2-Hydroxyglutaric acid

Base Information

• Chemical Name: 2-Hydroxyglutaric acid
• CAS No.: 2889-31-8
• Molecular Formula: C5H8O5
• Molecular Weight: 148.116
• UNII: RS4M3UYS95
• DSSTox Substance ID: DTXSID40864360
• Nikkaji Number: J527.822H
• Wikipedia: Alpha-Hydroxyglutaric_acid
• Wikidata: Q209412
• NCI Thesaurus Code: C116390
• Metabolomics Workbench ID: 77475
• ChEMBL ID: CHEMBL4870693
• Mol file: 2889-31-8.mol

Synonyms:2-hydroxyglutarate;2-hydroxyglutaric acid;alpha-hydroxyglutarate;alpha-hydroxyglutarate, (D)-isomer;alpha-hydroxyglutarate, (DL)-isomer;alpha-hydroxyglutarate, (L)-isomer;alpha-hydroxyglutarate, disodium salt;D-2-hydroxyglutarate

Chemical Property of 2-Hydroxyglutaric acid

Chemical Property:

• Melting Point: 98-100 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 394.2°Cat760mmHg
• PKA: 3.67±0.10(Predicted)
• Flash Point: 206.4°C
• PSA: 100.49000
• Density: 1.508g/cm³
• LogP: -3.37270
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 148.03717335
• Heavy Atom Count: 10
• Complexity: 141

Purity/Quality:

99%, ^*data from raw suppliers

α-Hydroxyglutaric Acid ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(=O)O)C(C(=O)O)O

Technology Process of 2-Hydroxyglutaric acid

There total 39 articles about 2-Hydroxyglutaric 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: 70.0%

α-ketoglutaric acid (328-50-7) → Glutamic acid (617-65-2,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + 2-hydroxyglutaric acid (2889-31-8,636-67-9)

Guidance literature:

With [Ir(III)Cp*(bpy)(OH₂)](SO₄); ammonium formate; In water; at 80 ℃; for 6h; pH=6.5;

DOI:10.1021/ja031633r

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + propene-1,1,3,3-tetracarboxylic acid tetraethyl ester (49597-05-9) → diethyl 3-hydroxypentanedioate (638-18-6) + 2-hydroxyglutaric acid (2889-31-8,636-67-9) + glutaconic acid (1724-02-3)

Guidance literature:

Reference yield:

1,5-pentanedioic acid (110-94-1) → 2-hydroxyglutaric acid (2889-31-8,636-67-9) + 2-Hydroxybutanoic acid (600-15-7,565-70-8)

Guidance literature:

With bromine; at 115 - 120 ℃; inactive α-oxy-glutaric acid; anschl. mit Zinkcarbonat;

upstream raw materials:

1,5-pentanedioic acid

Glutamic acid

D-Glutamic acid

diethyl 2-bromoglutarate

Downstream raw materials:

glutaconic acid

(+/-)-diethyl 2-hydroxypentandioate

1,5-pentanedioic acid

d,l-α,α'-dibromoglutaric acid

Refernces

• 1、 Ciceri, Daniele,Pierik, Antonio J.,Hartrampf, Guenter,Broeker, Gerd,Speranza, Giovanna,Buckel, Wolfgang,Cornforth, Sir John,Golding, Bernard T.. "Stereochemistry of the methyl group in (R)-3-methylitaconate derived by rearrangement of 2-methylideneglutarate catalysed by a coenzyme B12-dependent mutase". . p. 2550 - 2561. Retrieved 2000.
• 2、 -. "CONVERSION OF 1,2,5,6-HEXANETETROL (HTO) TO TETRAHYDROFURAN DICARBOXYLIC ACID (THFDCA)". Paragraph 46. . Retrieved 2019/11/04.
• 3、 Sergiy, M. Nadtochiy,Xenia, Schafer,Dragony, Fu,Keith, Nehrke,Joshua, Munger,Brookes, Paul S.. "Acidic pH is a metabolic switch for 2-Hydroxyglutarate generation and signaling". . p. 20188 - 20197. Retrieved 2016/11/03.