication No. 84-1779.

14 Toxicity

14.1 Toxicological Information

14.1.1 Hepatotoxicity

The low concentrations of eugenol and clove extracts used topically and in herbal products have not been convincingly linked to instances of liver injury, either in the form of serum enzyme elevations or clinically apparent liver injury. In high doses, however, eugenol appears to be a direct cytotoxin and several instances of severe acute liver and kidney injury have been reported after accidental overdose of eugenol containing herbal products, largely in children. Overdoses have been marked by the onset of agitation, decrease in consciousness and coma arising within hours on ingestion (10-30 mL of clove oil). There is typically an accompanying acidosis, respiratory depression and severe hypoglycemia requiring ventilation and intravenous glucose. Liver injury arises 12 to 24 hours after ingestion with marked elevations in serum aminotransferase levels and early coagulation abnormalities. Signs of hepatic failure arise rapidly, and jaundice can develop and deepen. The overall clinical presentation is typical of acute hepatic necrosis and similar to that of acetaminophen, iron or copper overdose. The liver injury generally worsens for several days but then rapidly improves and ultimately resolves within 1 to 3 weeks. Renal dysfunction may also occur but rarely requires intervention or dialysis. Long term injury or effects have not been described. Cases described in the literature have been in infants who swallowed clove oil being used by parents.

Likelihood score: C[H] (probable cause of clinically apparent liver injury in overdoses).

14.1.2 Evidence for Carcinogenicity

Classification of carcinogenicity: 1) evidence in humans: No adequate data. 2) evidence in animals: Limited evidence. Overall summary evaluation of carcinogenic risk to humans is Group 3: The agent is not classifiable as to its carcinogenicity to humans. /From table/
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. S7 63 (1987)

14.1.3 Carcinogen Classification

1 of 3
IARC Carcinogenic Agent
Eugenol
IARC Carcinogenic Classes
Group 3: Not classifiable as to its carcinogenicity to humans
IARC Monographs

Volume 36: (1985) Allyl Compounds, Aldehydes, Epoxides and Peroxides

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

2 of 3
Substance
NTP Technical Report
TR-223: Carcinogenesis Studies of Eugenol (CASRN 97-53-0) in F344/N Rats and B6C3F1 Mice (Feed Studies) (1983 )
Peer Review Date
Conclusion for Male Rat
No Evidence No Evidence
Conclusion for Female Rat
No Evidence No Evidence
Conclusion for Male Mice
Equivocal Evidence Equivocal Evidence
Conclusion for Female Mice
Equivocal Evidence Equivocal Evidence
Summary
3 of 3
Carcinogen Classification
3, not classifiable as to its carcinogenicity to humans. (L135)

14.1.4 Adverse Effects

Neurotoxin - Other CNS neurotoxin

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.

14.1.5 Acute Effects

14.1.6 Toxicity Data

LC50 > 2,580 mg/m3/4hr

14.1.7 Interactions

Mice treated with eugenol (400-600 mg/kg, orally) in combination with an inhibitor of glutathione synthesis, buthionine sulfoximine (1 hr before eugenol, 4 mmol/kg, ip) developed hepatotoxicity characterized by increases in relative liver weight and serum glutamic-pyruvic transaminase, hepatic congestion, and centrilobular necrosis of hepatocytes. Eugenol (up to 600 mg/kg) alone produced no hepatotoxicity. Drug metabolism inhibitors such as carbon disulfide, methoxsalen, and piperonyl butoxide prevented or significantly reduced the hepatotoxic effect of eugenol given in combination with buthionine sulfoximine.
Mizutani T et al; Res Commun Chem Pathol Pharmacol 71 (2): 219-30 (1991)
The present study was undertaken to evaluate the chemopreventive potential of eugenol alone and in combination with a chemotherapeutic agent such as gemcitabine. Eugenol showed dose-dependent selective cytotoxicity toward HeLa cells in comparison to normal cells, pointing to its safe cytotoxicity profile. A combination of eugenol and gemcitabine induced growth inhibition and apoptosis at lower concentrations, compared with the individual drugs. The analysis of the data using a combination index showed combination index values of <1 indicating strong synergistic interaction. The combination thus may enhance the efficacy of gemcitabine at lower doses and minimize the toxicity on normal cells. In addition, the expression analysis of genes involved in apoptosis and inflammation revealed significant downregulation of Bcl-2, COX-2, and IL-1beta on treatment with eugenol. Thus, the results suggest that eugenol exerts its anticancer activities via apoptosis induction and anti-inflammatory properties and also provide the first evidence demonstrating synergism between eugenol and gemcitabine, which may enhance the therapeutic index of prevention and/or treatment of cervical cancer.
Hussain A et al; Cancer Biother Radiopharm 26 (5): 519-27 (2011)
The biochemical mechanisms underlying the increased toxicity of several plant essential oils (thymol, eugenol, pulegone, terpineol, and citronellal) against fourth instar of Aedes aegypti L. when exposed simultaneously with piperonyl butoxide (PBO) were examined. Whole body biotransformational enzyme activities including cytochrome P450-mediated oxidation (ethoxyresorufin O-dethylase (EROD)), glutathione S-transferase (GST), and beta-esterase activity were measured in control, essential oil-exposed only (single chemical), and essential oil + PBO (10 mg/liter) exposed larvae. At high concentrations, thymol, eugenol, pulegone, and citronellal alone reduced EROD activity by 5-25% 16 h postexposure. Terpineol at 10 mg/liter increased EROD activity by 5 +/- 1.8% over controls. The essential oils alone reduced GST activity by 3-20% but PBO exposure alone did not significantly affect the activity of any of the measured enzymes. All essential oils in combination with PBO reduced EROD activity by 58-76% and reduced GST activity by 3-85% at 16 hr postexposure. This study indicates a synergistic interaction between essential oils and PBO in inhibiting the cytochrome P450 and GST detoxification enzymes in Ae. aegypti.
Waliwitiya R et al; J Med Entomol 49 (3): 614-23 (2012)
... Swiss albino mice were administered different doses of eugenol (75,150 and 300 mg/kg) before exposure to 1.5 Gy of gamma radiation. The micronucleus test was carried out to determine the genetic damage in bone marrow. Our results demonstrated significant reduction in the frequencies of micronucleated polychromatic erythrocytes (MnPCEs) with all three eugenol doses. Eugenol (150 mg/kg) was also tested against different doses of radiation (0.5, 1, 1.5, and 2 Gy) and was found to afford significant radioprotection. Reduction in the incidence of MnPCEs could be noticed up to 72 hr postirradiation (1.5 Gy). Moreover, the level of peroxidative damage and the specific activities of lactate dehydrogenase (LDH) and methylglyoxalase I (Gly I) were observed in the liver of mice treated with eugenol for seven days in comparison to untreated mice.
Tiku AB et al; J Radiat Res (Tokyo) 45 (3): 435-40 (2004)
For more Interactions (Complete) data for EUGENOL (7 total), please visit the HSDB record page.

