608-41-3

Basic information

• Product Name: 2-hydroxy-3-methylbutanedioic acid
• Synonyms: (R,S)-beta-Methylmalic acid; (R,S)-b-Methylmalic acid
• CAS NO: 608-41-3
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.114
• Mol File: 608-41-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 123 °C
• Boiling Point: 295.2°C at 760 mmHg
• Flash Point: 146.6°C
• Density: 1.502g/cm³
• Vapor Pressure: 0.000161mmHg at 25°C
• Refractive Index: 1.516
• PKA: 3.65±0.34(Predicted)
• CAS DataBase Reference: 2-hydroxy-3-methylbutanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-3-methylbutanedioic acid(608-41-3)
• EPA Substance Registry System: 2-hydroxy-3-methylbutanedioic acid(608-41-3)

Safety Data

• Hazardous Substances Data: 608-41-3(Hazardous Substances Data)

Usage

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).

Upstream product

• 100806-42-6 (E)-(2S,3S)-3-Hydroxy-2-methyl-hex-4-enoic acid 
• 113564-09-3 (E,2R^*,3S^*)-3-hydroxy-2-methyl-4-hexenoic acid 
• 642-92-2 D,L-threo-β-methylaspartic acid 
• 759-65-9 diethyl oxalpropionate 
• 93504-92-8 2-hydroxy-3-methylbutanedioic acid diethyl ester 
• 63921-06-2 3-methyl-2-oxo-butane-1,4-dioic acid dimethyl ester 

Downstream Products

• 85199-56-0 2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 89497-03-0 (2R,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 85249-22-5 (2S,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 50460-80-5 dimethyl 2-hydroxy-3-methylbutane-1,4-dioate 
• 50460-80-5 dimethyl 2-hydroxy-3-methylbutane-1,4-dioate 
• 50460-80-5 (2S,3R)-2-Hydroxy-3-methylbernsteinsaeure-dimethylester 
• 5380-37-0 (2S,3R)-2-Hydroxy-3-methyl-succinic acid 
• 5380-36-9 (+)-erythro-3-Methylaepfelsaeure 
• 5380-36-9 (-)-threo-3-Methylaepfelsaeure 
• 5380-37-0 (2S,3S)-2-Hydroxy-3-methyl-succinic acid 
• 65-71-4 thymin 
• 15981-91-6 2-amino-5-methylpyrimidin-4-one 

Relevant articles and documents

On the Stereochemistry of E'- and E''-Reactions

The decarboxylative E'-dehydration of β,γ-unsaturated δ-hydroxy acids with DMF-dineopentylacetal shows SYN-faciality irrespective of whether the conformation of the hydroxy group relative to the double bond axis is anticlinal or synclinal.

The Use of Microorganisms in Organic Synthesis. II. Microbiological Asymmetric Reduction of 2-Methyl-3-oxosuccinates

In order to synthesize four optically active methyl 2-methylmalates (10-13), microbiological asymmetric reduction of the corresponding dimethyl 2-methyl-3-oxosuccinate (9) was carried out.The β-keto diester 9 was found to be reduced by fermenting baker's yeast (Saccharomyces cerevisiae) and Candida albicans to afford a mixture of the (2R,3R)-isomer 10 and the (2S,3R)-isomer 11.Although the optical purity of 10 produced by Candida albicans was reasonably high (95percent e.e.), optical yields of other products were unexpectedly low.However, identification of the four possible isomers 14-17 was found to be easily carried out by means of nuclear magnetic resonance spectroscopy.Keywords - α-methyl-β-keto ester; methylmalate; asymmetric reduction; microbiological reduction; yeast; methyl 2-methylmalate