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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:
89-65-6
Molecular Weight:
176.12
FEMA Number:
2410
Beilstein:
84271
EC Number:
201-928-0
Council of Europe no.:
30c
MDL number:
MFCD00005378
UNSPSC Code:
12164502
PubChem Substance ID:
24901050
NACRES:
NA.21

biological source

(Starch)

Quality Level

400

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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Christian Dolle et al.
The journal of physical chemistry. B, 115(40), 11638-11649 (2011-09-08)
The properties of novel bolaamphiphiles that carry epimers of vitamin C (L-ascorbic acid and/or D-isoascorbic acid) as hydrophilic head groups, and an interconnecting aliphatic C(12) chain (DD, DL, and LL) were investigated by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA)
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
Tuomas Salusjärvi et al.
Applied and environmental microbiology, 70(9), 5503-5510 (2004-09-04)
A D-erythorbic acid-forming soluble flavoprotein, gluconolactone oxidase (GLO), was purified from Penicillium cyaneo-fulvum strain ATCC 10431 and partially sequenced. Peptide sequences were used to isolate a cDNA clone encoding the enzyme. The cloned gene exhibits high levels of similarity with
Ingrid Undeland et al.
Journal of agricultural and food chemistry, 53(14), 5625-5634 (2005-07-07)
It has previously been found that a process based on solubilization at pH 2.7 gives high yields of herring muscle proteins with good functionality. In this study, the development of lipid oxidation during acid processing of herring mince was studied.
Moira Ambrosi et al.
The journal of physical chemistry. B, 113(5), 1404-1412 (2009-01-13)
L-(+)-Ascorbic acid and D-(-)-isoascorbic acid are epimers, with an opposite configuration at the C5 stereogenic chiral center. Single-chained surfactants that carry a L-ascorbic or d-isoascorbic acid residue as hydrophilic headgroup and an alkanoate tail as hydrophobic chain were synthesized. We
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