14.1.8 Antidote and Emergency Treatment

Treatment is primarily supportive as there is no antidote. If mucosal burns are present, consider endoscopy to look for other ulcerations.
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 65
Maintain and open airway and assist ventilations if necessary. Treat seizures and coma if they occur There are no specific antidote for /these essential oils/. Administer activated charcoal, if available. Do not induce vomiting because of the risk of abrupt onset of seizures. Gastric emptying is not necessary for small ingestions if activated charcoal can be given promptly. /Camphor and Other Essential Oils/
OLSON, K.R. (Ed). Poisoning and Drug Overdose, Sixth Edition. McGraw-Hill, New York, NY 2012, p. 158
The volumes of distribution of camphor and other essential oils is extremely large, and it is unlikely that any enhanced removal procedure will remove significant amounts of /these essential oils/. Poorly substantiated case reports have recommended hemoperfusion. /Camphor and Other Essential Oils/
OLSON, K.R. (Ed). Poisoning and Drug Overdose, Sixth Edition. McGraw-Hill, New York, NY 2012, p. 158
N-Acetylcysteine may be beneficial in preventing or treating the hepatotoxicity /of clove oil/. /Clove oil/
OLSON, K.R. (Ed). Poisoning and Drug Overdose, Sixth Edition. McGraw-Hill, New York, NY 2012, p. 159
For more Antidote and Emergency Treatment (Complete) data for EUGENOL (8 total), please visit the HSDB record page.

14.1.9 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ Patch tests for eugenol in patients suffering from 'cosmetic dermatitis' were positive in 2.6% (4/155) of cases.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 87 (1985)
/HUMAN EXPOSURE STUDIES/ ... During a five-year period 3,065 patients with contact dermatitis were patch tested using a specific mix of fragrances. 509 (16.6%) patients were allergic to the fragrance mix, while 258 (8.4%) patients exhibited an allergic reaction to Myroxylon pereirae (balsam of Peru). Between those 509 patients, 157 were patch tested with eight individual substances contained in the fragrance mix: cinnamal, cinnamyl alcohol, eugenol, isoeugenol, geraniol, hydroxycitronellal, alpha-amyl cinnamal and Evernia prunastri (oak moss). The most frequent allergens were isoeugenol 57.9% (91/157), eugenol 55.4% (87/157), cinnamyl alcohol 34.4% (54/157) and Evernia prunastri (oak moss) 24.2% (38/157). ...
Turic P et al; Coll Antropol. 2011 Mar;35(1):83-7 (2011)
/HUMAN EXPOSURE STUDIES/ 84 patients with contact dermatitis (38 dentists, 18 dental nurses and 28 dental technicians) were studied. All were patch tested with standard patch test series of the Council for Mutual Economic Assistance countries and with some professional allergens. 31 (36.9%) of them had allergic occupational contact dermatitis and 39 (46.2%) had irritant contact dermatitis. The highest prevalence of irritant contact dermatitis was found among dental surgeons. The percentage of atopics in the group of patients with irritant contact dermatitis was twice greater compared to that in the group of patients with allergic contact dermatitis. The contact allergens most frequently encountered were acrylic compounds, disinfectants (eugenol, thymol, trioxymethylene) mercury compunds and anesthetics.
Berova N et al; Dermatol Monatsschr 176 (1): 15-8 (1990)
/SIGNS AND SYMPTOMS/ Not corrosive like phenol but ingestion results in gastroenteritis. Systemic toxicity is similar to but less than that of phenol perhaps because of its insolubility in water. Aqueous emulsions by mouth induce vomiting in man ... promote/s/ gastric secretion of mucin.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-257
For more Human Toxicity Excerpts (Complete) data for EUGENOL (11 total), please visit the HSDB record page.

14.1.10 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ ... Animals that survived acute effects remained lethargic, showed kidney injury as manifested by urinary incontinence and sometimes hematuria and exhibited malfunction of hind legs for several days.
Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1692
/LABORATORY ANIMALS: Acute Exposure/ Eugenol "purified" by HPLC was compared to commercial USP eugenol to determine if any difference exists between the inflammatory response caused by each. ... Each material was injected subcutaneously beneath the abdominal skin of 40 Walter Reed white rats. Ten animals were sacrificed at four different dates, and the degree of necrosis and inflammation was compared. The purified eugenol caused less necrosis and inflammation at all times than did the commercial eugenol. ... This study suggests that the impurities in commercial eugenol do cause an increase in the inflammatory response in the rat system studied. This increase is most evident at day two and after day ten.
Webb JG et al; J Dent Res 60 (9): 1724 (1981)
/LABORATORY ANIMALS: Acute Exposure/ When instilled directly into the trachea of rats, eugenol caused interstitial hemorrhage, acute emphysema, and acute pulmonary edema.
Haddad, L.M. (Ed). Clinical Management of Poisoning and Drug Overdose 3rd Edition. Saunders, Philadelphia, PA. 1998., p. 1177
/LABORATORY ANIMALS: Acute Exposure/ Dogs given oral doses of 0.25 g/kg of eugenol demonstrated vomiting, weakness, lethargy, and ataxia. At 0.5 g/kg eugenol is capable of causing coma and death within 24 hr. The LD50 of eugenol in rats has been determined to be 1.8 mL/kg (1.93 g), with postmortem findings consistent with sudden cardiovascular collapse.
Haddad, L.M. (Ed). Clinical Management of Poisoning and Drug Overdose 3rd Edition. Saunders, Philadelphia, PA. 1998., p. 1176
For more Non-Human Toxicity Excerpts (Complete) data for EUGENOL (61 total), please visit the HSDB record page.

