1575-72-0

Basic information

• Product Name: 2-PROPYL-4-PENTENOIC ACID
• Synonyms: 2-allylpentanoicacid;2-allylvalericacid;2-propyl-4-pentenoicaci;4-en-valproicacid;2-PROPYL-4-PENTENOIC ACID;4-ENEVALPROIC ACID;2-n-Propyl-4-pentenoic Acid;4-ene-VPA
• CAS NO: 1575-72-0
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 1575-72-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 228.8°Cat760mmHg
• Flash Point: 126.2°C
• Appearance: /
• Density: 0.943g/cm³
• Vapor Pressure: 0.0257mmHg at 25°C
• Refractive Index: 1.448
• Storage Temp.: Refrigerator
• PKA: 4.70±0.20(Predicted)
• CAS DataBase Reference: 2-PROPYL-4-PENTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PROPYL-4-PENTENOIC ACID(1575-72-0)
• EPA Substance Registry System: 2-PROPYL-4-PENTENOIC ACID(1575-72-0)

Safety Data

• Hazardous Substances Data: 1575-72-0(Hazardous Substances Data)

Usage

Description

(±)-2-propyl-4-Pentenoic acid (4-ene VPA) is a major metabolite of valproic acid . It undergoes β-oxidation to form reactive metabolites that induce hepatotoxicity in rats. 4-ene VPA is also neuroteratogenic, reducing forebrain size and inducing deformation of the neural tube in mouse embryos.

Chemical Properties

Clear Colorless Oil

Uses

A metabolite of Valproic Acid

Hazard

Moderately toxic.

InChI:InChI=1/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h3,7H,1,4-6H2,2H3,(H,9,10)

Upstream product

• 868161-98-2 allyl-propyl-malonic acid 
• 106-95-6 allyl bromide 
• 109-52-4 valeric acid 
• 2049-80-1 (2-propenyl)propanedioic acid diethyl ester 
• 2163-48-6 diethyl propylmalonate 
• 18362-97-5 isopropyl pentanoate 
• 624-24-8 methyl valerate 
• 797753-91-4 2-propyl-pent-4-enoic acid isopropyl ester 
• 210690-89-4 methyl 2-allylpentanoate 
• 106-94-5 propyl bromide 
• 59726-38-4 2-propyl-2-ethoxycarbonylpenten-4-oic acid ethyl ester 

Downstream Products

• 25093-79-2 4,5-Dihydroxy-2-propylpentanoic acid-γ-lactone 

Relevant articles and documents

Copper(II)-Catalyzed Alkene Aminosulfonylation with Sodium Sulfinates for the Synthesis of Sulfonylated Pyrrolidones

A copper-catalyzed direct aminosulfonylation of unactivated alkenes with sodium sulfinates for the efficient synthesis of sulfonylated pyrrolidones is described. This reaction features good functional group tolerance and wide substrate scope, providing an efficient and straightforward protocol to access this kind of pyrrolidones. Moreover, preliminary mechanistic investigations disclosed that a free-radical pathway might be invovled in the process.

NHC-catalyzed ring expansion of oxacycloalkane-2-carboxaldehydes: A versatile synthesis of lactones

Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by the electronic nature of the carbene catalyst.

Further branching of valproate-related carboxylic acids reduces the teratogenic activity, but not the anticonvulsant effect

In the present study, compounds derived from the anticonvulsant drug valproic acid (VPA, 2-n-propylpentanoic acid) and analogues known to be teratogenic were synthesized with an additional carbon-branching in one of the side chains. The substances were tested for their ability to induce anticonvulsant activity and sedation in adult mice, and neural tube defects (exencephaly) in the offspring of pregnant animals (Han:NMRI mice). In all cases, the rates of exencephaly, embryolethality, and fetal weight retardation induced by the methyl-branched derivatives were very low when compared to those of the parent compounds. These novel compounds exhibited anticonvulsant activity which was not significantly different from that of VPA. Neurotoxicity was considerably lower for some compounds as compared to VPA. Anticonvulsant activity and neurotoxicity of branched short chain fatty acids are far less structure-dependent and not related to teratogenic potency. Within this series of compounds, (±)-4-methyl-2-n-propyl-4- pentenoic acid and (±)-2-isobutyl-4-pentenoic acid exhibited the most favorable profile in regard to high anticonvulsant effect, low sedation, and teratogenicity. Valproic acid analogues with additional methyl branching may be valuable antiepileptic agents with low teratogenic potential.