Synonym: β-Caryophyllene epoxide; (−)-Epoxycaryophyllene; (−)-Epoxydihydrocaryophyllene; (1R,4R,6R,10S)-9-Methylene-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecane; trans-Caryophyllene oxide
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/c1-10-5-6-13-15(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 |
| 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([H])CC(C)(C)[C@]3([H])CC[C@@]1(C)O2 |
| 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 |
| Purity |
≥99.0% (sum of enantiomers, GC) |
| mp |
61-63 °C; 62-63 °C (lit.) |
| Storage Temp. |
2-8°C |
| UNSPSC |
12352212 |
