Record Information
Version2.0
Creation Date2012-05-31 10:24:52 -0600
Update Date2015-09-13 12:56:07 -0600
Secondary Accession Numbers
  • ECMDB00247
Identification
Name:Sorbitol
DescriptionSorbitol, also known as glucitol, is a sugar alcohol. It is obtained by reduction of glucose changing the aldehyde group to an additional hydroxyl group. Sorbitol is a polyhydric alcohol with about half the sweetness of sucrose. It occurs naturally and is also produced synthetically from glucose.
Structure
Thumb
Synonyms:
  • (-)-Sorbitol
  • Cystosol
  • D-Glucitol
  • D-Sorbitol
  • D-Sorbol
  • Diakarmon
  • Esasorb
  • Foodol D 70
  • Glucarine
  • Glucitol
  • Iso-sorbide
  • Karion
  • Karion instant
  • Kyowa Powder 50M
  • L-Gulitol
  • Meglumine
  • Multitol
  • Neosorb
  • Neosorb 20/60DC
  • Neosorb 70/02
  • Neosorb 70/70
  • Neosorb P 20/60
  • Neosorb P 60
  • Neosorb P 60W
  • Nivitin
  • Resulax
  • Sionit
  • Sionit K
  • Sionite
  • Sionon
  • Siosan
  • Sorbex M
  • Sorbex R
  • Sorbex Rp
  • Sorbex S
  • Sorbex X
  • Sorbilande
  • Sorbilax
  • Sorbit
  • Sorbit D 70
  • Sorbit D-Powder
  • Sorbit DP
  • Sorbit DP 50
  • Sorbit Kyowa Powder 50M
  • Sorbit L 70
  • Sorbit S
  • Sorbit T 70
  • Sorbit W 70
  • Sorbit W-Powder
  • Sorbit W-Powder 50
  • Sorbit WP
  • Sorbite
  • Sorbitol
  • Sorbitol F
  • Sorbitol FK
  • Sorbitol FP
  • Sorbitol S
  • Sorbitol syrup C
  • Sorbitur
  • Sorbo
  • Sorbogem 712
  • Sorbol
  • Sorbostyl
Chemical Formula:C6H14O6
Weight:Average: 182.1718
Monoisotopic: 182.07903818
InChI Key:FBPFZTCFMRRESA-JGWLITMVSA-N
InChI: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
CAS number:50-70-4
IUPAC Name:(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional IUPAC Name:D-sorbitol
SMILES:OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
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
State:Liquid
Charge:0
Melting point:11 °C
Experimental Properties:
PropertyValueSource
Water Solubility:2750.0 mg/mL [MULLIN,JW (1972)]PhysProp
LogP:-2.20 [SANGSTER (1994)]PhysProp
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
Polarizability17.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0ldj-0941000000-19d96a9ba7ba0c482c83View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1973000000-d907b75f68a7927501a7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldj-0941000000-19d96a9ba7ba0c482c83View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1973000000-d907b75f68a7927501a7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-4ffadb4b25e8e2510d93View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03k9-9500000000-97c5853d3e9b96f9d054View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-0a6s-7141193000-dcd9245e12314ee0ced4View 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
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ik9-2900000000-26a16e983791be7818f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ik9-2900000000-6513771e890cbff9c402View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0900000000-58e6917626e28d1830a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-83169b2192f847cc0636View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0900000000-4cd721d87e359527adf3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0900000000-b44f68c64bc74e79e9fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-bbb5e957a9e67ddc411eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-772c3052966c05f29842View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-d1fbea514e7f1c1628f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0790000000-b5b098cd5b4b4ec10821View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0690000000-41d4e48d49836c63485cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-ef92b9091ecf5d15cdeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-47f19bd4e51bff726536View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9100000000-60d5147d8e349337fe97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07ju-8900000000-36f0fe0f346a6424162aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c0c-9200000000-36e85b5ec098a45204c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-77703ee971336704163fView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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. Pubmed: 2533041
  • 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. Pubmed: 3090107
  • Belanger DR, Tierney MG, Dickinson G: Effect of sodium polystyrene sulfonate on lithium bioavailability. Ann Emerg Med. 1992 Nov;21(11):1312-5. Pubmed: 1416324
  • 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. Pubmed: 11102741
  • Ciuchi E, Odetti P, Prando R: Relationship between glutathione and sorbitol concentrations in erythrocytes from diabetic patients. Metabolism. 1996 May;45(5):611-3. Pubmed: 8622605
  • 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. Pubmed: 9059767
  • 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. Pubmed: 7963139
  • 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. Pubmed: 11856099
  • 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. Pubmed: 1908433
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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. Pubmed: 15748598
  • 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. Pubmed: 15707277
  • Nau R: Osmotherapy for elevated intracranial pressure: a critical reappraisal. Clin Pharmacokinet. 2000 Jan;38(1):23-40. Pubmed: 10668857
  • 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. Pubmed: 3515121
  • 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. Pubmed: 10840171
  • 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
  • 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. Pubmed: 9657347
  • 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. Pubmed: 7864160
  • 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. Pubmed: 19212411
  • 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. Pubmed: 10821291
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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. Pubmed: 8529328
  • 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. Pubmed: 3301442
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Liu, 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)
External Links:
ResourceLink
CHEBI ID17924
HMDB IDHMDB00247
Pubchem Compound ID5780
Kegg IDC00794
ChemSpider ID5576
WikipediaSorbitol
BioCyc IDSORBITOL
EcoCyc IDSORBITOL
Ligand ExpoSOR

Enzymes

General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucitol/sorbitol transport
Gene Name:
srlB
Uniprot ID:
P05706
Molecular weight:
13304
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing alpha-D- galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids
Gene Name:
melA
Uniprot ID:
P06720
Molecular weight:
50657
Reactions
Hydrolysis of terminal, non-reducing alpha-D-galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids.
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucitol/sorbitol transport
Gene Name:
srlE
Uniprot ID:
P56580
Molecular weight:
33332
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in glucitol/sorbitol transport
Gene Name:
srlA
Uniprot ID:
P56579
Molecular weight:
20580
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.

Transporters

General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in glucitol/sorbitol transport
Gene Name:
srlA
Uniprot ID:
P56579
Molecular weight:
20580
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368