33786-47-9

Basic information

• Product Name: 2-N-PROPYL-2(E)-PENTENOICACID
• Synonyms: 2-N-PROPYL-2(E)-PENTENOICACID;(2E)-2-Propyl-2-pentenoic acid;(E)-2-En-vpa;2-Pentenoic acid, 2-propyl-, (E)-;delta-2(E)-Valproate;E-2-En-valproic acid;trans-2-Ene-valproic acid;trans-2-Propyl-2-pentenoic acid
• CAS NO: 33786-47-9
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• Mol File: 33786-47-9.mol

Chemical Properties

• Melting Point: 38-40 °C
• Boiling Point: 242.9°Cat760mmHg
• Flash Point: 149.8°C
• Appearance: /
• Density: 0.956g/cm³
• Vapor Pressure: 0.0109mmHg at 25°C
• Refractive Index: 1.458
• PKA: 5.00±0.19(Predicted)
• CAS DataBase Reference: 2-N-PROPYL-2(E)-PENTENOICACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-PROPYL-2(E)-PENTENOICACID(33786-47-9)
• EPA Substance Registry System: 2-N-PROPYL-2(E)-PENTENOICACID(33786-47-9)

Safety Data

• Hazardous Substances Data: 33786-47-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h5H,3-4,6H2,1-2H3,(H,9,10)/b7-5+

Upstream product

• 63718-45-6 2-propyl-2-pentenoic acid ethyl ester 
• 99174-91-1 2-bromo-2-propyl pentanoic acid ethyl ester 
• 123-19-3 4-heptanone 
• 78435-49-1 methyl (E)-2-propyl-2-pentenoate 
• 3639-22-3 2,2-dipropylglycolic acid 

Downstream Products

• 615-83-8 2-bromo-pentanoic acid ethyl ester 
• 63718-45-6 2-propyl-2-pentenoic acid ethyl ester 
• 33786-53-7 (E)-2-Propyl-2-pentensaeure-(p-isopropylphenyl)ester 

Relevant articles and documents

Examining the correlations between GSK-3 inhibitory properties and anti-convulsant efficacy of valproate and valproate-related compounds

A family of compounds based upon the chemical structure of valproate were synthesized and assayed for their ability to inhibit glycogen synthase kinase (GSK)-3 α and β activity in vitro. A family of compounds based upon the chemical structure of valproate were synthesized and assayed for their ability to inhibit glycogen synthase kinase (GSK)-3 α and β activity in vitro. This data is correlated to the known anti-convulsant properties of these compounds in order to determine the potential role of GSK-3 inhibition in the therapeutic efficacy of these drugs.

Structure-activity relationships of unsaturated analogues of valproic acid

The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED50 or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.

Process for preparing (E)-2-propyl-2-pentenoic acid and intermediate compounds

Composition consisting of a mixture of (E) and (Z) isomers of esters of general formula: STR1 in which R represents a C1 -C4 alkyl radical, containing at least 85% of (E) isomer. A process for preparing such a composition. The use of such a composition for preparing (E)-2-propyl-2-pentenoic acid of formula: STR2 and also its pharmaceutically acceptable salts.

Valproic and (E)-2-valproenoic acid derivatives, and pharmaceutical compositions therefrom

2-Propyl-2-pentanoic acid (valproic acid) esters and (E)-2-propyl-2-pentenoic acid [(E)-2-valproenoic acid] esters surprisingly proved to have valuable properties, in that they show anticonvulsive and antiepileptic activities comparable with those of valproic acid, as well as an improved bioavailability and a markedly reduced toxicity.

Process for the preparation of E-2-propyl-2-pentenoic acid and physiologically compatible salts thereof

A novel process for the preparation of E-2-propyl-2-pentenoic acid, as well as the physiologically compatible salts thereof is described, in which 2-bromo-2-propyl-pentenoic acid ethyl ester is used as the starting compound. The bromine is split off with a cyclic tertiary amine in acetonitrile as the solvent and preferably the E-isomer of the ethyl ester is formed. The free acid is obtained by subsequent saponification under careful conditions and optionally, preferably using the corresponding carbon dioxide salts in aqueous acetone solution, is converted into the salt form.

Process for the preparation of E-2-propyl-2-pentenoic acid and physiologically compatible salts thereof

A novel process for the preparation of E-2-propyl-2-pentenoic acid and its physiologically compatible salts is described, in which di-n-propyl-ketone-cyanohydrin is used as the starting compound. The compound is either (a) dehydrated with thionyl chloride and the acid nitrile formed is subsequently saponified with a stoichiometric excess of potassium hydroxide, or (b) is initially converted into 2-hydroxy-2-propyl-pentanoic acid and the latter is subsequently dehydrated in the presence of a less than stoichiometric quantity of a tertiary amine at a temperature of at least 200° C. The free acid is optionally converted into the salt form, preferably using the corresponding salts of carbon dioxide in an aqueous acetone solution.

Process for the preparation of 2-propyl-2-pentenoic acid and its esters

The process for the preparation of the E isomers of the compounds of formula A: STR1 in which R 1 is selected from H or C 1 -C 4 alkyl, comprises according to the invention the reaction of propionaldehyde with a phosphorus derivative of formula: STR2 in which R 1 designates C 1 -C 4 alkyl and R 2 is selected from C 1 -C 4 alkyl or phenyl, and, optionally, the hydrolysis of the compound of formula A in which R 1 is alkyl in order to form the compounds of formula A in which R 1 is H.Pharmaceutical industry.

Valproic and (E)-2-valproenoic acid derivatives, processes for the preparation thereof and pharmaceutical compositions therefrom

2-Propyl-2-pentanoic acid (valproic acid) esters and (E)-2-propyl-2-pentenoic acid [(E)-2-valproenoic acid] esters surprisingly proved to have valuable properties, in that they show anticonvulsive and antiepileptic activities comparable with those of valproic acid, as well as an im-proved bioavailability and a markedly reduced toxicity.