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Carvacrol

PubChem CID
10364
Structure
Carvacrol_small.png
Carvacrol_3D_Structure.png
Molecular Formula
Synonyms
  • CARVACROL
  • 5-Isopropyl-2-methylphenol
  • 499-75-2
  • Isopropyl-o-cresol
  • Antioxine
Molecular Weight
150.22 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-04
Description
Carvacrol is a phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1). It has a role as a volatile oil component, a flavouring agent, an antimicrobial agent, an agrochemical and a TRPA1 channel agonist. It is a member of phenols, a p-menthane monoterpenoid and a botanical anti-fungal agent. It derives from a hydride of a p-cymene.
Carvacrol has been reported in Callistemon citrinus, Perilla frutescens, and other organisms with data available.
Carvacrol is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Carvacrol.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-methyl-5-propan-2-ylphenol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CC1=C(C=C(C=C1)C(C)C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H14O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

499-75-2

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 FEMA Number

2.3.9 HMDB ID

2.3.10 JECFA Number

710

2.3.11 KEGG ID

2.3.12 Lipid Maps ID (LM_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 Pharos Ligand ID

2.3.18 Wikidata

2.3.19 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5-isopropyl-2-methylphenol
  • carvacrol

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
150.22 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.1
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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
150.104465066 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
150.104465066 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
20.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
120
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

Thick colorless liquid; [Hawley] Clear, deep yellow liquid; [MSDSonline]
Liquid
Colourless to pale yellow liquid, pungent, spicy odour

3.2.2 Color / Form

NEEDLES
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-166
COLORLESS OR YELLOWISH, THICK LIQUID
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. 83

3.2.3 Odor

THYMOL ODOR
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 239
MEDICINAL SMOKE ODOR
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Volume 2. Boca Raton, Florida: CRC Press, Inc., 1980., p. 263

3.2.4 Taste

EXCELLENT SMOKE TASTE, @ 1-5 PPM
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Volume 2. Boca Raton, Florida: CRC Press, Inc., 1980., p. 263

3.2.5 Boiling Point

237-238 °C @ 760 MM HG
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 239
237.70 °C. @ 760.00 mm Hg
The Good Scents Company Information System

3.2.6 Melting Point

1 °C
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-166
3.5 °C

3.2.7 Flash Point

100 °C
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. 83

3.2.8 Solubility

SLIGHTLY SOL IN WATER; SOL IN ETHANOL, ETHER, ALKALIS; VERY SOLUBLE IN ACETONE
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-166
1.25 mg/mL at 25 °C
insoluble in water; miscible in oils
miscible (in ethanol)

3.2.9 Density

0.976 @ 20 °C/4 °C
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 239
0.974-0.979

3.2.10 LogP

3.49

3.2.11 Refractive Index

INDEX OF REFRACTION: 1.5230 @ 20 °C/D; MAX ABSORPTION (ALCOHOL): 277.5 NM (LOG E= 3.26); SADTLER REFERENCE NUMBER: 2470 (IR, PRISM)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-166
1.521-1.528

