5837-73-0

Basic information

• Product Name: DL-2-HYDROXY-3-BUTENOIC ACID METHYL ESTER
• Synonyms: DL-2-HYDROXY-3-BUTENOIC ACID METHYL ESTER;METHYL DL-2-HYDROXY-3-BUTENOATE;2-HYDROXY-3-BUTENOIC ACID METHYL ESTER 96+%;METHYL 2-HYDROXY BUT-3-ENOATE;Methyl DL-2-Hydroxy-3-butenoate
• CAS NO: 5837-73-0
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.12
• Mol File: 5837-73-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 64°C 10mm
• Flash Point: 64.4°C
• Appearance: /
• Density: 1,11 g/cm3
• Vapor Pressure: 0.539mmHg at 25°C
• Refractive Index: 1.4370-1.4420
• PKA: 12.26±0.20(Predicted)
• CAS DataBase Reference: DL-2-HYDROXY-3-BUTENOIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-HYDROXY-3-BUTENOIC ACID METHYL ESTER(5837-73-0)
• EPA Substance Registry System: DL-2-HYDROXY-3-BUTENOIC ACID METHYL ESTER(5837-73-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 5837-73-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 2908, 1983 DOI: 10.1021/ja00347a071

InChI:InChI=1/C5H8O3/c1-3-4(6)5(7)8-2/h3-4,6H,1H2,2H3

Upstream product

• 67-56-1 methanol 
• 57-48-7 D-Fructose 
• 533-50-6 L-erythrulose 
• 57-50-1 Sucrose 
• 141-46-8 Glycolaldehyde 
• 59-23-4 D-Galactose 
• 50-99-7 D-glucose 
• 1114-34-7 D-lyxose 
• 50-69-1 D-ribose 
• 10323-20-3 D-Arabinose 
• 3458-28-4 D-Mannose 
• 58-86-6 D-xylose 
• 57-48-7 fructose 

Downstream Products

• 1117-71-1 methyl-4-bromo-2-butenoate 
• 137207-24-0 Methyl α-bromoacrylate 
• 573713-67-4 4-(1-formyl-cyclohexyl)-but-2-enoic acid methyl ester 
• 1335133-99-7 C₁₂H₁₄O₄S 
• 74-85-1 ethene 
• 499-75-2 carvacrol 
• 600-18-0 2-Oxobutyric acid 
• 600-17-9 vinyl glycolic acid 

Relevant articles and documents

PROCESS FOR THE CONVERSION OF SUGARS TO LACTIC ACID AND 2-HYDROXY-3-BUTENOIC ACID OR ESTERS THEREOF COMPRISING A METALLO-SILICATE MATERIAL AND A METAL ION

The present invention regards metallo-silicate materials comprising a metal ion selected from one or more of the group consisting of potassium ions, sodium ions, lithium ions, rubidium ions and caesium ions. The materials are useful preparing lactic acid and 2-hydroxy-3-butenoic acid or esters thereof from a sugar.

Sn-Beta catalysed conversion of hemicellulosic sugars

Conversions of various pentoses and hexoses into methyl lactate has been demonstrated for the Sn-Beta catalyst. It is found that pentoses are converted to methyl lactate in slightly lower yields (～40%) than what is obtained for hexoses (～50%), but higher yields of glycolaldehyde dimethyl acetal are observed for the pentoses. This finding is in accordance to a reaction pathway that involves the retro aldol condensation of the sugars to form a triose and glycolaldehyde for the pentoses, and two trioses for hexoses. When reacting glycolaldehyde (formally a C2-sugar) in the presence of Sn-Beta, aldol condensation occurs, leading to the formation of methyl lactate, methyl vinylglycolate and methyl 2-hydroxy-4-methoxybutanoate. In contrast, when converting the sugars in water at low temperatures (100 °C), Sn-Beta catalyses the isomerisation of sugars (ketose-aldose epimers), rather than the formation of lactates. The Royal Society of Chemistry 2012.

ZEOLITE-CATALYZED PREPARATION OF ALPHA-HYDROXY CARBOXYLIC ACIDS AND ESTERS THEREOF

A process for the production of lactic acid and 2-hydroxy-3-butenoic acid or esters thereof by conversion of glucose, fructose, sucrose, xylose and glycolaldehyde dissolved in a solvent in presence of a solid Lewis acidic catalyst.