14.1.11 Non-Human Toxicity Values

LD50 Guinea pig oral 2130 mg/kg
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 85 (1985)
LD50 Mouse ip 1109 mg/kg (7.5% eugenol in saline)
Woolverton CJ et al; J Oral Pathol 15 (8): 450-3 (1986)
LD50 Rat oral 1930 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1735
LD50 Mouse intraperitoneal 500 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1735
For more Non-Human Toxicity Values (Complete) data for EUGENOL (6 total), please visit the HSDB record page.

14.1.12 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of June 21, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=97-53-0]

14.1.13 National Toxicology Program Studies

Carcinogenesis studies of eugenol (>99% pure), ... were conducted by feeding diets containing 6,000 or 12,500 ppm of eugenol to groups of 50 female F344/N rats and by feeding diets containing 3,000 or 6,000 ppm to groups of 50 male F344/N rats and B6C3Fl mice of each sex for 103 weeks. Groups of 40 rats and 50 mice of each sex served as controls. ... Eugenol was given in the diets of female F344/N rats (0, 0.6, or 1.25%) and of male F344/N rats and male and female B6C3F1 mice (0, 0.3, or 0.6%) for 103 weeks. Under these experimental conditions, there was no evidence of carcinogenicity observed for male or female rats. For mice there was equivocal evidence of carcinogenicity since eugenol caused increase incidences of both carcinomas and adenomas of the liver in male mice at the 3,000 ppm dietary level and because eugenol was associated with an increase in the combined incidences of hepatocellular carcinomas or adenomas in female mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Equivocal; Female Mice: Equivocal.
Carcinogenesis Bioassay of Eugenol in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 223 (1983) NIH Publication No. 84-1779 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709

14.2 Ecological Information

14.2.1 Ecotoxicity Values

LC50 Oncorhynchus kisutch (Coho salmon, juvenile approximately 2-3 months old) 67.6 mg/L/24, 48, 72 hr; 66.1 mg/L/96 hr; static, 15 +/-1 °C, mean hardness 95 mg/L CaCO3, average fish loading density was 0.4 (0.3-0.5) g/L, within a bioassay test volume of 20 L.
Stroh J et al; Bull Environ Contam Toxicol 60 (6): 923-30 (1998)
LC50 Oncorhynchus mykiss (Rainbow trout, juvenile approximately 2-3 months old) 61.5 mg/L/24 hr; 60.8 mg/L/48, 72, 96 hr; static, 15 +/-1 °C, mean hardness 95 mg/L CaCO3, average fish loading density was 0.4 (0.3-0.5) g/L, within a bioassay test volume of 20 L.
Stroh J et al; Bull Environ Contam Toxicol 60 (6): 923-30 (1998)
LC50 Pimephales promelas (Fathead minnow) 24 mg/L/1, 24, 48, 72, 96 hr; static /formulated product/
Mattson VR et al; EPA-600/3-76-097:12 (1976). ECOTOX database on Eugenol (97-53-0). Available from, as of April 20, 2005

14.2.2 Ecotoxicity Excerpts

/AQUATIC SPECIES/ /Investigators/ evaluated eugenol on the nerve and muscle in crayfish. Using concentrations up to 1000 ppm in water, /it has been/ reported that eugenol is an effective reversible anesthetic.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 p. 921

14.2.3 Environmental Fate / Exposure Summary

Eugenol is the main component of several essential oils such as clove leaf oil and cinnamon leaf oil. It has been identified as a component of particulate and gas-phase emissions from the combustion of wood, wheat and grass. Eugenol's production and use as a perfume and essential oil, as a flavoring agent, as an intermediate in the production of isoeugenol for the manufacture of vanillin, as an ingredient in temporary dental cements and fillings and as an insect attractant will result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.0221 mm Hg at 25 °C indicates eugenol will exist solely as a vapor in the atmosphere. Vapor-phase eugenol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 5.9 hours. Vapor-phase eugenol will also be degraded in the atmosphere by reaction with ozone; the half-life for this reaction in air is estimated to be 23 hours. Eugenol absorbs UV light at wavelengths >290 nm and is expected to be susceptible to direct photolysis by sunlight. If released to soil, eugenol is expected to have moderate mobility based upon an estimated Koc value of 340. Volatilization from moist soil surfaces is expected given an estimated Henry's Law constant of 1.92X10-6 atm-cu m/mole. A theoretical model of soil volatilization predicts that 4-33% of eugenol applied to a soil surface will volatilize during the first 10 days with the the fastest volatilization rates occurring with lowest soil organic content and moisture content. Isoeugenol, which is structurally similar to eugenol, was found to be readily biodegradable using a Manometric Respirometry Test in which isoeugenol reached 79% biodegradation after 28 days; by analogy, eugenol may also be readily biodegradable. Photodegradation may occur on surfaces exposed to sunlight. If released into water, eugenol is expected to adsorb to suspended solids and sediment based upon the estimated Koc values. Volatilization from water surfaces is expected based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 25 and 183 days, respectively. An estimated BCF of 20 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Photodegradation may occur in water exposed to sunlight. Occupational exposure to eugenol may occur through inhalation and dermal contact with this compound at workplaces where eugenol is produced or used. Monitoring and use data indicate the general population can be exposed to eugenol through dermal contact and inhalation of perfumes and other consumer products containing the compound and through ingestion of foods and plants containing eugenol. (SRC)

