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Valencene

From Wikipedia, the free encyclopedia
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 InfoCard100.022.770Edit 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 mass204.357 g·mol−1
Appearancecolorless oil
Boiling point123 °C (253 °F; 396 K) at 11 mmHg
organic solvents
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Valencene is asesquiterpene that is an aroma component ofcitrus fruit and citrus-derived odorants. It is obtained inexpensively from Valenciaoranges.[1] Valencene isbiosynthesized fromfarnesyl pyrophosphate (FPP) by theCVS enzyme.

It is used as a precursor tonootkatone, the main contributor to the aroma and flavor ofgrapefruit.[2][3]

References

[edit]
  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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