261556

(L)-Dehydroascorbic acid

• Synonym(s): DHAA, Dehydro-L-ascorbate, Dehydro-L-ascorbic acid, L-threo-Dehydroascorbic acid, oxidized ascorbic acid, oxidized vitamin C
• Empirical Formula (Hill Notation): C₆H₆O₆
• CAS Number: 490-83-5
• Molecular Weight: 174.11
• EC Number: 207-720-6
• MDL number: MFCD00066467
• UNSPSC Code: 12352205
• PubChem Substance ID: 24855820
• NACRES: NA.22

Properties

• form: powder
• Quality Level: 200
• 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

Description

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.

Safety Information

• 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