caryophyllene

Also known as β-Caryophyllene, 4,11,11-trimethyl-8-methylene- bicyclo[7.2.0]undec-4-ene, trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene, trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene, trans-caryophyllene, (E)-beta-caryophyllene

Caryophyllene (), more formally (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene that occurs widely in nature. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

Chemical data

Formula: C15H24
Molecular weight: 204.35 g/mol
IUPAC name: (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
SMILES: C/C/1=C\CCC(=C)[C@H]2CC([C@@H]2CC1)(C)C
InChIKey: NPNUFJAVOOONJE-GFUGXAQUSA-N
XLogP: 4.4
Polar surface area: 0 Å²
H-bond donors: 0
H-bond acceptors: 0
Formal charge: 0

via PubChem

Research

4,146 papers

Beta-caryophyllene in psychiatric and neurological diseases: Role of blood-brain barrier.Vitamins and hormones · 2024
β-Caryophyllene suppresses ferroptosis induced by cerebral ischemia reperfusion via activation of the NRF2/HO-1 signaling pathway in MCAO/R rats.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2022
Beta-Caryophyllene, a Cannabinoid Receptor Type 2 Selective Agonist, in Emotional and Cognitive Disorders.International journal of molecular sciences · 2024
β-caryophyllene Delivery Systems: Enhancing the Oral Pharmacokinetic and Stability.Current pharmaceutical design · 2018
Protective Effects of (E)-β-Caryophyllene (BCP) in Chronic Inflammation.Nutrients · 2020

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Wikidata facts

Has part: carbon
Mass: 204.187801

Show 6 more facts

found in taxon: Petasites hybridus
chemical formula: C₁₅H₂₄
Commons category: Caryophyllene
canonical SMILES: CC1=CCCC(=C)C2CC(C2CC1)(C)C
isomeric SMILES: C/C/1=C\CCC(=C)[C@H]2CC([C@@H]2CC1)(C)C
subject has role: non-steroidal anti-inflammatory drug

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Encyclopedic overview

9 sections

Contents

Production
Basic research
Safety
Metabolism and derivatives
Natural sources
Biosynthesis
Compendial status
Further reading
Notes and references

== Production == Caryophyllene can be produced synthetically, but it is invariably obtained from natural sources because it is widespread. It is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, copaiba, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer.

Excerpted from Wikipedia’s “caryophyllene” article, available under the CC BY-SA 4.0 licence.

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