A bicyclic sesquiterpene; a metabolite of β-caryophyllene that has been found in C. sativa; does not bind to the cannabinoid (CB) receptor CB2 (Ki = >20 µM); induces calcium currents in HL-60 cells expressing CB2 receptors but also does so in CB2-deficient cells; cytotoxic to HepG2

(−)-Caryophyllene oxide – 1 g

Brand:
Cayman
CAS:
1139-30-6
Storage:
-20
UN-No:
Non-Hazardous - /

(–)-Caryophyllene oxide is a bicyclic sesquiterpene and a metabolite of β-caryophyllene that has been found in C. sativa and has anticancer properties.{34255,34256} Unlike β-caryophyllene, (−)-caryophyllene oxide does not bind to the cannabinoid (CB) receptor CB2 (Ki = >20 µM). It induces calcium currents in HL-60 cells expressing CB2 receptors but also does so in CB2-deficient cells. (−)-Caryophyllene oxide is cytotoxic to HepG2, AGS, HeLa, SNU-1 and SNU-16 cells (IC50s = 3.95, 12.6, 13.55, 16.79, and 27.39 µM, respectively).{37661} It is the volatile component of C. sativa sensed by narcotic detection dogs.{34255} Formulations containing (–)-caryophyllene have been used as flavoring agents.  

 

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Description

A bicyclic sesquiterpene; a metabolite of β-caryophyllene that has been found in C. sativa; does not bind to the cannabinoid (CB) receptor CB2 (Ki = >20 µM); induces calcium currents in HL-60 cells expressing CB2 receptors but also does so in CB2-deficient cells; cytotoxic to HepG2, AGS, HeLa, SNU-1 and SNU-16 cells (IC50s = 3.95, 12.6, 13.55, 16.79, and 27.39 µM, respectively); the volatile component of C. sativa sensed by narcotic detection dogs

Formal name: (1R,6R,10S)-4R,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane

Synonyms:  BCP oxide|β-Caryophyllene epoxide|β-Caryophyllene oxide

Molecular weight: 220.4

CAS: 1139-30-6

Purity: ≥98%

Formulation: A crystalline solid

Application||Product Type|Biochemicals|Natural Products|Phytocannabinoids||Product Type|Biochemicals|Natural Products|Terpenes||Research Area|Cancer|Cell Death

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