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Key Documents

W241008

Sigma-Aldrich

D-Isoascorbic acid

FG

Synonym(s):

D-(−)-Isoascorbic acid, D-erythro-Hex-2-enoic acid γ-lactone, D-Araboascorbic acid, Erythorbic acid, Glucosaccharonic acid, NSC 8117

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About This Item

Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
Molecular Weight:
176.12
FEMA Number:
2410
Beilstein:
84271
EC Number:
Council of Europe no.:
30c
MDL number:
UNSPSC Code:
12164502
PubChem Substance ID:
NACRES:
NA.21

biological source

(Starch)

Quality Level

grade

FG
Kosher

reg. compliance

EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 117
FDA 21 CFR 175.105
FDA 21 CFR 182.3041

Assay

99%

optical activity

[α]20/D −16.8°, c = 10 in H2O

mp

169-172 °C (dec.) (lit.)

application(s)

flavors and fragrances

food allergen

no known allergens

Organoleptic

odorless

SMILES string

[H][C@@]1(OC(=O)C(O)=C1O)[C@H](O)CO

InChI

1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1

InChI key

CIWBSHSKHKDKBQ-DUZGATOHSA-N

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Application


  • The Vitamin C Enantiomers Possess a Comparable Potency in the Induction of Oxidative Stress in Cancer Cells but Differ in Their Toxicity.: The research compares the biochemical effects of Vitamin C enantiomers, including D-Isoascorbic acid, on oxidative stress in cancer cells, providing insights into their differential toxicity (Begimbetova et al., 2024).

  • Synthesis and potential antidiabetic and lipid-lowering activities of putative asperidine B and its desmethyl analogue.: This article discusses the synthesis of asperidine B analogues and their potential applications in biochemistry for antidiabetic and lipid-lowering activities (Thongpat et al., 2023).

  • Effects of Different Bacteriostats on the Dynamic Germination of Clostridium perfringens Spores.: The study investigates the impact of various bacteriostats, including D-Isoascorbic acid, on the germination dynamics of Clostridium perfringens spores, relevant to biochemical research in food safety (Liang et al., 2023).

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Daiki Kyotani et al.
Bioscience, biotechnology, and biochemistry, 73(4), 954-956 (2009-04-09)
We found that a strain of Penicillium sp. effectively converted L-ascorbic acid to a five-carbon analog, which was identified as L-erythroascorbic acid based on spectroscopic analysis. The conversion was achieved by growing culture or washed mycelia, with a yield of
Andrew C Clark et al.
Journal of agricultural and food chemistry, 58(2), 1004-1011 (2009-12-31)
The stereochemical influence of antioxidant and flavanol compounds on oxidation processes in a model wine system was studied. The diastereoisomers, ascorbic acid and erythorbic acid, were used as antioxidants in a model wine system containing either (+)-catechin or (-)-epicatechin as
Ravi S Talluri et al.
Current eye research, 31(6), 481-489 (2006-06-14)
To investigate the mechanism of L-ascorbic acid uptake by rabbit corneal epithelial cells and to functionally characterize the specific transporter involved in this translocation process. Uptake studies were carried out with SIRC (Statens Seruminstitut Rabbit Cornea) and rPCEC (rabbit Primary
Akihiro Tai et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 853(1-2), 214-220 (2007-04-10)
A new hydrophilic interaction liquid chromatography method for the simultaneous determination of ascorbic acid (AA), erythorbic acid (EA), 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) and 2-O-beta-D-glucopyranosyl-L-ascorbic acid (AA-2betaG) was developed using a diol column with an isocratic solution of acetonitrile-66.7 mM ammonium acetate
Katsumi Amako et al.
FEBS letters, 580(27), 6428-6434 (2006-11-14)
Erythroascorbic acid (eAsA) is a five-carbon analog of ascorbic acid, and it is synthesized from D-arabinose by D-arabinose dehydrogenase (ARA) and D-arabinono-gamma-lactone oxidase. We found an NAD+-specific ARA activity which is operative under submillimolar level of d-arabinose in the extracts

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