Dehydroascorbic acid

This article is about the vitamin C metabolite. For the omega-3 fatty acid also abbreviated as DHA, see Docosahexaenoic acid.
Dehydroascorbic acid
Names
IUPAC name
L-threo-Hexo-2,3-diulosono-1,4-lactone
Systematic IUPAC name
(5R)-5-[(1S)-1,2-Dihydroxyethyl]oxolane-2,3,4-trione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.019 Edit this at Wikidata
UNII
  • InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1 checkY
    Key: SBJKKFFYIZUCET-JLAZNSOCSA-N checkY
  • InChI=1/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1
    Key: SBJKKFFYIZUCET-JLAZNSOCBE
  • O=C1C(=O)C(=O)O[C@@H]1[C@@H](O)CO
Properties
C6H6O6
Molar mass 174.108 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid (vitamin C). It is actively imported into the endoplasmic reticulum of cells via glucose transporters.[1] It is trapped therein by reduction back to ascorbic acid by glutathione and other thiols.[2] The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids.

  1. ^ May, J. M. (1998). "Ascorbate function and metabolism in the human erythrocyte". Frontiers in Bioscience. 3 (4): d1–10. doi:10.2741/a262. PMID 9405334.
  2. ^ Welch, R. W.; Wang, Y.; Crossman, A. Jr.; Park, J. B.; Kirk, K. L.; Levine, M. (1995). "Accumulation of Vitamin C (Ascorbate) and Its Oxidized Metabolite Dehydroascorbic Acid Occurs by Separate Mechanisms". Journal of Biological Chemistry. 270 (21): 12584–12592. doi:10.1074/jbc.270.21.12584. PMID 7759506.