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Sorbitol

February 15, 2024

Sorbitol (/ˈsɔː(r)bɪtɒl/), less commonly known as glucitol (/ˈɡluːsɪtɒl/), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes.[4] It is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. Sorbitol is an isomer of mannitol, another sugar alcohol; the two differ only in the orientation of the hydroxyl group on carbon 2.[5] While similar, the two sugar alcohols have very different sources in nature, melting points, and uses.

Sorbitol
Names
IUPAC name
D-Glucitol[1]
Systematic IUPAC name
(2S,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol
Other names
D-Sorbitol; Sorbogem; Sorbo
Identifiers
  • 50-70-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17924 N
ChEMBL
  • ChEMBL1682 N
ChemSpider
  • 5576 N
DrugBank
  • DB01638 Y
ECHA InfoCard 100.000.056
E number E420 (thickeners, ...)
KEGG
  • C00794
MeSH Sorbitol
  • 5780
UNII
  • 506T60A25R Y
  • DTXSID5023588
  • 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 N[pubchem]
    Key: FBPFZTCFMRRESA-JGWLITMVSA-N N[pubchem]
  • InChI=1/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
    Key: FBPFZTCFMRRESA-JGWLITMVSA
  • OC([C@H](O)[C@@H](O)[C@H](O)CO)CO
Properties
C6H14O6
Molar mass 182.17 g/mol
Appearance White crystalline powder
Density 1.49 g/cm3[2]
Melting point 94–96 °C (201–205 °F; 367–369 K)[2]
2350 g/L[2]
log P -4.67[3]
-107.80·10−6 cm3/mol
Pharmacology
A06AD18 (WHO) A06AG07 (WHO) B05CX02 (WHO) V04CC01 (WHO)
Hazards
NFPA 704 (fire diamond)
Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point > 100 °C (212 °F; 373 K)[2]
420 °C (788 °F; 693 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

As an over-the-counter drug, sorbitol is used as a laxative to treat constipation.[6]

Synthesis edit

Sorbitol may be synthesised via a glucose reduction reaction[7] in which the converted aldehyde group is converted into a hydroxyl group. The reaction requires NADH and is catalyzed by aldose reductase. Glucose reduction is the first step of the polyol pathway of glucose metabolism, and is implicated in multiple diabetic complications.

 

The mechanism involves a tyrosine residue in the active site of aldehyde reductase. The hydrogen atom on NADH is transferred to the electrophilic aldehyde carbon atom; electrons on the aldehyde carbon-oxygen double bond are transferred to the oxygen that abstracts the proton on tyrosine side chain to form the hydroxyl group. The role of aldehyde reductase tyrosine phenol group is to serve as a general acid to provide proton to the reduced aldehyde oxygen on glucose.

 

Glucose reduction is not the major glucose metabolism pathway in a normal human body, where the glucose level is in the normal range. However, in diabetic patients whose blood glucose level is high, up to 1/3 of their glucose could go through the glucose reduction pathway. This will consume NADH and eventually leads to cell damage.

Sorbitol also may be synthesized through a catalytic hydrogenation of d-glucose to form d-sorbitol.[8][not specific enough to verify] This reaction has a 100% yield of d-sorbitol when d-glucose is reacted with hydrogen in water at 120 degrees Celsius, under 150001.5 Torr, for 1 hour.[citation needed]

Uses edit

Sweetener edit

Sorbitol is a sugar substitute, and when used in food it has the INS number and E number 420. Sorbitol is about 60% as sweet as sucrose (table sugar).[9]

Sorbitol is referred to as a nutritive sweetener because it provides some dietary energy. It is partly absorbed from the small intestine and metabolized in the body, and partly fermented in the large intestine. The fermentation produces short-chain fatty acids, acetic acid, propionic acid, and butyric acid, which are mostly absorbed and provide energy, but also carbon dioxide, methane, and hydrogen which do not provide energy. Even though the heat of combustion of sorbitol is higher than that of glucose (having two extra hydrogen atoms), the net energy contribution is between 2.5 and 3.4 kilocalories per gram, versus the approximately 4 kilocalories (17 kilojoules) for carbohydrates.[10] It is often used in diet foods (including diet drinks and ice cream), mints, cough syrups, and sugar-free chewing gum.[11] Most bacteria cannot use sorbitol for energy, but it can be slowly fermented in the mouth by Streptococcus mutans, a bacterium that causes tooth decay. In contrast, many other sugar alcohols such as isomalt and xylitol are considered non-acidogenic.[12][13]

