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Geranylgeraniol

Geranylgeraniol is a diterpene alcohol that is a cell permeable analog of geranylgeranyl pyrophosphate; it is used in the biosynthesis of vitamin E, vitamin K, and other diterpenes. Geranylgeraniol is a bee pheromone and a substrate for geranylgeranyl transferase. This compound exhibits anticancer, antibacterial, and cytoprotective activities. Geranylgeraniol induces apoptosis and inhibits growth of various tumor cells. Separately, geranylgeraniol inhibits growth of Mycobacterium in vitro and protects monocytes against statin-induced cytotoxicity.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18926762

Cas No.

24034-73-9

Purity

≥95%

Formula

C20H34O

Formula Wt.

290.49

Chemical Name

3,7,11,15-Tetramethyl-2,6,10,14-hexadecatraen-1-ol

IUPAC Name

(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol

Synonym

all trans-3,7,11-15-Tetramethyl-2,6,10,14-hexadecatetraen- 1-ol

Solubility

Soluble in chloroform, alcohols, acetone, or ethyl acetate.

Appearance

Light Yellow Oil

Campia I, Lussiana C, Pescarmona G, et al. Geranylgeraniol prevents the cytotoxic effects of mevastatin in THP-1 cells, without decreasing the beneficial effects on cholesterol synthesis. Br J Pharmacol. 2009 Dec;158(7):1777-86. PMID: 19888963.

Vik A, James A, Gundersen LL. Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro. Planta Med. 2007 Oct;73(13):1410-2. PMID: 17924309.

Shibayama-Imazu T, Sakairi S, Watanabe A, et al. Vitamin K(2) selectively induced apoptosis in ovarian TYK-nu and pancreatic MIA PaCa-2 cells out of eight solid tumor cell lines through a mechanism different from geranylgeraniol. J Cancer Res Clin Oncol. 2003 Jan;129(1):1-11. PMID: 12618894.

GLPG-0634