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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:35 UTC
NP-MRD IDNP0000500
Secondary Accession NumbersNone
Natural Product Identification
Common NameMannitol
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
Thumb
Synonyms
ValueSource
(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexaolChEBI
(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexolChEBI
D-(-)-MannitolChEBI
DulciteChEBI
e 421ChEBI
e-421ChEBI
e421ChEBI
Manna sugarChEBI
ManniteChEBI
OsmitrolChEBI
D-MannitolKegg
TobrexKegg
BronchitolKegg
1,2,3,4,5,6-HexanehexolHMDB
CordycepateHMDB
Cordycepic acidHMDB
DiosmolHMDB
HexahydroxyhexaneHMDB
HexanhexolHMDB
InvenexHMDB
IsotolHMDB
ManicolHMDB
Maniton SHMDB
Maniton-SHMDB
MannazuckerHMDB
MannidexHMDB
MannigenHMDB
MannistolHMDB
MannitHMDB
Mannit pHMDB
Mannogem 2080HMDB
Marine crystalHMDB
Mushroom sugarHMDB
OsmofundinHMDB
OsmosalHMDB
ResectisolHMDB
SDM No. 35HMDB
(L)-MannitolHMDB
MannitolChEBI
Chemical FormulaC6H14O6
Average Mass182.1718 Da
Monoisotopic Mass182.07904 Da
IUPAC Name(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
Traditional Namemannitol
CAS Registry Number69-65-8
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI Identifier
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
InChI KeyFBPFZTCFMRRESA-KVTDHHQDSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Acanthopanax giraldiiKNApSAcK Database
Allium tuberosum Rottl.ex Spreng.KNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Aragoa cundinamarcensisPlant
Arisaema consanguineumKNApSAcK Database
Averrhoa carambolaPlant
Bergera koenegii-
Brassica oleracea L. ssp. BotrytisKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Carum carviPlant
Carum carvi L.KNApSAcK Database
Cinnamosma fragransKNApSAcK Database
Cinnamosma madagascariensisKNApSAcK Database
Cistanche tubulosaKNApSAcK Database
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
Clerodendrum serratumKNApSAcK Database
Cocos nuciferaPlant
Commelina communisKNApSAcK Database
Cordia sinensisKNApSAcK Database
Crataegus spp.Plant
Cuminum cymimum LKNApSAcK Database
Escherichia coli K12Bacteria
Euonymus atropurpureusPlant
Fraxinus ornusKNApSAcK Database
Gardenia jasminoides var.grandifloraKNApSAcK Database
Globularia vulgaris L.KNApSAcK Database
Gymnosporia deflexaPlant
Itea ilicifoliaPlant
Kickxia ramosissimaKNApSAcK Database
Laminaria japonicaKNApSAcK Database
Ligustrum lucidumKNApSAcK Database
Medicago sativaKNApSAcK Database
Melampyrum nemorosumPlant
Murraya paniculataKNApSAcK Database
Neopicrorhiza scrophulariifloraPlant
Nyctanthes arbor-tristis Linn.KNApSAcK Database
Panax ginsengKNApSAcK Database
Pedicularis muscicolaKNApSAcK Database
Pedicularis resupinata oppositifoliaKNApSAcK Database
Phasianus colchicus-
Picrorhiza kurrooaKNApSAcK Database
Picrorhiza scrophulariifloraKNApSAcK Database
Plantago creticaPlant
Plantago subspathulataPlant
Prunus aviumKNApSAcK Database
Rehmannia glutinosaKNApSAcK Database
Saccharina japonicaPlant
Sonchus arvensisKNApSAcK Database
Sorbus-
Sorbus aucupariaPlant
Tamarix gallicaKNApSAcK Database
Tarenna gracilipes (HAY.) OHWIKNApSAcK Database
Theonella swinhoei-
Tylopilus plumbeoviolaceusFungi
Typha angustataKNApSAcK Database
Veronica austriaca L.KNApSAcK Database
Veronica hederifoliaPlant
Veronica ligustrifolia A.CunnKNApSAcK Database
Veronica persicaPlant
Veronica spuriaKNApSAcK Database
Veronica x andersonii Lindl. et PaxKNApSAcK Database
Veronicastrum sibiricumKNApSAcK Database
Veronicastrum virginicum (L.) Farw.KNApSAcK Database
Wulfenia baldaccii DegenKNApSAcK Database
Wulfenia orientalis BOISS.KNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point166 °CNot Available
Boiling Point290.00 to 295.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility216 mg/mL at 25 °CYalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP-3.10Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m³·mol⁻¹ChemAxon
Polarizability17.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000765
DrugBank IDDB00742
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112364
KNApSAcK IDC00001165
Chemspider ID6015
KEGG Compound IDC00392
BioCyc IDMANNITOL
BiGG IDNot Available
Wikipedia LinkMannitol
METLIN ID142
PubChem Compound6251
PDB IDNot Available
ChEBI ID16899
Good Scents IDrw1030941
References
General References
  1. Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [PubMed:7710082 ]
  2. Polderman KH, van de Kraats G, Dixon JM, Vandertop WP, Girbes AR: Increases in spinal fluid osmolarity induced by mannitol. Crit Care Med. 2003 Feb;31(2):584-90. [PubMed:12576970 ]
  3. Zunkeler B, Carson RE, Olson J, Blasberg RG, DeVroom H, Lutz RJ, Saris SC, Wright DC, Kammerer W, Patronas NJ, Dedrick RL, Herscovitch P, Oldfield EH: Quantification and pharmacokinetics of blood-brain barrier disruption in humans. J Neurosurg. 1996 Dec;85(6):1056-65. [PubMed:8929495 ]
