Geranylgeraniol

Last updated
Geranylgeraniol
Geranylgeraniol.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
Appearancecolorless 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.