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CHEBI:10357 - (−)-β-caryophyllene

ChEBI IDCHEBI:10357
ChEBI Name(−)-β-caryophyllene
Stars
ASCII Name(-)-beta-caryophyllene
DefinitionA 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.
Last Modified23 August 2021
DownloadsMolfile
FormulaC15H24
Net Charge0
Average Mass204.357
Monoisotopic Mass204.18780
SMILES[H][C@@]12CC/C(C)=C/CCC(=C)[C@@]1([H])CC2(C)C
InChIInChI=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
InChIKeyNPNUFJAVOOONJE-GFUGXAQUSA-N
Wikipedia
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
insect attractant  A chemical that attracts insects.
Applications:
fragrance  A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.
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.
ChEBI Ontology
Outgoing Relation(s)
(−)-β-caryophyllene (CHEBI:10357) has role fragrance (CHEBI:48318)
(−)-β-caryophyllene (CHEBI:10357) has role insect attractant (CHEBI:24850)
(−)-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 Relation(s)
(+)-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  Source
beta-CaryophylleneKEGG COMPOUND
CaryophylleneKEGG COMPOUND
trans-caryophylleneChEBI
trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-eneChEBI
caryophylleneChEBI
(E)-β-caryophylleneMetaCyc
UniProt Name  Source
(−)-(E)-β-caryophylleneUniProt
Manual XrefsDatabases
C09629KEGG COMPOUND
CPD-8230MetaCyc
CaryophylleneWikipedia
C00003110KNApSAcK
Registry NumbersSources
Reaxys:2044564Reaxys
CAS:87-44-5KEGG COMPOUND
CAS:87-44-5ChemIDplus
CAS:87-44-5NIST Chemistry WebBook
Citations