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Sigma-Aldrich

(−)-Caryophyllenoxid

≥99.0% (sum of enantiomers, GC)

Synonym(e):

β-Caryophyllenepoxid, (−)-Epoxycaryophyllen, (−)-Epoxydihydrocaryophyllen, (1R,4R,6R,10S)-9-Methylen-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecan, trans-Caryophyllenoxid

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About This Item

Empirische Formel (Hill-System):
C15H24O
CAS-Nummer:
1139-30-6
Molekulargewicht:
220.35
Beilstein:
148213
EG-Nummer:
214-519-7
MDL-Nummer:
MFCD00134216
UNSPSC-Code:
12352212
PubChem Substanz-ID:
57647961
NACRES:
NA.25

Qualitätsniveau

100

Assay

≥99.0% (sum of enantiomers, GC)

Form

solid

Optische Aktivität

[α]20/D −71±1°, c = 2% in chloroform

mp (Schmelzpunkt)

61-63 °C
62-63 °C (lit.)

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

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

InChIKey

NVEQFIOZRFFVFW-RGCMKSIDSA-N

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Allgemeine Beschreibung

(−)-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.

Anwendung

(−)-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. Wirkung

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.

Sonstige Hinweise

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

Piktogramme

Exclamation markEnvironment
GHS07,GHS09

Signalwort

Warning

Gefahreneinstufungen

Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Flammpunkt (°F)

230.0 °F - closed cup

Flammpunkt (°C)

110 °C - closed cup

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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