3.2.12 Kovats Retention Index

Standard non-polar
1278 , 1275 , 1280 , 1276 , 1275 , 1289 , 1273 , 1278 , 1297 , 1275 , 1272 , 1275 , 1275 , 1298 , 1277 , 1279 , 1275 , 1278 , 1278 , 1272 , 1272 , 1297 , 1299 , 1269.4 , 1277 , 1278 , 1283 , 1279 , 1293 , 1302 , 1288 , 1288 , 1295 , 1274 , 1273.8 , 1278 , 1289 , 1286 , 1300 , 1278 , 1278 , 1299 , 1298 , 1301 , 1284 , 1289 , 1298 , 1269 , 1278 , 1278 , 1286 , 1286 , 1278 , 1277 , 1299 , 1274 , 1274 , 1273 , 1278 , 1275 , 1297 , 1297 , 1299 , 1276 , 1286 , 1297 , 1286 , 1278 , 1300 , 1286 , 1279 , 1273 , 1295 , 1276 , 1275 , 1287 , 1275 , 1277 , 1277 , 1277 , 1292 , 1278 , 1280 , 1254 , 1277 , 1291 , 1282 , 1282 , 1273 , 1272 , 1275 , 1282 , 1282 , 1283 , 1291 , 1272 , 1277 , 1278 , 1277 , 1271 , 1271 , 1297 , 1297 , 1279 , 1286 , 1280 , 1329 , 1287 , 1299 , 1329 , 1286 , 1277.8 , 1283 , 1282 , 1278 , 1278 , 1301 , 1271 , 1296 , 1282 , 1275 , 1277 , 1294 , 1294 , 1286 , 1284 , 1307 , 1280 , 1290 , 1277 , 1278 , 1275 , 1278 , 1278 , 1275 , 1278 , 1297 , 1278 , 1278 , 1302 , 1300
Semi-standard non-polar
1304 , 1300 , 1294 , 1299 , 1291 , 1299 , 1300 , 1294.3 , 1285 , 1295 , 1300 , 1315 , 1315.8 , 1317 , 1311 , 1299 , 1302 , 1299 , 1304 , 1293 , 1298 , 1299 , 1298 , 1297 , 1300 , 1295 , 1299 , 1300 , 1297 , 1302 , 1304 , 1305 , 1302 , 1298 , 1293 , 1299 , 1299 , 1300 , 1299 , 1296 , 1301 , 1298 , 1304 , 1299 , 1299 , 1299 , 1299 , 1299 , 1299 , 1305 , 1298 , 1298 , 1300 , 1298 , 1300 , 1298 , 1298 , 1298 , 1301 , 1300 , 1301 , 1298 , 1299 , 1298 , 1306 , 1302 , 1299 , 1292 , 1302 , 1305 , 1297 , 1302 , 1312 , 1317 , 1298 , 1298 , 1301 , 1299 , 1300 , 1307 , 1316 , 1299 , 1300 , 1309 , 1307 , 1298 , 1298 , 1298 , 1296 , 1298 , 1298 , 1299 , 1309 , 1300 , 1300 , 1301 , 1301 , 1301 , 1302 , 1302 , 1302 , 1303 , 1303 , 1304 , 1305 , 1306 , 1307 , 1308 , 1309 , 1308 , 1304 , 1302 , 1299 , 1300 , 1290 , 1304 , 1306 , 1300 , 1312 , 1298 , 1301 , 1303 , 1296 , 1299 , 1299 , 1299 , 1287 , 1305 , 1327 , 1304 , 1290 , 1299 , 1301 , 1293 , 1299 , 1299 , 1298 , 1296 , 1303 , 1298 , 1300 , 1297 , 1299 , 1299 , 1317 , 1326 , 1297 , 1298 , 1298 , 1305 , 1297 , 1322 , 1300 , 1299 , 1299 , 1302 , 1303 , 1303 , 1299 , 1304 , 1300 , 1299 , 1303.2 , 1279 , 1283 , 1297 , 1299 , 1312 , 1300 , 1298 , 1298 , 1318 , 1314 , 1299 , 1299 , 1314 , 1280 , 1280 , 1297 , 1299 , 1302 , 1301 , 1315 , 1297 , 1297 , 1297 , 1301 , 1301 , 1297 , 1299 , 1298 , 1299 , 1288 , 1289 , 1297 , 1298 , 1312 , 1281 , 1299 , 1292 , 1300 , 1298 , 1299 , 1297 , 1295 , 1299 , 1298 , 1298 , 1297 , 1300 , 1299 , 1303 , 1294 , 1272 , 1275 , 1284 , 1328 , 1296 , 1298 , 1298 , 1298 , 1299 , 1291 , 1299 , 1297 , 1299 , 1298 , 1314 , 1296 , 1298 , 1325 , 1298 , 1295 , 1302 , 1299 , 1292 , 1314 , 1297 , 1299 , 1296 , 1298 , 1296 , 1298 , 1287 , 1297 , 1289 , 1299 , 1303 , 1291 , 1292 , 1299 , 1300 , 1299.5 , 1298 , 1307 , 1307 , 1298 , 1299 , 1299 , 1314 , 1325 , 1300 , 1307 , 1299 , 1300 , 1298 , 1310.1 , 1311 , 1303 , 1299 , 1299 , 1298.9 , 1313 , 1302 , 1299 , 1297.6 , 1295 , 1301
Standard polar
2219 , 2225 , 2183 , 2215 , 2212 , 2214 , 2222 , 2195 , 2183 , 2219 , 2215 , 2209 , 2189 , 2186 , 2223 , 2219 , 2219 , 2191 , 2191 , 2219 , 2225 , 2186 , 2238 , 2233 , 2225 , 2239 , 2224 , 2239 , 2215 , 2239 , 2222 , 2239 , 2239 , 2187 , 2192 , 2229 , 2239 , 2235 , 2201 , 2239 , 2239 , 2239 , 2201 , 2239 , 2239 , 2239 , 2239 , 2239 , 2239 , 2239 , 2212 , 2239 , 2239 , 2233 , 2239 , 2221 , 2221 , 2220 , 2239 , 2181 , 2239 , 2239 , 2239 , 2190 , 2239 , 2239 , 2189 , 2206 , 2246 , 2239 , 2246 , 2181 , 2210 , 2227 , 2181 , 2239 , 2239 , 2239 , 2220 , 2239 , 2236 , 2181 , 2239 , 2239 , 2239 , 2239 , 2239 , 2239 , 2239 , 2215 , 2221 , 2239 , 2239 , 2239 , 2181 , 2239 , 2239 , 2239 , 2239 , 2246 , 2239 , 2239 , 2239 , 2239 , 2189 , 2186 , 2240 , 2239 , 2246 , 2239 , 2239 , 2240 , 2240 , 2240 , 2240 , 2194 , 2246 , 2217 , 2210 , 2246 , 2246 , 2246 , 2246 , 2235 , 2229 , 2246 , 2205 , 2211 , 2246 , 2223 , 2222 , 2224 , 2246 , 2229 , 2177 , 2222 , 2173 , 2199 , 2240 , 2200 , 2181