It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus.[4][14]

Medical applications edit

Laxative edit

As is the case with other sugar alcohols, foods containing sorbitol can cause gastrointestinal distress. Sorbitol can be used as a laxative when taken orally or as an enema.[6] Sorbitol works as a laxative by drawing water into the large intestine, stimulating bowel movements.[6][15] Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a physician.[6][16]

Sorbitol is commonly used orally as a one-time dose of 30–150 millilitres (1.1–5.3 imp fl oz; 1.0–5.1 US fl oz) 70% solution.[6] It may also be used as a one-time rectal enema.[6]

Other medical applications edit

Sorbitol is used in bacterial culture media to distinguish the pathogenic Escherichia coli O157:H7 from most other strains of E. coli, because it is usually unable to ferment sorbitol, unlike 93% of known E. coli strains.[17]

A treatment for hyperkalaemia (elevated blood potassium) uses sorbitol and the ion-exchange resin sodium polystyrene sulfonate (tradename Kayexalate).[18] The resin exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. In 2010, the U.S. FDA issued a warning of increased risk for gastrointestinal necrosis with this combination.[19]

Sorbitol is also used in the manufacture of softgel capsules to store single doses of liquid medicines.[20]

Health care, food, and cosmetic uses edit

Sorbitol often is used in modern cosmetics as a humectant and thickener.[21] It is also used in mouthwash and toothpaste. Some transparent gels can be made only with sorbitol, because of its high refractive index.

Sorbitol is used as a cryoprotectant additive (mixed with sucrose and sodium polyphosphates) in the manufacture of surimi, a processed fish paste.[22] It is also used as a humectant in some cigarettes.[23]

Beyond its use as a sugar substitute in reduced-sugar foods, sorbitol is also used as a humectant in cookies and low-moisture foods like peanut butter and fruit preserves.[24] In baking, it is also valuable because it acts as a plasticizer, and slows down the staling process.[24]

Miscellaneous uses edit

A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel.[25]

Sorbitol is identified as a potential key chemical intermediate[26] for production of fuels from biomass resources. Carbohydrate fractions in biomass such as cellulose undergo sequential hydrolysis and hydrogenation in the presence of metal catalysts to produce sorbitol.[27] Complete reduction of sorbitol opens the way to alkanes, such as hexane, which can be used as a biofuel. Hydrogen required for this reaction can be produced by aqueous phase catalytic reforming of sorbitol.[28]

19 C6H14O6 → 13 C6H14 + 36 CO2 + 42 H2O

The above chemical reaction is exothermic, and 1.5 moles of sorbitol generate approximately 1 mole of hexane. When hydrogen is co-fed, no carbon dioxide is produced.

Sorbitol based polyols are used in the production of polyurethane foam for the construction industry.

It is also added after electroporation of yeasts in transformation protocols, allowing the cells to recover by raising the osmolarity of the medium.

Medical importance edit

Aldose reductase is the first enzyme in the sorbitol-aldose reductase pathway[29] responsible for the reduction of glucose to sorbitol, as well as the reduction of galactose to galactitol. Too much sorbitol trapped in retinal cells, the cells of the lens, and the Schwann cells that myelinate peripheral nerves, is a frequent result of long-term hyperglycemia that accompanies poorly controlled diabetes. This can damage these cells, leading to retinopathy, cataracts and peripheral neuropathy, respectively.

Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health.[30]

Potential adverse effects edit

Sorbitol may cause allergic reactions in some people.[6] Common side effects from use as a laxative are stomach cramps, vomiting, diarrhea or rectal bleeding.[6]

