A bicyclic sesquiterpene
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(−)-Caryophyllene oxide

Item No. 21573

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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
  • β-Caryophyllene epoxide
  • β-Caryophyllene oxide
Molecular Formula
C15H24O
Formula Weight
220.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 10 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (–)-Caryophyllene oxide is a bicyclic sesquiterpene and a metabolite of β-caryophyllene that has been found in C. sativa and has anticancer properties.1,2 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).3 It is the volatile component of C. sativa sensed by narcotic detection dogs.1 Formulations containing (–)-caryophyllene have been used as flavoring agents.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gertsch, J., Leonti, M., Raduner, S., et al. Beta-caryophyllene is a dietary cannabinoid. Proc. Natl. Acad. Sci. USA 105(26), 9099-9104 (2008).

    2. Fidyt, K., Fiedorowicz, A., Stradala, L., et al. β-caryophyllene and β-caryophyllene oxide-natural compounds of anticancer and analgesic properties. Cancer Med. 5(10), 3007-3017 (2016).

    3. Jun, N.J., Mosaddik, A., Moon, J.Y., et al. Cytotoxic activity of β-caryophyllene oxide isolated from Jeju guava (Psidium cattleianum Sabine) leaf. Rec. Nat. Prod. 5(3), 242-246 (2011).