14.2.4 Natural Pollution Sources

Eugenol is the main component of several essential oils; clove leaf oil and cinnamon leaf oil may contain >90% and eugenol occurs in small amounts in many other essential oils(1) such as pimento, bay, sassafras, massoy bark oils as well as oil of camphor and chamchwi plants(2). Clove leaf oil from Madagascar has eugenol content in the range of 82-92%; in Indonesia, the eugenol content is somewhat lower, 78-86%(3). Eugenol has been identified as a component of particulate and gas-phase emissions from the combustion of wood, wheat and grass(4-9).
(1) Fahlbusch KG et al; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2012). New York, NY: John Wiley & Sons; Flavors and Fragrances. Online Posting Date: Jan 15, 2003
(2) Osol A, ed; Remington's Pharmaceutical Sciences. 14th ed. Easton, PA: Mack Publ Co, p. 1070 (1970)
(3) Schreiber WL; Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2012). New York, NY: John Wiley & Sons; Perfumes. Online Posting Date: Sept 23, 2005
(4) Fine PM et al; Environ Sci Technol 35: 2665-2675 (2001)
(5) Fine PM et al; Environ Sci Technol 36: 1442-1451 (2002)
(6) Rogge WF et al; Environ Sci Technol 32: 13-22 (1998)
(7) Hayes MD et al; Environ Sci Technol 36: 2281-2295 (2002)
(8) Schauer JJ et al; Environ Sci Technol 35: 1716-1728 (2001)
(9) Jimenez JR et al; Environ Sci Technol 41: 7824-7829 (2007)
Eugenol is obtained from many natural sources including clove, cinnamon leaf, pimento, bay, sassafras, massoy bark oils as well as oil of camphor and chamchwi plants(1).
(1) Osol A, ed; Remington's Pharmaceutical Sciences. 14th ed. Easton, PA: Mack Publ Co, p. 1070 (1970)
... PRESENT IN OIL OF CAMPHOR, JAVA CITRONELLA, CALIFORNIA LAUREL & ACACIA FLOWERS. ... REMARKABLE AMT ... IN OCIMUM SANCTUM (70%) AND OCIMUM GRATISSIMUM (60%). EUGENOL IS ... FOUND IN OIL FROM VIOLET FLOWERS (21%). IN SOME PLANTS PROBABLY OCCURS AS GLUCOSIDE.
Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 198
EUGENOL ... OCCURS IN PIMENTO OIL (80%), & BAY OIL (60%).
Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1690
For more Natural Pollution Sources (Complete) data for EUGENOL (6 total), please visit the HSDB record page.

14.2.5 Artificial Pollution Sources

Eugenol's production and use as a perfume and essential oil, as a flavoring agent, as an intermediate in the production of isoeugenol for the manufacture of vanillin(1), as an ingredient in temporary dental cements and fillings(2) and as an insect attractant(3) will result in its release to the environment through various waste streams(SRC).
(1) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary 15th ed. New York, NY: John Wiley & Sons, Inc., p. 543 (2007)
(2) Tesk JA et al; Kirk-Othmer Encyclopedia of Chemical Technology. (1999-2012). New York, NY: John Wiley & Sons; Dental Materials. Online Posting Date: Oct 18, 2002
(3) Metcalf RL; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2012). New York, NY: John Wiley & Sons; Insect Control. Online Posting Date: Jun 15, 2000

14.2.6 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 340(SRC), determined from a log Kow of 2.49(2) and a regression-derived equation(3), indicates that eugenol is expected to have moderate mobility in soil(SRC). Volatilization of eugenol from moist soil surfaces is expected to occur(SRC) given a an estimated Henry's Law constant of 1.92X10-6 atm-cu m/mole(SRC), estimated from its vapor pressure, 0.0221 mm Hg at 25 °C(4), and water solubility, 2460 mg/L(5). A theoretical model of soil volatilization predicts that 4-33% of eugenol applied to a soil surface will volatilize during the first 10 days(6); the fastest volatilization rates occur with lowest soil organic content and moisture content(6). Isoeugenol, which is structurally similar to eugenol, was found to be readily biodegradable using a Manometric Respirometry Test in which isoeugenol reached 79% biodegradation after 28 days(7); by analogy, eugenol may also be readily biodegradable(SRC). Eugenol absorbs uv light at wavelengths >290 nm(8), and therefore may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Dias NC et al; Analyst 128: 427-433 (2003)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Jun 26, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(4) Van Roon A et al; Chemosphere 61: 599-609 (2005)
(5) Yalkowky SH et al; Handbook of Aqueous Solubility Data 2nd ed., Boca Raton, FL: CRC Press, p. 687 (2010)
(6) Van Roon A et al; Chemosphere 61: 129-138 (2005)
(7) HERA; HERA Risk Assessment of Isoeugenol (Draft). Human and Environmental Risk Assessment on ingredients of Household Cleaning Products. Isoeugenol (CAS 97-54-1). Available from, as of June 23, 2012: https://www.heraproject.com/
(8) NIST; NIST Chemistry WebBook. Eugenol (97-53-0). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of Jun 26, 2012: https://webbook.nist.gov
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 340(SRC), determined from a log Kow of 2.49(2) and a regression-derived equation(3), indicates that eugenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected to occur slowly(4) based upon an estimated Henry's Law constant of 1.92X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.0221 mm Hg at 25 °C(5), and water solubility, 2460 mg/L(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 25 and 183 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 20(SRC), from its log Kow and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Eugenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Eugenol absorbs UV light at wavelengths >290 nm(8), and therefore may be susceptible to direct photolysis by sunlight in water(SRC). Isoeugenol, which is structurally similar to eugenol, was found to be readily biodegradable using a Manometric Respirometry Test (OECD Guideline 301F) in which isoeugenol reached 79% biodegradation after 28 days(9); by analogy, eugenol may also be readily biodegradable(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Dias NC et al; Analyst 128: 427-433 (2003)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Jun 26, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 15-1 to 15-29 (1990)
(5) Van Roon A et al; Chemosphere 61: 599-609 (2005)
(6) Yalkowky SH et al; Handbook of Aqueous Solubility Data 2nd ed., Boca Raton, FL: CRC Press, p. 687 (2010)
(7) Franke C et al; Chemosphere 29: 1501-14 (1994)
(8) NIST; NIST Chemistry WebBook. Eugenol (97-53-0). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of Jun 26, 2012: https://webbook.nist.gov
(9) HERA; HERA Risk Assessment of Isoeugenol (Draft). Human and Environmental Risk Assessment on ingredients of Household Cleaning Products. Isoeugenol (CAS 97-54-1). Available from, as of June 23, 2012: https://www.heraproject.com/
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), eugenol, which has a vapor pressure of 0.0221 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase eugenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5.9 hours(SRC), calculated from its rate constant of 6.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase eugenol is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 23 hours(SRC), calculated from its rate constant of 1.2X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Eugenol absorbs UV light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Irradiation of eugenol in methanol solution yields 4-cyclopropyl-2-methoxyphenol as the main photodegradation product(5); sunlight degrades the main constituents of essential oils(5).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Van Roon A et al; Chemosphere 61: 599-609 (2005)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Jun 26, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(4) NIST; NIST Chemistry WebBook. Eugenol (97-53-0). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of Jun 26, 2012: https://webbook.nist.gov
(5) Mihura S, Shibamoto T; J Agric Food Chem 30: 1215-1218 (1982)

