Synthesis and antiscorbutic activity of vitamin C analogue: L-threo-hex-2-enaro-1,4-lactone ethyl ester in the guinea pig.
L-threo-hex-2-enaro-1,4-lactone ethyl ester (II) was synthesized by the modified Fisher's esterification and its sodium salt was obtained almost quantitatively. Confirmation of the compound was made by elementary analysis, as well as IR, UV, MS and NMR spectra. The antiscorbutic activity was compared to that of ascorbic acid and the result showed that (II) did not have Vitamin C activity. The results of this investigation indicate that a close relationship exists between the chemical structure of the C-6 position of ascorbic acid analogues and the development of vitamin C activity.
Kasai
T
T
Department of Food Science, Faculty of Bioindustry, Tokyo University of Agriculture, Hokkaido, Japan.
Inoue
K
K
Komatsubara
H
H
Tsujimura
M
M
D000469:Alkaline Phosphatase / Q000097:blood; D000818:Animals; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000493:pharmacokinetics / Q000494:pharmacology / Q000627:therapeutic use*; D001835:Body Weight / Q000187:drug effects; D001923:Brain Chemistry; D006168:Guinea Pigs; D006909:Hydroxyproline / Q000097:blood; D007668:Kidney / Q000737:chemistry; D008099:Liver / Q000737:chemistry; D008297:Male; D012614:Scurvy / Q000188:drug therapy*
C085694:hex-2-enaro-1,4-lactone ethyl ester; D000469:Alkaline Phosphatase; D001205:Ascorbic Acid; D006909:Hydroxyproline