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DEHYDROASCORBIC ACID

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DEHYDROASCORBIC ACID Basic information

Product Name:
DEHYDROASCORBIC ACID
Synonyms:
  • (5R)-5β-[(S)-1,2-Dihydroxyethyl]tetrahydrofuran-2,3,4-trione
  • C05422
  • Dehydroascorbate
  • L-Dehydroascorbate
  • L-threo-2,3-Hexodiulosonic Acid γ-Lactone
  • Oxidized Ascorbic Acid
  • L-ASCORBIC ACID OXIDIZED
  • DEHYDROASCORBIC ACID
CAS:
490-83-5
MF:
C6H6O6
MW:
174.11
EINECS:
207-720-6
Product Categories:
  • Carbohydrates & Derivatives
  • Intermediates & Fine Chemicals
  • Carbohydrate Synthesis
  • Monosaccharides
  • Specialty Synthesis
  • Pharmaceuticals
Mol File:
490-83-5.mol
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DEHYDROASCORBIC ACID Chemical Properties

Melting point:
228 °C (dec.)(lit.)
alpha 
D20 +56°
Boiling point:
389.3±38.0 °C(Predicted)
Density 
1.743±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO (Slightly, Heated), Methanol (Slightly, Sonicated)
form 
Solid
pka
3.90(at 25℃)
color 
White to Dark Orange
Merck 
13,2886
Stability:
Light Sensitive
LogP
-1.702 (est)
CAS DataBase Reference
490-83-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
1-8-10
HS Code 
2936270000

MSDS

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DEHYDROASCORBIC ACID Usage And Synthesis

Chemical Properties

Orange Solid

Uses

The reversibly oxidized form of ascorbic acid.

Definition

ChEBI: Dehydroascorbic acid having the L-configuration.

Purification Methods

Crystallise dehydro-L(+)-ascorbic acid from MeOH. The anhydrous acid is formed by heating it in a vacuum at 100o/1hour to give a crisp glassy product which when shaken with absolute EtOH and then kept at 0o for 2days gives microcrystals of the anhydrous acid. This is then washed with absolute EtOH and dried in a vacuum. It has m 225o(dec) and is stable in acidic solution but decomposes rapidly in alkaline solution. A 1% solution of the anhydrous acid when dissolved in phthalate/HCl buffer pH 3.5 at 60o and cooled to 20o has [] 20D +56o(0minutes), +53.5o(2hours), +19o(3days), -2o(5days) and -6o(6days); then it becomes orange in colour. A freshly prepared 1% solution in H2O has [] D +50o(0minutes), +44o(2hours), +16o(3days) and 0o(5days). [Herbert et al. J Chem Soc 1270 1933, Kenyon et al. J Chem Soc 158 1948, Beilstein 18/5 V 411.]

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