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 KharaschSosnovsky allylic oxidation method.
- (+)-Lineariifolianone, a natural product.
Preparation
By a Wolf–Kishner reduction of nootkatone.
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).
benefits
Strains high in Valencene produce euphoria and mood elevation, aid with alertness, and promote cognitive functions. Valencene is a powerful insecticide often found in tick and mosquito repellent. It is also used in pest control, cleaning, personal care, and cosmetics.
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.
References
[1] S. NAZ. Impact of Supercritical Fluid Extraction and Traditional Distillation on the Isolation of Aromatic Compounds from Cannabis indica and Cannabis sativa[J]. Journal of Essential Oil Bearing Plants, 2017, 106 1: 175-184. DOI:
10.1080/0972060x.2017.1281766[2] áSLAUG HGNADóTTIR Russell L R. Identification of aroma active compounds in orange essence oil using gas chromatography–olfactometry and gas chromatography–mass spectrometry[J]. Journal of Chromatography A, 2003, 998 1: Pages 201-211. DOI:
10.1016/s0021-9673(03)00524-7[3] KONSTANTIN TSOYI . (+)-Nootkatone and (+)-valencene from rhizomes of Cyperus rotundus increase survival rates in septic mice due to heme oxygenase-1 induction[J]. Journal of ethnopharmacology, 2011, 137 3: Pages 1311-1317. DOI:
10.1016/j.jep.2011.07.062[4] JULIA KOLWEK. Cell-free one-pot conversion of (+)-valencene to (+)-nootkatone by a unique dye-decolorizing peroxidase combined with a laccase from Funalia trogii.[J]. Journal of Industrial Microbiology & Biotechnology, 2018, 45 2: 89-101. DOI:
10.1007/s10295-017-1998-9
