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

• ChemBase ID: 73005
• Molecular Formular: C6H14O6
• Molecular Mass: 182.17176
• Monoisotopic Mass: 182.07903817
• SMILES: OC[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O
• InChI: InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
• InChIKey: FBPFZTCFMRRESA-KVTDHHQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
• IUPAC Traditional name: mannitol
• Synonyms: Mannitolum; D-Mannitol, ACS; Mannitol; Osmitrol; Osmofundin; D-Mannitol(Osmitrol); Manna sugar; Mannite; D-MANNITOL; 1,2,3,4,5,6-Hexahexol, Mannite; D-MANNITOL, ACS; Mannitol; D-Mannitol; 甘露蜜醇; D-甘露醇, ACS; D-甘露醇; 甘露醇; D-甘露糖醇

Database IDs

• CAS Number: 69-65-8; 69–65–8
• EC Number: 200-711-8
• MDL Number: MFCD00064287
• Beilstein Number: 1721898
• Merck Index: 145745
• PubChem SID: 24896902; 24882727; 24896586; 22435040; 24897257; 162037925; 24882728; 24897341; 24897346; 24860225; 24882729
• PubChem CID: 6251
• CHEBI ID: 16899
• ATC CODE: A06AD16; B05CX04; B05BC01; R05CB16
• CHEMBL: 689
• Chemspider ID: 6015
• DrugBank ID: DB00742
• KEGG ID: D00062
• Unique Ingredient Identifier: 3OWL53L36A
• Wikipedia Title: Mannitol

CALCULATED PROPERTIES

• Acid pKa: 12.585201
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -3.7300189
• LogD (pH = 7.4): -3.7300217
• Log P: -3.7300189
• Molar Refractivity: 38.4036 cm^3
• Polarizability: 15.776147 Å^3
• Polar Surface Area: 121.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless; H2O: soluble1 M at 20 °C, clear, colorless; H2O: soluble1 M, clear, colorless; Soluble in water, alcohol, pyridine, aniline. Insoluble in ether
• Apperance: Crystalline
• Melting Point: 165°C; 165-167 °C; 165-167°C; 165-167°C; 165-168 °C; 166-168 °C; 167-169°C; 167-170 °C(lit.)
• Boiling Point: (at 3.5 mm) 290-295°C; 290-295°C/3.5mm; 295°C
• Density: 1.489; 1.52 g/ml
• Optical Rotation: [α]/D +24.0±1° in borax solution acc. to ACS; [α]20/D +23 to +25°, c = 8% in Na2B4O7; [α]20/D +24.0±1° in borax solution acc. to ACS; [α]20/D +24.0±1° in borax solution acc. to Ph Eur; [α]20/D +24±1° in borax solution acc. to Ph Eur; [α]22/D +141.0°, c = 0.4 in acidified ammonium molybdate; [α]25/D +137 to +145; [α]25/D +141°, c = 0.4 in acidified ammonium molybdate; [α]25/D +23.3 to +24.3°(lit.); +24 (in borax solution)
• Absorption Wavelength: λ: 260 nm Amax: 0.04; λ: 280 nm Amax: 0.04
• Conductivity: 20 μS/cm at 20 °C
• pH: 5.0-6.5 (25 °C, 1 M in H2O); 5-7.5 (20 °C, 10%)

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: OP2060000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2; 3
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: Intravenous; Oral
• Bioavailability: ~7%
• Excretion: Renal: 90%
• Half Life: 100 minutes
• Metabolism: Hepatic, negligible.
• Pregnancy Category: C: (USA)

