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G3278

Sigma-Aldrich

Geranylgeraniol

≥85% (GC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H34O
CAS Number:
24034-73-9
Molecular Weight:
290.48
Beilstein/REAXYS Number:
1913779
MDL number:
MFCD00129083
UNSPSC Code:
12352202
PubChem Substance ID:
24895120
NACRES:
NA.77

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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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
GHS07

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

Certificates of Analysis (COA)

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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
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
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
Jianzhong Wen et al.
Biochemistry, 49(26), 5455-5463 (2010-06-05)
The Fenna-Matthews-Olson light-harvesting antenna (FMO) protein has been a model system for understanding pigment-protein interactions in the energy transfer process in photosynthesis. All previous studies have utilized wild-type FMO proteins from several species. Here we report the purification and characterization
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
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