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Merck
CN

91034

(−)-Caryophyllene oxide

analytical standard

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:
85151701
NACRES:
NA.24
PubChem Substance ID:
329769995
EC Number:
214-519-7
Beilstein/REAXYS Number:
148213
MDL number:
MFCD00134216

Key Documents

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Product Name

(−)-Caryophyllene oxide, analytical standard

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

grade

analytical standard

assay

≥98.5% (GC)

optical activity

[α]/D -71.0±1°, c = 2 in chloroform

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

62-63 °C (lit.)

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

storage temp.

2-8°C

Quality Level

100

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Application

(−)-Caryophyllene oxide may be used as an analytical standard in: Investigating its effect on the heart muscle, its ability as a calcium channel blocker, inhibition of potassium currents by experiments performed on the isolated papillary muscles and ventricular myocytes of the guinea-pig. Determining its efficiency as a contact irritant and its non-contact repellent activity against laboratory strains of Aedes aegypti and Anopheles minimus using an excito-repellency test system. The results are compared with the synthetic repellent N, N-diethyl-3-methylbenzamide (DEET).

General description

(−)-Caryophyllene oxide (BCPO) belongs to the class of flavor and fragrance standards used for the quality control of food and cosmetic products. It is an oxidation derivative of β-caryophyllene (BCP), and a bicyclic sesquiterpene molecule, identified as an important component of essential oils from various medicinal and edible plants, including clove oil, Salvia miltiorrhiza flower oil, etc. This compound shows relaxant effects in smooth muscle preparations and acts as a calcium channel blocker in the heart, thereby used in treating hypertension. It finds a variety of applications as an analgesic, tumor-suppressing agent, food flavoring agent, as a fragrance and cosmetic ingredient, etc.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3739
BCCM4387
BCCL5305
BCCL1331
BCCJ4573

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Excito-repellent activity of ?-caryophyllene oxide against Aedes aegypti and Anopheles minimus
Nararak J, et al.
Acta Tropica, 197 (2019)
Essential oil composition of Salvia miltiorrhiza flower
Liang Q, et al.
Food Chemistry, 113(2), 592-594 (2009)
Effects of inhibition of calcium and potassium currents in guinea?pig cardiac contraction: comparison of ??caryophyllene oxide, eugenol, and nifedipine
Sensch O, et al.
British Journal of Pharmacology, 131(6), 1089-1096 (2000)
Linus Svenberg et al.
Plants (Basel, Switzerland), 10(11) (2021-11-28)
In recent work, it was shown that the graminoid plants Cynodon dactylon (Poaceae), Cyperus exaltatus (Cyperaceae), and Panicum repens (Poaceae) have an ovipositional effect on the malaria vector Anopheles gambiae in olfactometric bioassays. In order to get a view of
??caryophyllene and ??caryophyllene oxide?natural compounds of anticancer and analgesic properties
Fidyt K, et al.
Cancer medicine, 5(10), 3007-3017 (2016)
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