zingiberene
Sign in to saveZingiberene 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.
Wikidata facts
- Mass
- 204.187800768
Show 3 more facts
- chemical formula
- C₁₅H₂₄
- isomeric SMILES
- C[C@@H](CCC=C(C)C)[C@H]1CC=C(C)C=C1
- canonical SMILES
- C1=CC(CC=C1C)C(C)CCC=C(C)C
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Article
3 sectionsContents
- Biosynthesis
- See also
- References
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== thumb|left|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.