6809-52-5

Basic information

• Product Name: Teprenone
• Synonyms: 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;Tetraprenylacetone;Teprenone(mixture of isomers)
• CAS NO: 6809-52-5
• Molecular Formula: C₂₃H₃₈O
• Molecular Weight: 661.09
• EINECS: 1308068-626-2
• Product Categories: Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 6809-52-5.mol
• Article Data: 18

Chemical Properties

• Boiling Point: bp0.01 155-160°
• Flash Point: 168 °C
• Appearance: clear/
• Density: d420.5 0.9081
• Vapor Pressure: 5.12E-08mmHg at 25°C
• Refractive Index: nD20 1.4947
• Storage Temp.: ?20°C
• Solubility: DMSO: >5mg/mL
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
• Merck: 14,9228
• CAS DataBase Reference: Teprenone(CAS DataBase Reference)
• NIST Chemistry Reference: Teprenone(6809-52-5)
• EPA Substance Registry System: Teprenone(6809-52-5)

Safety Data

• WGK Germany: 3
• RTECS: RA5391300
• Hazardous Substances Data: 6809-52-5(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 6809-52-5 differently. You can refer to the following data:
1. 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.
2. 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

Uses

Different sources of media describe the Uses of 6809-52-5 differently. You can refer to the following data:
1. 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.
2. 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

InChI:InChI=1/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+

Upstream product

• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 1066-26-8 sodium acetylide 
• 1113-21-9 (6E,10E)-geranyllinalool 
• 141-97-9 ethyl acetoacetate 
• 50848-64-1 2E,6E,10E-geranylgeranyl bromide 
• 3796-70-1 trans geranyl acetone 
• 72324-39-1 5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 51921-98-3 (4E,8E)-ethyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate 
• 1206897-24-6 C₂₄H₃₈O₃ 
• 71668-81-0 (4E,8E,12E)-ethyl 2-acetyl-5,9,13,17-tetramethyloctadeca-4,8,12,16-tetraenoate 
• 24163-93-7 farnesyl bromide 
• 24034-73-9 Geranylgeraniol 
• 1694-31-1 tert-butyl acetoacetate 
• 24035-35-6 (2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenoic acid ethyl ester 

Downstream Products

• 1182-68-9 2-Methyl-3-<3,7,11,15,19-pentamethyl-eicosapentaen-(2,6,10,14,18)-yl-(1)>-naphthochinon-(1,4) 
• 22488-05-7 geranylfarnesol 
• 64284-92-0 (E,E,E,E)-geranylfarnesoic acid 

Relevant articles and documents

Synthesis method of teprenone and intermediate thereof

The invention relates to synthesis methods of teprenone and an intermediate thereof. The synthesis of the intermediate all-trans (5E,9E)-farnesyl acetone comprises: 1) in the presence of a catalyst, carrying out a carroll rearrangement reaction on the mixture of 5E-nerolidol and 5Z-nerolidol and hydrocarbonyl acetoacetate to obtain the isomer mixture of (5Z,9Z)-farnesyl acetone, (5Z,9E)-farnesyl acetone, (5E,9Z)-farnesyl acetone, and (5E,9E)-farnesyl acetone, wherein the content of (5E,9E)-farnesyl acetone in the isomer mixture is controlled at more than 18%; and 2) carrying out low-temperature crystallization separation on the isomer mixture in a moderately polar solvent to obtain the all-trans (5E,9E)-farnesyl acetone. According to the present invention, the high-purity all-trans (5E,9E)-farnesyl acetone is obtained by using the mixture of 5E-nerolidol and 5Z-nerolidol as the raw material through the low-temperature crystallization separation, such that the teprenone with the qualified quality can be conveniently obtained.

A process for the preparation of Teprenone

The invention discloses a method for preparing teprenone. The method comprises the following steps: (a) mixing geranyl linalool, acetyl Meldrum's acid and aluminum isopropoxide according to a molar ratio of 1: (1.2-1.5): (0.02-0.1), dissolving the mixture in a paraxylene solvent, heating up to 50-160 DEG C, refluxing for 6-10 hours, cooling and removing the solvent to obtain a teprenone mixture; (b) washing and extracting the teprenone mixture, mixing organic layers, and drying to obtain a crude product of teprenone; (c) carrying out molecular distillation, impurity removal, decompression rectifying and impurity removal on the crude product of teprenone to obtain a teprenone product. The method is simple and easy to control, the conversion rate of the product is high, and the prepared product is high in purity, stable in quality and high in safety, thereby being convenient to promote and use in clinical and industrial production.

GGA DERIVATIVES

This invention relates to geranylgeranyl acetone (GGA) derivatives, pharmaceutical compositions comprising GGA derivatives and the use of GGA derivatives.