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
CAS Number	7614-21-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:46762
ChemSpider	4444726
ECHA InfoCard	100.152.315
PubChem CID	5281365
UNII	AIA02AJA3A^Y
InChI 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
SMILES OC/C=C(/CC/C=C(/CC\C=C(/C)CC\C=C(/C)C)C)C
Properties
Chemical formula	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 a diterpenoid alcohol. It is a colorless waxy solid.^[1]

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]

References

^ 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.
^ Fatty alcohols Archived 2012-06-25 at the Wayback Machine, cyberlipid.org
^ Semiochemical - geranylgeraniol, pherobase.com
^ 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 was last edited on 18 August 2022, at 16:26