(2R)-2-hydroxypentanedioic acid

Base Information

• Chemical Name: (2R)-2-hydroxypentanedioic acid
• CAS No.: 13095-47-1
• Molecular Formula: C5H8O5
• Molecular Weight: 148.116
• UNII: R9UK2G8Y79
• DSSTox Substance ID: DTXSID80897218
• Nikkaji Number: J1.280.876C
• Wikidata: Q27104222
• NCI Thesaurus Code: C179314
• Metabolomics Workbench ID: 37330
• ChEMBL ID: CHEMBL1614745
• Mol file: 13095-47-1.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 (2R)-2-hydroxypentanedioic acid

Chemical Property:

• Vapor Pressure: 7.55E-08mmHg at 25°C
• Refractive Index: 1.519
• Boiling Point: 394.2 °C at 760 mmHg
• PKA: 3.67±0.10(Predicted)
• Flash Point: 206.4 °C
• PSA: 94.83000
• Density: 1.508 g/cm³
• LogP: -0.70330
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• 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

(R)-2-Hydroxypentanedioicacid 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
• Isomeric SMILES: C(CC(=O)O)[C@H](C(=O)O)O
• Uses: 2-Hydroxypentanedioic Acid is a mouse metabolite

Technology Process of (2R)-2-hydroxypentanedioic acid

There total 16 articles about (2R)-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:

D-Glucose (2280-44-6) → α-ketoglutaric acid (328-50-7) + (2R)-hydroxyglutaric acid (13095-47-1,636-67-9) + 2-oxo-propionic acid (127-17-3)

Guidance literature:

With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate; In water; at 26 ℃; for 144h; Yield given. Yields of byproduct given; Yarrowia lipolytica R-2;

Reference yield:

pentadecane (629-62-9) → α-ketoglutaric acid (328-50-7) + (2R)-hydroxyglutaric acid (13095-47-1,636-67-9) + 2-oxo-propionic acid (127-17-3)

Guidance literature:

With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate; In water; at 26 ℃; for 144h; Yield given. Yields of byproduct given; Yarrowia lipolytica IFO 1659;

Reference yield:

Hexadecane (544-76-3) → α-ketoglutaric acid (328-50-7) + (2R)-hydroxyglutaric acid (13095-47-1,636-67-9) + 2-oxo-propionic acid (127-17-3)

Guidance literature:

With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate; In water; at 26 ℃; for 144h; Yield given. Yields of byproduct given; Yarrowia lipolytica IFO 1659;

upstream raw materials:

D-Glutamic acid

(-)(S)-2-chloro-glutaric acid

4-formyl-4-oxobutanoic acid

D-Glucose

Downstream raw materials:

α-ketoglutaric acid

(S)-5-tosyloxypentan-4-olide

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Refernces

• 1、 Wu, Fangrui,Jiang, Hong,Zheng, Baisong,Kogiso, Mari,Yao, Yuan,Zhou, Chao,Li, Xiao-Nan,Song, Yongcheng. "Inhibition of Cancer-Associated Mutant Isocitrate Dehydrogenases by 2-Thiohydantoin Compounds". . p. 6899 - 6908. Retrieved 2015/09/22.
• 2、 Rustoy, Eduardo M.,Pereyra, Elba N.,Moreno, Silvia,Baldessari, Alicia. "Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid". . p. 3763 - 3768. Retrieved 2007/10/03.