3.2.13 Other Experimental Properties

SOLIDIFICATION ABOUT 0 °C
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 239
UV: 6-304 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /o-Cresol, 6-isopropyl/
Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I and II. Boca Raton, FL: CRC Press Inc. 1985., p. V1 454

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Biological Agents -> Plant Oils and Extracts

3.4.1 Drugs

3.4.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Complementary Therapies; Food; Phytotherapy; Plants, Medicinal

3.4.2 Cosmetics

Cosmetic ingredients (Carvacrol) -> CIR (Cosmetic Ingredient Review)

3.4.3 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.4.4 Fragrances

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

3.4.5 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
NMR: 684 (Sadtler Research Laboratories Spectral Collection)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
W224502
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Varian
Frequency
25.16 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
121.21:453.00, 113.23:672.00, 130.92:687.00, 153.52:458.00, 148.42:398.00, 33.68:537.00, 23.95:1000.00, 15.35:517.00, 118.90:652.00
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2 of 3
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Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 14
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

135.0 99.99

150.0 35.60

91.0 16.40

107.0 8

136.0 8

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Notes
instrument=SHIMADZU LKB-9000B
2 of 14
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

135.0 99.99

150.0 35.60

91.0 16.40

136.0 8

107.0 8

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Notes
instrument=SHIMADZU LKB-9000B

4.2.2 MS-MS

1 of 3
View All
Spectra ID
Instrument Type
QTOF
Ionization Mode
positive
Top 5 Peaks

150.112 83.08

132.102 6.91

151.115 6.51

88.076 1.84

70.065 1.66

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Notes
adduct_type [M+H]+ original_collision_energy 3 CannabisDB spectra from NIST14 2020 June Agilent QTOF 6530
2 of 3
View All
Spectra ID
Instrument Type
n/a
Ionization Mode
positive
Top 5 Peaks

109.2 70.46

133.2 10.29

107.2 4.51

123.2 4.05

130.5 3.56

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Notes
adduct_type [M+H]+ original_collision_energy 35 % nominal CannabisDB spectra from NIST14 2020 June Thermo Finnigan LTQ

4.2.3 Other MS

1 of 4
View All
Other MS
MASS: 895 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Other MS
MASS: 106 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
2 of 4
View All
Authors
KAMEOKA H, DEPT. OF APPLIED CHEMISTRY, FAC. OF SCI. AND ENGINEERING, KINKI UNIV.
Instrument
SHIMADZU LKB-9000B
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

135 999

150 356

91 164

107 80

136 80

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License
CC BY-NC-SA

4.3 UV Spectra

UV: 653 (Sadtler Research Laboratories Spectral Collection)
Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I and II. Boca Raton, FL: CRC Press Inc. 1985., p. V1 454

