Record Information
public_id FDB021459
Chemical Information
name L-Dehydroascorbic acid
description Widespread in plants, as oxidn. prod. of Ascorbic acid BWR05-S. Formed reversibly in vivo from ascorbic acid and shows similar vitamin function Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid. It is actively imported into the endoplasmic reticulum of cells and generates the oxidative potential found there. Protein disulfide isomerases are known to reduce DHA back to ascorbic acid, oxidizing their disulfide bonds in the process. Therefore L-dehydroascorbic acid is a vitamin C compound much like L-ascorbic acid. Oxidized forms of esterified ascorbic acids can be numbered at C(5) or C(6) atoms and the (free) chemical radical semi-dehydroascorbate or semidehydro ascorbic acid (SDA) to the group of dehydroascorbic acids.; Dehydroascorbic acid is the oxidized form of vitamin C. Reduced Vitamin C concentrations in the brain exceed those in blood by 10 fold. Dehydroascorbic acid readily enters the brain and is retained in the brain tissue in the form of ascorbic acid (ascorbic acid is not able to cross the blood-brain barrier).; Therefore, transport of dehydroascorbic acid by the Glucose Transporter 1 (GLUT1, Glucose transporters are integral membrane glycoproteins involved in transporting glucose into most cells. GLUT1 is a major glucose transporter in the mammalian blood-brain barrier. It is present at high levels in primate erythrocytes and brain endothelial cells.) is a mechanism by which the brain acquires vitamin C. (OMIM 138140); Vitamin C does not pass from the blood stream into the brain, although the brain is one of the organs which has the greatest concentration of vitamin C. Instead it is dehydroascorbate that is transported through the blood-brain barrier via GLUT1 transporters, and then converted to vitamin C. Some research has suggested that administration of dehydroascorbic acid may confer protection from neuronal injury following an ischemic stroke.
cas_number 490-83-5
Properties
created_at 2010-04-08 22:15:43
updated_at 2011-11-07 17:40:27
moldb_smiles OCC(O)C1OC(=O)C(=O)C1=O
moldb_formula C6H6O6
moldb_average_mass 174.1082
moldb_inchi InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2
moldb_mono_mass 174.016437924
moldb_inchikey InChIKey=SBJKKFFYIZUCET-UHFFFAOYSA-N
moldb_iupac 5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione
Structure Thumb
Synonyms
Synonym Source
1-Dehydroascorbate biospider
1-Dehydroascorbic acid biospider
Dehydro-l-ascorbate biospider
Dehydro-l-ascorbic acid biospider
Dehydroascorbate biospider
Dehydroascorbic acid biospider
DHAA biospider
L-ascorbic acid, dehydro- biospider
L-dehydroascorbate biospider
L-dehydroascorbic acid biospider
L-threo-2,3-Hexodiulosonic acid gamma-lactone biospider
L-threo-2,3-Hexodiulosonic acid, gamma-lactone biospider
L-Threo-hexo-2,3-diulosono-1,4-lactone biospider
Oxidized ascorbate biospider
Oxidized ascorbic acid biospider
Oxidized vitamin c biospider