2-hydroxypentanedioic acid

Base Information

• Chemical Name: 2-hydroxypentanedioic acid
• CAS No.: 40951-21-1
• Molecular Formula: C₅H₆O₅*2Na
• Molecular Weight: 192.079
• Mol file: 40951-21-1.mol

Synonyms:Glutaricacid, 2-hydroxy-, disodium salt (7CI); Pentanedioic acid, 2-hydroxy-, disodiumsalt (9CI); Sodium a-hydroxyglutarate

Chemical Property of 2-hydroxypentanedioic acid

Chemical Property:

• Vapor Pressure: 7.55E-08mmHg at 25°C
• Melting Point: >290?C (dec.)
• Boiling Point: 394.2°Cat760mmHg
• Flash Point: 206.4°C
• PSA: 94.83000
• Density: 1.508g/cm³
• LogP: -0.70330
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly), Water (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-HYDROXYGLUTARIC ACID DISODIUM SALT 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: α-Hydroxyglutaric acid (2-HG) is an α-hydroxy acid. It is metabolized to 2-oxoglutarate by D- and L-2-hydroxyglutarate dehydrogenases, and mutations in these enzymes lead to 2-hydroxyglutaric aciduria, a neurometabolic disorder characterized by increased levels of L-2-hydroxyglutaric acid . 2-HG can also be metabolized from isocitrate by mutated forms of isocitrate dehydrogenase 1 (IDH1) and IDH2. 2-HG is structurally similar to α-ketoglutarate, the product of wild-type isocitrate dehydrogenases, and competitively inhibits α-ketoglutarate-dependent dioxygenases, including histone lysine demethylases and DNA hydroxylases.
• Uses: 2-Hydroxyglutaric acid is a potential inhibitor of glutamate carboxypeptidase.

Technology Process of 2-hydroxypentanedioic acid

There total 2 articles about 2-hydroxypentanedioic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (S)-2-hydroxypentanedioic acid, disodium salt (40951-21-1,55714-86-8,63512-50-5,103404-90-6)

Guidance literature:

L-glutamic acid; With potassium nitrite; sulfuric acid; In water; at -10 ℃;

With sodium hydroxide; Further stages.;

DOI:10.1002/hlca.200790195

Reference yield: 31.43%

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → (S)-2-hydroxypentanedioic acid, disodium salt (40951-21-1,55714-86-8,63512-50-5,103404-90-6)

Guidance literature:

With sodium hydroxide; In water; at 25 ℃; for 2h; pH=10;

DOI:10.7717/peerj.9438

Reference yield: 77.0%

4-nitrobenzyl chloride (100-14-1) + (S)-2-hydroxypentanedioic acid, disodium salt (40951-21-1,55714-86-8,63512-50-5,103404-90-6) → bis(4-nitrobenzyl) 2-hydroxypentanedioate

Guidance literature:

In N,N-dimethyl-formamide; at 120 ℃; for 6h;

DOI:10.1002/hlca.200790195

upstream raw materials:

L-glutamic acid

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

Downstream raw materials:

(R)-5-Oxo-tetrahydro-furan-2-carboxylic acid 4-bromo-phenyl ester

(R)-2-(2-Nitro-benzoyloxy)-pentanedioic acid dimethyl ester

(R)-2-(2,6-Dinitro-benzoyloxy)-pentanedioic acid dimethyl ester

(R)-2-(3,5-Dinitro-benzoyloxy)-pentanedioic acid dimethyl ester

Refernces

• 1、 Heizmann, Gerhard,Pfleiderer, Wolfgang. "Pteridines Part CXVIII. Methanopterin, chemical approach and partial synthesis". . p. 1856 - 1873. Retrieved 2008/03/12.