4.3.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 IR Spectra

IR Spectra
IR: 2471 (Sadtler Research Laboratories Prism Collection) /o-Cresol, 4-isopropyl/
IR Spectra
IR: 3528 (Documentation of Molecular Spectroscopy Collection) /o-Cresol, 6-isopropyl/
IR Spectra
IR: 325 (Sadtler Research Laboratories IR Grating Collection)

4.4.1 FTIR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
Neat
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
C0026
Lot Number
EXRFG
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker IFS 85
Technique
Cell
Source of Sample
Merck-Schuchardt Hohenbrunn
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Inc.
Catalog Number
W224502 SAMPLE-K
Lot Number
22896CJ
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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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
C0026
Lot Number
EXRFG
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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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.
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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.
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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.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
282197
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

1 of 2
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
C0026
Lot Number
EXRFG
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
W224502
Lot Number
22896CJ
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Classes

Breast Feeding; Lactation; Milk, Human; Complementary Therapies; Food; Phytotherapy; Plants, Medicinal

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

7.3 Reported Fatal Dose

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).
Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-126

8 Food Additives and Ingredients

8.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

8.2 FEMA Flavor Profile

Caraway, Spice, Thyme

8.3 FDA Substances Added to Food

Substance
Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
Document Number (21 eCFR)
FEMA Number
2245
GRAS Number
3
JECFA Flavor Number
710

8.4 Associated Foods

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

Chemical Name
2-HYDROXY-p-CYMENE
Evaluation Year
2000
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

9 Pharmacology and Biochemistry

9.1 Absorption, Distribution and Excretion

CARVACROL APPEARS TO BE SLOWLY ABSORBED FROM INTESTINE IN RABBIT, SINCE 22 HR AFTER ADMIN OF 1.5 G, SOME 30% WAS STILL IN GASTRO-INTESTINAL TRACT, ABOUT 25% OF DOSE HAVING BEEN EXCRETED IN URINE.
OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17 (SUPPL) 743 (1979)
CARVACROL APPLIED TO INTACT SHAVED ABDOMINAL SKIN OF MOUSE WAS NOT ABSORBED WITHIN 2 HR.
OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17 (SUPPL) 743 (1979)

9.2 Metabolism / Metabolites

/WHEN FED TO RABBITS,/ THE SUBSTITUTED MONOPHENOLS, THYMOL & CARVACROL, WHICH OCCUR IN ESSENTIAL OILS OF PLANTS...ARE...CONJUGATED WITH GLUCURONIC ACID & SULFATE.
Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 147
CARVACROL IS METABOLIZED BY CONJUGATION WITH GLUCURONIC ACID & SULFATE.
OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17 (SUPPL) 743 (1979)
Carvacrol has known human metabolites that include (2-methyl-5-propan-2-ylphenyl) hydrogen sulfate and (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(2-methyl-5-propan-2-ylphenoxy)oxane-2-carboxylic acid.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

9.3 Human Metabolite Information

9.3.1 Cellular Locations

  • Extracellular
  • Membrane

9.4 Biochemical Reactions

9.5 Transformations

10 Use and Manufacturing

10.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Carvacrol
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
Found in oil of origanum, thyme, marjoram, and summer savory; Used as a disinfectant, fungicide, and anthelmintic (nematodes); Also used in organic syntheses and in perfumes and flavorings; [Hawley] Origanum oil is about 60% carvacrol; [HSDB]
Hawley - Lewis RJ. _Hawley's Condensed Chemical Dictionary, _15th Ed. New York: John Wiley & Sons, 2007.
Industrial Processes with risk of exposure

Using Disinfectants or Biocides [Category: Clean]

Farming (Pesticides) [Category: Industry]

DISINFECTANT; IN ORGANIC SYNTHESES
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 239
MEDICATION: ANTIFUNGAL; ANTHELMINTIC AGENT
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 239
PERFUMES; FLAVORING
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 169

10.1.1 Use Classification

Food additives -> Flavoring Agents
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index

10.1.2 Household Products

Household & Commercial/Institutional Products

Information on 1 consumer products that contain Carvacrol in the following categories is provided:

