Zingiberene
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| Names | |
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| IUPAC name
2-Methyl-5-(6-methylhept-5-en-2-yl)cyclohexa-1,3-diene
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| Identifiers | |
495-60-3  |
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| 3DMet | B03248 |
| 2554989 | |
| ChEBI | CHEBI:10115  |
| ChEMBL | ChEMBL479020 |
| ChemSpider | 83751 |
| EC Number | 207-804-2 |
| Jmol 3D model | Interactive 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 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| 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]
