An official website of the United States government

Caryophyllene

PubChem CID
5281515
Structure
Caryophyllene_small.png
Caryophyllene_3D_Structure.png
Molecular Formula
Synonyms
  • BETA-CARYOPHYLLENE
  • Caryophyllene
  • (-)-trans-Caryophyllene
  • trans-Caryophyllene
  • 87-44-5
Molecular Weight
204.35 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-18
Description
Beta-caryophyllene is a pale yellow oily liquid with an odor midway between odor of cloves and turpentine. (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.
(-)-beta-caryophyllene is a beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. It has a role as a non-steroidal anti-inflammatory drug, a fragrance, a metabolite and an insect attractant. It is an enantiomer of a (+)-beta-caryophyllene.
Caryophyllene has been reported in Camellia sinensis, Trichogonia grazielae, and other organisms with data available.
See also: Humulene (related); Isocaryophyllene (related); (+)-beta-Caryophyllene (is enantiomer of) ... View More ...

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Caryophyllene.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

NPNUFJAVOOONJE-GFUGXAQUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C/C/1=C\CCC(=C)[C@H]2CC([C@@H]2CC1)(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H24
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

87-44-5

2.3.2 Deprecated CAS

1233519-47-5, 1407-53-0, 8007-38-3
1407-53-0, 8007-38-3

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

1324

2.3.12 KEGG ID

2.3.13 Lipid Maps ID (LM_ID)

2.3.14 Metabolomics Workbench ID

2.3.15 Nikkaji Number

2.3.16 RXCUI

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (E)-beta-caryophyllene
  • (E)-caryophyllene
  • beta-caryophyllene
  • caryophyllene
  • caryophyllene, (R*,4Z,9S*)-(+-)-isomer
  • caryophyllene, (R-(R*,4E,9S))-isomer
  • caryophyllene, (R-(R*,4Z,9S*))-isomer
  • caryophyllene, (S-(R*,4E,9S*))-isomer
  • caryophyllene, (S-(R*,4Z,9S*))-isomer
  • isocaryophyllene
  • trans-caryophyllene

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
204.35 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
204.187800766 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
204.187800766 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
293
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
2
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
1
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

Beta-caryophyllene is a pale yellow oily liquid with an odor midway between odor of cloves and turpentine. (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.
Liquid
Liquid with a terpene odor between cloves and turpentine; [Merck Index] Pale yellow oily liquid; [CAMEO] Clear colorless liquid with a sweet woody odor;
Solid
Colourless to slightly yellow oily liquid; woody-spicy, dry, clove-like aroma

3.2.2 Boiling Point

264 to 266 °F at 14 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.
256.00 to 259.00 °C. @ 760.00 mm Hg
The Good Scents Company Information System

3.2.3 Melting Point

< 25 °C

3.2.4 Flash Point

214 °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.

3.2.5 Solubility

less than 1 mg/mL at 70 °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.
Insoluble in water; soluble in oils, ether
Soluble (in ethanol)

3.2.6 Density

0.9075 at 68 °F (NTP, 1992) - Less dense than water; will float
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.
0.899-0.908

