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

• ChemBase ID: 126845
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O)[C@@H]([C@H]([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-LKPKBOIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
• IUPAC Traditional name: D-chiro-inositol
• Synonyms: DCI; 1,2,4/3,5,6-Hexahydroxycyclohexane; D-chiro-Inositol; D-(+)-chiro-Inositol; 1,2,4/3,5,6-六羟基环己烷; D-(+)-手性肌醇

Database IDs

• CAS Number: 643-12-9
• EC Number: 211-394-0
• MDL Number: MFCD00272608
• PubChem SID: 162221172; 24870460
• PubChem CID: 892
• CHEBI ID: 27372
• Chemspider ID: 10254647
• Wikipedia Title: D-chiro-Inositol

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

• Melting Point: 230 °C(lit.); 230°C
• Optical Rotation: [α]23/D +55°, c = 1.2 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Optical Purity: ee: 99% (GLC)
• Empirical Formula (Hill Notation): C6H12O6

DETAILS

Sigma Aldrich - 468045

Packaging
1 g in glass bottle
25, 100 mg in glass bottle
Application
The inositols and their phosphates have been used in the development of metabolically stable insulin mediators, inhibitors, and modulators of important metabolic functions such as glycolysis. Inositols are stable to degradative enzymes in vivo because they lack a hydrolytically labile glycosidic linkage.1,2,3,4,5,6