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G5048

Sigma-Aldrich

Geranylgeranylacetone

Synonyme(s) :

6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one, mixture of (5E,9E,13E) and (5Z,9E,13E) isomers, GGA, Selbex, Teprenone, UNII-S8S8451A4O

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About This Item

Formule empirique (notation de Hill):
C23H38O
Numéro CAS:
6809-52-5
Poids moléculaire :
330.55
Numéro MDL:
MFCD00869547
Code UNSPSC :
12352200
ID de substance PubChem :
329799745
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

oil

Conditions de stockage

protect from light

Couleur

clear

Solubilité

DMSO: >5 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

C\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CCC(C)=O

InChI

1S/C23H38O/c1-19(2)11-7-12-20(3)13-8-14-21(4)15-9-16-22(5)17-10-18-23(6)24/h11,13,15,17H,7-10,12,14,16,18H2,1-6H3/b20-13+,21-15+,22-17+

Clé InChI

HUCXKZBETONXFO-NJFMWZAGSA-N

Application

Geranylgeranylacetone has been used as an inducer of heat shock protein 70 (HSP70) to analyze its protective effects against cerebral ischemia/reperfusion (I/R).

Actions biochimiques/physiologiques

Geranylgeranylacetone can induce expression of HSP70, HSPB8, and HSPB1. Induction of HSP70 expression is protective against the development of various diseases, such as inflammatory bowel disease, hypoxic/ischemic brain injury and spinal and bulbar muscular atrophy (cytoprotective and anti-inflammatory effects). Reports indicate that GGA protects against NSAID-induced gastric and intestinal lesions by induction of HSP70 expression. Other studies have shown that GGA induces expression of HSPB8 and HSPB1 and reduces the formation of amyloid oligomers as well as insoluble aggregates in HSPB5 R120G TG mice.
Geranylgeranylacetone is an acyclic polyisoprenoid that has been studied to exhibit protective effects against reperfusion injury, inflammation and organ transplantation. It is an anti-ulcer agent that is involved in the protection of gastric mucosa.

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Fu-Cheng Luo et al.
Free radical biology & medicine, 52(7), 1218-1227 (2012-01-31)
There are few efficacious interventions to combat morphine dependence. Thioredoxin-1 (Trx-1) and heat shock protein 70 (Hsp70) are emerging as important modulators of neuronal function. They have been shown to be involved in cellular protective mechanisms against a variety of
Kylie Kavanagh et al.
American journal of physiology. Endocrinology and metabolism, 300(5), E894-E901 (2011-02-18)
We evaluated heat shock protein 70 (HSP70) changes in diabetes mellitus (DM) in a nonhuman primate model. To this end, two studies were conducted in DM vervet monkeys. 1) Normal control and streptozotocin-induced DM monkeys (Stz-DM) that were differentiated into
Yoko Ishii et al.
Investigative ophthalmology & visual science, 44(5), 1982-1992 (2003-04-26)
To study the effects of geranylgeranylacetone (GGA) on the expression of inducible (HSP72) and constitutive (HSC70) heat shock proteins (HSPs) on retinal ganglion cells (RGCs) in a rat model of glaucoma. Adult Wistar rats were given intraperitoneal injections of GGA
Noritaka Fujimura et al.
Arteriosclerosis, thrombosis, and vascular biology, 32(1), 153-160 (2011-10-15)
Geranylgeranylacetone (GGA) induces expression of heat shock protein 90 (Hsp90), an adaptor molecule for assembly of endothelial nitric oxide synthase (eNOS) phosphorylation complex. The purpose of this study was to determine whether GGA enhances Hsp90 expression and augments endothelium-dependent vasodilation
Tetsuro Marunouchi et al.
European journal of pharmacology, 730, 140-147 (2014-03-19)
The mechanisms underlying mitochondrial impairment in the failing heart are not yet clear. In a previous study, we found that the levels of small heat shock proteins (HSP) such as mitochondrial HSPB1 and HSPB8 in the failing heart following myocardial
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