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91034

Supelco

(−)-Caryophyllene oxide

analytical standard

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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:

grade

analytical standard

Quality Level

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

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
W50964722076W408588
vibrant-m

91034

(−)-Caryophyllene oxide

vibrant-m

W509647

(−)-Caryophyllene oxide

vibrant-m

22076

(−)-Caryophyllene oxide

vibrant-m

W408588

(−)-Caryophyllene oxide

grade

analytical standard

grade

Fragrance grade

grade

-

grade

FG, Fragrance grade, Halal, Kosher, natural (US)

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

application(s)

flavors and fragrances

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

flavors and fragrances

format

neat

format

-

format

-

format

-

assay

≥98.5% (GC)

assay

95%

assay

≥99.0% (sum of enantiomers, GC)

assay

≥95%

optical activity

[α]/D -71.0±1°, c = 2 in chloroform

optical activity

[α]20/D −70°, c = 2 in chloroform

optical activity

[α]20/D −71±1°, c = 2% in chloroform

optical activity

-

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.

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).

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


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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)
Essential oil composition of Salvia miltiorrhiza flower
Liang Q, et al.
Food Chemistry, 113(2), 592-594 (2009)
Excito-repellent activity of ?-caryophyllene oxide against Aedes aegypti and Anopheles minimus
Nararak J, et al.
Acta Tropica, 197 (2019)
??caryophyllene and ??caryophyllene oxide?natural compounds of anticancer and analgesic properties
Fidyt K, et al.
Cancer medicine, 5(10), 3007-3017 (2016)
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

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