FComEx: Dehydroascorbic acid (PC000617)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:31 UTC

Update date

2017-01-19 02:36:30 UTC

FoodComEx ID

PC000617

FoodDB Record

FDB011907

Chemical Information

Name

Dehydroascorbic acid

Description

Dehydroascorbic acid, also known as dehydroascorbate, is a member of the class of 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. Dehydroascorbic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Dehydroascorbic acid can be found in a number of food items such as white cabbage, gram bean, mexican groundcherry, and common pea, which makes dehydroascorbic acid a potential biomarker for the consumption of these food products. Dehydroascorbic acid may be a unique E.coli metabolite. 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. It is trapped therein by reduction back to ascorbate by glutathione and other thiols. The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids .

CAS Number

490-83-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
threo-2,3-Hexodiulosono-1,4-lactone, 9CI, 8CI	db_source

Chemical Formula

C6H6O6

IUPAC name

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

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