• Auto Products

10.2 Methods of Manufacturing

FROM P-CYMENE BY SULFONATION & SUBSEQUENT ALKALI FUSION. HIXSON & MCKEE, CHEM ZENTR, II: 851, 1919; GIBBS & PHILLIPS, J IND ENG CHEM, 12: 145, 1920.
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. 83
...BY CHLORINATION OF ALPHA-PINENE WITH TERT-BUTYL HYPOCHLORITE: RITTER, GINSBURG, J AM CHEM SOC 72, 2381 (1950); FROM 2-BROMO-P-CYMOL: STRUBELL, BAUMGARTEL, ARCH PHARM 291, 66 (1958).
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 238

10.3 Formulations / Preparations

THE COMMERCIAL PRODUCT CONSISTS OF A MIXTURE OF ISOMERS DIFFERING BECAUSE OF THE POSITION OF THE ISOPROPYL RADICAL. THE TECHNICAL & PURE QUALITY ARE DIFFERENT BECAUSE OF THE ODOR CHARACTERISTICS.
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. 83
THE MAIN CONSTITUENT/OF ORIGANUM OIL/IS CARVACROL (ca 60%)
KIRK-OTHMER ENCYC CHEM TECH 3RD ED 1978-PRESENT V16 p.325

10.4 General Manufacturing Information

EPA TSCA Commercial Activity Status
Phenol, 2-methyl-5-(1-methylethyl)-: ACTIVE
FLAVORS USEFUL IN: SMOKE FLAVORS, SPICE, MEAT FLAVORS.
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Volume 2. Boca Raton, Florida: CRC Press, Inc., 1980., p. 263
REPORTED USES: /IN/ NON-ALCOHOLIC BEVERAGES 26 PPM; ICE CREAM, ICES, ETC 34 PPM; CANDY 92 PPM; BAKED GOODS 120 PPM; CONDIMENTS 37 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. 83
FEMA NUMBER 2245
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 817

11 Identification

11.1 Analytic Laboratory Methods

BY USE OF (13)C NMR, GAS-CHROMATOGRAPHY, & GAS CHROMATOGRAPHY-MASS SPECTROMETRIC ANALYSIS, ESSENTIAL OIL COMPONENTS WERE IDENTIFIED.
BROSCHE T ET AL; ESSENTIAL OIL COMPONENTS FROM MAJORANA HORTENSIS MOENCH; Z NATURFORSCH, C: BIOSCI 36C(1-2) 23 (1981)
THYMOL & CARVACROL CONTENTS WERE DETERMINED WITH HIGH-PERFORMANCE LIQ CHROMATOGRAPHY.
VAN DEN BROUCKE CO, LEMLI JA; PHARMACOLOGICAL AND CHEMICAL INVESTIGATION OF THYME LIQUID EXTRACTS; PLANTA MED 41(2) 129 (1981)

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

Note
Pictograms displayed are for 99.9% (1808 of 1810) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 0.1% (2 of 1810) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (91.3%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (92.4%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (91.1%): 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 1810 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 2 of 1810 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 12 notifications provided by 1808 of 1810 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.

12.1.2 Hazard Classes and Categories

Acute Tox. 4 (99.8%)

Skin Irrit. 2 (91.3%)

Skin Sens. 1 (92.4%)

Eye Irrit. 2 (91.1%)

12.1.3 Hazards Summary

Emergency treatment: Irritants; [HSDB] Causes severe irritation on rabbit skin; Causes somnolence and convulsions at lethal doses; [RTECS] Safe when used as a flavoring agent in food; [JECFA]

12.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Phenol, 2-methyl-5-(1-methylethyl)-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
5-Isopropyl-2-methylphenol: Does not have an individual approval but may be used under an appropriate group standard

12.2.1 FDA Requirements

172.515
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Volume 2. Boca Raton, Florida: CRC Press, Inc., 1980., p. 263
121.1164; LIMITATIONS: SYNTHETIC FLAVOR.
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 817

12.3 Other Safety Information

12.3.1 Special Reports

REVIEW WITH 42 REF ON CARVACROL INCL TOXICITY, IRRITATION, SENSITIZATION, METAB, PERCUTANEOUS ABSORPTION, PHARMACOLOGY, CYTOTOXICITY, CHEMOTHERAPY, & EFFECT ON ISOLATED TISSUES & ORGANELLES.[OPDYKE DL J; MONOGRAPH ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17(ISS SUPPL) 743 (1979)]