  4. Dreher F, Patouillet C, Fouchard F, Zanini M, Messager A, Roguet R, Cottin M, Leclaire J, Benech-Kieffer F: Improvement of the experimental setup to assess cutaneous bioavailability on human skin models: dynamic protocol. Skin Pharmacol Appl Skin Physiol. 2002;15 Suppl 1:31-9. [PubMed:12476007 ]
  5. Schramm-Baxter J, Mitragotri S: Needle-free jet injections: dependence of jet penetration and dispersion in the skin on jet power. J Control Release. 2004 Jul 7;97(3):527-35. [PubMed:15212884 ]
  6. Megson GM, Stevens DA, Hamilton JR, Denning DW: D-mannitol in cerebrospinal fluid of patients with AIDS and cryptococcal meningitis. J Clin Microbiol. 1996 Jan;34(1):218-21. [PubMed:8748311 ]
  7. Koskela HO, Hyvarinen L, Brannan JD, Chan HK, Anderson SD: Responsiveness to three bronchial provocation tests in patients with asthma. Chest. 2003 Dec;124(6):2171-7. [PubMed:14665497 ]
  8. Zhao G, Wang CY, Wang F, Xiong JX: Clinical study on nutrition support in patients with severe acute pancreatitis. World J Gastroenterol. 2003 Sep;9(9):2105-8. [PubMed:12970916 ]
  9. Kiyoshima A, Kudo K, Hino Y, Ikeda N: Sensitive and simple determination of mannitol in human brain tissues by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):103-8. [PubMed:11482728 ]
  10. Ware ML, Nemani VM, Meeker M, Lee C, Morabito DJ, Manley GT: Effects of 23.4% sodium chloride solution in reducing intracranial pressure in patients with traumatic brain injury: a preliminary study. Neurosurgery. 2005 Oct;57(4):727-36; discussion 727-36. [PubMed:16239885 ]
  11. Tang H, Blankschtein D, Langer R: Effects of low-frequency ultrasound on the transdermal permeation of mannitol: comparative studies with in vivo and in vitro skin. J Pharm Sci. 2002 Aug;91(8):1776-94. [PubMed:12115805 ]
  12. Graefe H, Gutschow B, Gehring H, Dibbelt L: Sensitive and specific photometric determination of mannitol in human serum. Clin Chem Lab Med. 2003 Aug;41(8):1049-55. [PubMed:12964813 ]
  13. Koskela HO, Hyvarinen L, Brannan JD, Chan HK, Anderson SD: Sensitivity and validity of three bronchial provocation tests to demonstrate the effect of inhaled corticosteroids in asthma. Chest. 2003 Oct;124(4):1341-9. [PubMed:14555564 ]
  14. Barben J, Roberts M, Chew N, Carlin JB, Robertson CF: Repeatability of bronchial responsiveness to mannitol dry powder in children with asthma. Pediatr Pulmonol. 2003 Dec;36(6):490-4. [PubMed:14618640 ]
  15. Keating FK, Sobel BE, Schneider DJ: Effects of increased concentrations of glucose on platelet reactivity in healthy subjects and in patients with and without diabetes mellitus. Am J Cardiol. 2003 Dec 1;92(11):1362-5. [PubMed:14636925 ]
  16. Kiyoshima A, Kudo K, Goto Y, Tobimatsu S, Ikeda N: Changes of the cerebral mannitol concentrations in the course of brain death of a rodent model. Leg Med (Tokyo). 2004 Apr;6(2):117-24. [PubMed:15039055 ]
  17. Koskela HO, Hyvarinen L, Brannan JD, Chan HK, Anderson SD: Coughing during mannitol challenge is associated with asthma. Chest. 2004 Jun;125(6):1985-92. [PubMed:15189912 ]
  18. Rikitake Y, Liao JK: Rho-kinase mediates hyperglycemia-induced plasminogen activator inhibitor-1 expression in vascular endothelial cells. Circulation. 2005 Jun 21;111(24):3261-8. Epub 2005 Jun 13. [PubMed:15956119 ]
  19. Lee J, Chung BC: Simultaneous measurement of urinary polyols using gas chromatography/mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):126-31. Epub 2005 Dec 13. [PubMed:16356788 ]
  20. Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. [PubMed:6821187 ]
  21. 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:11564247 ]
  22. 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:12188940 ]
  23. 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:15035271 ]
  24. Wakai A, Roberts I, Schierhout G: Mannitol for acute traumatic brain injury. Cochrane Database Syst Rev. 2005 Oct 19;(4):CD001049. [PubMed:16235278 ]
  25. Roberts I, Smith R, Evans S: Doubts over head injury studies. BMJ. 2007 Feb 24;334(7590):392-4. [PubMed:17322250 ]
  26. Song SH, Vieille C: Recent advances in the biological production of mannitol. Appl Microbiol Biotechnol. 2009 Aug;84(1):55-62. doi: 10.1007/s00253-009-2086-5. Epub 2009 Jul 4. [PubMed:19578847 ]
  27. Wisselink HW, Mars AE, van der Meer P, Eggink G, Hugenholtz J: Metabolic engineering of mannitol production in Lactococcus lactis: influence of overexpression of mannitol 1-phosphate dehydrogenase in different genetic backgrounds. Appl Environ Microbiol. 2004 Jul;70(7):4286-92. doi: 10.1128/AEM.70.7.4286-4292.2004. [PubMed:15240312 ]
  28. Zhang M, Gu L, Cheng C, Ma J, Xin F, Liu J, Wu H, Jiang M: Recent advances in microbial production of mannitol: utilization of low-cost substrates, strain development and regulation strategies. World J Microbiol Biotechnol. 2018 Feb 26;34(3):41. doi: 10.1007/s11274-018-2425-8. [PubMed:29480337 ]