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Merck
CN

261556

(L)-Dehydroascorbic acid

Synonym(s):

DHAA, Dehydro-L-ascorbate, Dehydro-L-ascorbic acid, L-threo-Dehydroascorbic acid, oxidized ascorbic acid, oxidized vitamin C

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About This Item

Empirical Formula (Hill Notation):
C6H6O6
CAS Number:
490-83-5
Molecular Weight:
174.11
NACRES:
NA.22
PubChem Substance ID:
24855820
UNSPSC Code:
12352205
EC Number:
207-720-6
MDL number:
MFCD00066467

Key Documents

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InChI key

SBJKKFFYIZUCET-JLAZNSOCSA-N

InChI

1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1

SMILES string

OC[C@H](O)[C@H]1OC(=O)C(=O)C1=O

form

powder

mp

228 °C (dec.) (lit.)

storage temp.

−20°C

Quality Level

200

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Application

(L)-Dehydroascorbic acid can be used as a starting material to synthesize:
  • Pyrano[3,4-b]indole derivatives by reacting with 2-hydroxymethylindole.
  • (−)-ascorbyl phloroglucinol via stereoselective C-C bond formation reaction with phloroglucinol.

General description

(L)-Dehydroascorbic acid (DHA) is a potent glycation agent that is produced by the oxidation of ascorbic acid (vitamin C). In vitro studies revealed that DHA is significantly more reactive than glucose and fructose in the glycation of lens proteins. Thus, DHA could be a critical precursor for the in vivo formation of advanced glycation end products (AGEs).
DHA is a dimer when it is solid, but when it is dissolved in a solution, it becomes a monomer.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9188
BCCM8797
BCCL2356
BCCM2357
BCCK1396

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Jens Lykkesfeldt
Nutrition research (New York, N.Y.), 32(1), 66-69 (2012-01-21)
Ascorbate and dehydroascorbic acid are frequently used as biomarkers of oxidative stress, but their lack of stability ex vivo and rapid postsampling interconversion continue to result in erroneous reference values. One problem is the large variety of vacutainer devices used
Oliver Reihl et al.
Carbohydrate research, 339(3), 483-491 (2004-03-12)
Covalently cross-linked proteins are among the major modifications caused by the advanced Maillard reaction. So far, the chemical nature of these aggregates is largely unknown. L-dehydroascorbic acid (DHA, 5), the oxidation product of L-ascorbic acid (vitamin C), is known as
Els Vossen et al.
Meat science, 91(1), 29-35 (2012-01-10)
The effect of sodium ascorbate (SA; 500, 750, 1000 mg/kg) and sodium nitrite (SN; 40, 80, 120 mg/kg) doses on the shelf-life stability of liver pâtés was investigated in a full factorial design. Clear dose-dependent responses of the added SN
A biomimetic synthesis of (-)-ascorbyl phloroglucinol and studies toward the construction of ascorbyl-modified catechin natural products and analogues
Belapure SA, et al.
Tetrahedron, 67(48), 9265-9272 (2011)
Scheling Wibowo et al.
Food chemistry, 187, 140-151 (2015-05-16)
In view of understanding colour instability of pasteurised orange juice during storage, to the best of our knowledge, this study reports for the first time in a systematic and quantitative way on a range of changes in specific quality parameters
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Articles

Determination of Ascorbic Acid and Dehydroascorbic Acid in Different Food Products and Supplements - A Simple HPTLC Based Approach

Simultaneous analysis of ascorbic acid and dehydroascorbic acid in various food samples by High Performance Thin Layer Chromatography (HPTLC).

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