(1S,2r,4S)-cyclohexane-1,2,3,4,5,6-hexol

• ChemBase ID: 171643
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: C1([C@@H]([C@H](C([C@H](C1O)O)O)O)O)O
• Canonical SMILES: OC1C(O)[C@H](O)[C@H](C([C@H]1O)O)O
• InChI: InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2+,3?,4?,5+,6?/m0/s1
• InChIKey: CDAISMWEOUEBRE-QEZGZAACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2r,4S)-cyclohexane-1,2,3,4,5,6-hexol
• IUPAC Traditional name: (1S,2r,4S)-cyclohexane-1,2,3,4,5,6-hexol
• Synonyms: Cyclohexitol; Dambose; Inosital; Inosite; Inositene; Inositina; Inositol; MI; Mesoinosit; Mesoinosite; Mesoinositol; Mesol; Mesovit; Myoinosite; Myoinositol; Nucite; Phaseomannite; Phaseomannitol; Scyllite; cis-1,2,3,5-trans-4,6-Cyclohexanehexol; i-Inositol; myo-Inositol; Scyllitol; Cocositol; Quercinitol; 1,3,5/2,4,6-Hexahydroxycyclohexane; scyllo-Cyclohexanehexol; AZD 103; scyllo-Inositol

Database IDs

• CAS Number: 87-89-8; 488-59-5
• PubChem SID: 164227553
• PubChem CID: 892

CALCULATED PROPERTIES

• Acid pKa: 12.285498
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -3.7820098
• LogD (pH = 7.4): -3.7820153
• Log P: -3.7820096
• Molar Refractivity: 35.775 cm^3
• Polarizability: 15.092376 Å^3
• Polar Surface Area: 121.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Sil. Sol. Water; Water
• Apperance: White Crystalline Solid; White Solid
• Melting Point: 219-221°C; 348.5-350°C

Safety Information

• Storage Condition: -20°C Freezer; Refrigerator

DETAILS

Toronto Research Chemicals - I666050

scyllo-Inositol, acyclohexanehexol derivative used in the treatment of amyotrophic lateral sclerosis. Anti-Alzheimer's agent.

Toronto Research Chemicals - I665995

The structural basis for a number of signaling and secondary messenger molecules including; insulin signal transduction, cytoskeleton assembly, nerve guidance, membrane potentials, serotonin activity and the breaking down of fats and reducing cholesterol.

REFERENCES

• Fenili, D., et al.: J. Mol. Med., 85, 603 (2001)
• Chishti, M., et al.: J. Biol. Chem., 276, 21562 (2001)
• Fisher, S., et al.: J. Neurochem., 82, 736 (2001)
• McLaurin, J., et al.: Nat. Med., 12, 801 (2001)
• Graca, G., et al.: J. Prot. Res., 9, 6016 (2010)
• Rovio, S., et al.: Food Chem., 124, 1194 (2010)