Geranylgeraniol

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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).
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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

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