91034

(−)-Caryophyllene oxide

analytical standard

• Synonym(s): β-Caryophyllene epoxide, (−)-Epoxycaryophyllene, (−)-Epoxydihydrocaryophyllene, (1R,4R,6R,10S)-9-Methylene-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^4,6]dodecane, trans-Caryophyllene oxide
• Empirical Formula (Hill Notation): C₁₅H₂₄O
• CAS Number: 1139-30-6
• Molecular Weight: 220.35
• Beilstein: 148213
• EC Number: 214-519-7
• MDL number: MFCD00134216
• UNSPSC Code: 85151701
• PubChem Substance ID: 329769995
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 100
• Assay: ≥98.5% (GC)
• optical activity: [α]/D -71.0±1°, c = 2 in chloroform
• shelf life: limited shelf life, expiry date on the label
• technique(s): HPLC: suitable; gas chromatography (GC): suitable
• mp: 62-63 °C (lit.)
• application(s): cleaning products; cosmetics; flavors and fragrances; food and beverages; personal care
• format: neat
• storage temp.: 2-8°C
• SMILES string: [H][C@@]12CCC(=C)[C@@]3([H])CC(C)(C)[C@]3([H])CC[C@@]1(C)O2
• 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

Description

General description

(−)-Caryophyllene oxide (BCPO) belongs to the class of flavor and fragrance standards used for the quality control of food and cosmetic products. It is an oxidation derivative of β-caryophyllene (BCP), and a bicyclic sesquiterpene molecule, identified as an important component of essential oils from various medicinal and edible plants, including clove oil, Salvia miltiorrhiza flower oil, etc. This compound shows relaxant effects in smooth muscle preparations and acts as a calcium channel blocker in the heart, thereby used in treating hypertension. It finds a variety of applications as an analgesic, tumor-suppressing agent, food flavoring agent, as a fragrance and cosmetic ingredient, etc.

Application

(−)-Caryophyllene oxide may be used as an analytical standard in: Investigating its effect on the heart muscle, its ability as a calcium channel blocker, inhibition of potassium currents by experiments performed on the isolated papillary muscles and ventricular myocytes of the guinea-pig. Determining its efficiency as a contact irritant and its non-contact repellent activity against laboratory strains of Aedes aegypti and Anopheles minimus using an excito-repellency test system. The results are compared with the synthetic repellent N, N-diethyl-3-methylbenzamide (DEET).

Safety Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H315,H319,H411
• Precautionary Statements: P273 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): 230.0 °F - closed cup
• Flash Point(C): 110 °C - closed cup