CHEBI:10357 - (−)-β-caryophyllene

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ChEBI Name (−)-β-caryophyllene
ChEBI ID CHEBI:10357
ChEBI ASCII Name (-)-beta-caryophyllene
Definition A β-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 β-caryophyllene, occurring in many essential oils, particularly oil of cloves.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H24
Net Charge 0
Average Mass 204.35110
Monoisotopic Mass 204.188
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
InChIKey NPNUFJAVOOONJE-GFUGXAQUSA-N
SMILES [H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs 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.
fragrance
A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.
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ChEBI Ontology
Outgoing (−)-β-caryophyllene (CHEBI:10357) has role fragrance (CHEBI:48318)
(−)-β-caryophyllene (CHEBI:10357) has role metabolite (CHEBI:25212)
(−)-β-caryophyllene (CHEBI:10357) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
(−)-β-caryophyllene (CHEBI:10357) is a β-caryophyllene (CHEBI:63191)
(−)-β-caryophyllene (CHEBI:10357) is enantiomer of (+)-β-caryophyllene (CHEBI:63190)
Incoming (+)-β-caryophyllene (CHEBI:63190) is enantiomer of (−)-β-caryophyllene (CHEBI:10357)
IUPAC Name
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Synonyms Sources
(−)-β-caryophyllene UniProt
(E)-β-caryophyllene MetaCyc
beta-Caryophyllene KEGG COMPOUND
caryophyllene ChEBI
Caryophyllene KEGG COMPOUND
trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene ChEBI
trans-caryophyllene ChEBI
Database Links Databases
C00003110 KNApSAcK
C09629 KEGG COMPOUND
Caryophyllene Wikipedia
CPD-8230 MetaCyc
View more database links
Registry Numbers Types Sources
2044564 Reaxys Registry Number Reaxys
87-44-5 CAS Registry Number ChemIDplus
87-44-5 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
12409018 PubMed citation Europe PMC
18574142 PubMed citation Europe PMC
20015227 PubMed citation Europe PMC
20398787 PubMed citation Europe PMC
20433083 PubMed citation Europe PMC
21366052 PubMed citation Europe PMC
21425686 PubMed citation Europe PMC
21941920 PubMed citation Europe PMC
Last Modified
28 July 2014
General Comment
2011-11-16 Caryophyllene is a constituent of many essential oils, particularly oil of cloves, hemp, rosemary and hops, it is usually found as a mixture with isocaryophyllene (the cis-couble bond isomer) and α-humulene (also known as α-caryophyllene, a ring-openend isomer). The presence of the cyclobutane ring is noteworthyl - it is an uncommon feature in natural products.