VALENCENE Chemical Properties

Boiling point:

274 °C(lit.)

Density 

0.92 g/mL at 25 °C(lit.)

FEMA 

3443 | VALENCENE

refractive index 

n20/D 1.504(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless

Specific Gravity

0.92

Odor

at 10.00 % in dipropylene glycol. sweet fresh citrus grapefruit woody orange asprin dry green oily

Odor Type

citrus

optical activity

[α]22/D +90°, neat

Hydrolytic Sensitivity

1: no significant reaction with aqueous systems

JECFA Number

1337

BRN 

3539153

Stability:

Light Sensitive

LogP

6.29

EPA Substance Registry System

Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1R,7R,8aS)- (4630-07-3)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

VALENCENE Usage And Synthesis

Description

(+)-Valencene is a sesquiterpene that has been found in C. sativa and is an aromatic component of orange essence oil. (+)-Valencene (50 μM) induces heme oxgenase-1 (HO-1) expression in macrophages and inhibits the expression of inducible nitric oxide synthase (iNOS), the production of nitric oxide (NO), and the release of high-mobility group box-1 (HMGB1) in RAW 264.7 cells stimulated with LPS. It also increases the survival rate in a mouse model of sepsis induced by cecal ligation and puncture. (+)-Valencene has been used in the synthesis of nootkatone .

Chemical Properties

clear colorless to yellowish liquid

Occurrence

Reported found in citrus fruits, orange peel, orange juice, bitter orange peel oil, lemon peel oil, grapefruit juice, grapefruit peel oil, kumquat peel oil, leaves and stalk of celery, clove stem, Thymus vulgaris L., fresh mango, globe artichoke, cardamom, mangosteen and cocoa.

Uses

Valencene is a sesquiterpene and an essential oil component found in a variety of plants, and has been shown to have functional antioxidant, antiradical and antimicrobial properties.

Uses

(+)-Valencene can be used as a precursor to prepare:

• (+)-Nootkatone (a sesquiterpene) by dark singlet oxygenation.
• Benzoyloxyvalencene by reacting with tert-butyl peroxy benzoate via Kharasch?Sosnovsky allylic oxidation method.
• (+)-Lineariifolianone, a natural product.

Definition

ChEBI: A carbobicyclic compound and sesquiterpene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene which is substituted a prop-1-en-2-yl group at position 3 and by methyl groups at positions 4a and 5 (the 3R,4aS,5R diastereoisomer).

Preparation

By a Wolf–Kishner reduction of nootkatone.

General Description

Valencene is the major sesquiterpene aroma constituent of orange peel oil. It is mainly used as a starting material to synthesize nootkatone, an important flavor compound of grapefruit.

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