Geranylgeraniol

Geranylgeraniol
Names
Preferred IUPAC name
(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-ol
Other names
Tetraprenol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.152.315 Edit this at Wikidata
UNII
  • InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+
    Key: OJISWRZIEWCUBN-QIRCYJPOSA-N
  • InChI=1/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+
    Key: OJISWRZIEWCUBN-QIRCYJPOBA
  • OC/C=C(/CC/C=C(/CC\C=C(/C)CC\C=C(/C)C)C)C
Properties
C20H34O
Molar mass 290.491 g·mol−1
Appearance colorless liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Geranylgeraniol is a diterpenoid alcohol. It is a colorless waxy solid.[1] It is an important intermediate in the biosynthesis of other diterpenes, of vitamins E, and of K. It is a derivative of geranylgeraniol pyrophosphate, which is a precursor to carotenoids.[2]

Geranylgeraniol is synthesized in humans through the mevalonate pathway.[3][4]

As its pyrophosphate, it is also used in the post-translational modification by the process called geranylgeranylation.

Geranylgeraniol is a potent inhibitor of Mycobacterium tuberculosis in vitro.[5]

See also

References

  1. ^ Jin, Yinghua; Roberts, Frank G.; Coates, Robert M. (2007). "Stereoselective Isoprenoid Chain Extension with Acetoacetate Dianion: [(E, E, E)-Geranylgeraniol from (E, E)-Farnesol". Organic Syntheses. 84: 43. doi:10.15227/orgsyn.084.0043.
  2. ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  3. ^ Lange, B. Markus; Rujan, Tamas; Martin, William; Croteau, Rodney (2000-11-21). "Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes". Proceedings of the National Academy of Sciences. 97 (24): 13172–13177. doi:10.1073/pnas.240454797. PMC 27197. PMID 11078528.
  4. ^ Holstein, Sarah A.; Hohl, Raymond J. (2004-04-01). "Isoprenoids: Remarkable diversity of form and function". Lipids. 39 (4): 293–309. doi:10.1007/s11745-004-1233-3. ISSN 1558-9307. PMID 15357017.
  5. ^ Vik, A; James, A; Gundersen, LL (2007). "Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro". Planta Medica. 73 (13): 1410–2. doi:10.1055/s-2007-990238. PMID 17924309.

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