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Teprenone

CAS No.
6809-52-5
Chemical Name:
Teprenone
Synonyms
geranylgeranylacetone;Selbex;eprenone;TEPRENONE;Teprenone RS;UNII-S8S8451A4O;Teprenone, >=98%;Tetraprenylacetone;All trans-Teprenone;Teprenone USP/EP/BP
CBNumber:
CB8386175
Molecular Formula:
C23H38O
Molecular Weight:
330.55
MDL Number:
MFCD00866901
MOL File:
6809-52-5.mol
MSDS File:
SDS
Last updated:2024-03-28 17:11:29

Teprenone 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)
FDA UNII S8S8451A4O

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
WGK Germany  3
RTECS  RA5391300
HS Code  2914.19.0000
NFPA 704
3
2 0

Teprenone price More Price(26)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich G5048 Geranylgeranylacetone 6809-52-5 10mg $86 2024-03-01 Buy
Sigma-Aldrich G5048 Geranylgeranylacetone 6809-52-5 50mg $347 2024-03-01 Buy
TCI Chemical T2701 Teprenone [mixture of (5E,9E,13E)- and (5Z,9E,13E)- isomers] >95.0%(GC) 6809-52-5 1g $84 2024-03-01 Buy
TCI Chemical T2701 Teprenone [mixture of (5E,9E,13E)- and (5Z,9E,13E)- isomers] >95.0%(GC) 6809-52-5 5g $250 2024-03-01 Buy
Cayman Chemical 20218 Geranylgeranylacetone ≥98% (mixture of isomers) 6809-52-5 5mg $32 2024-03-01 Buy
Product number Packaging Price Buy
G5048 10mg $86 Buy
G5048 50mg $347 Buy
T2701 1g $84 Buy
T2701 5g $250 Buy
20218 5mg $32 Buy

Teprenone Chemical Properties,Uses,Production

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

71668-81-0
6809-52-5
Synthesis of Teprenone from ethyl (4E,8E,12E)-2-acetyl-5,9,13,17-tetramethyloctadeca-4,8,12,16-tetraenoate
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View Lastest Price from Teprenone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Teprenone pictures 2024-03-29 Teprenone
6809-52-5
US $35.00-1.20 / kg 1kg 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
Teprenone pictures 2023-07-29 Teprenone
6809-52-5
US $100.00 / kg 1kg 99% 500t/month Henan Bao Enluo International TradeCo.,LTD
Teprenone pictures 2023-03-20 Teprenone
6809-52-5
US $0.00 / kg 1kg 98.0%min 100kg LY Global chemicals co.,ltd .
  • Teprenone pictures
  • Teprenone
    6809-52-5
  • US $35.00-1.20 / kg
  • 99%
  • Henan Fengda Chemical Co., Ltd
  • Teprenone pictures
  • Teprenone
    6809-52-5
  • US $100.00 / kg
  • 99%
  • Henan Bao Enluo International TradeCo.,LTD
  • Teprenone pictures
  • Teprenone
    6809-52-5
  • US $0.00 / kg
  • 98.0%min
  • LY Global chemicals co.,ltd .
6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraen-2-one TEPRENONE 13,17-nonadecatetraen-2-one,6,10,14,18-tetramethyl-9 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetren-2-one Selbex Tetraprenylacetone Teprenone(mixture of isomers) Teprenone [mixture of (5E,9E,13E)- and (5Z,9E,13E)- isomers] 6,10,14,18-TetraMethyl- Geranylgeranylacetone 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one 5,9,13,17-Nonadecatetraen-2-one,6,10,14,18-tetraMethyl- 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one, mixture of (5E,9E,13E) and (5Z,9E,13E) isomers UNII-S8S8451A4O Teprenone, >=98% Teprenone (trans,trans) All trans-Teprenone (5Z,9Z,13Z)-6,10,14,18-tetramethyl-2-nonadeca-5,9,13,17-tetraenone Teprenone RS Teprenone USP/EP/BP 6,10,14,18-Tetramethylnonadeca-5,9,13,17-tetraen-2-one TeprenoneQ: What is Teprenone Q: What is the CAS Number of Teprenone Q: What is the storage condition of Teprenone Q: What are the applications of Teprenone NanoLiposomal Teprenone , Water-Soluble Teprenone geranylgeranylacetone eprenone Teprenone(Z/Emixture) Teprenone, mixture of (5E,9E,13E)- and (5Z,9E,13E)- isomers,≥ 95.0% 6809-52-5 2C23H38O Aliphatics Intermediates & Fine Chemicals Pharmaceuticals 6809-52-5