64769-66-0

Basic information

• Product Name: L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID
• Synonyms: L-TRANS-4-CARBOXY-L-PROLINE;L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID;L-TRANS-2,4-PDC;TRANS-4-CARBOXY-L-PROLINE;2,4-Pyrrolidinedicarboxylicacid,(2S,4R)-(9CI);Zinc03796127;(2S,4R)-pyrrolidine-2,4-dicarboxylic acid
• CAS NO: 64769-66-0
• Molecular Formula: C₆H₉NO₄
• Molecular Weight: 159.14
• Product Categories: PYRROLE;Glutamate receptor
• Mol File: 64769-66-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 355.3 °C at 760 mmHg
• Flash Point: 168.7 °C
• Appearance: /
• Density: 1.456 g/cm³
• Vapor Pressure: 5.28E-06mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Store at RT
• Solubility: Water (Slightly)
• CAS DataBase Reference: L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID(64769-66-0)
• EPA Substance Registry System: L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID(64769-66-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 64769-66-0(Hazardous Substances Data)

Usage

Uses

L-trans-Pyrrolidine-2,4-dicarboxylic Acid is an inhibitor of the glutamate transporter EAAT.

Biological Activity

Potent, competitive, transportable EAAT1-4 inhibitor/non-transportable EAAT5 inhibitor. Also available as part of the Excitatory Amino Acid Transporter Inhibitor Tocriset? .

InChI:InChI=1/C6H9NO4/c8-5(9)3-1-4(6(10)11)7-2-3/h3-4,7H,1-2H2,(H,8,9)(H,10,11)/t3-,4+/m1/s1

Upstream product

• 130830-74-9 N-(benzyloxycarbonyl)-trans-4-carboxy-L-proline 
• 64750-03-4 (2S,4R)-4-methoxycarbonylproline methyl ester 
• 220047-57-4 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine 
• 212266-75-6 (2S,4R)-1-tert-butoxycarbonyl-2-hydroxymethyl-4-hydroxymethylpyrrolidine 
• 212266-76-7 1-(tert-butyl) 2,4-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate 
• 212266-74-5 (2R,4R)-3-Benzenesulfonyl-2,4-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 220047-97-2 (2R,3S,4R)-3-Benzenesulfonyl-2,4-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 212266-72-3 ((3R,5R)-4-Benzenesulfonyl-1-benzyl-5-benzyloxymethyl-pyrrolidin-3-yl)-methanol 
• 220047-66-5 ((3R,4S,5R)-4-Benzenesulfonyl-1-benzyl-5-benzyloxymethyl-pyrrolidin-3-yl)-methanol 
• 212266-71-2 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-(S)-1-oxiranylmethyl-amine 
• 212266-69-8 (S)-3-[((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-amino]-propane-1,2-diol 
• 212266-68-7 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine 
• 130930-26-6 N-(benzyloxycarbonyl)-cis-4-hydroxy-L-proline ethyl ester 
• 130830-66-9 N-(benzyloxycarbonyl)-trans-4-cyano-L-proline ethyl ester 

Relevant articles and documents

Asymmetric synthesis of 4-substituted prolines as conformationally constrained amino acid analogues

Treatment of readily available chiral building block 1 with (2R)-2,3-O- isopropylideneglyceraldehyde (5) provides a new route for asymmetric synthesis of 2,4-disubstituted pyrrolidines. Several proline-amino acid chimeras: proline-leucine, proline-lysine, proline-arginine and proline- glutamic acid, are synthesized in highly diastereomerically pure forms.

Stereospecific synthesis of cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5-piperidinedicarboxylic acid

Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5- piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S,4S)-(-)-2,4-pyrrolidinedicarboxylic acid and (2R,4R)-(+)-2,4- pyrrolidinedicarboxylic acid were synthesized from (1S,4R)-(+)-2- azabicyclo[2.2.1]hept-5-en-3-one and (1R,4S)-(-)-2-azabicyclo[2.2.1]hept-5- en-3-one, respectively.

Synthesis of two cyclic analogs of glutamic acid: cis- and trans-pyrrolidine-2,4-dicarboxylic acids

The tosyl ester 2 of tetraethyl 1-acetamido-4-hydroxybutane- 1,1,3,3-tetracarboxylate gave 4-methylene glutammic acid in 90% yield by refluxing with concentrated HC1. Treatment of 2 with NaOEt, then with refluxing concentrated HC1 gave a 54% yield of cis