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Merck
CN

22076

(−)-Caryophyllene oxide

≥99.0% (sum of enantiomers, GC)

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

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About This Item

Empirical Formula (Hill Notation):
C15H24O
CAS Number:
1139-30-6
Molecular Weight:
220.35
UNSPSC Code:
12352212
NACRES:
NA.25
PubChem Substance ID:
57647961
EC Number:
214-519-7
Beilstein/REAXYS Number:
148213
MDL number:
MFCD00134216

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Product Name

(−)-Caryophyllene oxide, ≥99.0% (sum of enantiomers, GC)

InChI key

NVEQFIOZRFFVFW-RGCMKSIDSA-N

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

SMILES string

[H][C@@]12CCC(=C)[C@@]3([H])CC(C)(C)[C@]3([H])CC[C@@]1(C)O2

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

Quality Level

100

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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

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCF1348
BCCC5167
BCBN9883V
1399925V
1399925

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H.M.R. Hoffmann et al.
Synlett, 581-581 (1990)
Facundo Romani et al.
Current biology : CB, 30(14), 2815-2828 (2020-06-20)
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
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
Hebaallah Mamdouh Hashiesh et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 140, 111639-111639 (2021-06-07)
The endocannabinoid system (ECS), a conserved physiological system emerged as a novel pharmacological target for its significant role and potential therapeutic benefits ranging from neurological diseases to cancer. Among both, CB1 and CB2R types, CB2R have received attention for its
H.M.R. Hoffmann et al.
Synlett, 337-337 (1991)
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