4043-88-3

Basic information

• Product Name: 3,4-Dehydro-L-proline
• Synonyms: (s)-2,5-dihydro-1h-pyrrole-2-carboxylicacid;5-dihydro-(s)-1h-pyrrole-2-carboxylicaci;l-3,4-dehydroproline;l-3-pyrroline-2-carboxylicaci;3,4-DIDEHYDRO-L-PROLINE;3,4-DEHYDRO-L-PROLINE;3,4-DEHYDRO-L-PROLINE HYDROCHLORIDE;3,4-DEHYDRO-PROLINE
• CAS NO: 4043-88-3
• Molecular Formula: C₅H₇NO₂
• Molecular Weight: 113.11
• EINECS: 223-738-7
• Product Categories: Amino Acids;Chiral Compound
• Mol File: 4043-88-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 239-241 °C (dec.)
• Boiling Point: 211.82°C (rough estimate)
• Flash Point: 122.7°C
• Appearance: /
• Density: 1.2416 (rough estimate)
• Vapor Pressure: 0.00108mmHg at 25°C
• Refractive Index: 1.4200 (estimate)
• Storage Temp.: -15°C
• PKA: 2.04±0.20(Predicted)
• Water Solubility: Soluble in water
• BRN: 5376764
• CAS DataBase Reference: 3,4-Dehydro-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dehydro-L-proline(4043-88-3)
• EPA Substance Registry System: 3,4-Dehydro-L-proline(4043-88-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: UX9371345
• Hazardous Substances Data: 4043-88-3(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

Uses

3,4-Dehydro-L-proline is used to prepare morpholinyl-4-piperidinylacetic acid derivatives as potent oral active VLA-4 antagonist. It is also a β-Proline analog used as agonists at the strychnine-sensitive glycine receptor.

InChI:InChI=1/C5H7NO2/c7-5(8)4-2-1-3-6-4/h1-2,4,6H,3H2,(H,7,8)/t4-/m0/s1

Upstream product

• 22264-50-2 1-aminocyclobutane-1-carboxylic acid 
• 84062-30-6 methyl 1-benzyloxycarbonyl-(4S)-phenylseleno-(2S)-pyrrolidinylcarboxylate 
• 634-97-9 pyrrole-2-carboxyl acid 
• 5211-24-5 (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester 

Downstream Products

• 135837-63-7 3,4-dehydro-1-(9-fluorenylmethoxycarbonyl)-L-proline 
• 161813-74-7 (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester 
• 1386459-21-7 (2S,3R,4R)-3-hydroxy-4-methoxy-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 159651-34-0 (1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 159551-90-3 (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 159551-89-0 (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester 

Relevant articles and documents

Oxidative Degradation of Amino Acids and Aminophosphonic Acids by 2,2′-Bipyridine Complexes of Copper(II)

Copper(II)-amino acid (AA) complexes that contain 2,2′-bipyridine (bpy) as supporting ligand were investigated. X-ray structural analysis of three new bpy-based complexes revealed a bidentate coordination of the AAs on the copper(II) centers similar to that proposed for the substrate on the iron(II) center of the 1-aminocyclopropane-1-carboxylic acid oxidase (ACCO). Similar complexes with two aminophosphonic acids (APAs), 1-aminocyclopropane-1-phosphonic acid (ACP) and (1-amino-1-methyl)ethylphosphonic acid (AMEP), were also investigated, and the latter complex was structurally characterized. This structure reveals the bidentate coordination of α-aminophosphonate on the copper(II) ion. The oxidation of the bound amino acids (AAs) and aminophosphonates (APAs), which model the reaction catalyzed by ACCO, was investigated. The complexes react with H2O2 and give oxidation products that were identified by gas chromatography. Reduction of CuII to CuI was detected by UV/Vis spectroscopy upon reaction with H2O2 or ascorbate. This reduction is proposed to be the initial step for the peroxide/copper activation prior to the oxidation of the AA and APA ligands by means of a radical mechanism.

AN IMPROVED SYNTHESIS OF S-3,4-DEHYDROPROLINE

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