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Synthesis of ascorbic‐6‐ 14 C acid
Author(s) -
Karr Dale B.,
Baker Eugene M.,
Tolbert Bert M.
Publication year - 1970
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590060207
Subject(s) - ascorbic acid , sorbose , chemistry , yield (engineering) , sorbitol , decomposition , trifluoroacetic acid , dihydroxyacetone , acetone , nuclear chemistry , medicinal chemistry , organic chemistry , fructose , food science , materials science , glycerol , metallurgy
L‐ascorbic‐6‐ 14 C acid with a specific activity of 3.25 μCi/mg was prepared from D‐glucose‐1‐ 14 C in an overall yield of 10 %. Synthetic steps were : glucose to sorbitol, sorbose, diisopropylidene sorbose, potassium diisopropylidene 2‐ketogulonate, 2‐ketogulonic acid and ascorbic acid. In a similar manner L‐ascorbic‐5‐ 14 C acid was prepared from D‐glucose‐2‐ 14 C. Conversion of 2‐keto‐L‐gulonic acid to ascorbic acid was done in 0.5 M trifluoroacetic acid solution at 115°C with 2 % acetone as a decomposition inhibitor. The reaction probably proceeds via an enediol intermediate.