856061
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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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
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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
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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)
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)
The total synthesis of D-mycinose
AJ Poss
Tetrahedron Letters, 29, 5723-5724 (1988)
Total Synthesis of (3R, 4 S)-4-Hydroxylasiodiplodin via Ring Closing Metathesis Protocol
JS Reddy, et al.
ChemistrySelect, 4, 5345-5347 (2019)
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