Merck
CN
All Photos(2)

Documents

91034

Supelco

(−)-Caryophyllene oxide

analytical standard

Sign Into View Organizational & Contract Pricing
All Photos(2)
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:
1139-30-6
Molecular Weight:
220.35
Beilstein:
148213
EC Number:
214-519-7
MDL number:
MFCD00134216
PubChem Substance ID:
329769995

grade

analytical standard

Quality Level

100

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315 - H319 - H411

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

??caryophyllene and ??caryophyllene oxide?natural compounds of anticancer and analgesic properties
Fidyt K, et al.
Cancer medicine, 5(10), 3007-3017 (2016)
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)
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)
Getachew E Bokore et al.
Parasites & vectors, 14(1), 552-552 (2021-10-29)
Understanding the ecology and behaviour of disease vectors, including the olfactory cues used to orient and select hosts and egg-laying sites, are essential for the development of novel, insecticide-free control tools. Selected graminoid plants have been shown to release volatile
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service