Structure of ascorbic acid and its biological function. Determination of the conformation of ascorbic acid and isoascorbic acid by infrared and ultraviolet investigations.
The four O-H bands of ascorbic acid could be assigned by means of infrared investigations. It could be shown by electron spin resonance and nuclear magnetic resonance measurements that the radical sodium ascorbate is formed by a cyclic side-chain structure resulting in a loss of C(6)-OH and C(3)-OH. The C(2) = C(3) double bond is still maintained as could be shown by infrared and ultraviolet absorption spectroscopy. In the case of complete oxidation of ascorbic acid to dehydroascorbic acid, C(6)-OH is reestablished (indicating the reopening of the furanoid ring), while C(2)-OH as well as the C(2) = C(3) double bond have disappeared due to the deprotonation of C(2)-OH and C(3)-OH. In the case of isoascorbic acid and its radical potassium isoascorbate similar results are obtained with one distinct difference: in the case of isoascorbic acid, C(2)-OH does not appear while C(3)-OH exhibits a shoulder.
D001205:Ascorbic Acid / Q000032:analysis*; D055598:Chemical Phenomena; D002621:Chemistry; D004578:Electron Spin Resonance Spectroscopy; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
C005056:isoascorbic acid; D001205:Ascorbic Acid