(5R)-5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione

• ChemBase ID: 165608
• Molecular Formular: C6H6O6
• Molecular Mass: 174.10824
• Monoisotopic Mass: 174.01643791
• SMILES: C1(=O)[C@@H](C(CO)O)OC(=O)C1=O
• Canonical SMILES: OCC([C@H]1OC(=O)C(=O)C1=O)O
• InChI: InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2?,5-/m1/s1
• InChIKey: SBJKKFFYIZUCET-DOAHDZERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione
• IUPAC Traditional name: (5R)-5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione
• Synonyms: Dehydro-L-ascorbic Acid; L-threo-2,3-Hexodiulosonic Acid γ-Lactone; Oxidized Ascorbic Acid; Oxidized Vitamin C; L-Dehydro Ascorbic Acid

Database IDs

• CAS Number: 490-83-5
• PubChem SID: 162259741
• PubChem CID: 10280

CALCULATED PROPERTIES

• Acid pKa: 1.5571897
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.748775
• LogD (pH = 7.4): -3.8112833
• Log P: -0.67283064
• Molar Refractivity: 33.5458 cm^3
• Polarizability: 13.592451 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Orange Solid
• Melting Point: >220°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

Product Information

• Classification: Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - D229250

The reversibly oxidized form of ascorbic acid.

REFERENCES

• Moubasher, et al.: J. Biol. Chem., 176, 633 (1948)
• Sy, K., et al.: J. Food Prot., 68, 1176 (1948)
• Llorach, R., et al.: Food Chem., 2008, 108, 1028 (1948)