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G5048

Sigma-Aldrich

Geranylgeranylacetone

Synonym(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

Empirical Formula (Hill Notation):
C23H38O
CAS Number:
6809-52-5
Molecular Weight:
330.55
MDL number:
MFCD00869547
UNSPSC Code:
12352200
PubChem Substance ID:
329799745
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

100

form

oil

storage condition

protect from light

color

clear

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

SMILES string

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+

InChI key

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).

Biochem/physiol Actions

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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Yasuo M Tsutsumi et al.
Life sciences, 101(1-2), 43-48 (2014-03-04)
Geranylgeranylacetone (GGA) is commonly utilized to protect the gastric mucosa in peptic ulcer disease. Recently GGA has been shown to protect the myocardium from ischemia/reperfusion by activating heat shock proteins. However, the exact mechanism as to how GGA activates these
Deli Zhang et al.
Journal of molecular and cellular cardiology, 51(3), 381-389 (2011-07-13)
The most common clinical tachycardia, Atrial Fibrillation (AF), is a progressive disease, caused by cardiomyocyte remodeling, which finally results in contractile dysfunction and AF persistence. Recently, we identified a protective role of heat shock proteins (HSPs), especially the small HSPB1
Naoyuki Yoshikawa et al.
Anti-cancer drugs, 21(9), 850-860 (2010-08-21)
Geranylgeranylacetone (GGA), an isoprenoid compound, is a widely used antiulcer drug developed in Japan. GGA is structurally similar to plaunotol and geranylgeraniol, another isoprenoid reported to exert strong anticancer effects. In an earlier study, GGA was shown to inhibit ovarian
Masaki Yoda et al.
Journal of orthopaedic science : official journal of the Japanese Orthopaedic Association, 16(6), 791-798 (2011-08-13)
Osteoarthritis (OA) is a common disease, afflicting many sufferers with both pain and functional disorders. Various therapies have been attempted for OA, but no fully effective treatment has been established yet. Apoptosis of chondrocytes caused by reactive oxygen species (ROS)
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