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 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.
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.
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.
