(5R)-5-[1,2-dihydroxy(1,2-13C2)ethyl](2,3,4,5-13C4)oxolane-2,3,4-trione

• ChemBase ID: 165609
• Molecular Formular: C6H6O6
• Molecular Mass: 180.06416903
• Monoisotopic Mass: 180.03656694
• SMILES: [13C]1(=O)[13C@@H]([13CH]([13CH2]O)O)O[13C](=O)[13C]1=O
• Canonical SMILES: O[13CH2][13CH]([13C@H]1O[13C](=O)[13C](=O)[13C]1=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/i1+1,2+1,3+1,4+1,5+1,6+1
• InChIKey: SBJKKFFYIZUCET-HFEVONBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[1,2-dihydroxy(1,2-^1^3C₂)ethyl](2,3,4,5-^1^3C₄)oxolane-2,3,4-trione
• IUPAC Traditional name: (5R)-5-[1,2-dihydroxy(1,2-^1^3C₂)ethyl](2,3,4,5-^1^3C₄)oxolane-2,3,4-trione
• Synonyms: Dehydro-L-ascorbic Acid-13C6; L-threo-2,3-Hexodiulosonic Acid-13C6 γ-Lactone; Oxidized Ascorbic Acid-13C6; Oxidized Vitamin C-13C6; L-Dehydro Ascorbic Acid-13C6

Database IDs

• PubChem SID: 162259742
• PubChem CID: 57369509

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

DETAILS

Toronto Research Chemicals - D229252

The reversibly oxidized labelled 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)