Zingiberene

Source: Wikipedia, the free encyclopedia.
Zingiberene[1]
Stereo, skeletal formula of zingiberene
Names
Preferred IUPAC name
2-Methyl-5-(6-methylhept-5-en-2-yl)cyclohexa-1,3-diene
Identifiers
3D model (
JSmol
)
3DMet
2554989
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.007.096 Edit this at Wikidata
EC Number
  • 207-804-2
KEGG
MeSH zingiberene
UNII
  • InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15+/m0/s1 checkY
    Key: KKOXKGNSUHTUBV-LSDHHAIUSA-N checkY
  • Key: KKOXKGNSUHTUBV-LSDHHAIUBW
  • C[C@@H](CCC=C(C)C)[C@H]1CC=C(C)C=C1
Properties
C15H24
Molar mass 204.357 g·mol−1
Density 871.3 mg cm−3 (at 20 °C)
Boiling point 134 to 135 °C (273 to 275 °F; 407 to 408 K) at 2.0 kPa
log P 6.375
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Zingiberene is a monocyclic sesquiterpene that is the predominant constituent of the oil of ginger (Zingiber officinale),[1] from which it gets its name. It can contribute up to 30% of the essential oils in ginger rhizomes. This is the compound that gives ginger its distinct flavoring.

Biosynthesis

Pathway proposed for the biosynthesis of zingiberene

Zingiberene is formed in the

1,3-hydride shift then takes place to give a more stable allylic carbocation. The final step in the formation of zingiberene is the removal of the cyclic allylic proton and consequent formation of a double bond. Zingiberene synthase is the enzyme responsible for catalyzing the reaction forming zingiberene as well as other mono- and sesquiterpenes.[2]

See also

References

  1. ^
    doi:10.1135/cccc19530248
    .
  2. doi:10.1016/S0367-326X(99)00090-8
    .
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