Valencene
Names
IUPAC name
4α,5α-Eremophila-1(10),11-diene
Systematic IUPAC name
(3R,4aS,5R)-4a,5-Dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.022.770 Edit this at Wikidata
UNII
  • 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 checkY
    Key: QEBNYNLSCGVZOH-NFAWXSAZSA-N checkY
  • InChI=1/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
    Key: QEBNYNLSCGVZOH-NFAWXSAZBT
  • C\12=C\CC[C@H]([C@@]/1(C[C@H](\C(=C)C)CC2)C)C
Properties
C15H24
Molar mass 204.357 g·mol−1
Appearance colorless oil
Boiling point 123 °C (253 °F; 396 K) at 11 mmHg
organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Valencene is a sesquiterpene that is an aroma component of citrus fruit and citrus-derived odorants. It is obtained inexpensively from Valencia oranges.[1] Valencene is biosynthesized from farnesyl pyrophosphate (FPP) by the CVS enzyme.

It is used as a precursor to nootkatone, the main contributor to the aroma and flavor of grapefruit.[2][3]

References

  1. ^ Furusawa, Mai; Toshihiro Hashimoto; Yoshiaki Noma; Yoshinori Asakawa (November 2005). "Highly Efficient Production of Nootkatone, the Grapefruit Aroma from Valencene, by Biotransformation". Chem. Pharm. Bull. 53 (11): 1513–1514. doi:10.1248/cpb.53.1513. PMID 16272746.
  2. ^ M. M. Bomgardner (July 16, 2012). "Fragrances 101. A Fortuitous Field of Flavors and Fragrances". Chemical & Engineering News. 90 (29).
  3. ^ Leonhardt, Robin-Hagen; Berger, Ralf G. (2014). "Nootkatone". Biotechnology of Isoprenoids. Advances in Biochemical Engineering/Biotechnology. Vol. 148. pp. 391–404. doi:10.1007/10_2014_279. ISBN 978-3-319-20106-1. PMID 25326849.
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