Product Information

• Purity: ~99%; ≥98%; ≥98% (calc. to the dried substance, HPLC); ≥98% (GC); ≥98.0% (sum of enantiomers, HPLC); ≥99%; ≥99.0%; ≥99.0% (sum of enantiomers, HPLC); ≥99.9999% (metals basis); 98%; 98.0-101.5% (calc. to the dried substance, HPLC); 99%
• Grade: ACS; ACS reagent; for biotechnological purposes; for microbiology; Ph Eur; puriss. p.a.; REAGENT; SAJ first grade; SAJ special grade; TraceSELECT®
• Salt Data: Free Base
• Suitability: meets EP, FCC, USP testing specifications; passes test for identity (IR); plant cell culture tested
• Ignition Residue: ≤0.01%; ≤0.01% (as SO4); ≤0.05% (as SO4); ≤0.1% (as SO4)
• Impurities: ≤0.0005% Phosphorus (P); ≤0.0008 meq/g Titratable acid; ≤0.0072% free acid (as CH3COOH); ≤0.01% Insoluble matter; ≤0.3% water (Karl Fischer); ≤0.5% water (Karl Fischer); insoluble matter, passes filter test; reducing sugars, complies; Reducing sugars, passes test
• Cation Traces: Ag: ≤0.01 mg/kg; Al: ≤0.0005%; Al: ≤0.05 mg/kg; Al: ≤5 mg/kg; As: ≤0.01 mg/kg; As: ≤0.1 mg/kg; As: ≤1 mg/kg; Au: ≤0.01 mg/kg; B: ≤0.05 mg/kg; Ba: ≤0.05 mg/kg; Ba: ≤5 mg/kg; Be: ≤0.01 mg/kg; Bi: ≤0.01 mg/kg; Bi: ≤5 mg/kg; Ca: ≤0.0005%; Ca: ≤0.2 mg/kg; Ca: ≤10 mg/kg; Cd: ≤0.01 mg/kg; Cd: ≤5 mg/kg; Ce: ≤0.01 mg/kg; Co: ≤0.01 mg/kg; Co: ≤5 mg/kg; Cr: ≤0.01 mg/kg; Cr: ≤5 mg/kg; Cs: ≤0.01 mg/kg; Cu: ≤0.0005%; Cu: ≤0.01 mg/kg; Cu: ≤5 mg/kg; Dy: ≤0.01 mg/kg; Er: ≤0.01 mg/kg; Eu: ≤0.01 mg/kg; Fe: ≤0.0005%; Fe: ≤0.05 mg/kg; Fe: ≤10 mg/kg; Fe: ≤5 mg/kg; Ga: ≤0.01 mg/kg; Gd: ≤0.01 mg/kg; Ge: ≤0.01 mg/kg; heavy metals (as Pb): ≤5 ppm; Hf: ≤0.01 mg/kg; Hg: ≤0.001 mg/kg; Ho: ≤0.01 mg/kg; In: ≤0.01 mg/kg; Ir: ≤0.01 mg/kg; K: ≤0.005%; K: ≤0.1 mg/kg; K: ≤50 mg/kg; La: ≤0.01 mg/kg; Li: ≤0.01 mg/kg; Li: ≤5 mg/kg; Lu: ≤0.01 mg/kg; Mg: ≤0.0005%; Mg: ≤0.05 mg/kg; Mg: ≤5 mg/kg; Mn: ≤0.01 mg/kg; Mn: ≤5 mg/kg; Mo: ≤0.01 mg/kg; Mo: ≤5 mg/kg; Na: ≤0.005%; Na: ≤0.5 mg/kg; Na: ≤50 mg/kg; Nb: ≤0.01 mg/kg; Nd: ≤0.01 mg/kg; NH4+: ≤0.05%; Ni: ≤0.01 mg/kg; Ni: ≤1 mg/kg; Ni: ≤5 mg/kg; Os: ≤0.01 mg/kg; Pb: ≤0.001%; Pb: ≤0.01 mg/kg; Pb: ≤1 mg/kg; Pb: ≤5 mg/kg; Pd: ≤0.01 mg/kg; Pr: ≤0.01 mg/kg; Pt: ≤0.01 mg/kg; Rb: ≤0.01 mg/kg; Re: ≤0.01 mg/kg; Rh: ≤0.01 mg/kg; Ru: ≤0.01 mg/kg; Sb: ≤0.01 mg/kg; Sc: ≤0.05 mg/kg; Se: ≤0.01 mg/mL; Sm: ≤0.01 mg/kg; Sn: ≤0.01 mg/kg; Sr: ≤0.01 mg/kg; Sr: ≤5 mg/kg; Ta: ≤0.01 mg/kg; Tb: ≤0.01 mg/kg; Te: ≤0.01 mg/kg; Th: ≤0.01 mg/kg; Ti: ≤0.05 mg/kg; Tl: ≤0.01 mg/kg; Tm: ≤0.01 mg/kg; U: ≤0.01 mg/kg; V: ≤0.01 mg/kg; W: ≤0.01 mg/kg; Y: ≤0.01 mg/kg; Yb: ≤0.01 mg/kg; Zn: ≤0.0005%; Zn: ≤0.01 mg/kg; Zn: ≤10 mg/kg; Zn: ≤5 mg/kg; Zr: ≤0.01 mg/kg
• Antion Traces: bromide (Br-): ≤1000 μg/kg; chloride (Cl-): ≤0.05%; chloride (Cl-): ≤1000 μg/kg; chloride (Cl-): ≤50 mg/kg; fluoride (F-): ≤1000 μg/kg; nitrate (NO3-): ≤1000 μg/kg; nitrite (NO2-): ≤1000 μg/kg; phosphate (PO43-): ≤1000 μg/kg; sulfate (SO42-): ≤0.05%; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤1000 μg/kg; sulfate (SO42-): ≤50 mg/kg
• Loss on Drying: ≤0.05% loss on drying, 105°C; ≤0.05% loss on drying, 20 °C (HV); ≤0.3% loss on drying, 105 °C, 4 h
• Quality: meets analytical specification of Ph. Eur., USP, FCC, E421
• λ: 1 M in H2O
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioUltra
• Pharmacopeia Traceability: traceable to PhEur M0200000; traceable to USP 1375105
• Empirical Formula (Hill Notation): C6H14O6

