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Concept
Chemistry of ascorbic acid
Summary
Ascorbic acid is an organic compound with formula C6H8O6, originally called hexuronic acid. It is a white solid, but impure samples can appear yellowish. It dissolves well in water to give mildly acidic solutions. It is a mild reducing agent.
Ascorbic acid exists as two enantiomers (mirror-image isomers), commonly denoted "" (for "levo") and "" (for "dextro"). The isomer is the one most often encountered: it occurs naturally in many foods, and is one form ("vitamer") of vitamin C, an essential nutrient for humans and many animals. Deficiency of vitamin C causes scurvy, formerly a major disease of sailors in long sea voyages. It is used as a food additive and a dietary supplement for its antioxidant properties. The "" form can be made via chemical synthesis but has no significant biological role.
The antiscorbutic properties of certain foods were demonstrated in the 18th century by James Lind. In 1907, Axel Holst and Theodor Frølich discovered that the antiscorbutic factor was a water-soluble chemical substance, distinct from the one that prevented beriberi. Between 1928 and 1932, Albert Szent-Györgyi isolated a candidate for this substance, which he called it "hexuronic acid", first from plants and later from animal adrenal glands. In 1932 Charles Glen King confirmed that it was indeed the antiscorbutic factor.
In 1933, sugar chemist Walter Norman Haworth, working with samples of "hexuronic acid" that Szent-Györgyi had isolated from paprika and sent him in the previous year, deduced the correct structure and optical-isomeric nature of the compound, and in 1934 reported its first synthesis. In reference to the compound's antiscorbutic properties, Haworth and Szent-Györgyi proposed to rename it "a-scorbic acid" for the compound, and later specifically -ascorbic acid. Because of their work, in 1937 two Nobel Prizes: in Chemistry and in Physiology or Medicine were awarded to Haworth and Szent-Györgyi, respectively.
Independently, ascorbic acid was synthetized in 1933 by Tadeusz Reichstein (the Nobel Prize laureate in Physiology or Medicine in 1950).
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