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Zingiberene facts for kids

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Zingiberene
Zingiberene.png
Identifiers
CAS number 495-60-3
PubChem 92776
EC number 207-804-2
KEGG C09750
MeSH zingiberene
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.

Zingiberene Biosynthesis
Biosynthesis of zingiberene

See also

Kids robot.svg In Spanish: Zingibereno para niños

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