Formation of L-Threonolactone and Oxalic Acid in the Autoxidation Reaction of L-Ascorbic Acid

K Tadao; M Noriko; O Yuzuru

doi:10.1271/bbb.60.1212

Formation of L-Threonolactone and Oxalic Acid in the Autoxidation Reaction of L-Ascorbic Acid

Biosci Biotechnol Biochem. 1996 Jan;60(7):1212-4. doi: 10.1271/bbb.60.1212.

Authors

K Tadao¹, M Noriko¹, O Yuzuru^{1

2}

Affiliations

¹ a Institute of Environmental Science for Human Life, Ochanomizu University , Bunkyo-ku, Tokyo 112 , Japan.
² b Faculty of Education , Tottori University , Tottori-shi , Tottori 680 , Japan.

PMID: 27299726
DOI: 10.1271/bbb.60.1212

Abstract

The autoxidation of i-ascorbic acid (ASA) in methanol without heavy metal ion catalysts led to the formation of dehydro-L-ascorbic acid (DASA), the main oxidation product, together with minor oxidation products, L-threonoIactone (THL) and oxalic acid (OXA), which had been reported as the major oxidation products in the reaction of ASA with singlet oxygen. The facts suggested the possible involvement of the C(2) oxygen adduct of ASA as an important intermediate compound in this autoxidation process, and it was also supported by the semi-empirical molecular orbital calculation.

Keywords: L-ascorbic acid; L-threonolactone; autoxidation; oxalic acid; oxygen adduct of ascorbic acid.