3685-52-7

Usage

Uses

Used in Food Industry:
3-(3-Furyl)-DL-alanine is used as a flavoring agent for enhancing the taste and aroma of certain food products, contributing to a more appealing sensory experience for consumers.
Used in Pharmaceutical Development:
3-(3-Furyl)-DL-alanine is used as a potential therapeutic agent for the treatment of various health conditions such as diabetes, obesity, and inflammation. Its antioxidant properties and potential to modulate biological pathways make it a promising candidate for the development of new pharmaceuticals.
Used in Antioxidant Applications:
3-(3-Furyl)-DL-alanine is used as an antioxidant in various formulations to protect against oxidative stress and related health issues, thereby contributing to overall health and well-being.

Upstream product

• 498-60-2 furan-3-carboxaldehyde 
• 14497-29-1 3-(chloromethyl)furan 
• 4412-91-3 furan-3-methanol 
• 128941-45-7 2-formylamino-2-furan-3-yl-methyl-malonic acid 
• 128941-43-5 2-formylamino-2-furan-3-yl-methyl-malonic acid diethyl ester 
• 128941-47-9 (rac)-2-formylamino-3-furan-3-yl-propionic acid 
• 811860-60-3 3-(furan-3-yl)-2-(hydroxyimino)propanoic acid 

Relevant academic research and scientific papers

The interaction of heteroaryl-acrylates and alanines with phenylalanine ammonia-lyase from parsley

Acrylic acids and alanines substituted with heteroaryl groups at the β-position were synthesized and spectroscopically characterized (UV, HRMS, 1H NMR, and 13C NMR spectroscopy). The heteroaryl groups were furanyl, thiophenyl, benzofuranyl, and benzothiophenyl and contained the alanyl side chains either at the 2- or 3-positions. While the former are good substrates for phenylalanine ammonia lyase (PAL), the latter compounds are inhibitors. Exceptions are thiophen-3-yl-alanine, a moderate substrate and furan-3-yl-alanine, which is inert. Possible reasons for these exceptions are discussed. Starting from racemic het eroaryl-2-alanines their D-enantiomers were prepared by using a stereodestructive procedure. From the heteroaryl-2- acrylates, the L-enantiomers of the heteroaryl-2-alanines were prepared at high ammonia concentration. These results can be best explained by a Friedel - Crafts-type electrophilic attack at the aromatic part of the substrates as the initial step of the PAL reaction.

Improved preparation of racemic 2-amino-3-(heteroaryl)propanoic acids and related compounds containing a furan or thiophene nucleus

Racemic 2-amino-3-(heteroaryl)propanoic acids (1), mostly with a furan or thiophene nucleus as a heteroaryl group, were synthesized in 48-94% yield by the reduction of 3-(heteroaryl)-2-(hydroxyimino)propanoic acids (5) with zinc dust and formic acid in the presence of a catalytic amount of iron dust at 60°C for 2 h. Under these conditions, unfavorable hydrogenolysis of bromine on the thiophene nucleus does not occur. Traditional Nformylation of the prepared 3-(heteroaryl)alanine (1) with a mixture of formic acid and acetic anhydride afforded 2-(formylamino)-3-(heteroaryl)propanoic acids (6) in 51-95% yield.