Structure via PubChem · Public domain (PubChem)
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.
In the Vinony graph
Vinony's link graph records 6 inbound references to zingiberene, and connects out to ginger, mass density and digital object identifier.
It sits within the topics Alkene derivatives, Cyclohexadienes and ECHA InfoCard ID from Wikidata.
Vinony links it to 13 Wikipedia language editions.
Chemical data
- Formula
- C15H24
- Molecular weight
- 204.35 g/mol
- IUPAC name
- (5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
- SMILES
- CC1=CC[C@@H](C=C1)[C@@H](C)CCC=C(C)C
- InChIKey
- KKOXKGNSUHTUBV-LSDHHAIUSA-N
- XLogP
- 5.2
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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
via Wikidata · CC0
~1 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “zingiberene” article, available under the CC BY-SA 4.0 licence.