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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:22 UTC
HMDB IDHMDB00247
Secondary Accession NumbersNone
Metabolite Identification
Common NameSorbitol
DescriptionSorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. It is also used in many manufacturing processes, as a pharmaceutical aid, and in several research applications. Ascorbic acid fermentation; in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, tobacco, gelatin; bodying agent for paper, textiles, and liquid pharmaceuticals; softener for candy; sugar crystallization inhibitor; surfactants; urethane resins and rigid foams; plasticizer, stabilizer for vinyl resins; food additive (sweetener, humectant, emulsifier, thickener, anticaking agent); dietary supplement. (Hawley's Condensed Chemical Dictionary) Biological Source: Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus species Use/Importance: Used for manufacturing of sorbose, propylene glycol, ascorbic acid, resins, plasticizers and as antifreeze mixtures with glycerol or glycol. Tablet diluent, sweetening agent and humectant, other food uses. Sorbitol is used in photometric determination of Ru(VI) and Ru(VIII); in acid-base titration of borate (Dictionary of Organic Compounds).
Structure
Thumb
Synonyms
ValueSource
(-)-SorbitolChEBI
(2R,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexolChEBI
D-(-)-SorbitolChEBI
D-SorbitChEBI
e 420ChEBI
e-420ChEBI
e420ChEBI
g-OlChEBI
GLC-OlChEBI
L-GulitolChEBI
D-GlucitolHMDB
D-SorbolHMDB
DiakarmonHMDB
EsasorbHMDB
Foodol D 70HMDB
GlucarineHMDB
GlucitolHMDB
KarionHMDB
Karion instantHMDB
Kyowa powder 50mHMDB
MultitolHMDB
NeosorbHMDB
Neosorb 20/60dCHMDB
Neosorb 70/02HMDB
Neosorb 70/70HMDB
Neosorb P 20/60HMDB
Neosorb P 60HMDB
Neosorb P 60WHMDB
NivitinHMDB
ResulaxHMDB
SionitHMDB
Sionit KHMDB
SioniteHMDB
SiononHMDB
SiosanHMDB
Sorbex mHMDB
Sorbex RHMDB
Sorbex RPHMDB
Sorbex SHMDB
Sorbex XHMDB
SorbilandeHMDB
SorbilaxHMDB
SorbitHMDB
Sorbit D 70HMDB
Sorbit D-powderHMDB
Sorbit DPHMDB
Sorbit DP 50HMDB
Sorbit kyowa powder 50mHMDB
Sorbit L 70HMDB
Sorbit SHMDB
Sorbit T 70HMDB
Sorbit W 70HMDB
Sorbit W-powderHMDB
Sorbit W-powder 50HMDB
Sorbit WPHMDB
SorbiteHMDB
Sorbitol FHMDB
Sorbitol FKHMDB
Sorbitol FPHMDB
Sorbitol SHMDB
Sorbitol syrup CHMDB
SorbiturHMDB
SorboHMDB
Sorbogem 712HMDB
SorbolHMDB
SorbostylHMDB
Chemical FormulaC6H14O6
Average Molecular Weight182.1718
Monoisotopic Molecular Weight182.07903818
IUPAC Name(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional NameD-sorbitol
CAS Registry Number50-70-4
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 KeyInChIKey=FBPFZTCFMRRESA-JGWLITMVSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar alcohols
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Fructose and mannose metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point11 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2750.0 mg/mLNot Available
LogP-2.20SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility229.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m3·mol-1ChemAxon
Polarizability17.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0ldj-0941000000-19d96a9ba7ba0c482c83View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1973000000-d907b75f68a7927501a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-017j-8900000000-700285f86eac0a3501d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-9000000000-84676b839b145250d67dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9000000000-dce72cab270c488d65daView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Medulla
  • Bladder
  • Erythrocyte
  • Eye Lens
  • Fibroblasts
  • Kidney
  • Lens
  • Liver
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Red Blood Cell
  • Retina
  • Sciatic Nerve
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
Fructose intolerance, hereditarySMP00725Not Available
FructosuriaSMP00561Not Available
Galactose MetabolismSMP00043map00052
