(1S,3r,6R,8R,9R)-2,4,10-trioxatricyclo[3.3.1.13,7]decane-6,8,9-triol

• ChemBase ID: 138828
• Molecular Formular: C7H10O6
• Molecular Mass: 190.1507
• Monoisotopic Mass: 190.04773804
• SMILES: [C@@H]12O[C@H]3OC([C@H]1O)[C@H](C([C@H]2O)O3)O
• Canonical SMILES: O[C@@H]1C2O[C@H]3OC1[C@H]([C@@H]([C@@H]2O)O3)O
• InChI: InChI=1S/C7H10O6/c8-1-4-2(9)6-3(10)5(1)12-7(11-4)13-6/h1-10H/t1-,2-,3-,4+,5?,6?,7-/m0/s1
• InChIKey: WJJFNSGWGPSKAO-XEKWHFIDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3r,6R,8R,9R)-2,4,10-trioxatricyclo[3.3.1.1^3,^7]decane-6,8,9-triol
• IUPAC Traditional name: (1S,3r,6R,8R,9R)-2,4,10-trioxatricyclo[3.3.1.1^3,^7]decane-6,8,9-triol
• Synonyms: myo-Inositol monoorthoformate; 1,3,5-O-Methylidyne-myo-inositol; myo-纤维醇单原甲酸酯; 1,3,5-O-次甲基-myo-纤维醇

Database IDs

• CAS Number: 98510-20-4
• MDL Number: MFCD00134292
• PubChem SID: 162233079; 24885283
• PubChem CID: 1268065

CALCULATED PROPERTIES

• Acid pKa: 12.5465
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.482837
• LogD (pH = 7.4): -1.48284
• Log P: -1.4828368
• Molar Refractivity: 36.3295 cm^3
• Polarizability: 15.710125 Å^3
• Polar Surface Area: 88.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ≥270 °C (dec.); 260 °C (dec.)(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (HPLC); 98%
• Empirical Formula (Hill Notation): C7H10O6

DETAILS

Sigma Aldrich - 67550

Other Notes
Building block for the synthesis of inositol phosphates1,2,3
Packaging
5 g in glass bottle

Sigma Aldrich - 365076

Application
May be selectively dibenzylated at the C-4 and C-6 positions.1 Phosphorylation followed by deprotection provides inositol-2-phosphate.2