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Merck
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261556

Sigma-Aldrich

(L)-Dehydroascorbic acid

Sinónimos:

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

Fórmula empírica (notación de Hill):
C6H6O6
Número de CAS:
490-83-5
Peso molecular:
174.11
EC Number:
207-720-6
MDL number:
MFCD00066467
UNSPSC Code:
12352205
PubChem Substance ID:
24855820
NACRES:
NA.22

form

powder

mp

228 °C (dec.) (lit.)

storage temp.

−20°C

SMILES string

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

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

InChI key

SBJKKFFYIZUCET-JLAZNSOCSA-N

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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.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
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
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
A Wesley Burks et al.
Pediatric allergy and immunology : official publication of the European Society of Pediatric Allergy and Immunology, 26(4), 316-322 (2015-04-08)
Children with cow's milk allergy (CMA) are at risk for inadequate nutritional intake and growth. Dietary management of CMA, therefore, requires diets that are not only hypoallergenic but also support adequate growth in this population. This study assessed growth of
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Protocolos

HPLC Analysis of Ascorbic Acid on Ascentis® RP-Amide

Separation of (L)-Dehydroascorbic acid; L-Ascorbic acid 20 μg/mL

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