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:
Molecular Weight:
174.11
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
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
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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.
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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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
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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
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