(−)-Caryophyllene oxide
SIGMA/22076 - ≥99.0% (sum of enantiomers, GC)
Synonym: β-Caryophyllene epoxide; (−)-Epoxycaryophyllene; (−)-Epoxydihydrocaryophyllene; (1R,4R,6R,10S)
CAS Number: 1139-30-6
Empirical Formula (Hill Notation): C15H24O
Molecular Weight: 220.35
EC Number: 214-519-7
MDL Number: MFCD00134216
Linear Formula: C15H24O
Product Type: Chemical
| application(s) | metabolomics vitamins, nutraceuticals, and natural products |
| assay | ≥99.0% (sum of enantiomers, GC) |
| form | solid |
| InChI | 1S/C15H24O/c1-10-5-6-13-1 |
| InChI key | NVEQFIOZRFFVFW-RGCMKSIDSA |
| mp | 61-63 °C |
| 62-63 °C (lit.) | |
| optical activity | [α]20/D −71±1°, c = 2% in chloroform |
| Quality Level | 100  |
| SMILES string | [H][C@@]12CCC(=C)[C@@]3([ |
| storage temp. | 2-8°C |
| 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. |
| 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. |
| Other Notes: | Carefully purified sesquiterpene; Stereoselective rearrangement to an allyl alcohol; Transformation to an amine |
| Packaging: | 1 g in glass bottle |
| Symbol |   GHS07,GHS09 |
| Signal word | Warning |
| Hazard statements | H315 - H319 - H411 |
| Precautionary statements | P273 - P302 + P352 - P305 + P351 + P338 |
| Hazard Codes | Xi |
| Risk Statements | 36/38 |
| Safety Statements | 26 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 2 |
| Flash Point(F) | 230.0 °F - closed cup |
| Flash Point(C) | 110 °C - closed cup |
| Purity | ≥99.0% (sum of enantiomers, GC) |
| mp | 61-63 °C; 62-63 °C (lit.) |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352212 |