124400-08-4

Usage

Chiral form

3,4-dihydroxy-5-phenyl-2(5H)-furanone

Natural sources

Found in various fruits and vegetables

Aroma and flavor

Sweet, floral, and honey-like

Usage

Natural flavoring agent in food and fragrance industries

Health benefits

Potential antioxidant and anti-inflammatory properties

Biomedical research

Investigated for its potential role in inhibiting biofilm formation in bacteria

Safety

Considered safe for human consumption when used in food products

Upstream product

• 103-67-3 benzyl-methyl-amine 
• 124400-10-8 methyl (S)-(+)-2-phenyl-2-<(phenylmethoxy)acetoxy>-ethanoate 
• 21210-43-5 (S)-Methyl mandelate 
• 124400-12-0 (S)-(+)-4-hydroxy-5-phenyl-3-(phenylmethoxy)-2(5H)-furanone 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure stereogenically labile 4-aryl-2-hydroxytetronic acids from enantiomerically pure silyl-protected mandelaldehydes: Aci-reductone analogues of propionic acid nonsteroidal anti-inflammatory agents

Enantiomerically pure 4-aryl-2-hydroxytetronic acids (3) are expected to be useful tools for determining the mechanism by which corresponding racemic aci-reductones produce their multiple biological effects. Our published synthetic methods for the construction of the title compounds were only useful for the preparation of 4-alkyl analogues owing to facile racemization of the chiral benzylic proton with 4-aryl systems. The synthesis of these enantiomerically pure 4-aryl aci-reductones has now been accomplished in four steps by condensing enantiomerically pure tert-butyldimethylsilyl protected mandelaldehydes 16a-c with the anion of ethyl 1,3-dithiane-2-carboxylate in the presence of pivaloyl chloride to yield protected β,γ-dihydroxy-α-ketobutanoates 22a-c after dithiane hydrolysis. Reaction of 22a-c with tetrabutylammonium fluoride resulted in silyl deprotection, cyclization, and pivaloyl migration to afford 2-(pivaloyloxy)tetronic acids 25a-c. Pivaloate deprotection by either acid hydrolysis or selective hydride reduction produced enantiopure targets 3a-c.

Optically pure 4-aryl-2-hydroxytetronic acids

The present invention relates to a method for synthesis of optically pure stereogenically labile 4-aryl-2-hydroxytetronic acids from an optically pure aidehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase, and additionally as inhibitors of cyclooxygenase and 5-lipoxygenase. The invention further relates to the pharmaceutical use of such.compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis, and in the treatment of various inflammatory pathologies, especially arthritis.

Synthesis of optically pure 4-aryl-2-hydroxytetronic acids

The present invention relates to a method for synthesis of optically pure stereogenically labile 4-aryl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase. the invention further relates to the pharmaceutical use of such compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis.

Efficient synthesis for optically pure stereogenically labile 4-substituted-2-hydroxytetronic acids

The present invention relates to a method for synthesis of optically pure stereogenically labile 4-substituted-2-hydroxytetronic acids from an asymmetric α-hydroxy ester. The chiron approach of the present invention utilizes a non-nucleophilic lithium ami