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22076

Sigma-Aldrich

(−)-Caryophyllene oxide

≥99.0% (sum of enantiomers, GC)

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Synonym(s):
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
Empirical Formula (Hill Notation):
C15H24O
CAS Number:
Molecular Weight:
220.35
Beilstein/REAXYS Number:
148213
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

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

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This Item
W50964722075W408588
vibrant-m

22076

(−)-Caryophyllene oxide

vibrant-m

W509647

(−)-Caryophyllene oxide

vibrant-m

22075

(−)-trans-Caryophyllene

vibrant-m

W408588

(−)-Caryophyllene oxide

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

flavors and fragrances

application(s)

-

application(s)

flavors and fragrances

form

solid

form

-

form

liquid

form

-

assay

≥99.0% (sum of enantiomers, GC)

assay

95%

assay

≥98.0% (sum of enantiomers, GC)

assay

≥95%

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

optical activity

[α]20/D −71±1°, c = 2% in chloroform

optical activity

[α]20/D −70°, c = 2 in chloroform

optical activity

[α]20/D −10±1°, neat

optical activity

-

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

pictograms

Exclamation markEnvironment

signalword

Warning

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


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The origin of a terrestrial flora in the Ordovician required adaptation to novel biotic and abiotic stressors. Oil bodies, a synapomorphy of liverworts, accumulate secondary metabolites, but their function and development are poorly understood. Oil bodies of Marchantia polymorpha develop
H.M.R. Hoffmann et al.
Synlett, 337-337 (1991)
Jean-Jacques Filippi et al.
Journal of agricultural and food chemistry, 54(17), 6308-6313 (2006-08-17)
The essential oil of Achillea ligustica from Corsica was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 82 compounds representing 94.0% of the oil were tentatively identified. The main constituents were the camphane derivatives, representing

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