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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46762;
ChemSpider	4444726;
ECHA InfoCard	100.152.315
PubChem CID	5281365;
UNII	AIA02AJA3A ;
CompTox Dashboard (EPA)	DTXSID001345665 ;
	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] It has been researched as an agent to treat statin-induced muscle soreness and muscle fatigue.^[4]^[5]

Geranylgeraniol is a potent inhibitor of Mycobacterium tuberculosis in vitro.^[6]

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
^ Tan, Barrie; Chin, Kok-Yong (17 November 2023). "Potential role of geranylgeraniol in managing statin-associated muscle symptoms: a COVID-19 related perspective". Frontiers in Physiology. 14. doi:10.3389/fphys.2023.1246589. PMC 10691100. PMID 38046949.
^ Irwin, Jordon C.; Fenning, Andrew S.; Vella, Rebecca K. (January 2020). "Geranylgeraniol prevents statin-induced skeletal muscle fatigue without causing adverse effects in cardiac or vascular smooth muscle performance". Translational Research. 215: 17–30. doi:10.1016/j.trsl.2019.08.004. PMID 31491372.
^ 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.

[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] Tan, Barrie; Chin, Kok-Yong (17 November 2023). "Potential role of geranylgeraniol in managing statin-associated muscle symptoms: a COVID-19 related perspective". Frontiers in Physiology. 14. doi:10.3389/fphys.2023.1246589. PMC 10691100. PMID 38046949.

[5] Irwin, Jordon C.; Fenning, Andrew S.; Vella, Rebecca K. (January 2020). "Geranylgeraniol prevents statin-induced skeletal muscle fatigue without causing adverse effects in cardiac or vascular smooth muscle performance". Translational Research. 215: 17–30. doi:10.1016/j.trsl.2019.08.004. PMID 31491372.

[6] 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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[6]

Geranylgeraniol

See also

References