Caryophyllene oxide

The major and several minor constituents of essential oils were obtained from commercial sources. Sabinene, (−) linalool, hexanal, p-cymene-8-ol, 3,7-dimethyl-1,3,6-octatriene (β-ocimene), and MHDO were purchased from Sigma-Aldrich Chemical Co. (St. Loius, MO). Citronellol, (+)-limonene, trans-anethole, (−)-caryophyllene oxide, 4-allylanisole (estragole), 1,2-dimethoxy-4-(2-propenyl) (methyl eugenol), myrcene, isopropyl myristate, p-cymene, α-terpinene, and (−)-limonene were purchased from Acros Organics (Geel, Belgium). Myristic acid, α-pinene, and terpinolene were from Santa Cruz Biotechnology (Dallas, TX). Methyl cinnamate, 4-methoxystyrene (4-vinylanisole), palmitic (hexadecanoic) acid, and (1S)-(−)-β-pinene were from Alfa Aesar (Ward Hill, MA). For biological evaluation, compounds were dissolved in DMSO (20 mM stock solutions) and stored at −20°C.

The major and some minor compounds in the essential oils were obtained from commercial sources. Sabinene, p-cymen-8-ol, camphene, α-pinene oxide, α-terpineol, γ-terpinene, 4-carvomenthenol (terpinen-4-ol), myrtenol, and 3,7-dimethyl-1,3,6-octatriene (β-ocimene) were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA). Myrcene, (+)-limonene, (−)-limonene, p-cymene, (−)-caryophyllene oxide, and α-terpinene were purchased from Acros Organics (Geel, Belgium). Elemicin was from Toronto Research Chemicals (Toronto, Canada). Geraniol and (E)-2-nonenal were from AK Scientific Inc (Union City, CA, USA). Terpinolene and α-pinene were from Santa Cruz Biotechnology (Dallas, TX, USA). (E/Z)-geranylacetone and (1S)-(−)-β-pinene were from Alfa Aesar (Ward Hill, MA, USA). Thymol, (−)-menthol, (R)-(−)-carvone, isobornyl acetate, carvacrol, (−)-fenchone, and capsaicin were from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). Myristicin was from Cayman Chemical Co. (Ann Arbor, MI, USA). The compounds were dissolved in dimethyl sulfoxide (DMSO; 10 mM stock solutions) and stored at −20 °C.