3.2.7 LogP

6.300
The Good Scents Company Information System

3.2.8 Refractive Index

1.498-1.504

3.2.9 Collision Cross Section

151.93 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

3.2.10 Kovats Retention Index

Standard non-polar
1424 , 1421 , 1420 , 1447 , 1418 , 1419 , 1417 , 1414 , 1419 , 1419 , 1403 , 1409 , 1427 , 1420 , 1419 , 1408 , 1412 , 1421 , 1419 , 1419 , 1412 , 1408 , 1409 , 1410 , 1407 , 1410 , 1409 , 1424 , 1409 , 1418 , 1408 , 1405 , 1396 , 1399 , 1424 , 1391 , 1406 , 1419 , 1419 , 1419 , 1420 , 1409 , 1407 , 1428 , 1399 , 1420 , 1391.8 , 1404.3 , 1417.1 , 1408 , 1408 , 1418 , 1426 , 1398 , 1420 , 1417 , 1417 , 1400 , 1423 , 1408 , 1419 , 1400 , 1391 , 1410 , 1400 , 1414 , 1402.9 , 1409 , 1418 , 1405 , 1405 , 1420 , 1411 , 1406 , 1410 , 1410 , 1421 , 1415.1 , 1418 , 1423 , 1437 , 1418.3 , 1420 , 1420 , 1410 , 1410 , 1421 , 1424 , 1419 , 1423 , 1421 , 1420 , 1420 , 1401 , 1430 , 1419 , 1425 , 1420 , 1420 , 1420 , 1420 , 1426 , 1403 , 1435 , 1427 , 1421 , 1397 , 1406 , 1426 , 1426 , 1425 , 1422 , 1400 , 1420 , 1398 , 1431 , 1431 , 1429 , 1429 , 1422 , 1439 , 1440 , 1445 , 1448 , 1448 , 1449 , 1449 , 1450 , 1451 , 1451 , 1453 , 1455 , 1457 , 1459 , 1438 , 1425 , 1427 , 1416 , 1438 , 1414 , 1408.7 , 1414.8 , 1415.3 , 1430.2 , 1447.9 , 1427.5 , 1435.06 , 1427 , 1403 , 1414 , 1427 , 1422 , 1428 , 1420 , 1430 , 1432 , 1426 , 1413 , 1428 , 1392.14 , 1400 , 1407.76 , 1412.51 , 1419.57 , 1426.69 , 1433.93 , 1441.31 , 1449.01 , 1456.63 , 1464.5 , 1417 , 1432 , 1421 , 1423 , 1418 , 1425 , 1423 , 1423 , 1428 , 1425 , 1425 , 1411 , 1428 , 1419 , 1425 , 1420 , 1411 , 1422 , 1428 , 1418 , 1420 , 1422 , 1422 , 1422 , 1412 , 1433 , 1421 , 1420 , 1405 , 1420 , 1408 , 1419 , 1417 , 1420 , 1407 , 1414 , 1422 , 1422 , 1405 , 1414 , 1429 , 1424 , 1428 , 1417 , 1422 , 1422 , 1418 , 1418 , 1425 , 1432.6 , 1425 , 1403 , 1426 , 1410 , 1415 , 1403 , 1426 , 1424 , 1420 , 1449 , 1456 , 1424 , 1440 , 1408 , 1411 , 1430 , 1440 , 1426 , 1427 , 1434 , 1442 , 1449 , 1427 , 1434 , 1442 , 1449 , 1440 , 1442 , 1446 , 1446 , 1436 , 1417.5 , 1418 , 1422 , 1422 , 1424 , 1424 , 1417 , 1418 , 1421 , 1423 , 1435 , 1426 , 1467 , 1418 , 1420 , 1420 , 1424 , 1438 , 1409 , 1424 , 1422 , 1406 , 1427 , 1418 , 1415 , 1423 , 1419 , 1419 , 1425 , 1426 , 1427 , 1436 , 1425 , 1461 , 1415 , 1414 , 1414 , 1421 , 1424 , 1384 , 1414 , 1414 , 1419 , 1413 , 1419 , 1419 , 1421 , 1424 , 1424 , 1434 , 1414 , 1427 , 1414 , 1421 , 1418 , 1417 , 1400 , 1418 , 1410 , 1410 , 1403 , 1417 , 1423 , 1423 , 1427 , 1414 , 1429 , 1414 , 1417 , 1421 , 1415 , 1420 , 1413 , 1416 , 1423 , 1421 , 1421 , 1408 , 1412 , 1424 , 1415 , 1414 , 1413 , 1428 , 1428 , 1429 , 1419 , 1421 , 1412 , 1415 , 1415 , 1404 , 1419 , 1421 , 1408 , 1422 , 1397 , 1430 , 1423 , 1417 , 1418 , 1418 , 1416 , 1423 , 1419 , 1423 , 1422 , 1429 , 1439 , 1414 , 1412 , 1401 , 1412 , 1398 , 1414 , 1420 , 1416 , 1424 , 1429 , 1414 , 1422 , 1414 , 1423 , 1433 , 1435 , 1398 , 1402 , 1418 , 1423 , 1423 , 1418 , 1410 , 1410 , 1419 , 1419 , 1398 , 1430 , 1427 , 1424 , 1418 , 1414 , 1400 , 1423 , 1412 , 1419 , 1421 , 1416 , 1426 , 1416 , 1408 , 1424 , 1419 , 1420 , 1422 , 1422 , 1414 , 1419 , 1418 , 1419 , 1418 , 1409 , 1418 , 1418 , 1398 , 1429 , 1429 , 1415 , 1415 , 1422 , 1415 , 1412 , 1414 , 1420 , 1419 , 1402 , 1429 , 1428 , 1414 , 1414 , 1417 , 1417 , 1423 , 1413 , 1430 , 1455.4 , 1391.8 , 1420 , 1411 , 1423 , 1405 , 1414 , 1415 , 1419 , 1412 , 1406 , 1421 , 1414 , 1420 , 1423 , 1423 , 1409 , 1413 , 1416 , 1416 , 1415 , 1401 , 1423 , 1430 , 1421.7 , 1429.4 , 1415 , 1422 , 1414 , 1412 , 1424 , 1408 , 1422 , 1391 , 1423 , 1420 , 1428 , 1428 , 1419 , 1414 , 1423 , 1409 , 1413 , 1411 , 1414 , 1419 , 1400 , 1427 , 1411 , 1419 , 1414 , 1422 , 1417 , 1427 , 1428 , 1420 , 1403 , 1410 , 1415 , 1411 , 1411 , 1403 , 1418 , 1394 , 1422 , 1425 , 1425 , 1405 , 1434 , 1409 , 1418.5 , 1414 , 1440 , 1418 , 1460 , 1418 , 1398 , 1423 , 1429 , 1416 , 1420 , 1414 , 1420 , 1411 , 1423 , 1431 , 1396 , 1396 , 1397 , 1397 , 1417 , 1422 , 1423 , 1421 , 1418 , 1429 , 1419 , 1401 , 1420 , 1397 , 1401 , 1407 , 1404 , 1414 , 1428 , 1422 , 1432.1 , 1420 , 1422 , 1414 , 1424 , 1423 , 1424 , 1417 , 1423 , 1427 , 1415 , 1418 , 1414 , 1405 , 1403 , 1419 , 1419 , 1414 , 1435 , 1421 , 1418 , 1420 , 1423 , 1437 , 1414 , 1414 , 1396 , 1397 , 1437 , 1429 , 1414 , 1420 , 1420 , 1419 , 1419 , 1411 , 1414 , 1433 , 1410 , 1420 , 1408 , 1411 , 1420 , 1422 , 1423 , 1425 , 1419 , 1411 , 1416 , 1417 , 1415 , 1415 , 1416 , 1425 , 1427 , 1406 , 1417 , 1424 , 1424 , 1424 , 1424 , 1415 , 1417 , 1428 , 1429 , 1421 , 1423 , 1423 , 1409 , 1408 , 1409 , 1414 , 1414 , 1415 , 1420 , 1412 , 1422 , 1422 , 1397.4 , 1417.4 , 1417.4 , 1418 , 1418.5 , 1414 , 1415 , 1423 , 1415 , 1415 , 1412 , 1414 , 1415 , 1422 , 1422 , 1422 , 1410 , 1452 , 1414 , 1410 , 1413 , 1428 , 1445 , 1410 , 1414 , 1434 , 1435 , 1416 , 1414 , 1413 , 1412 , 1413 , 1413 , 1410 , 1442 , 1450 , 1417 , 1411 , 1414 , 1425 , 1428
Semi-standard non-polar
1423 , 1420 , 1420 , 1419 , 1423 , 1418 , 1421 , 1432 , 1457 , 1419 , 1419 , 1420 , 1427 , 1419 , 1419 , 1423 , 1419 , 1418 , 1411 , 1430 , 1431 , 1415 , 1418 , 1417 , 1420 , 1418 , 1414 , 1416 , 1425.6 , 1398 , 1417 , 1418 , 1418 , 1418 , 1418 , 1440 , 1413 , 1413 , 1413 , 1413 , 1413 , 1440 , 1418 , 1457 , 1415 , 1420 , 1467 , 1418 , 1420 , 1419 , 1421 , 1419 , 1417 , 1418 , 1438 , 1418 , 1411 , 1426 , 1467 , 1390 , 1412 , 1430 , 1419 , 1422 , 1414 , 1427 , 1413 , 1419 , 1419 , 1414 , 1417 , 1437.2 , 1442 , 1410 , 1423 , 1425 , 1421 , 1420 , 1428 , 1416 , 1420 , 1420 , 1419 , 1420 , 1412 , 1434 , 1418 , 1418 , 1419 , 1417 , 1412 , 1407 , 1404 , 1417.6 , 1426 , 1431.8 , 1417 , 1416 , 1418 , 1432 , 1435 , 1428 , 1420 , 1419 , 1418 , 1422 , 1420 , 1420 , 1420 , 1419 , 1420 , 1413 , 1417 , 1425 , 1425 , 1418 , 1418 , 1417 , 1425 , 1428 , 1441 , 1406 , 1420 , 1419 , 1420 , 1422 , 1418 , 1424 , 1397 , 1408 , 1427 , 1429 , 1426 , 1430 , 1422 , 1419 , 1419 , 1420 , 1420 , 1419 , 1419 , 1420 , 1418 , 1419 , 1419 , 1419 , 1407 , 1428 , 1420 , 1420 , 1420 , 1420 , 1419 , 1420 , 1418 , 1439 , 1417 , 1418 , 1419 , 1415 , 1420 , 1418 , 1423 , 1415 , 1420 , 1418 , 1418 , 1414 , 1418 , 1420 , 1423 , 1421 , 1418 , 1418 , 1419 , 1419 , 1418 , 1404 , 1417 , 1421 , 1418 , 1418 , 1419 , 1420 , 1420 , 1418 , 1418 , 1418 , 1416 , 1418 , 1412 , 1409 , 1410 , 1415 , 1418 , 1416 , 1390 , 1431 , 1418 , 1426 , 1417 , 1416 , 1423 , 1418 , 1411 , 1418 , 1418 , 1418 , 1421 , 1421 , 1414 , 1418 , 1420 , 