(1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol

• ChemBase ID: 130283
• Molecular Formular: C7H14O6
• Molecular Mass: 194.18246
• Monoisotopic Mass: 194.07903817
• SMILES: O[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1OC
• Canonical SMILES: CO[C@@H]1[C@@H](O)[C@@H](O)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5-,6+,7+/m0/s1
• InChIKey: DSCFFEYYQKSRSV-KLJZZCKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol
• IUPAC Traditional name: pinit
• Synonyms: D-Pinitol; 3-O-Methyl-D-chiro-inositol; D-(+)-chiro-Inositol; D-Pinitol; Inzitol; D-(+)-Pinitol; (+)-Pinitol; Sennitol; Pinnitol; (+/-)pinitol; Pinitol; 3-O-甲基-D-手性肌醇; D-松醇

Database IDs

• CAS Number: 10284-63-6
• MDL Number: MFCD00216659
• PubChem SID: 24867648; 162224562
• PubChem CID: 164619
• CHEBI ID: 28548
• CHEMBL: 493737
• Chemspider ID: 10369209
• Wikipedia Title: Pinitol

CALCULATED PROPERTIES

• Acid pKa: 12.360891
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.138883
• LogD (pH = 7.4): -3.138888
• Log P: -3.138883
• Molar Refractivity: 40.5262 cm^3
• Polarizability: 16.951847 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 179-185 °C(lit.); 179–185 °C
• Optical Rotation: [α]20/D 60.0 to 70.0°, c = 1% in H2O

Safety Information

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

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C7H14O6

DETAILS

Sigma Aldrich - 441252

Packaging
100, 500 mg in glass bottle
Application
Precursor to biologically active fluorinated isosteres of inositol, which show cell growth inhibitory properties.1 Has shown antidiabetic properties in mice.2 Believed to be a salt stress regulator in a wide range of plants.3