GalactosemiaSMP00182Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.09 +/- 0.37 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified13.0 (4.0-24.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified13.0 (9.49-16.5) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified19.43 +/- 5.65 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified19.4 +/- 5.6 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified15.6 +/- 1.9 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified17.2 +/- 4.6 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected and Quantified196.17 +/- 346.21 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified<1.00 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.9 (1.9-5.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified9.9 (2.5-18.7) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.5 +/- 2.24 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified46.064 +/- 38.805 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified9.74 +/- 10.36 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified23.3 +/- 3.3 uMAdult (>18 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified22.89 +/- 3.34 uMNot SpecifiedNot SpecifiedAlzheimer's disease details
UrineDetected and Quantified52.238 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [8595727 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011676
KNApSAcK IDC00001173
Chemspider ID5576
KEGG Compound IDC00794
BioCyc IDNot Available
BiGG ID36018
Wikipedia LinkSorbitol
NuGOwiki LinkHMDB00247
Metagene LinkHMDB00247
METLIN ID143
PubChem Compound5780
PDB IDSOR
ChEBI ID17924
References
Synthesis ReferenceLiu, Haichao; Luo, Chen. Method for manufacturing sorbitol and mannitol with cellulose. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  2. Airey CM, Price DE, Kemp JV, Perkins CM, Wales JK: The effect of aldose reductase inhibition on erythrocyte polyols and galactitol accumulation in diabetic patients. Diabet Med. 1989 Dec;6(9):804-8. [2533041 ]
  3. 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. [7710082 ]
  4. Sundkvist G, Dahlin LB, Nilsson H, Eriksson KF, Lindgarde F, Rosen I, Lattimer SA, Sima AA, Sullivan K, Greene DA: Sorbitol and myo-inositol levels and morphology of sural nerve in relation to peripheral nerve function and clinical neuropathy in men with diabetic, impaired, and normal glucose tolerance. Diabet Med. 2000 Apr;17(4):259-68. [10821291 ]
  5. Morenkova SA: [Comparative analysis of dependence of saliva sorbitol and fructosamine levels on blood glucose level in patients with diabetes] Biomed Khim. 2004;50(6):612-4. [15707277 ]
  6. Bareford D, Jennings PE, Stone PC, Baar S, Barnett AH, Stuart J: Effects of hyperglycaemia and sorbitol accumulation on erythrocyte deformability in diabetes mellitus. J Clin Pathol. 1986 Jul;39(7):722-7. [3090107 ]
  7. Ciuchi E, Odetti P, Prando R: Relationship between glutathione and sorbitol concentrations in erythrocytes from diabetic patients. Metabolism. 1996 May;45(5):611-3. [8622605 ]
  8. Kwang-Hyok S, Ui-Nam P, Sarkar C, Bhadra R: A sensitive assay of red blood cell sorbitol level by high performance liquid chromatography: potential for diagnostic evaluation of diabetes. Clin Chim Acta. 2005 Apr;354(1-2):41-7. Epub 2005 Jan 18. [15748598 ]
  9. Nau R: Osmotherapy for elevated intracranial pressure: a critical reappraisal. Clin Pharmacokinet. 2000 Jan;38(1):23-40. [10668857 ]
  10. Belanger DR, Tierney MG, Dickinson G: Effect of sodium polystyrene sulfonate on lithium bioavailability. Ann Emerg Med. 1992 Nov;21(11):1312-5. [1416324 ]
  11. Ciuchi E, Odetti P, Prando R: The effect of acute glutathione treatment on sorbitol level in erythrocytes from diabetic patients. Diabetes Metab. 1997 Feb;23(1):58-60. [9059767 ]
  12. Shinohara R, Ohta Y, Yamauchi M, Ishiguro I: Improved fluorometric enzymatic sorbitol assay in human blood. Clin Chim Acta. 1998 May 25;273(2):171-84. [9657347 ]
