Page last updated: 2024-12-04

dehydroascorbic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

Dehydroascorbic Acid: The reversibly oxidized form of ascorbic acid. It is the lactone of 2,3-DIKETOGULONIC ACID and has antiscorbutic activity in man on oral ingestion. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

L-dehydroascorbate : An organic anion and the conjugate base of L-dehydroascorbic acid, arising from deprotonation of the acidic C2-position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

L-dehydroascorbic acid : Dehydroascorbic acid having the L-configuration. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID440667
CHEBI ID27956
SCHEMBL ID66326
MeSH IDM0005759

Synonyms (49)

Synonym
dehydro-l-ascorbic acid
(5r)-5-[(1s)-1,2-dihydroxyethyl]furan-2,3,4(5h)-trione
l-threo-hexo-2,3-diulosono-1,4-lactone
l-threo-2,3-hexodiulosonic acid, gamma-lactone
dhaa
CHEBI:27956 ,
l-dehydroascorbic acid
C05422
dehydroascorbate
490-83-5
dehydroascorbic acid
l-dehydroascorbate
dehydro-l-(+)-ascorbic acid dimer, >=80% (enzymatic)
(l)-dehydroascorbic acid
dehydro-l-ascorbinsaure
F34401D0-9CF1-428F-ACB9-26935446580D
(5r)-5-[(1s)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
(r)-5-((s)-1,2-dihydroxyethyl)furan-2,3,4(5h)-trione ,
A827655
S3329
l-ascorbic acid, dehydro-
einecs 207-720-6
unii-y2z3ztp9um
y2z3ztp9um ,
EPITOPE ID:194981
gtpl4733
(5r)-5-((1s)-1,2-dihydroxyethyl)furan-2,3,4(5h)-trione
dehydroascorbic acid [mi]
dehydroascorbic-acid
dehyroascorbic acid
DB08830
bis-dehydro-l-ascorbic acid
SCHEMBL66326
mfcd00066467
l-threo-2,3-hexodiulosonic acid gamma-lactone
l-threo-dehydroascorbic acid
SBJKKFFYIZUCET-JLAZNSOCSA-N
l-threo-2,3-hexodiulosonic acid ?-lactone
AKOS027470272
1-dehydroascorbic acid
1-dehydroascorbate
CS-0033149
HY-110281
(5r)-5-[(1s)-1,2-dihydroxyethyl]furan-2,3,4(5h)-trione (non-preferred name)
dehydroascorbic acid; dha
DTXSID00912316
Q3116723
l-threo-2,3-hexodiulosonic acid, g-lactone
BS-28662

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Dehydroascorbate, an electron affinic metabolite of vitamin C, sensitized Ehrlich ascites tumor cells, in vivo, to radiation and was selectively toxic to V79 Chinese hamster lung cells under hypoxic conditions (without radiation)."( Toxicity, radiation sensitivity modification, and metabolic effects of dehydroascorbate and ascorbate in mammalian cells.
Biaglow, JE; Koch, CJ, 1978
)
0.26
"The goal of this randomized, double-blind crossover clinical trial in 50 healthy volunteers sensitive to acidic foods was to evaluate whether Ester-C calcium ascorbate causes fewer epigastric adverse effects than are produced by regular ascorbic acid (AA)."( Safety and tolerance of ester-C compared with regular ascorbic acid.
Bentley, C; Busch, R; Graubaum, HJ; Gruenwald, J,
)
0.13
" However, H(2)S is also highly toxic as it inhibits mitochondrial respiration at the level of cytochrome c oxidase, which additionally is involved in sulfide oxidation."( Modulation of sulfide oxidation and toxicity in rat mitochondria by dehydroascorbic acid.
Hildebrandt, TM, 2011
)
0.37

