DL-THREO-BETA-HYDROXYASPARTIC ACID

Base Information

• Chemical Name: DL-THREO-BETA-HYDROXYASPARTIC ACID
• CAS No.: 4294-45-5
• Molecular Formula: C4H7NO5
• Molecular Weight: 149.103
• Hs Code.: 2922509090
• European Community (EC) Number: 224-299-4
• UNII: Z9Q5W0U8VW
• DSSTox Substance ID: DTXSID301017241
• Nikkaji Number: J215.816G
• Wikipedia: 3-Hydroxyaspartic_acid
• Wikidata: Q4634147
• Pharos Ligand ID: 6D753VK9KFQ7
• Metabolomics Workbench ID: 53541
• ChEMBL ID: CHEMBL1231330
• Mol file: 4294-45-5.mol

Synonyms:Asparticacid, 3-hydroxy-, DL-threo- (8CI);DL-Aspartic acid, 3-hydroxy-, threo-;DL-threo-3-Hydroxyaspartic acid;threo-3-Hydroxy-DL-asparticacid;

Chemical Property of DL-THREO-BETA-HYDROXYASPARTIC ACID

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 6.2E-07mmHg at 25°C
• Melting Point: >230 °C
• Refractive Index: 1.583
• Boiling Point: 368.7 °C at 760 mmHg
• PKA: 2.13±0.27(Predicted)
• Flash Point: 176.8 °C
• PSA: 120.85000
• Density: 1.738 g/cm³
• LogP: -1.45590
• Storage Temp.: −20°C
• Solubility.: Aqueous Base (Slightly)
• XLogP3: -4.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 149.03242232
• Heavy Atom Count: 10
• Complexity: 156

Purity/Quality:

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

D,L-threo-b-Hydroxyaspartic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(=O)O)O)(C(=O)O)N
• Isomeric SMILES: [C@H]([C@@H](C(=O)O)O)(C(=O)O)N
• Uses: A glutamate uptake inhibitor L-aspartate beta-carboxylase inhibitor, neurotoxic DL-threo-β-Hydroxyaspartic acid (THA) has been used to block glutamate transport in cannulated sprague dawley rat.

Technology Process of DL-THREO-BETA-HYDROXYASPARTIC ACID

There total 56 articles about DL-THREO-BETA-HYDROXYASPARTIC 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: 87.0%

3-hydroxyaspartic acid (71653-06-0) → L-threo-3-hydroxyaspartic acid (1186-90-9,1860-87-3,4294-45-5,5174-55-0,5753-30-0,6532-76-9,7298-98-8,7298-99-9,16417-36-0,71653-06-0,81601-40-3) + threo-β-hydroxy-D-aspartic acid (1186-90-9,1860-87-3,4294-45-5,5174-55-0,5753-30-0,6532-76-9,7298-98-8,7298-99-9,71653-06-0,81601-40-3,16417-36-0)

Guidance literature:

With L-lysine; In water; for 0.0833333h; Reflux;

DOI:10.1002/anie.201509926

Reference yield: 87.0%

3-hydroxyaspartic acid (71653-06-0) → L-threo-3-hydroxyaspartic acid (1186-90-9,1860-87-3,4294-45-5,5174-55-0,5753-30-0,6532-76-9,7298-98-8,7298-99-9,16417-36-0,71653-06-0,81601-40-3) + threo-β-hydroxy-D-aspartic acid (1186-90-9,1860-87-3,4294-45-5,5174-55-0,5753-30-0,6532-76-9,7298-98-8,7298-99-9,71653-06-0,81601-40-3,16417-36-0)

Guidance literature:

With L-lysine; In water; for 0.0833333h; Reflux;

DOI:10.1002/anie.201509926

Reference yield: 80.0%

DL-threo-β-hydroxyaspartic acid (4294-45-5) → L-threo-3-hydroxyaspartic acid (1186-90-9,1860-87-3,4294-45-5,5174-55-0,5753-30-0,6532-76-9,7298-98-8,7298-99-9,16417-36-0,71653-06-0,81601-40-3)

Guidance literature:

DOI:10.1246/bcsj.56.2994

upstream raw materials:

3-hydroxyaspartic acid

lower-melting inactive 3-chloro-2-hydroxy-succinic acid

sodium glyoxylate

N-(DL-α-Methyl-benzyl)-threo-β-hydroxy-DL-asparaginsaeure

Downstream raw materials:

3-hydroxy-2-oxopropionic acid

Glyoxal

D,L-threo-β-Hydroxyasparaginsaeure-dimethylester

erythro-β-Hydroxy-DL-asparaginsaeuredimethylester

Refernces

• 1、 Hardy, Clifford D.,Butler, Alison. "Ambiguity of NRPS Structure Predictions: Four Bidentate Chelating Groups in the Siderophore Pacifibactin". . p. 990 - 997. Retrieved 2019/03/26.
• 2、 Fu, Haigen,Younes, Sabry H. H.,Saifuddin, Mohammad,Tepper, Pieter G.,Zhang, Jielin,Keller, Erik,Heeres, André,Szymanski, Wiktor,Poelarends, Gerrit J.. "Rapid chemoenzymatic route to glutamate transporter inhibitor l-TFB-TBOA and related amino acids". supporting information. p. 2341 - 2344. Retrieved 2017/03/20.