(-)-Caryophyllene oxide

(-)-Caryophyllene oxide is a bicyclic sesquiterpene and a metabolite of beta-caryophyllene that has been found in C. sativa and has anticancer properties. Unlike beta-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). It is the volatile component of C. sativa sensed by narcotic detection dogs. Formulations containing (-)-caryophyllene have been used as flavoring agents.Formal Name: (1R,6R,10S)-4R,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane. CAS Number: 1139-30-6. Synonyms: BCP oxide, beta-Caryophyllene epoxide, beta-Caryophyllene oxide. Molecular Formula: C15H24O. Formula Weight: 220.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMSO: 10 mg/ml, Ethanol: 30 mg/ml, Ethanol:PBS (pH 7.2) (1:3): 0.25 mg/ml. lambdamax: 242 nm. SMILES: CC(C1)(C)[C@@]2([H])[C@@]1([H])C(CC[C@@H]3[C@](C)(O3)CC2)=C. InChi Code: InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1. InChi Key: NVEQFIOZRFFVFW-RGCMKSIDSA-N.