Zingiberene

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
CAS Number
  • 495-60-3 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B03325
Beilstein Reference
 2554989
ChEBI
  • CHEBI:10115 checkY
ChEMBL
  • ChEMBL479020 ☒N
ChemSpider
  • 83751 checkY
ECHA InfoCard 100.007.096 Edit this at Wikidata
EC Number
  • 207-804-2
KEGG
  • C09750
MeSH zingiberene
PubChem CID
  • 92776
UNII
  • 8XOC63EI5F checkY
CompTox Dashboard (EPA)
  • DTXSID00197808 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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
Chemical compound

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 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. ^ a b 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.