13 Toxicity

13.1 Toxicological Information

13.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Oregano (Origanum vulgare) leaves and oil contain carvacrol, thymol, eugenol and rosmarinic acid. Oregano has been used in medicinal doses for respiratory and gastrointestinal disorders and as an antimicrobial. Oregano oil has been advocated as a treatment for lactation-related Candida infection of the nipples; however, no clinical studies have confirmed the safety or efficacy of this use. Oregano has been used as a galactogogue in Türkiye. No data exist on the safety or efficacy of oregano in nursing mothers or infants. Oregano and oregano oil are "generally recognized as safe" (GRAS) as food ingredients by the U.S. Food and Drug Administration. Oregano is generally well tolerated, but gastrointestinal upset and allergic skin reactions have been reported rarely. Because of a lack of data, oregano in amounts higher than those found in foods as a flavoring should probably be avoided during breastfeeding.

Dietary supplements do not require extensive pre-marketing approval from the U.S. Food and Drug Administration. Manufacturers are responsible to ensure the safety, but do not need to prove the safety and effectiveness of dietary supplements before they are marketed. Dietary supplements may contain multiple ingredients, and differences are often found between labeled and actual ingredients or their amounts. A manufacturer may contract with an independent organization to verify the quality of a product or its ingredients, but that does not certify the safety or effectiveness of a product. Because of the above issues, clinical testing results on one product may not be applicable to other products. More detailed information about dietary supplements is available elsewhere on the LactMed Web site.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

13.1.2 Adverse Effects

Neurotoxin - Other CNS neurotoxin

13.1.3 Acute Effects

13.1.4 Human Toxicity Excerpts

TECHNICAL GRADE (1.0 & 0.1% IN ETHANOL) PRODUCED POS PATCH TESTS IN PT WITH ACUTE DERMATITIS OF FACE, BUT NO POS RESPONSES IN CONTROL SUBJECTS. TESTED @ 4% IN PETROLATUM, IT PRODUCED NO IRRITATION AFTER 48-HR.
OPDYKE DL J; MONGRAPHS ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17 (SUPPL) 743 (1979)
CARVACROL SHOWED MODERATE CYTOTOXIC EFFECTS IN HELA CELLS.
OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17 (SUPPL) 743 (1979)

13.1.5 Non-Human Toxicity Excerpts

SOMEWHAT MORE TOXIC THAN THYMOL IN RATS & RABBITS.
Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-126
EVALUATED FOR MUTAGENIC EFFECTS TO 5 STRAINS OF SALMONELLA TYPHIMURIUM EMPLOYING PROCEDURES DESCRIBED BY AMES, ISOTHYMOL HAD PRONOUNCED MUTAGENICITY.
ERCEGOVICH CD, RASHID KA; MUTAGENESIS INDUCED IN MUTANT STRAINS OF SALMONELLA TYPHIMURIUM BY PESTICIDES; AMER CHEM SOC ABSTR PAP 174: PEST NO 43 (1977)
CARVACROL APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN FOR 24 HR UNDER OCCLUSION WAS SEVERELY IRRITATING.
OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17 (SUPPL) 743 (1979)
WHEN MIXT OF 93% CARVACROL & 7% THYMOL IN ARACHIS OIL WAS ADMIN BY GASTRIC INTUBATION TO CFE STRAIN RATS IN SINGLE DOSE OF 1.5 MMOL/KG, SLIGHT INCR IN PRODUCTION OF LIVER BIPHENYL-4-HYDROXYLASE WAS NOTED.
OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17 (SUPPL) 743 (1979)
CARVACROL SHOWED PAPAVERINE-LIKE ANTISPASMODIC ACTION ON ISOLATED SMALL INTESTINE OF MOUSE. ADDED TO BOVINE SEMINAL VESICLE MICROSOMES @ 4.1 UG/ML, IT INHIBITED THE IN VITRO FORMATION OF PROSTAGLANDIN E1 BY 50%.
OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17 (SUPPL) 743 (1979)

13.2 Ecological Information

13.2.1 Natural Pollution Sources

FOUND IN OIL OF ORIGANUM, THYME, MARJORAM, SUMMER SAVORY...
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 238
OCCURS IN BARK OIL OF THUJA ARTICULATA, CAMPHOR OIL, IN OILS OF MONARDA CITRIODORA & MONARDA FISTULOSA, IN SOME SPECIES OF SATUREJA, IN OIL OF VARIOUS SPECIES OF ORIGANUM, THYME, THYMBRA SPICATA L, IN SEED OIL OF PTYCHOTIS AJOWAN DC, & OTHERS.
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. 83

