(5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

• ChemBase ID: 160835
• Molecular Formular: C9H12O6
• Molecular Mass: 216.18798
• Monoisotopic Mass: 216.0633881
• SMILES: C1(=O)C(=C([C@H](O1)[C@H]1OC(OC1)(C)C)O)O
• Canonical SMILES: O=C1O[C@@H](C(=C1O)O)[C@@H]1COC(O1)(C)C
• InChI: InChI=1S/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3/t4-,7+/m0/s1
• InChIKey: POXUQBFHDHCZAD-MHTLYPKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
• IUPAC Traditional name: (5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-5H-furan-2-one
• Synonyms: 5,6-O-Isopropylidene-L-ascorbic Acid; NSC 252042; Ascorbic Acid Acetonide

Database IDs

• CAS Number: 15042-01-0
• PubChem SID: 162254970
• PubChem CID: 54691418

CALCULATED PROPERTIES

• Acid pKa: 4.5245724
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.2290365
• LogD (pH = 7.4): -3.000189
• Log P: -0.21113425
• Molar Refractivity: 49.2391 cm^3
• Polarizability: 19.215916 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 195-200°C

Safety Information

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

REFERENCES

• Shibayama, H., et al.: Biosci., Biotechnol., Biochem., 72, 1015 (2008)
• Choi, H., et al.: Bioorg. Med. Chem. Lett., 19, 2079 (2008)