136378-14-8

Basic information

• Product Name: (2S)-2-propylpent-4-ynoic acid
• CAS NO: 136378-14-8
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.1797
• Mol File: 136378-14-8.mol

Chemical Properties

• Boiling Point: 234.8°C at 760 mmHg
• Flash Point: 110.7°C
• Density: 1.005g/cm³
• Vapor Pressure: 0.0179mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: (2S)-2-propylpent-4-ynoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-propylpent-4-ynoic acid(136378-14-8)
• EPA Substance Registry System: (2S)-2-propylpent-4-ynoic acid(136378-14-8)

Safety Data

• Hazardous Substances Data: 136378-14-8(Hazardous Substances Data)

Upstream product

• 2163-48-6 diethyl propylmalonate 
• 106-96-7 propargyl bromide 
• 245079-02-1 2-propyl-2-prop-2-ynyl-malonic acid diethyl ester 
• 1540-28-9 ethyl 2-propylacetoacetate 
• 36477-24-4 α-Propyl-α-propargylacetoacetat-ethylester 

Relevant articles and documents

Antiproliferative and neurotrophic molecules

Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.

Antiproliferative and neurotrophic molecules

Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.

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).