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75056

Sigma-Aldrich

(+)-Valencene

technical, ≥70%

Synonym(s):
(3R,4aS,5R)-4a,5-Dimethyl-3-isopropenyl-1,2,3,4,4a,5,6,7-octahydronaphthalene
Empirical Formula (Hill Notation):
C15H24
CAS Number:
Molecular Weight:
204.35
Beilstein:
3539153
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

technical

assay

≥70%

form

liquid

optical activity

[α]20/D +100±25°, neat

refractive index

n20/D 1.504 (lit.)

bp

274 °C (lit.)

density

0.92 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@@H]1CCC=C2CC[C@H](C[C@@]12C)C(C)=C

InChI

1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3/t12-,13-,15+/m1/s1

InChI key

QEBNYNLSCGVZOH-NFAWXSAZSA-N

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General description

(+)-Valencene is a sesquiterpene, which contains decalin framework and two methyl-bearing stereocenters. It is an aroma component of citrus fruit.

Application

(+)-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.

Packaging

10, 50 g in glass bottle

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Asp. Tox. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

One-Pot Synthesis of (+)-Nootkatone via Dark Singlet Oxygenation of Valencene: The Triple Role of the Amphiphilic Molybdate Catalyst.
Hong B, et al.
Catalysts, 6(12), 184-184 (2016)
Optimization by Response Surface Methodology (RSM) of the Kharasch-Sosnovsky Oxidation of Valencene
Garcia-Cabeza AL, et al.
Organic Process Research & Development, 19(11), 1662-1666 (2015)
Jungho Lee et al.
Frontiers in microbiology, 11, 1655-1655 (2020-08-28)
Sesquiterpenoids are important secondary metabolites with various pharma- and nutraceutical properties. In particular, higher basidiomycetes possess a versatile biosynthetic repertoire for these bioactive compounds. To date, only a few microbial production systems for fungal sesquiterpenoids have been established. Here, we
CitAP2. 10 activation of the terpene synthase CsTPS1 is associated with the synthesis of (+)-valencene in 'Newhall'orange.
Shen SL, et al.
Journal of Experimental Botany, 67(14), 4105-4115 (2016)
Synthesis of (+)-Lineariifolianone and Related Cyclopropenone-Containing Sesquiterpenoids
Reber KP, et al.
The Journal of Organic Chemistry, 84(9), 5524-5534 (2019)

Protocols

GC Analysis of Sweet Orange Essential Oil on SLB®-5ms (10 m x 0.10 mm I.D., 0.10 µm), Fast GC Analysis

-β-Farnesene; α-Huµlene; Germacrene D; (+)-Valencene; Bicyclogermacrene; (+)-δ-Cadinene

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