Compendial status edit

See also edit

References edit

  1. ^ publications.iupac.org/pac/1996/pdf/6810x1919.pdf
  2. ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ "Sorbitol_msds".
  4. ^ a b Teo G, Suzuki Y, Uratsu SL, Lampinen B, Ormonde N, Hu WK, Dejong TM, Dandekar AM (2006). "Silencing leaf sorbitol synthesis alters long-distance partitioning and apple fruit quality". Proceedings of the National Academy of Sciences of the United States of America. 103 (49): 18842–7. Bibcode:2006PNAS..10318842T. doi:10.1073/pnas.0605873103. PMC 1693749. PMID 17132742.
  5. ^ Kearsley, M. W.; Deis, R. C. Sorbitol and Mannitol. In Sweeteners and Sugar Alternatives in Food Technology; Ames: Oxford, 2006; pp 249-249-261.
  6. ^ a b c d e f g h "Sorbitol". Drugs.com. 23 November 2021. Retrieved 8 July 2022.
  7. ^ "Reduction of Glucose". butane.chem.uiuc.edu.
  8. ^ SRINIVASAN, K.; GUNDEKARI, S. India Patent WO2017/60922. April 13, 2017.
  9. ^ Sugar substitute
  10. ^ Tsuneyuki Oku and Sadako Nakamura (2002). "Digestion, absorption, fermentation, and metabolism of functional sugar substitutes and their available energy" (PDF). Pure Appl. Chem. 74 (7): 1253–1261. doi:10.1351/pac200274071253.
  11. ^ Campbell, Farrell (2011). Biochemistry (Seventh ed.). Brooks/Cole. ISBN 978-1-111-42564-7.
  12. ^ Hayes C (October 2001). "The effect of non-cariogenic sweeteners on the prevention of dental caries: a review of the evidence". Journal of Dental Education. 65 (10): 1106–1109. doi:10.1002/j.0022-0337.2001.65.10.tb03457.x. ISSN 0022-0337. PMID 11699985.
  13. ^ Nicolas GG, Lavoie MC (January 2011). "[Streptococcus mutans and oral streptococci in dental plaque]". Canadian Journal of Microbiology. 57 (1): 1–20. doi:10.1139/w10-095. ISSN 1480-3275. PMID 21217792.
  14. ^ Nelson, Cox (2005). Lehninger Principles of Biochemistry (Fourth ed.). New York: W. H. Freeman. ISBN 0-7167-4339-6.
  15. ^ . Cancer Drug Guide. American Cancer Society. Archived from the original on 2007-06-30.
  16. ^ Lederle FA (1995). "Epidemiology of constipation in elderly patients. Drug utilisation and cost-containment strategies". Drugs & Aging. 6 (6): 465–9. doi:10.2165/00002512-199506060-00006. PMID 7663066. S2CID 43386314.
  17. ^ Wells JG, Davis BR, Wachsmuth IK, et al. (September 1983). "Laboratory investigation of hemorrhagic colitis outbreaks associated with a rare Escherichia coli serotype". Journal of Clinical Microbiology. 18 (3): 512–20. doi:10.1128/JCM.18.3.512-520.1983. PMC 270845. PMID 6355145. The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive
  18. ^ Rugolotto S, Gruber M, Solano PD, Chini L, Gobbo S, Pecori S (April 2007). "Necrotizing enterocolitis in a 850 gram infant receiving sorbitol-free sodium polystyrene sulfonate (Kayexalate): clinical and histopathologic findings". J Perinatol. 27 (4): 247–9. doi:10.1038/sj.jp.7211677. PMID 17377608.
