hexane-1,2,3,4,5,6-hexol

• ChemBase ID: 622
• Molecular Formular: C6H14O6
• Molecular Mass: 182.17176
• Monoisotopic Mass: 182.07903817
• SMILES: OC(C(O)C(O)CO)C(O)CO
• Canonical SMILES: OCC(C(C(C(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
• InChIKey: FBPFZTCFMRRESA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: hexane-1,2,3,4,5,6-hexol
• IUPAC Traditional name: sorbitol
• Brand Name: Diosmol; Hexanhexol; Hexitol; Isotol; Manicol; Maniton-S; Manna sugar; Mannazucker; Mannidex; Mannigen; Mannistol; Mannit; Mannite; Mannitol 10%; Mannitol 10% In Plastic Container; Mannitol 15%; Mannitol 15% In Plastic Container; Mannitol 20%; Mannitol 20% In Plastic Container; Mannitol 25%; Mannitol 5%; Mannitol 5% In Plastic Container; Mannitol BP; Mushroom sugar; Osmitrol; Osmitrol 10% In Water; Osmitrol 15% In Water; Osmitrol 20% In Water; Osmitrol 5% In Water; Osmosal; Resectisol; Resectisol In Plastic Container; SDM-25; d-mannitol extra pure; Bronchitol
• Synonyms: Galactitol; Dulcite; DULCITOL; D-Mannitol; Cordycepic acid; mannitol; Mannitol; Allodulcitol. allo-Hexitol; Allitol

Database IDs

• CAS Number: 69-65-8; 488-44-8; 608-66-2
• EC Number: 210-165-2
• PubChem SID: 160964085
• PubChem CID: 453

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.68
• LOG S: 0.1
• Solubility (Water): 2.29e+02 g/l

PROPERTIES

Physical Property

• Solubility: 216 mg/mL
• Apperance: Cryst.
• Melting Point: 188-191°C
• Boiling Point: 275-280°C
• Hydrophobicity(logP): -3.9

Safety Information

• Storage Condition: Room Temperature (15-30°C)

Product Information

• Purity: ~99%

DETAILS

MP Biomedicals - 02101629

Crystalline
Purified for use in bacteriology.

DrugBank - DB00742

• Drug Groups: approved; investigational
• Description: Mannitol is an osmotic diuretic that is metabolically inert in humans and occurs naturally, as a sugar or sugar alcohol, in fruits and vegetables. Mannitol elevates blood plasma osmolality, resulting in enhanced flow of water from tissues, including the brain and cerebrospinal fluid, into interstitial fluid and plasma. As a result, cerebral edema, elevated intracranial pressure, and cerebrospinal fluid volume and pressure may be reduced. Mannitol may also be used for the promotion of diuresis before irreversible renal failure becomes established; the promotion of urinary excretion of toxic substances; as an Antiglaucoma agent; and as a renal function diagnostic aid.
• Indication: Used for the promotion of diuresis before irreversible renal failure becomes established, the reduction of intracranial pressure, the treatment of cerebral edema, and the promotion of urinary excretion of toxic substances.
• Pharmacology: Chemically, mannitol is an alcohol and a sugar, or a polyol; it is similar to xylitol or sorbitol. However, mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this reason, it is not uncommon to add a substance to adjust its pH, such as sodium bicarbonate. Mannitol is commonly used to increase urine production (diuretic). It is also used to treat or prevent medical conditions that are caused by an increase in body fluids/water (e.g., cerebral edema, glaucoma, kidney failure). Mannitol is frequently given along with other diuretics (e.g., furosemide, chlorothiazide) and/or IV fluid replacement.
• Toxicity: LD₅₀=1700 mg/kg (rat oral)
• Affected Organisms: Humans and other mammals
• Biotransformation: Mannitol is metabolized only slightly, if at all, to glycogen in the liver.
• Absorption: Approximately 7% of ingested mannitol is absorbed during gastrointestinal perfusion in uremic patients.
• Half Life: 100 minutes
• Protein Binding: None
• Elimination: It is rapidly excreted in the urine.
• References: Cruz J, Minoja G, Okuchi K: Improving clinical outcomes from acute subdural hematomas with the emergency preoperative administration of high doses of mannitol: a randomized trial. Neurosurgery. 2001 Oct;49(4):864-71. [Pubmed] ; Cruz J, Minoja G, Okuchi K: Major clinical and physiological benefits of early high doses of mannitol for intraparenchymal temporal lobe hemorrhages with abnormal pupillary widening: a randomized trial. Neurosurgery. 2002 Sep;51(3):628-37; discussion 637-8. [Pubmed] ; Cruz J, Minoja G, Okuchi K, Facco E: Successful use of the new high-dose mannitol treatment in patients with Glasgow Coma Scale scores of 3 and bilateral abnormal pupillary widening: a randomized trial. J Neurosurg. 2004 Mar;100(3):376-83. [Pubmed] ; Roberts I, Smith R, Evans S: Doubts over head injury studies. BMJ. 2007 Feb 24;334(7590):392-4. [Pubmed] ; Wakai A, Roberts I, Schierhout G: Mannitol for acute traumatic brain injury. Cochrane Database Syst Rev. 2005 Oct 19;(4):CD001049. [Pubmed] ; Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Roberts I, Smith R, Evans S: Doubts over head injury studies. BMJ. 2007 Feb 24;334(7590):392-4. Pubmed
• Cruz J, Minoja G, Okuchi K, Facco E: Successful use of the new high-dose mannitol treatment in patients with Glasgow Coma Scale scores of 3 and bilateral abnormal pupillary widening: a randomized trial. J Neurosurg. 2004 Mar;100(3):376-83. Pubmed
• Cruz J, Minoja G, Okuchi K: Improving clinical outcomes from acute subdural hematomas with the emergency preoperative administration of high doses of mannitol: a randomized trial. Neurosurgery. 2001 Oct;49(4):864-71. Pubmed
• Cruz J, Minoja G, Okuchi K: Major clinical and physiological benefits of early high doses of mannitol for intraparenchymal temporal lobe hemorrhages with abnormal pupillary widening: a randomized trial. Neurosurgery. 2002 Sep;51(3):628-37; discussion 637-8. Pubmed
• Wakai A, Roberts I, Schierhout G: Mannitol for acute traumatic brain injury. Cochrane Database Syst Rev. 2005 Oct 19;(4):CD001049. Pubmed
• Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. Pubmed