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

• ChemBase ID: 102533
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H]([C@H]([C@@H]1O)O)O)O)O)O
• 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-
• InChIKey: CDAISMWEOUEBRE-GPIVLXJGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3S,4R,5S,6r)-cyclohexane-1,2,3,4,5,6-hexol
• IUPAC Traditional name: (1R,2S,3S,4R,5S,6r)-cyclohexane-1,2,3,4,5,6-hexol
• Synonyms: i-Inositol; myo-Inositol; meso-Inositol; 1,2,3,4,5,6-Hexahydroxycyclohexane; D-myo-INOSITOL; Hexahydroxycyclohexane; Myoinositol; myo-Inositol; cis-1,2,3,5-trans-4,6-Cyclohexanehexol; Cyclohexanehexol; Mouse antialopecia factor; Nucite; Phaseomannite; Phaseomannitol; Rat antispectacled eye factor; Scyllite (for the structural isomer scyllo-Inositol); Inositol; 纤维醇; meso-肌醇; 环己六醇; 肌糖; 肌醇

Database IDs

• CAS Number: 87-89-8
• EC Number: 201-781-2
• MDL Number: MFCD00077932
• Beilstein Number: 1907329
• Merck Index: 144978
• PubChem SID: 162088452; 24880822; 24880820; 24896020; 24895982; 24896116
• PubChem CID: 892
• CHEBI ID: 17268
• ATC CODE: A11HA07
• CHEMBL: 1222251
• Chemspider ID: 10239179
• KEGG ID: D08079
• Unique Ingredient Identifier: 4L6452S749
• Wikipedia Title: Inositol

CALCULATED PROPERTIES

• 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
• Acid pKa: 12.285498
• H Acceptors: 6

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear; H2O: soluble0.5 M at 20 °C, clear, colorless; H2O: soluble50 mg/mL
• Melting Point: 222-227 °C; 222-227 °C(lit.); 224-227 °C; 224-227°C; 225°C; 225–227 °C
• Flash Point: 143°C (289.4°F)
• Density: 1.75; 1.752 g/cm3; 6.2 g/ml
• Vapor Density: 6.2 (vs air)
• Absorption Wavelength: λ: 260 nm Amax: 0.1; λ: 280 nm Amax: 0.1
• pH: 5.0-7.0 (25 °C, 0.5 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: NM7520800
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: 是
• NFPA704:
  

  0

  1

  0
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); ≥99%; ≥99.0%; ≥99.0% (HPLC); ≥99.5% (HPLC); 98+%
• Grade: for microbiology; purum; SAJ special grade
• Suitability: plant cell culture tested; suitable for cell culture; suitable for insect cell culture
• Ignition Residue: ≤0.2%; ≤0.2% (as SO4)
• Impurities: insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Loss on Drying: ≤0.5% loss on drying, 110 °C; ≤0.5% loss on drying, 20 °C (HV)
• Quality Level: PREMIUM
• λ: 0.5 M in H2O
• Product Line: BioUltra
• Empirical Formula (Hill Notation): C6H12O6

DETAILS

MP Biomedicals - 02194688

Cell Culture Reagent
A lipotropic agent.

MP Biomedicals - 02102052

A lipotropic agent.

Sigma Aldrich - I7508

Biochem/physiol Actions
膜磷脂、糖基化磷脂酰肌醇锚定蛋白、磷酸肌醇酯第二信使的成分,其中锚定蛋白可将糖蛋白锚定到细胞膜上。

Sigma Aldrich - 57569

Biochem/physiol Actions
A component of membrane phospholipids, glycosyl-phosphatidyl-inositol anchors that bind glycoproteins to cell membranes, and inositol phosphate second messengers.
Other Notes
Metabolism and function of myo-inositol and inositol phospholipids1; Review 2,3; Component of the liquid stationary phase in the GLC separation of nitroxylene and xylenol isomers4
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 57569.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Application
Myo-Inositol, an organic osmolyte, is used to improve ovarian function in women with polycystic ovary syndrome (PCOS). Myo-Inositol may be used to study the H+-myo-inositol transporter SLC2A13, a Potential Marker for Cancer Stem Cells in an Oral Squamous Cell Carcinoma.

Sigma Aldrich - I5125

Biochem/physiol Actions
膜磷脂、糖基化磷脂酰肌醇锚定蛋白、磷酸肌醇酯第二信使的成分,其中锚定蛋白可将糖蛋白锚定到细胞膜上。
包装
1 kg in poly bottle
10 mg in autosmp vl
50, 100, 500 g in poly bottle

Sigma Aldrich - I3011

Biochem/physiol Actions
膜磷脂、糖基化磷脂酰肌醇锚定蛋白、磷酸肌醇酯第二信使的成分,其中锚定蛋白可将糖蛋白锚定到细胞膜上。

Sigma Aldrich - I6652

Biochem/physiol Actions
A component of membrane phospholipids, glycosyl-phosphatidyl-inositol anchors that bind glycoproteins to cell membranes, and inositol phosphate second messengers.

Sigma Aldrich - 57570

Biochem/physiol Actions
A component of membrane phospholipids, glycosyl-phosphatidyl-inositol anchors that bind glycoproteins to cell membranes, and inositol phosphate second messengers.

Sigma Aldrich - 57575

Biochem/physiol Actions
A component of membrane phospholipids, glycosyl-phosphatidyl-inositol anchors that bind glycoproteins to cell membranes, and inositol phosphate second messengers.

Sigma Aldrich - 15-0510

Biochem/physiol Actions
A component of membrane phospholipids, glycosyl-phosphatidyl-inositol anchors that bind glycoproteins to cell membranes, and inositol phosphate second messengers.