  19. ^ "Kayexalate (sodium polystyrene sulfonate) powder". fda.gov. Retrieved 12 July 2015.
  20. ^ "Home – Catalent". catalent.com. Retrieved 12 July 2015.
  21. ^ . bttcogroup.in. Archived from the original on 10 July 2020. Retrieved 12 July 2015.
  22. ^ Medina J, Garrote R (2002). "The effect of two cryoprotectant mixtures on frozen surubí surimi". Brazilian Journal of Chemical Engineering. 19 (4): 419–424. doi:10.1590/S0104-66322002000400010. ISSN 0104-6632.
  23. ^ . gallaher-group.com. Archived from the original on 27 December 2008. Retrieved 12 July 2015.
  24. ^ a b Chemical and functional properties of food saccharides. Tomasik, Piotr. Boca Raton: CRC Press. 2004. ISBN 9780203495728. OCLC 317752036.{{cite book}}: CS1 maint: others (link)
  25. ^ "Richard Nakka's Experimental Rocketry Web Site". nakka-rocketry.net. Retrieved 12 July 2015.
  26. ^ Metzger JO (2006). "Production of Liquid Hydrocarbons from Biomass". Angewandte Chemie International Edition. 45 (5): 696–698. doi:10.1002/anie.200502895. PMID 16374789.
  27. ^ Shrotri A, Tanksale, Akshat, Beltramini, Jorge Norberto, Gurav, Hanmant, Chilukuri, Satyanarayana V. (2012). "Conversion of cellulose to polyols over promoted nickel catalysts". Catalysis Science & Technology. 2 (9): 1852–1858. doi:10.1039/C2CY20119D.
  28. ^ Tanksale A, Beltramini, Jorge Norberto, Lu, GaoQing Max (2010). "A review of catalytic hydrogen production processes from biomass". Renewable and Sustainable Energy Reviews. 14 (1): 166–182. doi:10.1016/j.rser.2009.08.010.
  29. ^ Nishikawa T, Edelstein D, Du XL, Yamagishi S, Matsumura T, Kaneda Y, Yorek MA, Beebe D, et al. (2000). "Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage". Nature. 404 (6779): 787–90. Bibcode:2000Natur.404..787N. doi:10.1038/35008121. PMID 10783895. S2CID 4426750.
  30. ^ Islam MS, Sakaguchi E (2006). "Sorbitol-based osmotic diarrhea: Possible causes and mechanism of prevention investigated in rats". World Journal of Gastroenterology. 12 (47): 7635–7641. doi:10.3748/wjg.v12.i47.7635. PMC 4088045. PMID 17171792.
  31. ^ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Archived from the original on 5 July 2010. Retrieved 6 July 2009.
  32. ^ Sigma Aldrich. "D-Sorbitol". Retrieved 15 February 2022.
  33. ^ European Pharmacopoeia. (PDF). Archived from the original (PDF) on 20 July 2011. Retrieved 6 July 2009.
  34. ^ British Pharmacopoeia (2009). (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 6 July 2009.
  35. ^ National Institute of Health Sciences (2016). (PDF). Archived from the original (PDF) on 4 March 2018. Retrieved 17 August 2018.

