Zingiberene

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Zingiberene[1]
Stereo, skeletal formula of zingiberene
Names
IUPAC name
2-Methyl-5-(6-methylhept-5-en-2-yl)cyclohexa-1,3-diene
Identifiers
495-60-3 N
3D model (Jmol) Interactive image
3DMet B03248
2554989
ChEBI CHEBI:10115 YesY
ChEMBL ChEMBL479020 N
ChemSpider 83751 YesY
ECHA InfoCard 100.007.096
EC Number 207-804-2
MeSH zingiberene
PubChem 92776
Properties
C15H24
Molar mass 204.36 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 YesYN ?)
Infobox references

Zingiberene is a monocyclic sesquiterpene that is the predominant constituent of the oil of ginger (Zingiber officinale),[1][2] 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[edit]

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.[3]

Biosynthesis of zingiberene

References[edit]

  1. ^ a b Herout, Vlastimil; Benesova, Vera; Pliva, Josef (1953). "Terpenes. XLI. Sesquiterpenes of ginger oil". Collection of Czechoslovak Chemical Communications. 18: 297–300. 
  2. ^ Sultan, Misbah; Bhatti, Haq Nawaz; Iqbal, Zafar (2005). "Chemical analysis of essential oil of ginger (Zingiber officinale)". Pakistan Journal of Biological Sciences. 8 (11): 1576–1578. doi:10.3923/pjbs.2005.1576.1578. 
  3. ^ 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.