1419 , 1420 , 1427 , 1418 , 1401.3 , 1403.15 , 1439 , 1419 , 1423 , 1414 , 1419 , 1425 , 1415 , 1415 , 1414 , 1417 , 1417 , 1417 , 1418 , 1428 , 1418 , 1415 , 1415 , 1404 , 1404 , 1428 , 1418 , 1423 , 1427 , 1420 , 1418 , 1420 , 1400 , 1419 , 1427 , 1440 , 1418 , 1415 , 1417 , 1444 , 1420 , 1422 , 1419 , 1414 , 1451 , 1419 , 1418 , 1423 , 1423 , 1419 , 1420 , 1414 , 1418 , 1451 , 1417 , 1429.6 , 1419 , 1427 , 1416 , 1420 , 1419 , 1418 , 1418 , 1409 , 1431 , 1410 , 1418 , 1417 , 1419 , 1417 , 1431 , 1428 , 1446 , 1399 , 1419 , 1420 , 1394 , 1395 , 1408 , 1418 , 1420 , 1451 , 1420 , 1418 , 1420 , 1422 , 1411 , 1415 , 1419 , 1424 , 1418 , 1425 , 1418 , 1418 , 1418 , 1418 , 1418 , 1455 , 1417 , 1420 , 1418 , 1418 , 1419 , 1435 , 1418 , 1424 , 1420 , 1418 , 1455 , 1418 , 1399 , 1417 , 1419 , 1420 , 1418 , 1390 , 1396 , 1417 , 1418 , 1421 , 1405 , 1390 , 1419 , 1412 , 1412 , 1413 , 1417 , 1417 , 1423 , 1442 , 1427 , 1417 , 1419 , 1411 , 1438 , 1419 , 1424 , 1434 , 1419 , 1418 , 1418 , 1413 , 1413 , 1413 , 1419 , 1427 , 1427 , 1424 , 1438 , 1419 , 1418 , 1420 , 1414 , 1418 , 1418 , 1419 , 1458 , 1417 , 1431 , 1418 , 1419 , 1419 , 1420 , 1424 , 1429 , 1430 , 1421 , 1415 , 1414 , 1430 , 1432 , 1430 , 1431 , 1420 , 1462 , 1419 , 1393 , 1408 , 1418 , 1424 , 1422 , 1416 , 1423 , 1419 , 1419 , 1428 , 1420 , 1430 , 1427 , 1420 , 1411 , 1420 , 1421 , 1427 , 1428 , 1424 , 1420 , 1418 , 1420 , 1419 , 1416 , 1410 , 1420 , 1451 , 1416 , 1429 , 1442 , 1427 , 1411 , 1418 , 1459 , 1435 , 1439 , 1436 , 1411 , 1411 , 1419 , 1440 , 1411 , 1416 , 1439 , 1416 , 1418 , 1426 , 1419 , 1425 , 1414 , 1434 , 1415 , 1422 , 1423 , 1424 , 1426 , 1438 , 1426 , 1429 , 1429 , 1418 , 1413 , 1421 , 1410 , 1414 , 1420 , 1425 , 1419 , 1427 , 1422 , 1420 , 1419 , 1432 , 1432 , 1418 , 1416 , 1426 , 1465 , 1467 , 1427 , 1400 , 1407 , 1418 , 1418 , 1412 , 1418 , 1419 , 1403 , 1403 , 1403 , 1425 , 1418 , 1419 , 1418 , 1424 , 1424 , 1397 , 1425 , 1423 , 1417 , 1433 , 1419 , 1425 , 1449 , 1422 , 1436 , 1436 , 1420 , 1420 , 1421 , 1425 , 1420 , 1419 , 1428 , 1418 , 1458 , 1427 , 1423 , 1412 , 1414 , 1420 , 1422 , 1419 , 1433 , 1415 , 1410 , 1399 , 1401 , 1455 , 1414 , 1419 , 1436 , 1416 , 1418 , 1421 , 1417 , 1419 , 1418 , 1418 , 1419 , 1418 , 1411 , 1455 , 1414 , 1448 , 1424 , 1418 , 1412 , 1415 , 1415 , 1447 , 1422 , 1434 , 1414 , 1432 , 1396 , 1421 , 1406 , 1418 , 1458 , 1415 , 1390 , 1430 , 1422 , 1418 , 1412 , 1413 , 1419 , 1422 , 1389 , 1419 , 1421 , 1465 , 1419 , 1409 , 1420 , 1427 , 1428 , 1419 , 1419 , 1468 , 1468 , 1413 , 1419 , 1422 , 1419 , 1420 , 1396 , 1418 , 1424 , 1419 , 1419 , 1414 , 1418 , 1424 , 1419 , 1403 , 1412 , 1420 , 1414.5 , 1419 , 1408 , 1414 , 1417 , 1420 , 1430 , 1402 , 1417 , 1418 , 1415 , 1418 , 1412 , 1421 , 1417 , 1418 , 1418 , 1416 , 1414 , 1418 , 1422 , 1415 , 1414 , 1420 , 1420 , 1421 , 1422 , 1448 , 1417 , 1418 , 1418 , 1412 , 1416 , 1419 , 1414 , 1427 , 1428 , 1422 , 1424 , 1424 , 1418 , 1415 , 1415 , 1419 , 1418 , 1418 , 1399 , 1421 , 1419 , 1419 , 1421 , 1425 , 1418 , 1425 , 1427 , 1423 , 1418 , 1418 , 1418 , 1418 , 1420 , 1423 , 1419 , 1430 , 1415 , 1417 , 1441 , 1419 , 1420 , 1402 , 1417 , 1419 , 1420 , 1420 , 1420 , 1413 , 1413 , 1418 , 1415 , 1414 , 1431 , 1418 , 1420 , 1420 , 