Skip to Content
Merck
All Photos(3)

Key Documents

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
Molecular Weight:
176.12
Beilstein:
84271
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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.

Application

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Total Synthesis of (3R, 4 S)-4-Hydroxylasiodiplodin via Ring Closing Metathesis Protocol
JS Reddy, et al.
ChemistrySelect, 4, 5345-5347 (2019)
Erythorbic acid is a potent enhancer of nonheme-iron absorption
M Fidler
American Journal of Clinical Nutrition, 79, 99-102 (2004)
Enantiopure aminotriol from d-isoascorbic acid synthesis of d-threo-C-18-sphingosine
A Tuch
Tetrahedron Asymmetry, 7, 897-906 (1996)
The total synthesis of D-mycinose
AJ Poss
Tetrahedron Letters, 29, 5723-5724 (1988)
Chiral ?-hydroxy-and ?,?-dihydroxy-aldehydes from D-isoascorbic and L-ascorbic acids. Useful precursors for the synthesis of fatty acid metabolites.
Y Le Merrer, et.al.
Tetrahedron Letters, 31, 1003-1006 (1990)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service