FComEx: L-Dehydroascorbic acid (PC000618)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:32 UTC

Update date

2017-01-19 02:36:30 UTC

FoodComEx ID

PC000618

FoodDB Record

Not Available

Chemical Information

Name

L-Dehydroascorbic acid

Description

Widespread in plants, as oxidn. production 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. L-Dehydroascorbic acid is found in many foods, some of which are whisky, nutmeg, pepper (spice), and wild celery.

CAS Number

490-83-5

Structure

MOL SDF PDB SMILES InChI

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

Chemical Formula

Not Available

IUPAC name

Not Available

InChI Identifier

InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2

InChI Key

SBJKKFFYIZUCET-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)C1OC(=O)C(=O)C1=O

Average Molecular Weight

174.1082

Monoisotopic Molecular Weight

174.016437924

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents