140696-23-7

Basic information

• Product Name: (S)-2-hydroxy-4-phenyl-3-butenoic acid
• Synonyms: (S)-2-hydroxy-4-phenyl-3-butenoic acid
• CAS NO: 140696-23-7
• Molecular Weight: 178.188
• Mol File: 140696-23-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-2-hydroxy-4-phenyl-3-butenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-hydroxy-4-phenyl-3-butenoic acid(140696-23-7)
• EPA Substance Registry System: (S)-2-hydroxy-4-phenyl-3-butenoic acid(140696-23-7)

Safety Data

• Hazardous Substances Data: 140696-23-7(Hazardous Substances Data)

Upstream product

• 140653-89-0 (E)-benzylideneglyoxylic acid potassium salt 
• 3483-12-3 diothiothreitol 
• 129029-61-4 2-hydroxy-4-phenylbut-3-enoic acid 
• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 866251-36-7 (S)-2-acetoxy-4-phenyl-3-butenoic acid 
• 866251-33-4 (+/-)-2-acetoxy-4-phenyl-3-butenoic acid 

Downstream Products

• 99058-09-0 (2R,3S,4R)-3,4-dibromo-2-hydroxy-4-phenyl-butyric acid 
• 115016-95-0 (S)-2-hydroxy-4-phenylbutanoic acid 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 140632-55-9 (R)-(E)-2-hydroxy-4-phenyl-3-butenoic acid 
• 129029-61-4 2-hydroxy-4-phenylbut-3-enoic acid 

Relevant articles and documents

Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids

A challenging direct asymmetric hydrogenation of (E)-2-oxo-4-arylbut-3- enoic acids to give 2-hydroxy-4-arylbutanoic acids (85.4-91.8% ee) was achieved with a Ru catalyst based on SunPhos as the chiral ligand. Further investigation of the reaction revealed that partial isomerization of 2-hydroxy-4-arylbutenoic acids was involved in the hydrogenation process. Employing the reaction conditions to the hydrogenation of 2-oxo-4-phenylbutanoic acid resulted in better enantioselectivity (91.8% ee) and efficiency (TON = 2000, TOF = 200 h-1), which offers a useful method for the synthesis of a common intermediate for ACE inhibitors.

Synthesis of homochiral 2-hydroxy acids

A process for the production of a homochiral 2-hydroxy carboxylic acid or salt thereof corresponding to general formula (I), wherein R represents one of formulae (II), (III), (IV), (V), wherein R' represents straight- or branched-chain alkyl or phenyl opt