Synthesis of ascorbic acid from lactose

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound

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435138, 435190, C12N 904, C12P 758, C12P 760

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active

042594430

ABSTRACT:
A method of synthesizing vitamin C (ascorbic acid) directly from the hydrolysis products of lactose. Lactose, economically obtained from whey, undergoes hydrolysis with a warm aqueous slurry of lactase to produce D-galactose and D-glucose. Preparing the methyl glycosides of these two sugars protects a labile C-O linkage during the oxidation of the sugars to D-galacturonic acid and D-glucuronic acid. The mixture of these acids, after the removal of the methyl group through hydrolysis, undergoes reduction with gaseous hydrogen in the presence of an Adams catalyst or Raney nickel to produce a mixture of L-gulonic acid and L-galactonic acid. Removing the water from these acids forces their conversion into the corresponding lactones. Because of the applicable rate constants, adding water to the lactones does not result in their rapid reconversion to the acids. Accordingly, they can then undergo oxidation, in the presence of an enzyme obtained from pea seeds, to L-ascorbic acid.

REFERENCES:
patent: 2265121 (1941-12-01), Reichstein
patent: 2462251 (1949-02-01), Bassford et al.
patent: 2606186 (1952-08-01), Dean et al.
patent: 2681858 (1954-06-01), Stimpson
patent: 2917435 (1959-12-01), Perlman
patent: 4048018 (1977-09-01), Coughlin et al.
Cadotte et al., J. Amer. Chem. Soc., 74, 1501, (1952).

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