1421 , 1418 , 1412 , 1419 , 1458 , 1413 , 1403 , 1420 , 1414 , 1407 , 1430 , 1418 , 1421 , 1427 , 1416 , 1405 , 1395 , 1418 , 1417 , 1418 , 1419 , 1420 , 1417 , 1419 , 1454 , 1421 , 1418 , 1450 , 1414 , 1411 , 1420 , 1422 , 1416 , 1413 , 1418 , 1426 , 1428 , 1418 , 1413 , 1418 , 1421 , 1419 , 1425 , 1425 , 1414 , 1392 , 1419 , 1419 , 1419 , 1421 , 1418 , 1426 , 1415 , 1418 , 1444 , 1426 , 1431 , 1419 , 1406 , 1423 , 1418 , 1434 , 1416 , 1416 , 1421 , 1418 , 1414 , 1418 , 1418 , 1409 , 1409 , 1415 , 1420 , 1417 , 1419 , 1423 , 1417 , 1453 , 1418 , 1420 , 1410 , 1403 , 1421 , 1418 , 1413 , 1398 , 1404 , 1418 , 1418 , 1418 , 1419 , 1418 , 1441 , 1419 , 1426 , 1415 , 1418 , 1419 , 1409 , 1425 , 1418 , 1400 , 1418 , 1414 , 1414 , 1415 , 1415 , 1416 , 1394 , 1425 , 1412 , 1419 , 1413 , 1413 , 1418 , 1418 , 1421 , 1419 , 1412 , 1419 , 1420 , 1418 , 1415 , 1414 , 1431 , 1420 , 1419 , 1406 , 1414 , 1419 , 1419 , 1418 , 1443 , 1424 , 1437 , 1419 , 1416 , 1418 , 1431 , 1442 , 1431 , 1433 , 1418 , 1391 , 1421 , 1420.9 , 1419 , 1421 , 1426 , 1422 , 1418 , 1432 , 1437 , 1419 , 1427 , 1415 , 1426 , 1419 , 1420 , 1406 , 1410 , 1411 , 1425 , 1418 , 1418 , 1418 , 1418 , 1417.6 , 1413 , 1423.3 , 1418 , 1421 , 1418 , 1406 , 1417 , 1419 , 1425 , 1418 , 1416 , 1455 , 1414 , 1420 , 1420 , 1424 , 1424 , 1425 , 1418 , 1414 , 1419 , 1418.5 , 1425 , 1420 , 1419 , 1428 , 1418 , 1411 , 1419 , 1422 , 1422 , 1417 , 1426 , 1418 , 1419 , 1424 , 1413 , 1418 , 1438.8 , 1418 , 1418 , 1418 , 1426 , 1405 , 1416 , 1425 , 1414 , 1414 , 1433 , 1412 , 1415 , 1419 , 1420 , 1418 , 1418 , 1419 , 1419 , 1425 , 1425 , 1428 , 1428 , 1430 , 1406 , 1423 , 1425 , 1418 , 1418 , 1418 , 1418 , 1422 , 1410 , 1420 , 1414 , 1424 , 1404 , 1419 , 1420 , 1418 , 1414 , 1421 , 1384 , 1420 , 1415 , 1418 , 1416 , 1428 , 1431 , 1418 , 1417 , 1408 , 1420 , 1417 , 1454 , 1430 , 1434 , 1422.7 , 1438.2 , 1422 , 1411 , 1417 , 1419 , 1427 , 1419 , 1425 , 1418 , 1437 , 1418 , 1418 , 1451 , 1419 , 1418 , 1428 , 1419 , 1422 , 1424 , 1420 , 1420 , 1416 , 1428 , 1427 , 1400 , 1419 , 1418 , 1416.1 , 1418.3 , 1419 , 1457 , 1432 , 1429 , 1423 , 1425 , 1426 , 1437 , 1410 , 1425.7 , 1429 , 1422 , 1435 , 1430 , 1435 , 1444 , 1444 , 1468 , 1468 , 1418 , 1421 , 1419 , 1420 , 1420 , 1420 , 1418 , 1419 , 1416 , 1415 , 1423 , 1424 , 1411 , 1418 , 1419 , 1419 , 1433 , 1411 , 1412 , 1416 , 1455 , 1413 , 1419 , 1416 , 1421
Standard polar
1591 , 1592 , 1598 , 1592 , 1593 , 1594 , 1613 , 1600 , 1593 , 1604 , 1589 , 1558 , 1583 , 1568 , 1593 , 1593 , 1561 , 1598 , 1597 , 1597 , 1585 , 1587 , 1585 , 1598 , 1595 , 1605 , 1594 , 1590 , 1594 , 1622 , 1578 , 1562 , 1593 , 1604 , 1581 , 1591 , 1580 , 1584 , 1614 , 1593 , 1583 , 1571 , 1593 , 1555 , 1624 , 1644 , 1615 , 1620 , 1595 , 1590 , 1569 , 1605 , 1604 , 1604 , 1595 , 1595 , 1578 , 1587 , 1581 , 1579 , 1586 , 1597 , 1595 , 1604 , 1583 , 1583 , 1583 , 1589 , 1565 , 1604 , 1604 , 1604 , 1608 , 1580 , 1618 , 1583 , 1576 , 1557 , 1581 , 1581 , 1578 , 1572 , 1598 , 1578 , 1599 , 1555 , 1607 , 1565 , 1563 , 1588 , 1561 , 1576 , 1576 , 1576 , 1587 , 1594 , 1593 , 1610 , 1599 , 1618 , 1576 , 1557 , 1572 , 1588 , 1578 , 1576 , 1576 , 1588 , 1571 , 1594 , 1594 , 1594 , 1594 , 1596 , 1596 , 1588 , 1606 , 1587 , 1575 , 1584 , 