G5048

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
• 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

Properties

• Assay: ≥98% (HPLC)
• 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

Description

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.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable