Record Information
Version1.0
Creation date2010-04-08 22:15:43 UTC
Update date2018-05-29 01:51:23 UTC
Primary IDFDB021459
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Dehydroascorbic acid
DescriptionWidespread 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 Number490-83-5
Structure
Thumb
Synonyms
SynonymSource
DehydroascorbateChEBI
DehydroascorbatesChEBI
1-Dehydroascorbatebiospider
1-Dehydroascorbic acidbiospider
Dehydro-l-ascorbatebiospider
Dehydro-l-ascorbic acidbiospider
Dehydroascorbic acidbiospider
DHAAbiospider
L-ascorbic acid, dehydro-biospider
L-dehydroascorbatebiospider
L-dehydroascorbic acidbiospider
L-threo-2,3-Hexodiulosonic acid gamma-lactonebiospider
L-threo-2,3-Hexodiulosonic acid, gamma-lactonebiospider
L-Threo-hexo-2,3-diulosono-1,4-lactonebiospider
Oxidized ascorbatebiospider
Oxidized ascorbic acidbiospider
Oxidized vitamin cbiospider
Predicted Properties
PropertyValueSource
Water Solubility190 g/LALOGPS
logP-1.2ALOGPS
logP-0.67ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.55 m³·mol⁻¹ChemAxon
Polarizability14.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H6O6
IUPAC name5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione
InChI IdentifierInChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2
InChI KeySBJKKFFYIZUCET-UHFFFAOYSA-N
Isomeric SMILESOCC(O)C1OC(=O)C(=O)C1=O
Average Molecular Weight174.1082
Monoisotopic Molecular Weight174.016437924
Classification
DescriptionThis compound belongs to the class of chemical entities known as gamma butyrolactones. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassLactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • 3-furanone
  • Gamma butyrolactone
  • Tetrahydrofuran
  • 1,2-diol
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 41.39%; H 3.47%; O 55.14%DFC
Melting PointMp 225 dec. (196° dec.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +56 -> -6 (6d) (c, 1 in phthalate/HCl buffer at pH 3.5)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9200000000-0a414c4d59046ece51c1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fki-9831000000-c4b46024e1624e983ac3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-4900000000-25a652482451303b3ca4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-f1d23791c8a7b59576a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2900000000-5ebc67e43b07167f34cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-27ae8f5e1795d4f732a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-0900000000-ee719ada45193fc650a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0mbc-1900000000-d54b8e72e08e6ea1f7c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9200000000-d07ff0053ddc28ce1915View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID182283
ChEMBL IDNot Available
KEGG Compound IDC00425
Pubchem Compound ID210328
Pubchem Substance IDNot Available
ChEBI ID17242
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01264
CRC / DFC (Dictionary of Food Compounds) IDHBR64-G:NXM15-F
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34945
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDehydroascorbic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glutathione S-transferase omega-1GSTO1P78417
Glutathione S-transferase omega-2GSTO2Q9H4Y5
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).