1598 , 1588 , 1585 , 1594 , 1594 , 1582 , 1564 , 1581 , 1595 , 1588 , 1588 , 1591 , 1612 , 1590 , 1590 , 1601 , 1594 , 1594 , 1594 , 1600 , 1608 , 1582 , 1594 , 1594 , 1594 , 1625 , 1590 , 1582 , 1613 , 1642 , 1612 , 1619 , 1603 , 1606 , 1597 , 1610 , 1593 , 1594 , 1587 , 1591 , 1567 , 1583 , 1593 , 1595 , 1596 , 1612 , 1594.3 , 1611 , 1623.3 , 1620 , 1615 , 1589 , 1625 , 1576 , 1617 , 1570 , 1585 , 1575 , 1607 , 1599 , 1617 , 1632 , 1581 , 1584 , 1617 , 1579 , 1579 , 1588 , 1598 , 1617 , 1587 , 1585 , 1581 , 1617 , 1577 , 1570 , 1570 , 1580 , 1581 , 1570 , 1570 , 1568 , 1570 , 1632 , 1642 , 1594 , 1638 , 1638 , 1638 , 1618 , 1618 , 1618 , 1632 , 1612 , 1612 , 1586 , 1572 , 1585 , 1628 , 1612 , 1614 , 1623 , 1612 , 1612 , 1602 , 1634 , 1608 , 1616 , 1555 , 1595 , 1589 , 1612 , 1612 , 1632 , 1613 , 1582 , 1612 , 1607 , 1575 , 1590 , 1608 , 1558 , 1572 , 1612 , 1578 , 1600 , 1601 , 1604 , 1612 , 1564 , 1566 , 1594 , 1580 , 1574 , 1585 , 1593 , 1638 , 1612 , 1612 , 1612 , 1587 , 1584 , 1595 , 1608 , 1594 , 1610 , 1612 , 1612 , 1617 , 1617 , 1606 , 1558 , 1593 , 1594 , 1585 , 1586 , 1586 , 1597 , 1567 , 1580 , 1585 , 1594 , 1594 , 1607 , 1587 , 1589 , 1612 , 1612 , 1612 , 1571 , 1599 , 1574 , 1638 , 1612 , 1612 , 1612 , 1638 , 1587 , 1594 , 1586 , 1590 , 1628 , 1612 , 1612 , 1591 , 1555 , 1588 , 1608 , 1595 , 1612 , 1599 , 1602 , 1593 , 1554 , 1602 , 1587 , 1578 , 1578 , 1584 , 1603 , 1612 , 1612 , 1612 , 1612 , 1575 , 1612 , 1608 , 1583 , 1581 , 1602 , 1585 , 1578 , 1612 , 1612 , 1612 , 1570 , 1569 , 1615 , 1583 , 1609 , 1611 , 1628 , 1577 , 1578 , 1578 , 1614 , 1614 , 1594 , 1594 , 1618 , 1596 , 1596 , 1612 , 1569 , 1617 , 1612 , 1571 , 1612 , 1599 , 1592 , 1612 , 1612 , 1588 , 1590 , 1601 , 1598 , 1612 , 1612 , 1578 , 1598 , 1592 , 1592 , 1612 , 1612 , 1612 , 1580 , 1580 , 1612 , 1610 , 1587 , 1589 , 1596 , 1615 , 1588 , 1589 , 1618 , 1618 , 1612 , 1622 , 1595 , 1607 , 1612 , 1612 , 1605 , 1573 , 1612 , 1612 , 1612 , 1612 , 1611 , 1615 , 1612 , 1575 , 1583 , 1602 , 1597 , 1603 , 1572 , 1589 , 1589 , 1587 , 1588.1 , 1579 , 1618 , 1618 , 1618 , 1612 , 1587 , 1589 , 1612 , 1614 , 1616.2 , 1607 , 1612 , 1612 , 1612 , 1612 , 1644 , 1578 , 1608.8 , 1612 , 1617 , 1613 , 1616 , 1595 , 1609 , 1575 , 1612 , 1615 , 1600 , 1612 , 1574 , 1550 , 1578 , 1617 , 1612 , 1612 , 1588 , 1602.9 , 1598 , 1587 , 1589 , 1612 , 1612 , 1612 , 1612 , 1607 , 1615 , 1595 , 1615 , 1612 , 1612 , 1612 , 1594 , 1596 , 1612 , 1556 , 1558 , 1563 , 1609 , 1555 , 1612 , 1616 , 1590 , 1578 , 1591 , 1597 , 1617 , 1610 , 1591 , 1579 , 1588 , 1607 , 1566 , 1566 , 1566 , 1566 , 1566 , 1567 , 1582 , 1595 , 1611 , 1628 , 1612 , 1612 , 1607 , 1612 , 1612 , 1612 , 1579 , 1610 , 1612 , 1627 , 1617 , 1588 , 1606 , 1607 , 1611 , 1585 , 1623 , 1609 , 1577 , 1612 , 1607 , 1607 , 1615 , 1610 , 1628 , 1611 , 1611 , 1611 , 1611 , 1611 , 1611 , 1611 , 1571 , 1631 , 1631 , 1594 , 1591 , 1587 , 1611 , 1598 , 1607 , 1631 , 1591 , 1595 , 1604 , 1575 , 1582 , 1615 , 1595 , 1587 , 1577 , 1581 , 1592 , 1592 , 1594 , 1622 , 1600 , 1610 , 1592 , 1594 , 1619 , 1585 , 1633 , 1599 , 1598 , 1570 , 1617 , 1570 , 1573.2 , 1587 , 1587 , 1598 , 1570 , 1618 , 1570 , 1570 , 1572 , 1552 , 1570 , 1618 , 1633 , 1636 , 1642 , 1612 , 1598 , 1564 , 1628

