Zingiberene

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.

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
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).
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Infobox references

Biosynthesis
Pathway proposed for the biosynthesis of zingiberene

Zingiberene is formed in the isoprenoid pathway from farnesyl pyrophosphate (FPP). FPP undergoes a rearrangement to give nerolidyl diphosphate. After the removal of pyrophosphate, the ring closes leaving a carbocation on the tertiary carbon attached to the ring. A 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. Herout, Vlastimil; Benesova, Vera; Pliva, Josef (1953). "Terpenes. XLI. Sesquiterpenes of ginger oil". Collection of Czechoslovak Chemical Communications. 18: 297–300. doi:10.1135/cccc19530248.
  2. K. Rani (1999). "Cyclisation of farnesyl pyrophosphate into sesquiterpenoids in ginger rhizomes ("Zingiber officinale")". Fitoterapia. 70 (6): 568–574. doi:10.1016/S0367-326X(99)00090-8.
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