ChemFOnt: Showing chemical card for L-Dehydroascorbic acid (CFc000336836)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:13 UTC

Chemfont ID

CFc000336836

Molecule Identification

Common Name

L-Dehydroascorbic acid

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dehydroascorbate	ChEBI
Dehydroascorbates	ChEBI

Chemical Formula

C₆H₆O₆

Average Molecular Weight

174.1082

Monoisotopic Molecular Weight

174.016437924

IUPAC Name

5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione

Traditional Name

dehydroascorbic acid

CAS Registry Number

490-83-5

SMILES

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

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

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.

Showing chemical card for L-Dehydroascorbic acid (CFc000336836)

MOL for CFc000336836 (L-Dehydroascorbic acid)

3D MOL for CFc000336836 (L-Dehydroascorbic acid)

3D SDF for CFc000336836 (L-Dehydroascorbic acid)

3D-SDF for CFc000336836 (L-Dehydroascorbic acid)

PDB for CFc000336836 (L-Dehydroascorbic acid)

3D PDB for CFc000336836 (L-Dehydroascorbic acid)

SMILES for CFc000336836 (L-Dehydroascorbic acid)

INCHI for CFc000336836 (L-Dehydroascorbic acid)

Structure for CFc000336836 (L-Dehydroascorbic acid)

3D Structure for CFc000336836 (L-Dehydroascorbic acid)