(-)-Caryophyllene oxide - CAS 1139-30-6
Catalog number: 1139-30-6
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Molecular Formula:
C15H24O
Molecular Weight:
220.4
COA:
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Chemical Family:
Sesquiterpenoids
Description:
Caryophyllene oxide, isolated from the fruits of Eugenia caryophyllata, inhibited the mitochondrial electron transport chain. Caryophyllene oxide can be used as potent anti-inflammatory agent and modulators of a newly established therapeutic target.
Purity:
>98%
Appearance:
Powder
Synonyms:
(-)-5-Oxatricyclo[8.2.0.0(4,6)]dodecane,4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-; (-)-beta-Caryophyllene epoxide; (-)-beta-caryophylleneepoxid; (-)-beta-caryophylleneepoxide; (-)-Epoxydihydrocaryophyllene; (1r-(1r*,4r*,6r*,10s*))-4,12,12-trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane; (1r-(1r,4r,6r,10s))-4,12,12-trimethyl; (1r-(1r,4r,6r,10s))-4,12,12-trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane
MSDS:
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Application:
Analgesic/anti-inflammatory
Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
Density:
0.96 g/cm3
1.Chemosensitizing Properties of β-Caryophyllene and β-Caryophyllene Oxide in Combination with Doxorubicin in Human Cancer Cells.
DI Giacomo S;DI Sotto A;Mazzanti G;Wink M Anticancer Res. 2017 Mar;37(3):1191-1196.
BACKGROUND/AIM: ;The natural sesquiterpenes β-caryophyllene (CRY) and β-caryophyllene oxide (CRYO) were evaluated for their potential chemosensitizing properties.;MATERIALS AND METHODS: ;CRY and CRYO cytotoxicity was tested against the Caco-2, CCRF/CEM and CEM/ADR5000 human cancer cell lines. Furthermore, combination experiments were carried out in order to study the ability of the sesquiterpenes to increase doxorubicin cytotoxicity. The possible interference of CRY and CRYO with functionality of ATP-binding cassette (ABC)-transporters was also investigated by Rhodamine123 efflux assay.;RESULTS: ;Despite a low cytotoxicity, both substances were able to enhance the cytotoxicity of doxorubicin in all cell lines, with CRYO being the most effective reversal agent. Both sesquiterpenes were also able to increase the Rho123 content into cells, likely due to inhibition of the efflux pumps.;CONCLUSION: ;Our results highlight a potential role of CRY and CRYO as new chemosensitizing agents for doxorubicin chemotherapy and to re-sensitize cancer-resistant cells.;Copyright© 2017, International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.
2.Toxic effects of two essential oils and their constituents on the mealworm beetle, Tenebrio molitor.
Martínez LC;Plata-Rueda A;Colares HC;Campos JM;Dos Santos MH;Fernandes FL;Serrão JE;Zanuncio JC Bull Entomol Res. 2017 Dec 14:1-10. doi: 10.1017/S0007485317001262. [Epub ahead of print]
The study identified insecticidal effects from the cinnamon and clove essential oils in Tenebrio molitor L. (Coleoptera: Tenebrionidae). The lethal concentrations (LC50 and LC90), lethal time, and repellent effect on larvae, pupae, and adults of T. molitor after exposure to six concentrations of each essential oil and toxic compounds were evaluated. The chemical composition of the cinnamon oil was also determined and primary compounds were eugenol (10.19%), trans-3-caren-2-ol (9.92%), benzyl benzoate (9.68%), caryophyllene (9.05%), eugenyl acetate (7.47%), α-phellandrene (7.18%), and α-pinene (6.92%). In clove essential oil, the primary compounds were eugenol (26.64%), caryophyllene (23.73%), caryophyllene oxide (17.74%), 2-propenoic acid (11.84%), α-humulene (10.48%), γ-cadinene (4.85%), and humulene oxide (4.69%). Cinnamon and clove essential oils were toxic to T. molitor. In toxic chemical compounds, eugenol have stronger contact toxicity in larvae, pupae, and adult than caryophyllene oxide, followed by α-pinene, α-phellandrene, and α-humulene. In general, the two essential oils were toxic and repellent to adult T. molitor. Cinnamon and clove essential oils and their compounds caused higher mortality and repellency on T.
3.The strained sesquiterpene β-caryophyllene as a probe for the solvent-assisted epoxidation mechanism.
Steenackers B;Neirinckx A;De Cooman L;Hermans I;De Vos D Chemphyschem. 2014 Apr 4;15(5):966-73. doi: 10.1002/cphc.201300981. Epub 2014 Feb 24.
In our attempt to synthesize β-caryophyllene oxide in food-compatible conditions, we observed the uncatalyzed and highly selective epoxidation of β-caryophyllene, a strained bicyclic sesquiterpene, in ethanol with aqueous H2 O2 under radical-suppressing conditions without the addition of a catalyst. The unusual reactivity of β-caryophyllene allowed us to use it as a probe for the mechanism of the solvent-assisted epoxidation in a wide range of organic solvents. A kinetic study was performed to investigate the epoxidation mechanism; an excellent correlation was found between the observed epoxidation rates in different solvents and the Abraham's hydrogen bond formation parameters of these solvents. By means of computational analysis, it was found that the main role of the solvent consists of the stabilization of the elongated OO bond of H2 O2 in the transition state through hydrogen-bond donation to the leaving OH moiety of H2 O2 . α-Humulene was found to possess similar reactivity as β-caryophyllene whereas isocaryophyllene-the unstrained isomer of β-caryophyllene-was unreactive.
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CAS 1139-30-6 (-)-Caryophyllene oxide

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