Bioavailability

ExcerptReferenceRelevance
" There is no information on the mechanism of vitamin C transport across the intestinal barrier, a step that determines the bioavailability of vitamin C in humans."( Up-regulation and polarized expression of the sodium-ascorbic acid transporter SVCT1 in post-confluent differentiated CaCo-2 cells.
Bachem, M; Bustamante, ME; Cárcamo, JG; Grünert, A; Henríquez, EA; Kempe, S; Maulén, NP; Nualart, F; Schmid-Kotsas, A; Vera, JC, 2003
)
0.32
" It is well absorbed from the digestive system and easily reaches the tissues."( [Determination of ascorbic and dehydroascorbic acid concentration using HPLC method in smokers with stable coronary artery disease scheduled for coronary artery bypass grafting (CABG)].
Kleszczewska, E; Lisowski, P; Wiszowata, A, 2005
)
0.33
" Furthermore, dietary sugars and flavonoids in fruits and vegetables may modulate Asc bioavailability via inhibition of small intestinal GLUT2 and GLUT8."( Intestinal dehydroascorbic acid (DHA) transport mediated by the facilitative sugar transporters, GLUT2 and GLUT8.
Al-Hasani, H; Corpe, CP; Eck, P; Levine, M; Wang, J, 2013
)
0.39
" In this study, bioavailability of the oxidized form of vitamin C (l-dehydroascorbic acid or DHA)-commonly found in vitamin C containing food products prone to oxidation-was studied."( L-dehydroascorbic acid can substitute l-ascorbic acid as dietary vitamin C source in guinea pigs.
Frikke-Schmidt, H; Lykkesfeldt, J; Tveden-Nyborg, P, 2016
)
0.43
" However, high dose VC has shown limited efficacy in clinical trials, possibly due to the decreased bioavailability of oral VC."( Glutathione Depletion, Pentose Phosphate Pathway Activation, and Hemolysis in Erythrocytes Protecting Cancer Cells from Vitamin C-induced Oxidative Stress.
Deberardinis, RJ; Glass, D; Lee, EE; Sudderth, J; Wang, RC; Yue, Y; Zhang, ZZ; Zia, A, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" The official titration methods and TLC, colorimetric, and polarographic determinations correlate well and define accurately the stability of ascorbic acid in these dosage forms."( Stability of vitamin C (ascorbic acid) in tablets.
DeRitter, E; Johnson, JB; Rubin, SH, 1976
)
0.26
" As for HeLa cells in a tissue culture, tetraacetyl-bis-DHA, in a dosage of 125-250 mug/ml, demonstrated definitely its morphological degeration."( Effects of tetraacetyl-bis-dehydroascorbic acid, a derivative of ascorbic acid, on Ehrlich cells and HeLa cells (human carcinoma cells).
Hiyoshi, S; Jinnouchi, H; Takahashi, N; Yagishita, K; Yamamoto, H, 1976
)
0.26
" A dosage of 30-40 ng/mL TCDD induced maximal intracellular production of H2O2 at 30 minutes and led to severe cell death (0-31% survival) at two hours."( Alpha-tocopherol protects cultured human cells from the acute lethal cytotoxicity of dioxin.
Hirai, K; Kanamaru, T; Koyama, J; Pan, JH; Shimada, H; Shui, YB; Simamura, E, 2002
)
0.31
" The DHA impurity values found in dosage forms were < or =0."( Development and validation of a liquid chromatographic method for the determination of ascorbic acid, dehydroascorbic acid and acetaminophen in pharmaceuticals.
Andreatta, P; Boschetti, S; Gatti, R; Gioia, MG, 2008
)
0.35
" Unfortunately, enhanced EPR signal intensities were observed at 300 min after dosing in patients with serum molar ratio of deferiprone to iron less than 3, suggesting the formation of incomplete iron-deferiprone complexes and consequently free radical formation."( Pharmaco/ferrokinetic-related pro-oxidant activity of deferiprone in beta-thalassemia.
Chantharaksri, U; Fucharoen, S; Jirasomprasert, T; Limenta, LM; Morales, NP; Sirijaroonwong, S; Wilairat, P; Yamanont, P, 2009
)
0.35
" For Docetaxel and 5-FU, a linear correlation between this sensitizing effect and the ascorbate dosage is observed."( Ascorbate exerts anti-proliferative effects through cell cycle inhibition and sensitizes tumor cells towards cytostatic drugs.
Aigner, A; Czubayko, F; Frömberg, A; Gutsch, D; Schulze, D; Vollbracht, C; Weiss, G, 2011
)
0.37
" In terms of safety, based on all available animal information, DHAA is safe in the proposed dosing regimen."( Dehydroascorbic acid for the treatment of acute ischemic stroke.
Spector, R, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
coenzymeA low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
dehydroascorbic acid
vitamin CAny member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (5)

PathwayProteinsCompounds
Tyrosine metabolism ( Tyrosine metabolism )2841
ascorbate biosynthesis018
Catecholamine synthesis012
AtMetExpress overview0109
Biochemical pathways: part I0466

Research

Studies (1,072)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990332 (30.97)18.7374
1990's259 (24.16)18.2507
2000's277 (25.84)29.6817
2010's173 (16.14)24.3611
2020's31 (2.89)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials14 (1.22%)5.53%
Reviews51 (4.43%)6.00%
Case Studies1 (0.09%)4.05%
Observational0 (0.00%)0.25%
Other1,086 (94.27%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]