14 Associated Disorders and Diseases

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Chemical Co-Occurrences in Literature

15.6 Chemical-Gene Co-Occurrences in Literature

15.7 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Interactions and Pathways

17.1 Protein Bound 3D Structures

17.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

17.2 Chemical-Target Interactions

18 Biological Test Results

18.1 BioAssay Results

19 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

20 Classification

20.1 MeSH Tree

20.2 NCI Thesaurus Tree

20.3 ChEBI Ontology

20.4 LIPID MAPS Classification

20.5 KEGG: Lipid

20.6 KEGG: Phytochemical Compounds

20.7 ChemIDplus

20.8 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

20.9 ChEMBL Target Tree

20.10 UN GHS Classification

20.11 EPA CPDat Classification

20.12 NORMAN Suspect List Exchange Classification

20.13 EPA DSSTox Classification

20.14 Consumer Product Information Database Classification

20.15 EPA TSCA and CDR Classification

20.16 LOTUS Tree

20.17 EPA Substance Registry Services Tree

20.18 MolGenie Organic Chemistry Ontology

21 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
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    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
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  6. EPA Chemicals under the TSCA
    Phenol, 2-methyl-5-(1-methylethyl)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  7. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  8. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
  9. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. Hazardous Substances Data Bank (HSDB)
  11. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  12. International Fragrance Association (IFRA)
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    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  13. New Zealand Environmental Protection Authority (EPA)
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    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  14. BindingDB
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    https://www.bindingdb.org/rwd/bind/info.jsp
  15. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  16. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  17. Therapeutic Target Database (TTD)
  18. ChEBI
  19. LOTUS - the natural products occurrence database
    LICENSE
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    https://lotus.nprod.net/
  20. Yeast Metabolome Database (YMDB)
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    http://www.ymdb.ca/downloads
  21. ChEMBL
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  22. ClinicalTrials.gov
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    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  24. Cosmetic Ingredient Review (CIR)
  25. EPA Chemical and Products Database (CPDat)
  26. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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    https://creativecommons.org/publicdomain/zero/1.0/
  28. Drugs and Lactation Database (LactMed)
  29. EU Food Improvement Agents
  30. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  32. Flavor and Extract Manufacturers Association (FEMA)
  33. FooDB
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    https://foodb.ca/about
    5-Isopropyl-2-methylphenol
    https://foodb.ca/compounds/FDB014512
  34. NORMAN Suspect List Exchange
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    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    carvacrol
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  35. NMRShiftDB
  36. MassBank Europe
  37. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  38. NIST Mass Spectrometry Data Center
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    https://www.nist.gov/srd/public-law
    Phenol, 2-methyl-5-(1-methylethyl)-
    http://www.nist.gov/srd/nist1a.cfm
  39. SpectraBase
    PHENOL, 2-METHYL-5-(1-METHYLETHYL)-
    https://spectrabase.com/spectrum/3HhApBiakWP
    PHENOL, 2-METHYL-5-(1-METHYLETHYL)-
    https://spectrabase.com/spectrum/FL9yvT0g1r1
    Phenol, 2-methyl-5-(1-methylethyl)-
    https://spectrabase.com/spectrum/53BkqszINtu
    Phenol, 2-methyl-5-(1-methylethyl)-
    https://spectrabase.com/spectrum/4uBgczCpohM
  40. Japan Chemical Substance Dictionary (Nikkaji)
  41. KEGG
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    https://www.kegg.jp/kegg/legal.html
  42. KNApSAcK Species-Metabolite Database
  43. Natural Product Activity and Species Source (NPASS)
  44. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  45. Metabolomics Workbench
  46. NCI Thesaurus (NCIt)
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  47. Pharos
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  48. Protein Data Bank in Europe (PDBe)
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  51. Springer Nature
  52. SpringerMaterials
  53. Thieme Chemistry
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  58. GHS Classification (UNECE)
  59. EPA Substance Registry Services
  60. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  61. PATENTSCOPE (WIPO)
CONTENTS