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Biological Agents -> Plant Oils and Extracts

3.4.1 Cosmetics

Cosmetics ingredient -> Flavor; Fragrance

3.4.2 Food Additives

COLOR OR COLORING ADJUNCT, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.4.3 Fragrances

Fragrance Ingredient (beta-Caryophyllene) -> IFRA transparency List

3.4.4 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 2
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
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 3
View All
Spectra ID
Instrument Type
GC-EI-Q
Ionization Mode
Positive
Top 5 Peaks

91.1 6.68

93.1 6.34

133.1 6.01

41.1 5.74

79.1 5.74

Thumbnail
Thumbnail
Notes
Collected by Yilin Wang May 2020 for CannabisDB, instrument= Agilent 7890B GC, Agilent 5977A MSD
2 of 3
View All
Source of Spectrum
Adams' Essential Oil Components (GC-MS), Version 4
Copyright
Database Compilation Copyright © 2023-2024 John Wiley and Sons, Inc. Copyright © 2023-2024 John Wiley and Sons, Inc., Portions Copyright Wiley-VCH GmbH, Adams Library under license from Diablo Analytical. All Rights Reserved.
Thumbnail
Thumbnail

4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
CAPILLARY CELL: NEAT
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Catalog Number
22075
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Clinical Trials

7.1.1 ClinicalTrials.gov

8 Food Additives and Ingredients

8.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

8.2 FEMA Flavor Profile

Fried, Spice, Wood

8.3 FDA Substances Added to Food

Used for (Technical Effect)
COLOR OR COLORING ADJUNCT, FLAVORING AGENT OR ADJUVANT
Document Number (21 eCFR)
FEMA Number
2252
GRAS Number
3
JECFA Flavor Number
1324

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

Chemical Name
beta-CARYOPHYLLENE
Evaluation Year
2004
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

9.2 Human Metabolite Information

9.2.1 Cellular Locations

  • Extracellular
  • Membrane

9.3 Biochemical Reactions

10 Use and Manufacturing

10.1 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
Found in many essential oils, especially clove oil; Used in perfumes; [Merck Index] Used as flavoring agent or adjuvant and coloring agent for foods; [FDA] Also used to suppress intestinal bacteria; [NTP]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

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 Industry Uses

  • Fragrance
  • Flavoring and nutrient

10.1.3 Consumer Uses

Fragrance

10.1.4 Household Products

California Safe Cosmetics Program (CSCP)

Cosmetics product ingredient: (1R,4E,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene (Beta-Caryophyllene)

Beta-Caryophyllene 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: 633

Household & Commercial/Institutional Products

Information on 27 consumer products that contain Beta-Caryophyllene in the following categories is provided:

• Auto Products

• Commercial / Institutional

• Inside the Home

• Personal Care

10.2 U.S. Production

Aggregated Product Volume

2019: <1,000,000 lb

2018: 13,889 lb

2017: 18,518 lb

2016: 11,188 lb

10.3 General Manufacturing Information

Industry Processing Sectors
  • All Other Chemical Product and Preparation Manufacturing
  • All Other Basic Organic Chemical Manufacturing
  • Food, beverage, and tobacco product manufacturing
EPA TSCA Commercial Activity Status
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-: ACTIVE

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Note
Pictograms displayed are for > 99.9% (2042 of 2044) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for < 0.1% (2 of 2044) of reports.
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H304 (99.5%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

H317 (78.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Precautionary Statement Codes

P261, P272, P280, P301+P316, P302+P352, P321, P331, P333+P317, P362+P364, P405, 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 2044 reports by companies from 10 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 2044 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 9 notifications provided by 2042 of 2044 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.

