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Teprenone

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Teprenone Basic information

Product Name:
Teprenone
Synonyms:
  • All trans-Teprenone
  • (5Z,9Z,13Z)-6,10,14,18-tetramethyl-2-nonadeca-5,9,13,17-tetraenone
  • 6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraen-2-one
  • TEPRENONE
  • 13,17-nonadecatetraen-2-one,6,10,14,18-tetramethyl-9
  • geranylgeranylacetone
  • 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetren-2-one
  • Selbex
CAS:
6809-52-5
MF:
C23H38O
MW:
330.55
EINECS:
614-276-0
Product Categories:
  • Aliphatics
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • 6809-52-5
Mol File:
6809-52-5.mol
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Teprenone Chemical Properties

Boiling point:
bp0.01 155-160°
Density 
d420.5 0.9081
refractive index 
nD20 1.4947
storage temp. 
-20°C
solubility 
DMSO: >5mg/mL
form 
liquid
color 
clear
Merck 
14,9228
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChIKey
SBOCYPUKNYDTSX-DMLVRTFPSA-N
LogP
8.200 (est)
CAS DataBase Reference
6809-52-5(CAS DataBase Reference)
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Safety Information

WGK Germany 
3
RTECS 
RA5391300
HS Code 
2914.19.0000
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Teprenone Usage And Synthesis

Description

Teprenone (geranylgeranylacetone) is an antiulcer agent whose synthesis was inspired by the gastric protecting properties of Coenzyme Q10. Teprenone is reported to act via enhancement of gastric mucosal glycoprotein secretion.

Description

Geranylgeranylacetone is an inducer of heat shock protein (Hsp) expression that has been shown to increase Hsp70 (also known as Hsp72 and HspA1A), Hsp22 (HspB8), Hsp27 (HspB1), Hsp90 (HspC), and Hsp105 (HspH1) levels in various cells and tissues. It is orally bioavailable and has diverse effects in vivo, including hepatoprotective, neuroprotective, and antiulcerative effects. The effects of geranylgeranylacetone on Hsp expression are more pronounced under stress conditions.

Chemical Properties

Yellow Oil

Originator

Eisai (Japan)

Uses

An anti-ulcerative. 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.

Uses

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

Definition

ChEBI: A terpene ketone in which a (9E,13E)-geranylgernayl group is bonded to one of the alpha-methyls of acetone (it is a mixture of 5E- and 5Z-geoisomers in a 3:2 ratio).

brand name

SELBEX

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.

References

1) Kamal and Omran (2013) The role of heat shock protein 70 induced by geranylgeranylacetone in carbon tetrachloride-exposed adult rat testes; Pathophysiology, 20 139 2) Lennikov et al. (2013) Induction of heat chock protein 70 ameliorates ultraviolet-induced photokeratitis in mice; Int. J. Mol. Sci., 14 2175 3) Adache et al. (2010) An acyclic polyisoprenoid derivative, geranylgeranylacetone, protects against visceral adiposity and insulin resistance in high fat fed mice; Am. J. Physiol. Endocrinol. Metab., 299 E764 4) Marunouchi et al. (2014) Protective effect of geranylgeranylacetone via enhanced induction of HSPB1 and HSPB8 in mitochondria of the failing heart following myocardial infarction in rats; Eur. J. Pharmacol. 730 140

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