261556
(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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Fórmula empírica (notación de Hill):
C6H6O6
Número CAS:
Peso molecular:
174.11
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352205
EC Number:
207-720-6
MDL number:
Servicio técnico
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powder
Quality Level
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
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.
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.
Clase de almacenamiento
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
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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
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