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Synthesis of ascorbic-6-14C acid

✍ Scribed by Dale B. Karr; Eugene M. Baker; Bert M. Tolbert

Publisher
John Wiley and Sons
Year
1970
Tongue
French
Weight
604 KB
Volume
6
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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