74046-07-4

Basic information

• Product Name: S(+)-4-AMINOHEXENOIC ACID
• Synonyms: S(+)-GAMMA-VINYL GABA;S(+)-4-AMINOHEXENOIC ACID;S(+)-Y-VINYL GABA GABA TRANSAMINASE;s(+)-γ-vigabatrin;s(+)-γ-vinyl gaba;S(+)-γ-Vinyl GABA, S(+)-4-Aminohexenoic acid;(4S)-4-Amino-5-hexenoic acid;(S)-4-Amino-5-hexenoic acid
• CAS NO: 74046-07-4
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.16
• Product Categories: Amines;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74046-07-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 162-165 °C
• Boiling Point: 277.701°C at 760 mmHg
• Flash Point: 121.749°C
• Appearance: off-white/solid
• Density: 1.064g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.483
• Storage Temp.: 2-8°C
• Solubility: H2O: >20 mg/mL
• PKA: 4.36±0.10(Predicted)
• Stability: Hygroscopic, Light Sensitive
• CAS DataBase Reference: S(+)-4-AMINOHEXENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: S(+)-4-AMINOHEXENOIC ACID(74046-07-4)
• EPA Substance Registry System: S(+)-4-AMINOHEXENOIC ACID(74046-07-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 74046-07-4(Hazardous Substances Data)

Usage

Uses

Vigabatrin is a novel anti-epileptic drug. Antidepressant; antipsychotic; anxiolytic.

Biochem/physiol Actions

γ-Vigabatrin has the potential to treat infantile spasms and seizures. It exhibits therapeutic effects against cocaine and other addictions.

InChI:InChI=1/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m1/s1

Upstream product

• 93288-23-4 (5S)-5-ethenyl-2-pyrrolidinone 
• 139694-78-3 (S)-(-)-5-ethenyl-1-butenyl-2-pyrrolidinone 
• 139694-78-3 (S)-5-ethenyl-1-butenyl-2-pyrrolidinone 
• 148073-34-1 (S)-ethyl 4--5-hexenoate 
• 197231-54-2 methyl (4S)-4-[(tert-butoxycarbonyl)amino]hex-5-enoate 
• 611182-50-4 (S)-4-(2,2,2-Trichloro-acetylamino)-hex-5-enoic acid methyl ester 
• 916677-49-1 C₁₃H₁₇NO₄S 
• 916677-44-6 3-(4-methylphenylsulfonyl)-4-vinyl-[1,3]oxazinan-6-one 
• 916677-46-8 N-[1-(2-hydroxyethyl)allyl]-4-methylphenylsulfonylamide 
• 916677-48-0 N-[1-(2-oxoethyl)allyl]-4-methylbenzenesulfonamide 
• 881405-68-1 (2S)-2-methoxycarbonylmethyl-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester 
• 881405-70-5 (2R)-2-methoxycarbonylmethyl-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester 
• 881405-69-2 (2S)-2-methoxycarbonylmethyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 881405-71-6 (1R,5R,6R)-4-bromo-3-oxo-2-azabicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-tert-butyl ester 6-methyl ester 

Downstream Products

• 526-63-6 (-)-isoretronecanol 

Relevant articles and documents

Scalable Synthesis of Both Enantiomers of Vigabatrin, an Antiepileptic Drug

Vigabatrin is a potent inhibitor of gamma-aminobutyric acid (GABA) catabolism used for the treatment of epilepsy. Here we have synthesized both enantiomers of the drug vigabatrin in five steps from known intermediates using Wittig olefination and pyrolytic elimination as key steps. The target compounds are synthesized in gram scale amounts with >98 % enantiopurity.

Enantioselective iridium-catalyzed allylic aminations of allylic carbonates with functionalized side chains. Asymmetric total synthesis of (S)-vigabatrin

Indium-catalyzed aminations of allylic carbonates containing a variety of O-functional groups have been explored. High degrees of regio- as well as enantioselectivity were achieved with diacylamides under salt-free conditions and with arylamines. The results allowed the antiepilepsy drug (5)-vigabatrin to be prepared via a very short route.

Synthesis of functionalized pyrrolidin-2-ones and (S)-vigabatrin from pyrrole

Starting from pyrrole, the novel 3,4-didehydropyrohomoglutamate 8 or (ent)-8 can be efficiently synthesized in up to 91% ee, which can be utilized as a versatile building block toward functionalized pyrrolidin-2-ones. Moreover, (ent)-8 can be readily converted to (S)-Vigabatrin, being an irreversible inhibitor for GABA-T, which is used as adjunctive therapy in patients that suffer from epilepsy.