Common NameD-mannitol
DescriptionMannitol, or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6), is an alcohol and a sugar (sugar alcohol), or a polyol, it is a stereoisomer of sorbitol and is similar to the C5 xylitol. The structure of mannitol is made of a straight chain of six carbon atoms, each of which is substituted with a hydroxyl group. Mannitol is one of the most abundant energy and carbon storage molecules in nature, it is produced by a wide range of organisms such as bacteria, fungi and plants (PMID: 19578847 ). In medicine, mannitol is used as a diuretic and renal diagnostic aid. Mannitol has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. Mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this, it is not uncommon to add a weak base, such as sodium bicarbonate, to the solution to adjust its pH. Mannitol is a non-permeating molecule i.e., it cannot cross biological membranes. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. Mannitol is found to be associated with cytochrome c oxidase deficiency and ribose-5-phosphate isomerase deficiency, which are inborn errors of metabolism. Mannitol is also a microbial metabolite found in Aspergillus, Candida, Clostridium, Gluconobacter, Lactobacillus, Lactococcus, Leuconostoc, Pseudomonas, Rhodobacteraceae, Saccharomyces, Streptococcus, Torulaspora and Zymomonas (PMID: 15240312 ; PMID: 29480337 ).
Structure
Molecular FormulaC6H14O6
Average Mass182.17180
Monoisotopic Mass182.07904
IUPAC Name(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
Traditional NameMannitol
CAS Registry Number69-65-8
SMILESOC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI IdentifierInChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
InChI KeyFBPFZTCFMRRESA-KVTDHHQDSA-N
CHEBI IDCHEBI:16899
HMDB IDHMDB0000765
StateNot Available
Water Solubility2.29e+02 g/l
logP-2.68
logS0.10
pKa (Strongest Acidic)12.59
pKa (Strongest Basic)-2.97
Hydrogen Acceptor Count6
Hydrogen Donor Count6
Polar Surface Area121.38 Ų
Rotatable Bond Count5
Physiological Charge0
Formal Charge0
Refractivity38.40 m³·mol⁻¹
Polarizability17.24

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