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856061

Sigma-Aldrich

D-(−)-Isoascorbic acid

98%

Synonym(s):

D-erythro-Hex-2-enoic acid γ-lactone, D-Araboascorbic acid, Erythorbic acid, Glucosaccharonic acid, NSC 8117

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500 G
RM 264.00

About This Item

Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
89-65-6
Molecular Weight:
176.12
Beilstein:
84271
EC Number:
201-928-0
MDL number:
MFCD00005378
UNSPSC Code:
12352205
PubChem Substance ID:
24888398
NACRES:
NA.22

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Quality Level

200

Assay

98%

form

crystals

optical activity

[α]25/D −16.8°, c = 2 in H2O

mp

169-172 °C (dec.) (lit.)

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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1 of 4

This Item
W24100879469D804
D-(−)-Isoascorbic acid 98%

856061

D-(−)-Isoascorbic acid

D-Isoascorbic acid FG

W241008

D-Isoascorbic acid

D-Arabino-1,4-lactone ≥97.0% (HPLC)

79469

D-Arabino-1,4-lactone

γ-Decanolactone 98%

D804

γ-Decanolactone

assay

98%

assay

99%

assay

≥97.0% (HPLC)

assay

98%

Quality Level

200

Quality Level

400

Quality Level

200

Quality Level

100

form

crystals

form

-

form

crystals

form

liquid

mp

169-172 °C (dec.) (lit.)

mp

169-172 °C (dec.) (lit.)

mp

94 - 100  °C ( (201 - 212 °F ))

mp

-

optical activity

[α]25/D −16.8°, c = 2 in H2O

optical activity

[α]20/D −16.8°, c = 10 in H2O

optical activity

[α]/D 72.0±3.0°, c = 1 in H2O

optical activity

-

General description

D-(−)-Isoascorbic acid, also known as erythorbic acid, is widely utilized as a chiral building block in organic synthesis for the preparation of various chiral compounds. It is also used as a reducing agent in various organic reactions.[1]

Application

D-(−)-Isoascorbic acid can be used as a reactant in the synthesis of various chiral compounds such as:
  • enantiopure aminotriol[2]
  • (3R, 4S)-4-hydroxylasiodiplodin and D-mycinose [3] [4]
  • enantiomerically pure stereoisomers of α,β-dihydroxy-aldehydes or acids[5]

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    MKBC7773
    1404010
    11731CJ
    06620BJ
    10920LH

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    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
    Manuel Bueno et al.
    Carbohydrate research, 344(15), 2100-2104 (2009-07-17)
    l-Ascorbic and d-isoascorbic acids have been used as the starting materials for the preparation of (3R,4'S)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1,4-dioxane-2,5-dione (IPTA), (3R and S, 4'S,6R)-3-methyl-6-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1,4-dioxane-2,5-dione (IPTP) and (3R,4'R)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1,4-dioxane-2,5-dione (IPEA), three novel 1,4-dioxane-2,5-dione-type monomers. Ring-opening homopolymerisation and copolymerisation of the IPTA monomer, derived from l-ascorbic
    Spyros Drivelos et al.
    Analytical and bioanalytical chemistry, 397(6), 2199-2210 (2010-04-16)
    A new hydrophilic interaction liquid chromatographic (HILIC) method for the simultaneous determination of isoascorbic (IAA) and ascorbic acid (AA) was developed. The separation of IAA and AA was studied in various HILIC stationary phases and the influence of the composition
    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
    Alberto Baroja-Mazo et al.
    Fungal genetics and biology : FG & B, 42(5), 390-402 (2005-04-06)
    D-Erythroascorbate and D-erythroascorbate glucoside have been identified in the Zygomycete fungus Phycomyces blakesleeanus. Ascomycete and Basidiomycete fungi also synthesise D-erythroascorbate instead of l-ascorbate, suggesting that D-erythroascorbate synthesis evolved in the common ancestor of the fungi. Both compounds accumulate in P.
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