(1R,2S,3S,4R,5S,6R)-2,3,6-tris(acetyloxy)-4,5-dihydroxycyclohexyl acetate

• ChemBase ID: 178227
• Molecular Formular: C14H20O10
• Molecular Mass: 348.3026
• Monoisotopic Mass: 348.10564684
• SMILES: [C@@H]1([C@H]([C@H]([C@H]([C@@H]([C@@H]1O)O)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](OC(=O)C)[C@H]([C@H]([C@@H]1OC(=O)C)O)O
• InChI: InChI=1S/C14H20O10/c1-5(15)21-11-9(19)10(20)12(22-6(2)16)14(24-8(4)18)13(11)23-7(3)17/h9-14,19-20H,1-4H3/t9-,10+,11+,12-,13+,14-
• InChIKey: ZQLBHQSQMQLFBM-KXSLGULGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3S,4R,5S,6R)-2,3,6-tris(acetyloxy)-4,5-dihydroxycyclohexyl acetate
• IUPAC Traditional name: (1R,2S,3S,4R,5S,6R)-2,3,6-tris(acetyloxy)-4,5-dihydroxycyclohexyl acetate
• Synonyms: 1,4,5,6-Tetraacetate myo-Inositol; 1,4,5,6-Tetraacetate DL-myo-Inositol; NSC 269405; 3,4,5,6-Tetra-O-acetyl myo-Inositol

Database IDs

• CAS Number: 90366-30-6
• PubChem SID: 164234137
• PubChem CID: 71752395

CALCULATED PROPERTIES

• Acid pKa: 12.725458
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.017508
• LogD (pH = 7.4): -2.0175102
• Log P: -2.017508
• Molar Refractivity: 72.381 cm^3
• Polarizability: 30.498955 Å^3
• Polar Surface Area: 145.66 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 81-83°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T282950

Used in the synthesis of seven novel myo-inositol ferulic acid ester derivatives.

REFERENCES

• Z. Physiol. Chem., 349, 767 (1968)
• Biochem. Biophys. Res. Commun., 67, 85 (1968)
• Biochem. Biophys. Res. Commun., 152, 155 (1988).