16635-19-1

Basic information

• Product Name: Benzoic acid, 4-hydroxy-3-[3-(4-methoxyphenyl)-1-oxo-2-propenyl]-
• CAS NO: 16635-19-1
• Molecular Formula: C17H14O5
• Molecular Weight: 298.295
• Mol File: 16635-19-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-hydroxy-3-[3-(4-methoxyphenyl)-1-oxo-2-propenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-hydroxy-3-[3-(4-methoxyphenyl)-1-oxo-2-propenyl]-(16635-19-1)
• EPA Substance Registry System: Benzoic acid, 4-hydroxy-3-[3-(4-methoxyphenyl)-1-oxo-2-propenyl]-(16635-19-1)

Safety Data

• Hazardous Substances Data: 16635-19-1(Hazardous Substances Data)

Upstream product

• 16357-40-7 3-acetyl-4-hydroxybenzoic acid 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 145602-99-9 2-(4-Methoxyphenyl)-4-oxo-chroman-6-carbonsaeure 

Relevant articles and documents

Chalcone-5'- and flavanone-6-carboxylic acids

While 3-acetyl-4-hydroxybenzoic acid (1) reacts with the aldehydes 2a-c by Claisen-Schmidt reaction to the chalcone carboxylic acids 3a-c, the parent reaction with 2d is not successful. The chalcones 3a-b but not 3c can be transformed to the isomeric flavanone carboxylic acids 4a-b by common methods. 3c in MeOH/H2SO4 forms the methyl flavanone-carboxylate 4c which does not lead to the carboxylic acid of 4c by acid hydrolysis. Instead, 4c is split to chalcone carboxylic acid 3c quantitatively. 4'-nitroflavanone-6-carboxylic acid (4d) can only be obtained by condensation of the diketones 5a-h with 4-nitrobenzaldehyd (2d) as the methyl carboxylate, too. Here, instead of the expected α-aroylchalcone 6 or its tautomeric 3-aroylflavanone derivative, 4d is formed by hydrolytic removal of the arylcarboxylic acids 7a-b. The alkaline hydrolysis of compound 4d does not quantitatively afford the chalconecarboxylic acid 3d but results in destruction to a complex mixture of several compounds.