14.2.7 Environmental Biodegradation

AEROBIC: At a concentration of 100 mg/L, isoeugenol (which is structurally similar to eugenol) was found to be readily biodegradable using a Manometric Respirometry Test (OECD Guideline 301F) in which isoeugenol reached 79% biodegradation after 28 days. The biodegradation started on day 2 and reached 79% at the end of the 10-day window period(1).
(1) HERA; HERA Risk Assessment of Isoeugenol (Draft). Human and Environmental Risk Assessment on ingredients of Household Cleaning Products. Isoeugenol (CAS 97-54-1). Available from, as of June 23, 2012: https://www.heraproject.com/
PURE CULTIRE: Various strains of bacteria (Pseudomonas sp. strain HR199, Ralstonia eutropha H16, Bacillus Cereus Strain PN24) have been isolated that can biotransform eugenol. Biometabolites include protocatechuic acid, ferulic acid, coniferyl alcohol, coniferyl aldehyde, vanillin, and vanillic acid(1,2).
(1) Overhage J et al; Appl Environ Microbiol 68: 4315-4321 (2002)
(2) Kadakol JC, Kamanavalli CM; E-Journal of Chemistry 7(S1): S474-S480 (2010)

14.2.8 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of eugenol with photochemically-produced hydroxyl radicals has been estimated as 6.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of isoeugenol with ozone has been estimated as 1.2X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). Eugenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Eugenol absorbs UV light at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Irradiation of eugenol in methanol solution yields 4-cyclopropyl-2-methoxyphenol as the main photodegradation product(4); sunlight degrades the main constituents of essential oils(4).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Jun 26, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
(3) NIST; NIST Chemistry WebBook. Eugenol (97-53-0). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of Jun 26, 2012: https://webbook.nist.gov
(4) Mihura S, Shibamoto T; J Agric Food Chem 30: 1215-1218 (1982)

14.2.9 Environmental Bioconcentration

An estimated BCF of 20 was calculated in fish for eugenol(SRC), using a log Kow of 2.49(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Dias NC et al; Analyst 128: 427-433 (2003)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Jun 26,2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

14.2.10 Soil Adsorption / Mobility

The Koc of eugenol is estimated as 340(SRC), using a log Kow of 2.49(1) and a regression-derived equation(2). According to a classification scheme(3), these estimated Koc values suggest that eugenol is expected to have moderate to lowmobility in soil.
(1) Dias NC et al; Analyst 128: 427-433 (2003)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011.Available from, as of Jun 26, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Swann RL et al; Res Rev 85: 17-28 (1983)

14.2.11 Volatilization from Water / Soil

The Henry's Law constant for eugenol is estimated as 1.92X10-6 atm-cum/mole(SRC) derived from its extrapolated vapor pressure, 0.0221 mm Hg at 25deg C(1), and water solubility, 2460 mg/L at 25 °C(2). This Henry's Law constant indicates that eugenol is expected to volatilize slowly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 25 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 183 days(SRC). Eugenol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). A theoretical model of soil volatilization predicts that 4-33% of eugenol applied to a soil surface will volatilize during the first 10 days(4); the fastest volatilization rates occur with lowest soil organic content and moisture content(4). Although eugenol's vapor pressure might suggest that volatilization from dry soil will not occur, the compound is used in fragrance and odorant applications that result in inhalation exposure(SRC); therefore, volatilization from dry soil is expected to occur(SRC).
(1) Van Roon A et al; Chemosphere 61: 599-609 (2005)
(2) Yalkowky SH et al; Handbook of Aqueous Solubility Data 2nd ed., Boca Raton, FL: CRC Press, p. 687(2010)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(4) Van Roon A et al; Chemosphere 61: 129-138 (2005)

14.2.12 Effluent Concentrations

Eugenol was qualitatively detected in the wastewater effluent from one of ten publicly-owned treatment works in Illinois in 1980(1). A eugenol concentration of 0.18 ug/L was detected in the secondary effluent from a rapid infiltration site in Fort Polk, LA in 1980(2). A eugenol concentration of 0.025 mg/L was detected in the effluent from a kraft paper mill in GA(3). Eugenol was detected in 8 effluents collected from 13 paper and pulp in Quebec, Canada in1990 at a concentration of 0 (detection limit not specified) to 18743 ug/L(2).
(1) Arch Environ Contam Toxicol 11: 373-382 (1982)
(2) Hutchins SR et al; Environ Toxicol Chem 2: 195-216 (1983)
(3) Keith LH; Environ Sci Technol 10:555-564 (1976)
(4) Lavallee HC et al; Sci Tech Eau 25: 501-510 (1992)
The eugenol concentration in the fine particle emissions from the fireplace combustion of six species of wood grown in the northeastern US ranged from0.059 to 0.254 mg/g organic content emitted(1). The eugenol concentration in the fine particle emissions from the fireplace combustion of six species of wood grown in the southern US ranged from 0.044 to 0.161 mg/g organic content emitted(2). The emission rate of eugenol in wood smoke from the combustion of pine wood logs, oak wood logs and synthetic logs was reported as 1.44 mg/kg, not detected and not detected respectively(3). The eugenol concentration in the particle emissions from the open-burning of six biomass fuels ranged from 0.0012-0021 percent of particle mass(4); the eugenol concentration in the gas-phase emissions from the open-burning of six biomass fuels ranged from 10.11-37.32 mg/kg(4). Eugenol concentrations in emissions from the combustion of wood (pine, oak, eucalyptus) was 10.8-57.2 mg/kg burned wood in the gas-phase and 0.381 mg/kg in the particle phase(5). Eugenol concentrations of 0.01-0.09 ug/mg were detected in the PM2.5 particulates from the combustion of wheat and Kentucky bluegrass(6).
(1) Fine PM et al; Environ Sci Technol 35: 2665-2675 (2001)
(2) Fine PM et al; Environ Sci Technol 36: 1442-1451 (2002)
(3) Rogge WF et al; Environ Sci Technol 32: 13-22 (1998)
(4) Hayes MD et al; Environ Sci Technol 36: 2281-2295(2002)
(5) Schauer JJ et al; Environ Sci Technol 35: 1716-1728 (2001)
(6) Jimenez JR et al; Environ Sci Technol 41: 7824-7829 (2007)

