22076

(−)-Caryophyllene oxide

≥99.0% (sum of enantiomers, GC)

• 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/REAXYS Number: 148213
• EC Number: 214-519-7
• MDL number: MFCD00134216
• UNSPSC Code: 12352212
• PubChem Substance ID: 57647961
• NACRES: NA.25

Properties

• assay: ≥99.0% (sum of enantiomers, GC)
• form: solid
• optical activity: [α]20/D −71±1°, c = 2% in chloroform
• mp: 61-63 °C; 62-63 °C (lit.)
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• 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 or β-caryophyllene oxide (BCPO) is a natural plant compound, bicyclic sesquiterpene, and oxidation derivative of β-caryophyllene (BCP). It has a strong wooden odor. BCPO is commonly found in many food and spice plants and essential oils, such as basil, salvia, and Syzygium cordatum. It is widely used as a cosmetic and food additive.

Application

(−)-Caryophyllene oxide has been used:

• as an antimicrobial agent to study its effects against Gram-positive, Gram-negative and yeast strains
• as a commercial standard to perform quantification analysis of constitutes from Marchantia polymorpha extracts using gas chromatography with flame-ionization detection (GC-FID)
• as a reference standard to analyze the enantiomeric ratios of Achillea ligustica essential oil constituents using gas chromatography-mass spectrometry (GC-MS)

Biochem/physiol Actions

β-caryophyllene oxide is a potent anti-cancer agent which also exerts antioxidant, anti-inflammatory, and antiviral properties. It is a strong inhibitor of drug-metabolizing enzyme cytochromes P4503A (CYP3A) activities both in rat and human hepatic microsomes. BCPO also exerts analgesic, antifungal, antibacterial, and genoprotective activities.

Other Notes

Carefully purified sesquiterpene; Stereoselective rearrangement to an allyl alcohol; Transformation to an amine

Safety Information

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H315,H319,H411
• pcodes: P264 - P273 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313
• Hazard Classifications: Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: 230.0 °F - closed cup
• flash_point_c: 110 °C - closed cup
• ppe: dust mask type N95 (US), Eyeshields, Gloves