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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352205
EC Number:
207-720-6
MDL number:
form
powder
Quality Segment
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.
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signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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