14.2.13 Atmospheric Concentrations

SOURCE DOMINATED: Eugenol has been detected in fine particle emissions smoke generated from wood burning fireplaces at concentrations ranging from 0.044-0.161 mg/g(1) in the southern states to 0.059-0.254 mg/g(2) in the north eastern United States. Eugenol is found in the gas phase of smoke from burning pine, oak and eucalyptus in concentrations of 57.2, 20.7 and 10.8 mg/kg respectively(3).
(1) Fine PM et al; Environ Sci Technol 36: 1442-51 (2002)
(2) Fine PM et al; Environ Sci Technol 35: 2665-75 (2001)
(3) Schauer JJ et al; Environ Sci Technol 35: 1716-28 (2001)

14.2.14 Food Survey Values

Eugenol was identified as a volatile aroma component from frankfurters and sausages(1,2). Eugenol was identified as a volatile component from the edible Korean Chamchwi plant(3). A red wine with an initial eugenol concentration of 15 mg/L had the eugenol concentration increase to 23.6 to 80.95 mg/L after aging in Spanish, French and American oak barrels(4).
(1) Chevance FFV, Farmer LJ; J Agric Food Chem 47: 5161-5168 (1999)
(2) Chevance FFV, Farmer LJ; J Agric Food Chem 47: 5151-5160 (1999)
(3) Chung TY et al; J Agric Food Chem 41: 1693-1697 (1993)
(4) Fernandez de Simon,B et al; J Agric Food Chem 51: 7671-7678 (2003)
REPORTED USED IN NON-ALCOHOLIC BEVERAGES 1.4 PPM; ICE CREAM, ICES, ETC 3.1 PPM; CANDY 32 PPM; BAKED GOODS 33 PPM; GELATINS & PUDDINGS 0.60 PPM; CHEWING GUM 500 PPM; CONDIMENTS 9.6-100 PPM; MEATS 40-2000 PPM.
Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 198
The Flavor and Extract Manufacturers' Association of the United States (1978) has reported the occurrence of eugenol, without specific concentrations, in the following food sources: cocoa, Japanese ginger oil, loganberries, mace essential oil, sweet marjoram dried mushrooms, nutmeg, yellow passion fruit, black pepper, peppermint, pimento berry oil and tomatoes.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 80 (1985)