11.1.2 Hazard Classes and Categories

Asp. Tox. 1 (99.5%)

Skin Sens. 1 (78.7%)

11.1.3 Health Hazards

SYMPTOMS: This chemical causes irritation of the skin.

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and irritating fumes. (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.

11.1.4 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.

11.1.5 Hazards Summary

A skin irritant; [NTP] Safe when used as a flavoring agent in food; [JECFA] Causes local anesthesia in acute ocular studies of rabbits; Causes inflammation in acute oral studies of mice; [RTECS] beta-Caryophyllene (oxidized) included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] A skin irritant; Harmful by ingestion (may cause lung damage by aspiration); [Good Scents MSDS]

11.2 First Aid Measures

11.2.1 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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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: 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. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. 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.

11.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical carbon dioxide or Halon extinguisher. (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.

11.4 Handling and Storage

11.4.1 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 store this material under ambient 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.

11.5 Exposure Control and Personal Protection

11.5.1 Personal Protective Equipment (PPE)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate 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.

11.6 Stability and Reactivity

11.6.1 Air and Water Reactions

Insoluble in water.

11.6.2 Reactive Group

Hydrocarbons, Aliphatic Unsaturated

11.6.3 Reactivity Profile

The unsaturated aliphatic hydrocarbons, such as BETA-CARYOPHYLLENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions.

11.7 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-
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)

REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-: Does not have an individual approval but may be used under an appropriate group standard

12 Toxicity

12.1 Toxicological Information

12.1.1 Adverse Effects

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

13 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact dermatitis, allergic [Category: Skin Disease]

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Chemical Co-Occurrences in Literature

14.6 Chemical-Gene Co-Occurrences in Literature

14.7 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

16.2 Pathways

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

19 Classification

19.1 MeSH Tree

19.2 ChEBI Ontology

19.3 LIPID MAPS Classification

19.4 KEGG: Lipid

19.5 KEGG: Phytochemical Compounds

19.6 CAMEO Chemicals

19.7 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

19.8 ChEMBL Target Tree

19.9 UN GHS Classification

19.10 EPA CPDat Classification

19.11 NORMAN Suspect List Exchange Classification

19.12 CCSBase Classification

19.13 EPA DSSTox Classification

19.14 Consumer Product Information Database Classification

19.15 EPA TSCA and CDR Classification

19.16 LOTUS Tree

19.17 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-
    https://services.industrialchemicals.gov.au/search-inventory/
  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. 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
  5. 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
    Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
    https://www.epa.gov/chemical-data-reporting
  6. EPA Chemicals under the TSCA
    Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
    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)
    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
  9. 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
  10. 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
  11. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  12. 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/
  13. California Safe Cosmetics Program (CSCP) Product Database
    (1R,4E,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
    https://www.cdph.ca.gov/Programs/CCDPHP/DEODC/OHB/CSCP/Pages/About-CSCP.aspx
    (1R,4E,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene (Beta-Caryophyllene)
    https://cscpsearch.cdph.ca.gov/search/detailresult/4465
  14. 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/
  15. 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
  16. 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
  17. ChEBI
  18. 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/
  19. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  20. 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
  21. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  22. 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
  23. 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
  24. Therapeutic Target Database (TTD)
  25. EPA Chemical and Products Database (CPDat)
  26. EU Food Improvement Agents
  27. 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
  28. Flavor and Extract Manufacturers Association (FEMA)
  29. SpectraBase
    Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)-
    https://spectrabase.com/spectrum/ASz64Nn5XiZ
    (E)-(1R,9S)-(-)-8-methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
    https://spectrabase.com/spectrum/4L23Jh4eAiE
    (E)-(1R,9S)-(-)-8-METHYLENE-4,11,11-TRIMETHYLBICYCLO[7.2.0]UNDEC-4-ENE
    https://spectrabase.com/spectrum/BqIV07BQtSe
  30. Japan Chemical Substance Dictionary (Nikkaji)
  31. 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
  32. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  33. Natural Product Activity and Species Source (NPASS)
  34. Metabolomics Workbench
  35. 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
  36. 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
  37. NMRShiftDB
  38. 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
  39. Springer Nature
  40. SpringerMaterials
  41. 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/
  42. Wikidata
  43. Wikipedia
  44. PubChem
  45. 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
    Anti-Inflammatory Agents, Non-Steroidal
    https://www.ncbi.nlm.nih.gov/mesh/68000894
  46. GHS Classification (UNECE)
  47. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  48. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  49. PATENTSCOPE (WIPO)
CONTENTS