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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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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
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
Michio Hongo et al.
Journal of gastroenterology and hepatology, 27(1), 62-68 (2011-10-19)
Functional dyspepsia (FD) is a common condition seen in primary gastroenterology practice. The present study was conducted to compare the clinical effectiveness of mosapride and teprenone in patients with FD. Prospective clinical comparative study with random allocation of open labeled
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
Wangjun Qin et al.
Behavioural pharmacology, 31(2&3), 179-185 (2019-11-27)
The clinical use of opioid analgesics, such as morphine, is limited by analgesic tolerance, molecular mechanism of which is not well understood. Recently, molecular chaperone heat shock protein 70 (Hsp70) has been demonstrated to play important roles in morphine-induced neuroadaptation.
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