14.2.15 Plant Concentrations

Eugenol was detected in the skin and pulp of Queen Anne's pocket melon (Cucumis melo var dudaim (L.) Naudin) at respective concentrations of 2302.4 mg/kg and 225.1 mg/kg(1).
(1) Aubert C, Pitrat M; J Agric Food Chem 54: 8177-8182 (2006)
Eugenol concentrations in various plants(1).
Genus species
Syzygium aromaticum (L.)
Plant
Clove, Clovetree
Part
Flower
Concn (ppm)
180,000
Genus species
Pimenta dioica (L.)
Plant
Allspice, Clover-Pepper, Jamaica- Pepper, Pimenta, Pimento
Part
Fruit
Concn (ppm)
36,000
Genus species
Pimenta racemosa
Plant
Bayrum Tree, West Indian Bay
Part
Leaf
Concn (ppm)
19,100
Genus species
Piper betel L.
Plant
Betel Pepper
Part
Leaf
Concn (ppm)
17,850
Genus species
Alpinia galanga (L.)
Plant
Greater Galangal, Languas, Siamese Ginger
Part
Rhizome
Concn (ppm)
12,000
Genus species
Syzygium aromaticum (L.)
Plant
Clove, Clovetree
Part
Leaf; Stem
Concn (ppm)
9,000; 9,000
Genus species
Ocimum basilicum L.
Plant
Basil, Cuban Basil, Sweet Basil
Part
Leaf
Concn (ppm)
8,575
Genus species
Pimenta dioica (L.)
Plant
Allspice, Clover-Pepper, Jamaica- Pepper, Pimenta, Pimento
Part
Leaf
Concn (ppm)
8,348
Genus species
Daucus carota L.
Plant
Carrot
Part
Seed
Concn (ppm)
7,000
Genus species
Cinnamomum verum
Plant
Ceylon Cinnamon, Cinnamon
Part
Bark
Concn (ppm)
3,520
Genus species
Ocimum gratissimum L.
Plant
Agbo, Shrubby Basil
Part
Plant
Concn (ppm)
0-5,340
Genus species
Ocimum sanctum L.
Plant
Holy Basil, Tulsi
Part
Leaf
Concn (ppm)
4,200-4,970
Genus species
Curcuma longa L.
Plant
Indian Saffron, Turmeric
Part
Essential Oil
Concn (ppm)
2,100
Genus species
Ocimum gratissimum L.
Plant
Agbo, Shrubby Basil
Part
Shoot
Concn (ppm)
0-4,045
Genus species
Ocimum kilimandscharicum
Plant
African Blue Basil, Kenyan Perennial Basil
Part
Shoot
Concn (ppm)
0-3,000
Genus species
Ocimum suave
Plant
Kenyan Tree Basil
Part
Shoot
Concn (ppm)
110-2,860
Genus species
Laurus nobilis L.
Plant
Bay, Bay Laurel, Bayleaf, Grecian Laurel, Laurel, Sweet Bay
Part
Leaf
Concn (ppm)
1,335
Genus species
Origanum majorana L.
Plant
Marjoram, Sweet Marjoram
Part
Plant
Concn (ppm)
1,152
Genus species
Cistus ladaniferus L.
Plant
Ambreine, Gum Cistus, Labdanum, Rockrose
Part
Leaf
Concn (ppm)
1,050
Genus species
Ocimum gratissimum L.
Plant
Agbo, Shrubby Basil
Part
Seed
Concn (ppm)
0-1,670
Genus species
Hyssopus officinalis L.
Plant
Hyssop
Part
Flower; Leaf
Concn (ppm)
624; 443
Genus species
Ageratum conyzoides L.
Plant
Mexican ageratum
Part
Shoot
Concn (ppm)
0-800
Genus species
Alpinia officinarum
Plant
Chinese Ginger, Lesser Galangal
Part
Rhizome
Concn (ppm)
400
Genus species
Viola odorata L.
Plant
Common Violet, Sweet Violet
Part
Flower
Concn (ppm)
357
Genus species
Mentha pulegium L.
Plant
European Pennyroyal
Part
Plant
Concn (ppm)
320
Genus species
Myristica fragrans
Plant
Mace, Muskatnussbaum (Ger.), Nutmeg, nogal moscado (Sp.), nuez moscada (Sp.)
Part
Seed
Concn (ppm)
320
Genus species
Cymbopogon winterianus
Plant
Java Citronella, Mahapengiri
Part
Plant
Concn (ppm)
233
Genus species
Pycnanthemum setosum
Plant
Setose Mountain Mint
Part
Shoot
Concn (ppm)
93
Genus species
Acorus calamus L.
Plant
Calamus, Flagroot, Myrtle Flag, Sweet Calamus, Sweetflag, Sweetroot
Part
Rhizome
Concn (ppm)
84
Genus species
Origanum minutiflorum
Plant
Small-Flowered Oregano
Part
Shoot
Concn (ppm)
55-125
Genus species
Umbellularia californica
Plant
California Bay
Part
Plant
Concn (ppm)
40
Genus species
Ocimum kilimandscharicum
Plant
African Blue Basil, Kenyan Perennial Basil
Part
Flower
Concn (ppm)
0-35
Genus species
Micromeria fruticosa subsp. barbata
Plant
Tea Hyssop, Zopha, Zuta
Part
Shoot
Concn (ppm)
0-26
Genus species
Thymus capitatus (L.)
Plant
'Sicilian' Thyme, Spanish Origanum, Spanish Thyme
Part
Shoot
Concn (ppm)
0-21
Genus species
Jasminum officinale L.
Plant
Jasmine, Poet's Jessamine
Part
Flower
Concn (ppm)
10
Genus species
Lavandula latifolia
Plant
Aspic, Broad-Leaved Lavender, Spike Lavender
Part
Plant
Concn (ppm)
9
Genus species
Micromeria congesta
Plant
Kaya Yarpuzu
Part
Leaf
Concn (ppm)
5-15
Genus species
Ocimum basilicum L.
Plant
Basil, Cuban Basil, Sweet Basil
Part
Plant
Concn (ppm)
0-14
Genus species
Hyacinthus orientalis L.
Plant
Hyacinth
Part
Flower
Concn (ppm)
4.6
Genus species
Calamintha nepeta subsp. glandulosa
Plant
Turkish Calamint
Part
Shoot
Concn (ppm)
0-8
Genus species
Syzygium aromaticum (L.)
Plant
Clove, Clovetree
Part
Flower
Concn (ppm)
180,000
Genus species
Rosa gallica L.
Plant
French Rose
Part
Flower
Concn (ppm)
4
Genus species
Glycyrrhiza glabra L.
Plant
Commom Licorice, Licorice, Licorice- Root, Smooth Licorice
Part
Root
Concn (ppm)
1
Genus species
Elsholtzia blanda
Plant
Bantaluki, Bantulsi
Part
Shoot
Genus species
Vaccinium corymbosum L.
Plant
Blueberry
Part
Fruit
(1) USDA; Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical. Eugenol. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of Aug 1, 2012: https://www.ars-grin.gov/duke/

14.2.16 Other Environmental Concentrations

An air freshener formulation containing eugenol was applied as a spray in an environmental controlled room(1); eugenol air concentrations in the breathing-zone heights ranged from about 60-347 ug/cu m during the first 10 minutes post-application(1). Eugenol was identified as a component of soot from residential wood stoves(2). Eugenol was qualitatively detected in the volatile emissions from biodegradable household waste and infected building materials(3).
(1) Rogers IH et al; Environ Sci Technol 39: 7810-7816 (2005)
(2) Hawthorne SB et al; Environ Sci Technol 22: 1191-1196 (1988)
(3) Wilkins CK, Larsen K; J High Resolut Chromatogr 18: 373-377 (1995)

14.2.17 Probable Routes of Human Exposure

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of eugenol is 100 to 999; the data may be greatly underestimated(1).
(1) US EPA; Inventory Update Reporting (IUR). Non-confidential 2006 IUR Records by Chemical, including Manufacturing, Processing and Use Information. Washington, DC: U.S. Environmental Protection Agency. Available from, as of June 25, 2012: https://cfpub.epa.gov/iursearch/index.cfm
NIOSH (NOES Survey 1981-1983) has statistically estimated that 187,937 workers (83,766 of these were female) were potentially exposed to eugenol in the US(1). Occupational exposure to eugenol may occur through inhalation and dermal contact with this compound at workplaces where eugenol is produced or used(SRC). Monitoring and use data indicate the general population can be exposed to eugenol through dermal contact and inhalation of perfumes and other consumer products containing the compound and through ingestion of foods and plants containing eugenol(SRC).
(1) NIOSH; NOES. National Occupational Exposure Survey conducted from 1981-1983. Estimated numbers of employees potentially exposed to specific agents by 2-digit standard industrial classification (SIC). Available from, as of June 25, 2012: https://www.cdc.gov/noes/
... LIKELY TO OCCUR BY DIRECT CONTACT OF SKIN & EYES WITH OIL OR SOLUTIONS OF OIL. EXCESSIVE EXPOSURE TO VAPORS DOES NOT SEEM LIKELY IN VIEW OF LOW VOLATILITY & PUNGENT ODOR ... IN HIGH CONCN.
Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1691
Occupational exposure to eugenol may occur through inhalation and dermal contact with this compound at workplaces where eugenol is produced or used. One likely pathway by which the general public is exposed to eugenol is by inhalation due to the release of this substance from perfumes and flavorings. The general population may be exposed to eugenol via inhalation of wood fire smoke, perfumes, dermal contact with perfumes, essential oils, analgesics containing this compound, and ingestion of certain foods. (SRC)

