PRODUCT IDENTIFICATION

H.S. CODE

TOXICITY

CLASSIFICATION

Flavor, Cannabinoid, Sesquiterpene,

EXTRA NOTES

FEMA No: 2252

PHYSICAL AND CHEMICAL PROPERTIES

129 - 130 C

AUTOIGNITION

NFPA RATINGS

REFRACTIVE INDEX

96 C

Stable under ordinary conditions

GENERAL DESCRIPTION & APPLICATIONS

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Caryophyllene

PubChem Compound Summary - Caryophyllene

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Caryophyllene

http://www.ebi.ac.uk/chebi/ -  Caryophyllene

http://www.ncbi.nlm.nih.gov/ -  Caryophyllene

Human Metabolome Database - Caryophyllene

http://www.ch.ic.ac.uk/
Caryophyllene, a constituent of many essential oils, include clove oil, has a trans alkene contained in a 9-membered ring. One interesting property is that it has 4 diastereoisomers possible, originating from a total of three disymmetric centres present in the molecule. Two of these are conventional chiral centres, one is present in the form of a disymmetric trans double bond. To understand why such a bond can result in two configurations, one must appreciate that (concurrent) rotation about the two C-C single bonds adjacent to the alkene is in fact restricted. This phenomenon, also known as atropisomerism, is a feature of a number of natural products, and arises from a combination of angle strain in a medium sized ring caused by the rotation, together with trans-annular steric effects.

http://ntp.niehs.nih.gov/
Metabolism: Asakawa and coworkers (1981,1986) characterized the metabolism of beta-caryophyllene in rabbits as shown in the following scheme. The main metabolite, (10S)-(-)-14-hydroxycaryophyllene-5,6-oxide, was separated as an acetate, (10S)-(-)-14-acetoxycaryophyllene-5,6-oxide, using column chromatography by n-hexane-ethyl acetate. A second acetate, identified as (-)-caryophyllene-5,6-oxide-2,12-diol monoacetate, was the hydroxyacetate derivative of an additional metabolite, caryophyllene-5,6-oxide-2,12-glycol. The metabolic pathway shown as A was confirmed by administering (-)-caryophyllene-5,6-oxide to rabbits. After being acetylated compound IV was identified and compound III was established as the major metabolite. The authors note that the presence of the route B remains to be clarified and that route A may be favorable to route B since the oxide is often found in essential oils. The stereoselective biohydroxylation of the gem-dimethyl group on the four-membered ring in mammals had not previously been reported. Other Biological Effects: Several studies have documented the anti-inflammatory, cytoprotective, and enzyme-inducing activities of beta-caryophyllene, as well as its in vitro cytotoxicity against several solid tumor cells.

APPEARANCE

ASSAY

90.0% min

REFRACTIVE INDEX

1.498 - 1.504

SPECIFIC GRAVITY

0.90 - 0.91

OPTICAL ROTATION

-10° ~ -5°