Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Zingiberene: Difference between pages

| verifiedrevid = 470637284

| Reference = <ref name=herout>{{cite journal|title=Terpenes. XLI. Sesquiterpenes of ginger oil|author1=Herout, Vlastimil |author2=Benesova, Vera |author3=Pliva, Josef |journal=Collection of Czechoslovak Chemical Communications|year=1953|volume=18|pages=297–300|doi=10.1135/cccc19530248 }}</ref>

| PIN= 2-Methyl-5-(6-methylhept-5-en-2-yl)cyclohexa-1,3-diene

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 495-60-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8XOC63EI5F

| PubChem = 92776

| ChemSpiderID = 83751

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 207-804-2

| MeSHName = zingiberene

| ChEBI = 10115

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 479020

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| KEGG = C09750

| Beilstein = 2554989

| 3DMet = B03325

| SMILES = C[C@@H](CCC=C(C)C)[C@H]1CC=C(C)C=C1

| StdInChI = 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KKOXKGNSUHTUBV-LSDHHAIUSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey = KKOXKGNSUHTUBV-LSDHHAIUBW

|Section2={{Chembox Properties

| C=15 | H=24

| Density = 871.3 mg cm⁻³ (at 20&nbsp;°C)

| BoilingPtC = 134 to 135

| BoilingPt_notes = at 2.0&nbsp;kPa

| LogP = 6.375

'''Zingiberene''' is a [[cyclic compound|monocyclic]] [[sesquiterpene]] that is the predominant constituent of the oil of [[ginger]] (''Zingiber officinale''),<ref name="herout"/> from which it gets its name. It can contribute up to 30% of the [[Essential oil|essential oils]] in ginger [[Rhizome|rhizomes]]. This is the compound that gives ginger its distinct flavoring.

==Biosynthesis==

[[File:ZingibereneBiosyn.svg|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.<ref>{{cite journal | author = K. Rani | title = Cyclisation of farnesyl pyrophosphate into sesquiterpenoids in ginger rhizomes ("Zingiber officinale") | journal = [[Fitoterapia]] | year = 1999 | volume = 70 | pages = 568–574 | doi = 10.1016/S0367-326X(99)00090-8 | issue = 6}}</ref>

==See also==

* [[Gingerol]]

* sequiphellandrene

== References ==

{{Reflist}}

[[Category:Sesquiterpenes]]

[[Category:Alkene derivatives]]

[[Category:Ginger]]

[[Category:Cyclohexadienes]]