15 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound

Contact dermatitis, allergic [Category: Skin Disease]

Contact urticaria [Category: Skin Disease]

Asthma, occupational [Category: Airway Disease]

16 Literature

16.1 Consolidated References

16.2 NLM Curated PubMed Citations

16.3 Springer Nature References

16.4 Thieme References

16.5 Wiley References

16.6 Chemical Co-Occurrences in Literature

16.7 Chemical-Gene Co-Occurrences in Literature

16.8 Chemical-Disease Co-Occurrences in Literature

17 Patents

17.1 Depositor-Supplied Patent Identifiers

17.2 WIPO PATENTSCOPE

17.3 Chemical Co-Occurrences in Patents

17.4 Chemical-Disease Co-Occurrences in Patents

17.5 Chemical-Gene Co-Occurrences in Patents

18 Interactions and Pathways

18.1 Protein Bound 3D Structures

18.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

18.2 Chemical-Target Interactions

18.3 Pathways

19 Biological Test Results

19.1 BioAssay Results

20 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
S29 | PHYTOTOXINS | Toxic Plant Phytotoxin (TPPT) Database | DOI:10.5281/zenodo.2652993

21 Classification

21.1 MeSH Tree

21.2 NCI Thesaurus Tree

21.3 ChEBI Ontology

21.4 KEGG: Phytochemical Compounds

21.5 KEGG: Risk Category of Japanese OTC Drugs

21.6 KEGG: OTC drugs

21.7 KEGG: Animal Drugs

21.8 FDA Pharm Classes

21.9 ChemIDplus

21.10 CAMEO Chemicals

21.11 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

21.12 ChEMBL Target Tree

21.13 UN GHS Classification

21.14 EPA CPDat Classification

21.15 NORMAN Suspect List Exchange Classification

21.16 CCSBase Classification

21.17 EPA DSSTox Classification

21.18 International Agency for Research on Cancer (IARC) Classification

21.19 Consumer Product Information Database Classification

21.20 EPA TSCA and CDR Classification

21.21 LOTUS Tree

21.22 EPA Substance Registry Services Tree

21.23 MolGenie Organic Chemistry Ontology

22 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  6. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  7. EPA Chemical Data Reporting (CDR)
    LICENSE
    The U.S. Government retains a nonexclusive, royalty-free license to publish or reproduce these documents, or allow others to do so, for U.S. Government purposes. These documents may be freely distributed and used for non-commercial, scientific and educational purposes.
    https://www.epa.gov/web-policies-and-procedures/epa-disclaimers#copyright
    Phenol, 2-methoxy-4-(2-propen-1-yl)-
    https://www.epa.gov/chemical-data-reporting
  8. EPA Chemicals under the TSCA
    Phenol, 2-methoxy-4-(2-propen-1-yl)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  9. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  11. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  12. Hazardous Substances Data Bank (HSDB)
  13. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  14. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  15. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  16. California Safe Cosmetics Program (CSCP) Product Database
    Phenol, 2-methoxy-4-(2-propenyl)- (EUGENOL)
    https://cscpsearch.cdph.ca.gov/search/detailresult/2942
  17. EU Pesticides Database
  18. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  19. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  20. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  21. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  22. Therapeutic Target Database (TTD)
  23. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  24. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  25. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    EUGENOL
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  26. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  27. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  28. ChEBI
  29. FDA Pharm Classes
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  30. LiverTox
  31. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  32. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  33. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  34. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  35. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  36. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  37. DailyMed
  38. EPA Chemical and Products Database (CPDat)
  39. EU Food Improvement Agents
  40. Hazardous Chemical Information System (HCIS), Safe Work Australia
  41. NITE-CMC
  42. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  43. FDA Substances Added to Food
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  44. Flavor and Extract Manufacturers Association (FEMA)
  45. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  46. IUPAC Digitized pKa Dataset
  47. NMRShiftDB
  48. MassBank Europe
  49. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  50. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  51. SpectraBase
    PHENOL, 2-METHOXY-4-(2-PROPENYL)-
    https://spectrabase.com/spectrum/3FkDevS943m
    PHENOL, 2-METHOXY-4-(2-PROPENYL)-
    https://spectrabase.com/spectrum/7BQ4w9tK3sr
    Phenol, 2-methoxy-4-(2-propenyl)-
    https://spectrabase.com/spectrum/KCGXK8b07H4
    Phenol, 2-methoxy-4-(2-propenyl)-
    https://spectrabase.com/spectrum/3OiK9Yq5b96
  52. International Agency for Research on Cancer (IARC)
    LICENSE
    Materials made available by IARC/WHO enjoy copyright protection under the Berne Convention for the Protection of Literature and Artistic Works, under other international conventions, and under national laws on copyright and neighbouring rights. IARC exercises copyright over its Materials to make sure that they are used in accordance with the Agency's principles. All rights are reserved.
    https://publications.iarc.fr/Terms-Of-Use
    IARC Classification
    https://www.iarc.fr/
  53. NTP Technical Reports
  54. Japan Chemical Substance Dictionary (Nikkaji)
  55. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Risk category of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08312.keg
    Classification of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08313.keg
  56. KNApSAcK Species-Metabolite Database
  57. Natural Product Activity and Species Source (NPASS)
  58. Metabolomics Workbench
  59. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  60. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  61. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  62. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  63. Protein Data Bank in Europe (PDBe)
  64. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  65. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  66. Springer Nature
  67. SpringerMaterials
  68. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  69. Wikidata
  70. Wikipedia
  71. Wiley
  72. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  73. PubChem
  74. GHS Classification (UNECE)
  75. EPA Substance Registry Services
  76. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  77. PATENTSCOPE (WIPO)
  78. NCBI
CONTENTS