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G3278

Sigma-Aldrich

Geranylgeraniol

≥85% (GC)

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Synonym(s):
all trans-3,7,11-15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol
Empirical Formula (Hill Notation):
C20H34O
CAS Number:
Molecular Weight:
290.48
Beilstein/REAXYS Number:
1913779
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥85% (GC)

form

liquid

solubility

ethanol: 50 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

SMILES string

C\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO

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+

InChI key

OJISWRZIEWCUBN-QIRCYJPOSA-N

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1 of 4

This Item
G6025277541W247804
Geranylgeraniol ≥85% (GC)

G3278

Geranylgeraniol

trans,trans-Farnesol 96%

277541

trans,trans-Farnesol

Farnesol mixture of isomers, ≥95%, stabilized, FG

W247804

Farnesol

form

liquid

form

solution

form

liquid

form

-

solubility

ethanol: 50 mg/mL, clear, colorless to light yellow

solubility

-

solubility

-

solubility

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

-

Biochem/physiol Actions

As the pyrophosphate, the metabolic precursor of all diterpenes. Screening in vitro shows this to be a potent and selective agent against Mycobacterium tuberculosis.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Chikara Ohto et al.
Applied microbiology and biotechnology, 87(4), 1327-1334 (2010-04-16)
An acyclic diterpene alcohol, (E,E,E)-geranylgeraniol (GGOH), is one of the important compounds used as perfume and pharmacological agents. A deficiency of squalene (SQ) synthase activity allows yeasts to accumulate an acyclic sesquiterpene alcohol, (E,E)-farnesol, in their cells. Since sterols are
E L Scheller et al.
Journal of dental research, 90(7), 894-899 (2011-05-10)
Osteonecrosis of the jaw (ONJ), a side-effect of bisphosphonate therapy, is characterized by exposed bone that fails to heal within eight weeks. Healing time of oral epithelial wounds is decreased in the presence of amino-bisphosphonates; however, the mechanism remains unknown.
Kenro Tokuhiro et al.
Applied and environmental microbiology, 75(17), 5536-5543 (2009-07-14)
(E, E, E)-Geranylgeraniol (GGOH) is a valuable starting material for perfumes and pharmaceutical products. In the yeast Saccharomyces cerevisiae, GGOH is synthesized from the end products of the mevalonate pathway through the sequential reactions of farnesyl diphosphate synthetase (encoded by
Miu Iijima et al.
Plant physiology, 174(4), 2213-2230 (2017-07-07)
Daurichromenic acid (DCA) synthase catalyzes the oxidative cyclization of grifolic acid to produce DCA, an anti-HIV meroterpenoid isolated from
Aida Hiseni et al.
Applied microbiology and biotechnology, 91(4), 1029-1036 (2011-05-19)
Two carotenoid 1,2-hydratase (CrtC) genes from the photosynthetic bacteria Rubrivivax gelatinosus and Thiocapsa roseopersicina were cloned and expressed in Escherichia coli in an active form and purified by affinity chromatography. The biochemical properties of the recombinant enzymes and their substrate

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