Zingiberene
 | |
| Names | |
|---|---|
| IUPAC name
2-Methyl-5-(6-methylhept-5-en-2-yl)cyclohexa-1,3-diene | |
| Identifiers | |
495-60-3  | |
| 3DMet | B03248 |
| 2554989 | |
| ChEBI | CHEBI:10115  |
| ChEMBL | ChEMBL479020 |
| ChemSpider | 83751 |
| EC Number | 207-804-2 |
| Jmol interactive 3D | Image |
| MeSH | zingiberene |
| PubChem | 92776 |
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| |
| 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). | |
| verify (what is ?) | |
| 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
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
- 1 2 Herout, Vlastimil; Benesova, Vera; Pliva, Josef (1953). "Terpenes. XLI. Sesquiterpenes of ginger oil". Collection of Czechoslovak Chemical Communications 18: 297–300.
- ↑ 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.
- ↑ 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.