DETAILS

MP Biomedicals - 02152540

ACS Reagent Grade

MP Biomedicals - 02102248

Crystalline
Purity: ~99%

Selleck Chemicals - S2381

Research Area: Cardiovascular Disease
Biological Activity:
D-Mannitol(Osmitrol) is an osmotic diuretic agent and a weak renal vasodilator. It is used clinically to reduce acutely raised intracranial pressure until more definitive treatment can be applied, e.g., after head trauma. It is also used to treat patients with oliguric renal failure. Mannitol can also be used as a facilitating agent for the transportation of pharmaceuticals directly into the brain. The arteries of the blood-brain barrier are much more selective than normal arteries. It is commonly used in the circuit prime of a heart lung machine during cardiopulmonary bypass. The presence of mannitol preserves renal function during the times of low blood flow and pressure, while the patient is on bypass. [1]

Sigma Aldrich - 63565

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - M9546

Biochem/physiol Actions
糖醇甜促味剂。用于甜味抑制研究。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M9546.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 63559

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.
Other Notes
Used in discontinuous gradient centrifugation for purification of plant protoplasts1. Plasmolyticum that reversibly inhibits phenylalanine ammonia-lyase activity of protoplasts at concentrations exceeding 50 mM2. Component of the liquid stationary phase in the GLC separation of nitroxylene and xylenol isomers3.
Application
D-Mannitol is used as an osmolyte and transport facilitator in a variety of biological in vivo and in vitro applications, such as improvement of blood-brain barrier transport and hyperosmolar therapy. D-Mannitol is used as a substrate to identify, differentiate and characterized enzymes such as mannitol dehydrogenase(s). D-Mannitol is used in identify mannitol metabolizing bacteria.

Sigma Aldrich - M1902

Biochem/physiol Actions
糖醇甜促味剂。用于甜味抑制研究。

Sigma Aldrich - M2357

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - 33440

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - 63560

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.
Other Notes
Important starting material for the synthesis of many chiral building blocks1,2,3,4.

Sigma Aldrich - 15719

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - M9647

Biochem/physiol Actions
糖醇甜促味剂。用于甜味抑制研究。
包装
1 kg in poly bottle
10 kg in poly drum
250, 500 g in poly bottle

Sigma Aldrich - 17311

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - M4125

Biochem/physiol Actions
糖醇甜促味剂。用于甜味抑制研究。
包装
1 kg in poly bottle
10 mg in autosmp vl
100, 500 g in poly bottle
5 kg in poly drum

Sigma Aldrich - 78513

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.
Legal Information
TraceSELECT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 43618

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - 19-1070

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - 240184

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - 19-1080

Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.

Sigma Aldrich - M8429

Biochem/physiol Actions
糖醇甜促味剂。用于甜味抑制研究。

REFERENCES

• http://en.wikipedia.org/wiki/Mannitol