  13. Peterson MJ, Page MG, Just LJ, Aldinger CE, Malone JI: Applicability of red blood cell sorbitol measurements to monitor the clinical activity of sorbinil. Metabolism. 1986 Apr;35(4 Suppl 1):93-5. [3515121 ]
  14. Vertommen J, Rillaerts E, Gysels M, De Leeuw I: Erythrocyte sorbitol content in diabetic patients: relation to metabolic control. Diabete Metab. 1987 Jun;13(3):182-6. [3301442 ]
  15. Cunningham JJ, Mearkle PL, Brown RG: Vitamin C: an aldose reductase inhibitor that normalizes erythrocyte sorbitol in insulin-dependent diabetes mellitus. J Am Coll Nutr. 1994 Aug;13(4):344-50. [7963139 ]
  16. Kamon N, Mabuchi H, Takeda R, Terashima H: Effects of aldose reductase inhibitor (ONO-2235) on human erythrocyte sorbitol concentrations in 75 g oral glucose tolerance tests. Horm Metab Res. 1991 May;23(5):226-9. [1908433 ]
  17. Sizeland PC, Chambers ST, Lever M, Bason LM, Robson RA: Short-term response of nonurea organic osmolytes in human kidney to a water load and water deprivation. Am J Physiol. 1995 Feb;268(2 Pt 2):F227-33. [7864160 ]
  18. van Griensven JM, Jusko WJ, Lemkes HH, Kroon R, Verhorst CJ, Chiang ST, Cohen AF: Tolrestat pharmacokinetic and pharmacodynamic effects on red blood cell sorbitol levels in normal volunteers and in patients with insulin-dependent diabetes. Clin Pharmacol Ther. 1995 Dec;58(6):631-40. [8529328 ]
  19. Regenold WT, Kling MA, Hauser P: Elevated sorbitol concentration in the cerebrospinal fluid of patients with mood disorders. Psychoneuroendocrinology. 2000 Aug;25(6):593-606. [10840171 ]
  20. Gehring H, Hornberger C, Dibbelt L, Dorges V, Eichenauer R, Schmucker P: Detecting and quantifying absorbed irrigation fluid by measuring mannitol and sorbitol concentrations in serum samples, and by ethanol monitoring. BJU Int. 2002 Feb;89(3):202-7. [11856099 ]
  21. Burggraaf J, Schoemaker RC, Lentjes EG, Cohen AF: Sorbitol as a marker for drug-induced decreases of variable duration in liver blood flow in healthy volunteers. Eur J Pharm Sci. 2000 Dec;12(2):133-9. [11102741 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Reactions
Sorbitol + NADP → Alpha-D-Glucose + NADPH + Hydrogen Iondetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the initial step in utilization of glucose by the beta-cell and liver at physiological glucose concentration. Glucokinase has a high Km for glucose, and so it is effective only when glucose is abundant. The role of GCK is to provide G6P for the synthesis of glycogen. Pancreatic glucokinase plays an important role in modulating insulin secretion. Hepatic glucokinase helps to facilitate the uptake and conversion of glucose by acting as an insulin-sensitive determinant of hepatic glucose usage.
Gene Name:
GCK
Uniprot ID:
P35557
Molecular weight:
52191.07
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK3
Uniprot ID:
P52790
Molecular weight:
99024.56
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK2
Uniprot ID:
P52789
Molecular weight:
102379.06
General function:
Involved in zinc ion binding
Specific function:
Converts sorbitol to fructose. Part of the polyol pathway that plays an important role in sperm physiology. May play a role in the sperm motility by providing an energetic source for sperm (By similarity).
Gene Name:
SORD
Uniprot ID:
Q00796
Molecular weight:
38324.25
Reactions
Sorbitol + NAD → D-Fructose + NADH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GLA
Uniprot ID:
P06280
Molecular weight:
Not Available
Reactions
Melibiitol + Water → Sorbitol + Beta-D-Galactosedetails
General function:
Not Available
Specific function:
This protein is a minor sialoglycoprotein in erythrocyte membranes
Gene Name:
GYPB
Uniprot ID:
P06028
Molecular weight:
9795.6
General function:
Not Available
Specific function:
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:
AKR1B10
Uniprot ID:
O60218
Molecular weight:
Not Available
Reactions
Sorbitol + NADP → Alpha-D-Glucose + NADPH + Hydrogen Iondetails