Zingiberene facts for kids
Quick facts for kids Zingiberene |
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Preferred IUPAC name
2-Methyl-5-(6-methylhept-5-en-2-yl)cyclohexa-1,3-diene
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| Identifiers | |
| CAS number | |
| PubChem | |
| EC number | 207-804-2 |
| KEGG | C09750 |
| MeSH | |
| ChEBI | CHEBI:10115 |
| SMILES | C[C@@H](CCC=C(C)C)[C@H]1CC=C(C)C=C1 |
| Beilstein Reference | 2554989 |
| 3DMet | B03325 |
| Properties | |
| Molecular formula | C15H24 |
| Molar mass | 204.35 g mol-1 |
| Density | 871.3 mg cm−3 (at 20 °C) |
| Boiling point |
134 to 135 °C, Expression error: Unrecognized word "to". K, Expression error: Unrecognized word "to". °F |
| log P | 6.375 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Zingiberene is a monocyclic sesquiterpene that is the predominant constituent of the oil of ginger (Zingiber officinale), 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.
See also
In Spanish: Zingibereno para niños
