140632-55-9

Basic information

• Product Name: (R)-(E)-2-hydroxy-4-phenyl-3-butenoic acid
• Synonyms: (R)-(E)-2-hydroxy-4-phenyl-3-butenoic acid
• CAS NO: 140632-55-9
• Molecular Weight: 178.188
• Mol File: 140632-55-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (R)-(E)-2-hydroxy-4-phenyl-3-butenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(E)-2-hydroxy-4-phenyl-3-butenoic acid(140632-55-9)
• EPA Substance Registry System: (R)-(E)-2-hydroxy-4-phenyl-3-butenoic acid(140632-55-9)

Safety Data

• Hazardous Substances Data: 140632-55-9(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 129029-61-4 2-hydroxy-4-phenylbut-3-enoic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 140653-89-0 (E)-benzylideneglyoxylic acid potassium salt 
• 100-52-7 benzaldehyde 
• 117306-12-4 (2R,3E)-2-hydroxy-4-phenyl-3-butenenitrile 
• 866251-33-4 (+/-)-2-acetoxy-4-phenyl-3-butenoic acid 
• 140696-23-7 (S)-2-hydroxy-4-phenyl-3-butenoic acid 
• 866251-39-0 (R)-2-acetoxy-4-phenyl-3-butenoic acid 
• 107969-82-4 (2R)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid methyl ester 

Downstream Products

• 129029-61-4 2-hydroxy-4-phenylbut-3-enoic acid 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 866251-36-7 (S)-2-acetoxy-4-phenyl-3-butenoic acid 
• 866251-39-0 (R)-2-acetoxy-4-phenyl-3-butenoic acid 
• 1346260-93-2 C₁₅H₁₉NO₄ 
• 1346260-91-0 (R)-3-(2-acetoxy-4-phenylbut-3-enoylamino)propionic acid 
• 85254-48-4 (2R,3S,4R)-2,3-dihydroxy-4-phenyl-γ-butyrolactone 
• 85254-48-4 (2R,3R,4S)-2,3-dihydroxy-4-phenyl-γ-butyrolactone 
• 140479-61-4 (R)-2-(t-butyldimethylsiloxy)-4-phenyl-3-butenoic acid methylester 
• 140479-81-8 (2S)-5-(1',2'-dibromo-2'-phenylethenyl)-1,3-dioxolanone-4 
• 140479-80-7 (2S,3R,4S)-2-hydroxy-3,4-dibromo-4-phenyl-butanoic acid methylester 
• 99058-09-0 (2S,3R,4S)-2-hydroxy-3,4-dibromo-4-phenyl-butanoic acid 
• 140479-76-1 (2S,3R,4S)-2-hydroxy-3-iodo-4-phenyl-γ-butyrolactone 
• 140479-71-6 (2S,3R,4S)-2-hydroxy-3-bromo-4-phenyl-γ-butyrolactone 

Relevant articles and documents

Structure and absolute configuration of new acidic metabolites from Stachys ehrenbergii

Two novel metabolites have been isolated from the aerial parts of Stachys ehrenberiigii. Their structures and stereochemistry were elucidated using a combination of 13C and 1H homo and heteronuclear 2D NMR experiments and mass analysis. The development of an enantioselective synthesis of 3-(2′-acetoxy-4-phenylbut-3′-enoylamino)propionic acid allowed to confirm the structure and assign the (R) absolute configuration at C-2′ of the natural product.

The substrate spectrum of mandelate racemase: Minimum structural requirements for substrates and substrate model

Mandelate racemase (EC 5.1.2.2) is one of the few biochemically well-characterized racemases. The remarkable stability of this cofactor-independent enzyme and its broad substrate tolerance make it an ideal candidate for the racemization of non-natural α-hydroxycarboxylic acids under physiological reaction conditions to be applied in deracemization protocols in connection with a kinetic resolution step. This review summarizes all aspects of mandelate racemase relevant for the application of this enzyme in preparative-scale biotransformations with special emphasis on its substrate tolerance. Collection and evaluation of substrate structure-activity data led to a set of general guidelines, which were used as basis for the construction of a general substrate model, which allows a quick estimation of the expected activity for a given substrate.

Enzymatic resolution of 2-hydroxy-4-phenylbutanoic acid and 2-hydroxy-4-phenylbutenoic acid

Racemic 2-hydroxy-4-phenylbutanoic acid and 2-hydroxy-4-phenyl-butenoic acid have been resolved using a lipase. In each case, the (R)-2-hydroxy and the (S)-2-acetoxy acids were isolated with high enantiomeric excess and yield.