2-Hydroxy-3-methylbutanedioic acid

Base Information

• Chemical Name: 2-Hydroxy-3-methylbutanedioic acid
• CAS No.: 608-41-3
• Molecular Formula: C5H6O5-2
• Molecular Weight: 148.116
• European Community (EC) Number: 809-241-3
• DSSTox Substance ID: DTXSID80976274
• Nikkaji Number: J94.860H
• Wikidata: Q27109877
• Mol file: 608-41-3.mol

Synonyms:beta-methylmalate

Chemical Property of 2-Hydroxy-3-methylbutanedioic acid

Chemical Property:

• Vapor Pressure: 0.000161mmHg at 25°C
• Melting Point: 123 °C
• Boiling Point: 295.2°Cat760mmHg
• PKA: 3.65±0.34(Predicted)
• Flash Point: 146.6°C
• PSA: 94.83000
• Density: g/cm³
• LogP: -0.84740
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 148.03717335
• Heavy Atom Count: 10
• Complexity: 152

Purity/Quality:

99%, ^*data from raw suppliers

2-Hydroxy-3-methyl-butanedioicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)O)O)C(=O)O
• Uses: 2-Hydroxy-3-methyl-butanedioic Acid is used as a sole C source when metabolized by soil bacterium; Also, it is an intermediate used in the synthesis of 5-Methyl-2’-deoxy Cytidine-13C,15N2 (M295904), which is an isotopic analog of 5-Methyl-2’-deoxy Cytidine (M295900), a Cytidine (C998300) analog and also an isostere of Thymidine (T412000).

Technology Process of 2-Hydroxy-3-methylbutanedioic acid

There total 9 articles about 2-Hydroxy-3-methylbutanedioic 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:

2-hydroxy-3-methylbutanedioic acid diethyl ester (93504-92-8) → (2S,3S)-2-Hydroxy-3-methyl-succinic acid (608-41-3,13398-38-4,13398-39-5,13398-40-8,13398-41-9,13398-42-0,34017-12-4,56272-29-8,61391-24-0,85026-06-8,5380-37-0) + erythro-2-hydroxy-3-methylbutane-1,4-dioic acid (608-41-3,13398-38-4,13398-39-5,13398-40-8,13398-41-9,13398-42-0,34017-12-4,56272-29-8,61391-24-0,85026-06-8,5380-36-9,5380-37-0)

Guidance literature:

With hydrogenchloride; In water; for 6h; Yield given. Yields of byproduct given; Heating;

Reference yield:

2-hydroxy-3-methylbutanedioic acid diethyl ester (93504-92-8) → (2S,3S)-2-Hydroxy-3-methyl-succinic acid (608-41-3,13398-38-4,13398-39-5,13398-40-8,13398-41-9,13398-42-0,34017-12-4,56272-29-8,61391-24-0,85026-06-8,5380-37-0) + erythro-2-hydroxy-3-methylbutane-1,4-dioic acid (608-41-3,13398-38-4,13398-39-5,13398-40-8,13398-41-9,13398-42-0,34017-12-4,56272-29-8,61391-24-0,85026-06-8,5380-36-9,5380-37-0)

Guidance literature:

With hydrogenchloride; In water; for 6h; Yield given. Yields of byproduct given; Heating;

Reference yield:

D,L-threo-β-methylaspartic acid (642-92-2,1114-07-4,2955-50-2,4846-45-1,5941-19-5,6061-13-8,6667-60-3,7298-96-6,31571-69-4,86562-29-0,121570-10-3,127001-58-5) → (2S,3S)-2-Hydroxy-3-methyl-succinic acid (608-41-3,13398-38-4,13398-39-5,13398-40-8,13398-41-9,13398-42-0,34017-12-4,56272-29-8,61391-24-0,85026-06-8,5380-37-0)

Guidance literature:

With hydrogenchloride; sodium nitrite;

DOI:10.1246/bcsj.39.1818

upstream raw materials:

(E)-(2S,3S)-3-Hydroxy-2-methyl-hex-4-enoic acid

(E,2R^*,3S^*)-3-hydroxy-2-methyl-4-hexenoic acid

D,L-threo-β-methylaspartic acid

diethyl oxalpropionate

Downstream raw materials:

2-amino-5-methylpyrimidin-4-one

thymin

(2S,3R)-2-Hydroxy-3-methylbernsteinsaeure-dimethylester

dimethyl 2-hydroxy-3-methylbutane-1,4-dioate

Refernces

• 1、 Bhat, K. S.,Dixit, K. N.,Rao, A. S.. "Synthesis of erythro-2-Hydroxy-3-methylbutane-1,4-dioic Acid". . p. 509 - 512. Retrieved 2007/10/02.