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Human Metabolome Database Version 3.5

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Showing metabocard for Sorbitol (HMDB00247)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:10 -0700
HMDB ID HMDB00247
Secondary Accession Numbers None
Metabolite Identification
Common Name Sorbitol
Description Sorbitol 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-Sorbitol
  2. D-Glucitol
  3. D-Sorbitol
  4. D-Sorbol
  5. Diakarmon
  6. Esasorb
  7. Foodol D 70
  8. Glucarine
  9. Glucitol
  10. Karion
  11. Karion instant
  12. Kyowa Powder 50M
  13. L-Gulitol
  14. Multitol
  15. Neosorb
  16. Neosorb 20/60DC
  17. Neosorb 70/02
  18. Neosorb 70/70
  19. Neosorb P 20/60
  20. Neosorb P 60
  21. Neosorb P 60W
  22. Nivitin
  23. Resulax
  24. Sionit
  25. Sionit K
  26. Sionite
  27. Sionon
  28. Siosan
  29. Sorbex M
  30. Sorbex R
  31. Sorbex Rp
  32. Sorbex S
  33. Sorbex X
  34. Sorbilande
  35. Sorbilax
  36. Sorbit
  37. Sorbit D 70
  38. Sorbit D-Powder
  39. Sorbit DP
  40. Sorbit DP 50
  41. Sorbit Kyowa Powder 50M
  42. Sorbit L 70
  43. Sorbit S
  44. Sorbit T 70
  45. Sorbit W 70
  46. Sorbit W-Powder
  47. Sorbit W-Powder 50
  48. Sorbit WP
  49. Sorbite
  50. Sorbitol F
  51. Sorbitol FK
  52. Sorbitol FP
  53. Sorbitol S
  54. Sorbitol syrup C
  55. Sorbitur
  56. Sorbo
  57. Sorbogem 712
  58. Sorbol
  59. Sorbostyl
Chemical Formula C6H14O6
Average Molecular Weight 182.1718
Monoisotopic Molecular Weight 182.07903818
IUPAC Name (2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional IUPAC Name D-sorbitol
CAS Registry Number 50-70-4
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 Key FBPFZTCFMRRESA-JGWLITMVSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Alcohols
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • glucitol(ChEBI)
Substituents
  • 1,2 Diol
  • Primary Alcohol
  • Saccharide
  • Secondary Alcohol
  • Sugar Alcohol
Direct Parent Fatty Alcohols
Ontology
Status Detected 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
State Liquid
Experimental Properties
Property Value Reference
Melting Point 11 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2750.0 mg/mL Not Available
LogP -2.20 SANGSTER (1994)
Predicted Properties
Property Value Source
Water Solubility 229 g/L ALOGPS
LogP -2.68 ALOGPS
LogP -3.7 ChemAxon
LogS 0.10 ALOGPS
pKa (strongest acidic) 12.59 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 121.38 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 38.4 ChemAxon
Polarizability 17.12 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Neuron
  • Placenta
  • Erythrocyte
  • Kidney
  • Liver
  • Prostate
  • Adipose Tissue
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Eye Lens
  • Lens
  • Red Blood Cell
  • Retina
  • Sciatic Nerve
Pathways
Name SMPDB Link KEGG Link
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Galactose Metabolism SMP00043 map00052 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
1.09 +/- 0.37 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
13.0 (4.0-24.0) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
13.0 (9.49-16.5) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
19.43 +/- 5.65 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
19.4 +/- 5.6 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
15.6 +/- 1.9 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
17.2 +/- 4.6 uM Adult (>18 years old) Both Normal Not Available
Saliva Detected and Quantified
Article_icon
<1.00 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
3.9 (1.9-5.1) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
Article_icon
9.9 (2.5-18.7) umol/mmol creatinine Adult (>18 years old) Both Normal by NMR
Urine Detected and Quantified
Article_icon
3.5 +/- 2.24 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
9.74 +/- 10.36 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
23.3 +/- 3.3 uM Adult (>18 years old) Both Alzheimer's disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
22.89 +/- 3.34 uM Not Specified Not Specified Alzheimer's disease Not Available
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • 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. Pubmed: 8595727 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB011676
    KNApSAcK ID C00001173 Link_out
    Chemspider ID 5576 Link_out
    KEGG Compound ID C00794 Link_out
    BioCyc ID Not Available
    BiGG ID 36018 Link_out
    Wikipedia Link Sorbitol Link_out
    NuGOwiki Link HMDB00247 Link_out
    Metagene Link HMDB00247 Link_out
    METLIN ID 143 Link_out
    PubChem Compound 5780 Link_out
    PDB ID SOR Link_out
    ChEBI ID 17924 Link_out
    References
    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)
    General References
    1. 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 Link_out
    2. 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 Link_out
    3. 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 Link_out
    4. 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 Link_out
    5. 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 Link_out
    6. Nau R: Osmotherapy for elevated intracranial pressure: a critical reappraisal. Clin Pharmacokinet. 2000 Jan;38(1):23-40. Pubmed: 10668857 Link_out
    7. 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 Link_out
    8. 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 Link_out
    9. 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 Link_out
    10. 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 Link_out
    11. 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 Link_out
    12. 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 Link_out
    13. 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 Link_out
    14. 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 Link_out
    15. 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 Link_out
    16. 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 Link_out
    17. 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 Link_out
    18. 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 Link_out
    19. 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 Link_out
    20. 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 Link_out
    21. 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 Link_out
    Enzymes
    Name: Aldose reductase
    Reactions:
    • alditol + NAD(P)+ = aldose + NAD(P)H + H+ [RN:R02819 R02820]
    Gene Name: AKR1B1
    Uniprot ID: P15121 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glucokinase
    Reactions:
    • ATP + D-glucose = ADP + D-glucose 6-phosphate [RN:R00299]
    Gene Name: GCK
    Uniprot ID: P35557 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Hexokinase-3
    Reactions:
    • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
    Gene Name: HK3
    Uniprot ID: P52790 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Hexokinase-2
    Reactions:
    • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
    Gene Name: HK2
    Uniprot ID: P52789 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sorbitol dehydrogenase
    Reactions:
    • L-iditol + NAD+ = L-sorbose + NADH + H+ [RN:R07145]
    Gene Name: SORD
    Uniprot ID: Q00796 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alpha-galactosidase A
    Reactions:
    • Hydrolysis of terminal, non-reducing alpha-D-galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids ALL_REAC (other) R01101 R01103 R01104 R01194 R01329 R02926 R03618 R03634 R04019 R04470 R05549 R05961(G) R06070(G) R06091(G) R06093(G) R06094(G) R06096(G) R06142(G) R06152(G)
    Gene Name: GLA
    Uniprot ID: P06280 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycophorin-B
    Reactions:
      Gene Name: GYPB
      Uniprot ID: P06028 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA