Zingiberene is a monocyclicsesquiterpene that is the predominant constituent of the oil of ginger (Zingiber officinale),[1] 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.
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.[2]
^ abHerout, Vlastimil; Benesova, Vera; Pliva, Josef (1953). "Terpenes. XLI. Sesquiterpenes of ginger oil". Collection of Czechoslovak Chemical Communications. 18: 297–300. doi:10.1135/cccc19530248.
^K. Rani (1999). "Cyclisation of farnesyl pyrophosphate into sesquiterpenoids in ginger rhizomes ("Zingiber officinale")". Fitoterapia. 70 (6): 568–574. doi:10.1016/S0367-326X(99)00090-8.
February 16, 2024
zingiberene, monocyclic, sesquiterpene, that, predominant, constituent, ginger, zingiber, officinale, from, which, gets, name, contribute, essential, oils, ginger, rhizomes, this, compound, that, gives, ginger, distinct, flavoring, namespreferred, iupac, name,. Zingiberene is a monocyclic sesquiterpene that is the predominant constituent of the oil of ginger Zingiber officinale 1 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 Zingiberene 1 NamesPreferred IUPAC name 2 Methyl 5 6 methylhept 5 en 2 yl cyclohexa 1 3 dieneIdentifiersCAS Number 495 60 3 Y3D model JSmol Interactive image3DMet B03325Beilstein Reference 2554989ChEBI CHEBI 10115 YChEMBL ChEMBL479020 NChemSpider 83751 YECHA InfoCard 100 007 096EC Number 207 804 2KEGG C09750MeSH zingiberenePubChem CID 92776UNII 8XOC63EI5F YCompTox Dashboard EPA DTXSID00197808InChI 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 YKey KKOXKGNSUHTUBV LSDHHAIUSA N YKey KKOXKGNSUHTUBV LSDHHAIUBWSMILES C C H CCC C C C C H 1CC C C C C1PropertiesChemical formula C 15H 24Molar mass 204 357 g mol 1Density 871 3 mg cm 3 at 20 C Boiling point 134 to 135 C 273 to 275 F 407 to 408 K at 2 0 kPalog P 6 375Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesBiosynthesis edit nbsp Pathway proposed for the biosynthesis of zingibereneZingiberene 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 2 See also editGingerol sequiphellandreneReferences edit a b Herout Vlastimil Benesova Vera Pliva Josef 1953 Terpenes XLI Sesquiterpenes of ginger oil Collection of Czechoslovak Chemical Communications 18 297 300 doi 10 1135 cccc19530248 K Rani 1999 Cyclisation of farnesyl pyrophosphate into sesquiterpenoids in ginger rhizomes Zingiber officinale Fitoterapia 70 6 568 574 doi 10 1016 S0367 326X 99 00090 8 Retrieved from https en wikipedia org w index php title Zingiberene amp oldid 1129850987, wikipedia, wiki, book, books, library,
