FORMATION OF A NEW ACETOXY DERIVATIVE OF α-LIPOIC ACID BY MILD REACTION OF β-LIPOIC ACID WITH ACETIC ANHYDRIDE

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1. A reaction of β-lipoic acid with acetic anhydride under mild conditions yielded an unknown product which liberated acetic acid by hydrolysis with NaOH. The product showed almost the same microbiological activity for Streptococcus faecalis 10 C1 and Corynebacterium bovis as α-lipoic acid and β-lipoic acid.2. The results of ultraviolet and infrared spectrophotometry and other tests confirmed the identity of the acetylated product with an acetoxy derivative of α-lipoic acid.3. Deuterium exchange studies revealed the possibility of a proton attracted to the carbon adjacent to the sulfoxide group in β-lipoic acid. A possible steric hindrance caused by the bulky side chain suggests that the acetylated product is 8-C-acetoxy-lipoic acid, the formation mechanism of which is thought to be analogous to that of the Pummerer reaction.4. Associated with the competitive inhibitory effect of 8-C-methyllipoic acid, the results obtained in this experiment would suggest the possible reactivity at carbon 8 of β-lipoic acid which may play an unknown interesting role in biological systems.
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