(-)-CARYOPHYLLENE OXIDE >=99.0% GC SUM OF ENANTIOMERS (C005B-009600)

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

Molecular Weight: 220.35. Empirical Formula: C₁₅H₂₄O. Quality Level: 100. 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. Pictograms: GHS07,GHS09. Signal Word: Warning. Hazard Statements: H315 - H319 - H411. Precautionary Statements: P264 - P273 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313. 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. Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves.