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Mannitol (FDB112364)

Record Information
Version1.0
Creation date2020-04-20 19:55:37 UTC
Update date2020-09-17 15:42:10 UTC
Primary IDFDB112364
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMannitol
DescriptionMannitol, also known ashexan-1,2,3,4,5,6-hexol (C6H8(OH)6), osmitrol or tobrex, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Mannitol is one of the most abundant energy and carbon storage molecules in nature, and is produced by a plethora of organisms, including bacteria, fungi, algae, lichens. Mannitol is commonly used as a sweetener in diabetic foods as it is poorly absorbed by the intestines. Mannitol is also used as medication to decrease pressure in the eyes, (i.e. glaucoma) and to lower increased intracranial pressure. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. Mannitol can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function. Mannitol is commonly used as a research tool in cell biological studies, usually to control osmolarity. Chemically, mannitol as a sugar alcohol, is similar to xylitol or sorbitol and is considered an isomer of 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 base to adjust its pH, such as sodium bicarbonate. Mannitol is a non-permeating molecule, meaning that it cannot cross biological membranes. Because of this inability to cross biological membranes, mannitol has been used for the determination of glomerular filtration rate (GFR). Altered levels of mannitol have been 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).
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
Chemical FormulaC6H14O6
IUPAC name(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
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
Isomeric SMILESOC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Average Molecular Weight182.1718
Monoisotopic Molecular Weight182.07903818
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00di-9000000000-d5db4fbf6c1eb9dd35642018-05-25View Spectrum
GC-MSMannitol, 6 TMS, GC-MS Spectrumsplash10-0ktb-0931000000-b481d576c5f24dd1b1d5Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-066s-0942000000-20043a375d72ca08dce9Spectrum
GC-MSMannitol, 6 TMS, GC-MS Spectrumsplash10-066r-1974000000-38a4beaca17ab8c750b6Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-0229-9100000000-5655e9df8e0fdcaa72a0Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-001i-9200000000-0dad802ab0000303cb33Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-0ktb-0931000000-b481d576c5f24dd1b1d5Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-066s-0942000000-20043a375d72ca08dce9Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-066r-1974000000-38a4beaca17ab8c750b6Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-066s-0942000000-f4df881aeebac32de5c7Spectrum
Predicted GC-MSMannitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03k9-9500000000-97c5853d3e9b96f9d054Spectrum
Predicted GC-MSMannitol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6s-7141193000-dcd9245e12314ee0ced4Spectrum
Predicted GC-MSMannitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014j-9600000000-26f4335f7ef7c81ca2612012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-9000000000-73db1fbd51fb8c061bec2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9000000000-45a4dea1d21286c4b8da2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0089-6900000000-961d76d6550bc342ffa12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0089-6900000000-061f88989a6ac71321e32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ik9-1900000000-eb8ea056f3b1dfe2fb1f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-1900000000-6768b4744e1a4e56b18b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-1900000000-0765563624accf132d032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0900000000-e159f4e76b7847313f352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0900-0910000000-8d56394cbc78dd3b5ca02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0900000000-63517bff4abfbf09e1ca2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w2l-0940000000-dc20c851073dcbc4dba92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-05ar-9500000000-c82bc4e2d1e173359c3e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9000000000-47357f9a38864cba96682021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-066r-9000000000-9cd6979ccf800d067e032021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-02tj-9400000000-b72fa250b3caa4a876822021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-fc27b5c54b0dd6fc8a392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-9100000000-0436dafd7f39b7c910e92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-066u-9000000000-fb4a8654ee07a1dcc56c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-ef92b9091ecf5d15cdee2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-47f19bd4e51bff7265362016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9100000000-60d5147d8e349337fe972016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07ju-8900000000-36f0fe0f346a6424162a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c0c-9200000000-36e85b5ec098a45204c32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-77703ee971336704163f2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference