1575-72-0

Usage

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Electrophilic rearrangements of chiral amides: A traceless asymmetric α-allylation

A one-pot protocol for the asymmetric α-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched α-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.

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.

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.

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.

Anticonvulsant and neurotoxic activities of twelve analogues of valproic acid.

Twelve racemic analogues of the antiepileptic drug valproic acid (VPA) were tested and compared with VPA for anticonvulsant activity by the subcutaneous pentylenetetrazol (PTZ) seizure threshold test and for neurotoxicity by the rotorod test. Four compounds produced maximal anticonvulsant activity (100% protection) in equimolar doses (1.5 mmol/kg) to VPA and two compounds showed a similar effect with lower doses (1.0 mmol/kg). Four compounds produced lower activity (38-80% protection), and two compounds showed no anticonvulsant activity at the dose used (1.5 mmol/kg). Two of the 12 compounds, (+/-)-2-n-propyl-4-hexynoic acid (11) and (+/-)-4-methyl-2-n-propyl-4-pentenoic acid (12), showed no sedation at doses that produced the maximum anticonvulsant effect. For the first time we succeeded to develop two compounds with higher protective index and safety ratios than VPA. Compound 11 had a longer duration of action and higher protective index but a lower safety ratio than 12. Comparisons of the anticonvulsant and minimal neurotoxic effects of these compounds with their calculated lipophilicity (C log P) revealed that compounds with the desired high anticonvulsant activity and minimal neurotoxicity showed C log P values between 1.84 and 2.64 and had nine carbon atoms (in contrast to eight carbon atoms for VPA).