Geranylgeraniol

Geranylgeraniol is a diterpenoid alcohol. It is a colorless waxy solid.[1]

Geranylgeraniol
Names
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
Properties
C20H34O
Molar mass 290.491 g·mol−1
Appearance Clear liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Geranylgeraniol is an important intermediate in the biosynthesis of other diterpenes, of vitamins E, and of K.[2] It also used in the post-translational modification known as geranylgeranylation. Geranylgeraniol is a pheromone for bumblebees and a variety of other insects.[3]

Geranylgeraniol is a potent inhibitor of Mycobacterium tuberculosis in vitro.[4]

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. Fatty alcohols Archived 2012-06-25 at the Wayback Machine, cyberlipid.org
  3. Semiochemical - geranylgeraniol, pherobase.com
  4. 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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