(5R)-5-[1,2-dihydroxy(1,2-13C2)ethyl]-3,4-dihydroxy-2,5-dihydro(2,3,4,5-13C4)furan-2-one

• ChemBase ID: 160834
• Molecular Formular: C6H8O6
• Molecular Mass: 182.08004903
• Monoisotopic Mass: 182.052217
• SMILES: [13C]1(=[13C](O)[13C](=O)O[13C@@H]1[13CH]([13CH2]O)O)O
• Canonical SMILES: O[13CH2][13CH]([13C@H]1O[13C](=O)[13C](=[13C]1O)O)O
• InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2?,5-/m1/s1/i1+1,2+1,3+1,4+1,5+1,6+1
• InChIKey: CIWBSHSKHKDKBQ-HFEVONBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[1,2-dihydroxy(1,2-^1^3C₂)ethyl]-3,4-dihydroxy-2,5-dihydro(2,3,4,5-^1^3C₄)furan-2-one
• IUPAC Traditional name: (5R)-5-[1,2-dihydroxy(1,2-^1^3C₂)ethyl]-3,4-dihydroxy(2,3,4,5-^1^3C₄)-5H-furan-2-one
• Synonyms: (+)-Ascorbic Acid-13C6; 100M-13C6; 3-Oxo-L-gulofuranolactone-13C6; 3-keto-L-Gulofuranolactone-13C6; Adenex-13C6; Allercorb-13C6; Ascorbajen-13C6; Cantan-13C6; Cantaxin-13C6; Vitacimin-13C6; Davitamon C-13C6; Laroscorbine-13C6; Vitamisin-13C6; Vitascorbol-13C6; L-Ascorbic Acid-13C6

Database IDs

• PubChem SID: 162254969
• PubChem CID: 57369508

CALCULATED PROPERTIES

• Acid pKa: 4.3599176
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.082243
• LogD (pH = 7.4): -4.8322015
• Log P: -1.9135588
• Molar Refractivity: 37.0321 cm^3
• Polarizability: 14.376429 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 187-189°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A786992

Labelled Ascorbic Acid. Physiological antioxidant. Coenzyme for a number of hydroxylation reactions; required for collagen synthesis. Widely distributed in plants and animals. Inadequate intake results in deficiency syndromes such as scurvy. Used as antim

REFERENCES

• Al-Meshal, I.A., et al.: Anal. Profiles Drug Subs., 11, 45 (1982)
• Levine, M., et al.: N. Engl. J. Med., 314, 892 (1982)
• Prust, C., et al.: Nature Biotech., 23, 195 (1982)