Zingiberene

Zingiberene
Preferred IUPAC name 2-Methyl-5-(6-methylhept-5-en-2-yl)cyclohexa-1,3-diene[citation needed]
Identifiers
CAS number	495-60-3 N
PubChem	92776
ChemSpider	83751 Y
EC number	207-804-2
MeSH	zingiberene
ChEBI	CHEBI:10115 Y
ChEMBL	CHEMBL479020 N
Beilstein Reference	2554989
3DMet	B03248
Jmol-3D images	Image 1
SMILES C[C@@H](CCC=C(C)C)[C@H]1CC=C(C)C=C1
InChI InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15+/m0/s1 Y Key: KKOXKGNSUHTUBV-LSDHHAIUSA-N Y
Properties
Molecular formula	C15H24
Molar mass	204.35 g mol−1
Density	871.3 mg cm-3 (at 20 °C)
Boiling point	134-135 °C, 407-408 K, 273-275 °F (at 2.0 kPa)
log P	6.375
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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 flavouring.

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