Page last updated: 2024-11-13

isoascorbic acid

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

Description

isoascorbic acid: food antioxidant; (L)-isomer is ascorbic acid; RN given refers to (D)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID54675810
CHEMBL ID486293
CHEBI ID51438
SCHEMBL ID18678
SCHEMBL ID3700961
MeSH IDM0046353

Synonyms (95)

Synonym
d-erythro-hex-2-enonic acid gamma-lactone
CHEBI:51438 ,
d-erythro-hex-2-enono-1,4-lactone
e315
CHEMBL486293
isoascorbic acid
erythorbic acid
saccharosonic acid
araboascorbic acid
d-erythro-hex-2-enonic acid, .gamma.-lactone
isovitamin c
89-65-6
erycorbin
neo-cebicure
d-araboascorbic acid
glucosaccharonic acid
d-ascorbic acid, iso
nsc-8117
d-erythorbic acid
d-isoascorbic acid
(5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5h)-one
einecs 201-928-0
2,3-didehydro-d-erythro-hexono-1,4-lactone
ccris 6568
fema no. 2410
erythroascorbic acid, d-
d-erythro-3-oxohexonic acid lactone
d-erythro-3-ketohexonic acid lactone
brn 0084271
hsdb 584
fema number: 2410
3-keto-d-erythro-hexonic acid gamma-lactone
3-oxohexonic acid lactone, d-erythro-
hex-2-enonic acid gamma-lactone, d-erythro-
nsc 8117
d-erythro-hex-2-enonic acid, gamma-lactone,
mercate 5
d-isoascorbic acid, >=99%, fcc, fg
d-(-)-isoascorbic acid, 98%
1F9G
7179C406-7CCF-4C07-9125-AA71E28FB983
A0520
A843272
ec 201-928-0
erythorbic acid [nf]
unii-311332oii1
5-18-05-00026 (beilstein handbook reference)
311332oii1 ,
NCGC00258663-01
tox21_201111
dtxcid306537
cas-89-65-6
dtxsid6026537 ,
C20364
AKOS015856346
(r)-5-((r)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5h)-one
isoascorbic-acid
ins-315
ins no.315
erythorbic acid [mart.]
isoascorbic acid [mi]
e-315
erythorbic acid [fhfi]
d-erythro-hex-2-enoic acid gamma-lactone
erythorbic acid [inci]
ascorbic acid impurity f [ep impurity]
erythorbate
erythorbic acid [ii]
erythorbic acid [fcc]
(5r)-5-((1r)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5h)-one
erythorbic acid [hsdb]
erythorbic acid [usp-rs]
SCHEMBL18678
SCHEMBL3700961
d-(-)-isoascorbic acid
J-506944
mfcd00005378
erythorbic acid, united states pharmacopeia (usp) reference standard
(5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5h)-one (d-isoascorbic acid); ascorbic acid impurity f; sodium ascorbate impurity f
(5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5h)-one (non-preferred name)
(2r)-2-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one
Q424531
d-erythro-hex-2-enoic acid ?-lactone
Z1255372411
d-iso-ascorbic acid
HY-N7079
CS-0014152
d-erythro-hex-2-enonic acid, g-lactone
AC8021
d-isoascorbic acid 1000 microg/ml in acetonitrile
d(-)-isoascorbic acid (erythorbic acid)
d-soascorbic acid
(5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5h)-one (d-isoascorbic acid)
EN300-251979
(5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

Research Excerpts

Overview

Isoascorbic acid is an epimer of ascorbic acid. It has the same reduction-oxidation potential as ascorBic acid, but is less biologically active.

ExcerptReferenceRelevance
"Isoascorbic acid is an epimer of ascorbic acid, having the same reduction-oxidation potential as ascorbic acid, but is less biologically active."( Ascorbic acid potentiates the inhibitory effect of dopamine on prolactin release in primary cultured rat pituitary cells.
Shin, SH; Stirling, R, 1988
)
1

Toxicity

ExcerptReferenceRelevance
" L-Ascorbate and its oxidative product dehydroascorbate were cytotoxic or lethal to the fast-growing malignant cells, but they were less toxic to nonmalignant cells."( Cytotoxic effect of ascorbate and its derivatives on cultured malignant and nonmalignant cell lines.
Leung, PY; Miyashita, K; Tsao, CS; Young, M,
)
0.13

Bioavailability

ExcerptReferenceRelevance
" The absorption rate of AsA in the small intestine of guinea pigs was higher than that of ErA; however, Km of AsA absorption was lower than that of ErA in normal guinea pigs."( Comparison of absorption of erythorbic acid and ascorbic acid in guinea pig small intestine.
Arakawa, N; Kurata, T; Suzuki, E, 1991
)
0.28
" In the erythorbic acid-treated mice, erythorbic acid is well absorbed by the gastrointestinal tract, enters the blood stream, and is rapidly excreted in the urine."( Influence of erythorbic acid on ascorbic acid retention and elimination in the mouse.
Salimi, SL; Tsao, CS, 1983
)
0.27
" It is concluded that D-isoascorbic acid is a "weakly" antiscorbutic agent on the basis that it is both poorly absorbed and retained by the tissue; that in fact it may, to the degree that it is taken up by the tissues and retained, be equal in antiscorbutic potency to L-ascorbic acid."( The antiscorbutic action of L-ascorbic acid and D-isoascorbic acid (erythorbic acid) in the guinea pig.
Goldman, HM; Gould, BS; Munro, HN, 1981
)
0.82
" There were no significant effects of smoking or supplementation on relative bioavailability (difference in area under curve, AUC 0-infinity) of erythorbic acid (smokers 357 (sd 119), non-smokers 414 (sd 142) micromol."( Effect of smoking on erythorbic acid pharmacokinetics.
Bolbjerg, ML; Lykkesfeldt, J; Poulsen, HE, 2003
)
0.32
" However, it may play a major role in enhancing iron bioavailability from mixed diets that include foods preserved with erythorbic acid."( Erythorbic acid is a potent enhancer of nonheme-iron absorption.
Davidsson, L; Fidler, MC; Hurrell, RF; Zeder, C, 2004
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
ascorbic acid
[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 (1)

PathwayProteinsCompounds
Biochemical pathways: part I0466

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency43.71590.000221.22318,912.5098AID743035
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency24.36130.000657.913322,387.1992AID1259377
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HYALURONATE LYASEStreptococcus pneumoniaeKi53,000.000053,000.000053,000.000053,000.0000AID977610
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2001The Journal of biological chemistry, May-04, Volume: 276, Issue:18
Vitamin C inhibits the enzymatic activity of Streptococcus pneumoniae hyaluronate lyase.
AID1811Experimentally measured binding affinity data derived from PDB2001The Journal of biological chemistry, May-04, Volume: 276, Issue:18
Vitamin C inhibits the enzymatic activity of Streptococcus pneumoniae hyaluronate lyase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (167)

TimeframeStudies, This Drug (%)All Drugs %
pre-199059 (35.33)18.7374
1990's34 (20.36)18.2507
2000's35 (20.96)29.6817
2010's25 (14.97)24.3611
2020's14 (8.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 58.18

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index58.18 (24.57)
Research Supply Index5.19 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index95.62 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (58.18)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (1.70%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other173 (98.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
An Exploratory Phase I/II Single-center Clinical Trial of the Efficacy, Tolerability and Safety of Intravenous D-isoascorbic Acid With Arsenic Trioxide in Patients With Advanced/Metastatic Colorectal Cancer Who Have Exhausted Standard Therapy [NCT05721872]Phase 1/Phase 238 participants (Anticipated)Interventional2023-02-15Recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]