External links edit

  •   Media related to Sorbitol at Wikimedia Commons

February 15, 2024
sorbitol, ɔː, less, commonly, known, glucitol, sugar, alcohol, with, sweet, taste, which, human, body, metabolizes, slowly, obtained, reduction, glucose, which, changes, converted, aldehyde, group, primary, alcohol, group, ch2oh, most, sorbitol, made, from, po. Sorbitol ˈ s ɔː r b ɪ t ɒ l less commonly known as glucitol ˈ ɡ l uː s ɪ t ɒ l is a sugar alcohol with a sweet taste which the human body metabolizes slowly It can be obtained by reduction of glucose which changes the converted aldehyde group CHO to a primary alcohol group CH2OH Most sorbitol is made from potato starch but it is also found in nature for example in apples pears peaches and prunes 4 It is converted to fructose by sorbitol 6 phosphate 2 dehydrogenase Sorbitol is an isomer of mannitol another sugar alcohol the two differ only in the orientation of the hydroxyl group on carbon 2 5 While similar the two sugar alcohols have very different sources in nature melting points and uses Sorbitol NamesIUPAC name D Glucitol 1 Systematic IUPAC name 2S 3R 4R 5R Hexane 1 2 3 4 5 6 hexolOther names D Sorbitol Sorbogem SorboIdentifiersCAS Number 50 70 4 Y3D model JSmol Interactive imageChEBI CHEBI 17924 NChEMBL ChEMBL1682 NChemSpider 5576 NDrugBank DB01638 YECHA InfoCard 100 000 056E number E420 thickeners KEGG C00794MeSH SorbitolPubChem CID 5780UNII 506T60A25R YCompTox Dashboard EPA DTXSID5023588InChI 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 N pubchem Key FBPFZTCFMRRESA JGWLITMVSA N N pubchem InChI 1 C6H14O6 c7 1 3 9 5 11 6 12 4 10 2 8 h3 12H 1 2H2 t3 4 5 6 m1 s1Key FBPFZTCFMRRESA JGWLITMVSASMILES OC C H O C H O C H O CO COPropertiesChemical formula C 6H 14O 6Molar mass 182 17 g molAppearance White crystalline powderDensity 1 49 g cm3 2 Melting point 94 96 C 201 205 F 367 369 K 2 Solubility in water 2350 g L 2 log P 4 67 3 Magnetic susceptibility x 107 80 10 6 cm3 molPharmacologyATC code A06AD18 WHO A06AG07 WHO B05CX02 WHO V04CC01 WHO HazardsNFPA 704 fire diamond 110Flash point gt 100 C 212 F 373 K 2 Autoignitiontemperature 420 C 788 F 693 K 2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references As an over the counter drug sorbitol is used as a laxative to treat constipation 6 Contents 1 Synthesis 2 Uses 2 1 Sweetener 2 2 Medical applications 2 2 1 Laxative 2 2 2 Other medical applications 2 3 Health care food and cosmetic uses 2 4 Miscellaneous uses 3 Medical importance 4 Potential adverse effects 5 Compendial status 6 See also 7 References 8 External linksSynthesis editSorbitol may be synthesised via a glucose reduction reaction 7 in which the converted aldehyde group is converted into a hydroxyl group The reaction requires NADH and is catalyzed by aldose reductase Glucose reduction is the first step of the polyol pathway of glucose metabolism and is implicated in multiple diabetic complications nbsp The mechanism involves a tyrosine residue in the active site of aldehyde reductase The hydrogen atom on NADH is transferred to the electrophilic aldehyde carbon atom electrons on the aldehyde carbon oxygen double bond are transferred to the oxygen that abstracts the proton on tyrosine side chain to form the hydroxyl group The role of aldehyde reductase tyrosine phenol group is to serve as a general acid to provide proton to the reduced aldehyde oxygen on glucose nbsp Glucose reduction is not the major glucose metabolism pathway in a normal human body where the glucose level is in the normal range However in diabetic patients whose blood glucose level is high up to 1 3 of their glucose could go through the glucose reduction pathway This will consume NADH and eventually leads to cell damage Sorbitol also may be synthesized through a catalytic hydrogenation of d glucose to form d sorbitol 8 not specific enough to verify This reaction has a 100 yield of d sorbitol when d glucose is reacted with hydrogen in water at 120 degrees Celsius under 150001 5 Torr for 1 hour citation needed Uses editSweetener edit Sorbitol is a sugar substitute and when used in food it has the INS number and E number 420 Sorbitol is about 60 as sweet as sucrose table sugar 9 Sorbitol is referred to as a nutritive sweetener because it provides some dietary energy It is partly absorbed from the small intestine and metabolized in the body and partly fermented in the large intestine The fermentation produces short chain fatty acids acetic acid propionic acid and butyric acid which are mostly absorbed and provide energy but also carbon dioxide methane and hydrogen which do not provide energy Even though the heat of combustion of sorbitol is higher than that of glucose having two extra hydrogen atoms the net energy contribution is between 2 5 and 3 4 kilocalories per gram versus the approximately 4 kilocalories 17 kilojoules for carbohydrates 10 It is often used in diet foods including diet drinks and ice cream mints cough syrups and sugar free chewing gum 11 Most bacteria cannot use sorbitol for energy but it can be slowly fermented in the mouth by Streptococcus mutans a bacterium that causes tooth decay In contrast many other sugar alcohols such as isomalt and xylitol are considered non acidogenic 12 13 It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus 4 14 Medical applications edit Laxative edit As is the case with other sugar alcohols foods containing sorbitol can cause gastrointestinal distress Sorbitol can be used as a laxative when taken orally or as an enema 6 Sorbitol works as a laxative by drawing water into the large intestine stimulating bowel movements 6 15 Sorbitol has been determined safe for use by the elderly although it is not recommended without the advice of a physician 6 16 Sorbitol is commonly used orally as a one time dose of 30 150 millilitres 1 1 5 3 imp fl oz 1 0 5 1 US fl oz 70 solution 6 It may also be used as a one time rectal enema 6 Other medical applications edit Sorbitol is used in bacterial culture media to distinguish the pathogenic Escherichia coli O157 H7 from most other strains of E coli because it is usually unable to ferment sorbitol unlike 93 of known E coli strains 17 A treatment for hyperkalaemia elevated blood potassium uses sorbitol and the ion exchange resin sodium polystyrene sulfonate tradename Kayexalate 18 The resin exchanges sodium ions for potassium ions in the bowel while sorbitol helps to eliminate it In 2010 the U S FDA issued a warning of increased risk for gastrointestinal necrosis with this combination 19 Sorbitol is also used in the manufacture of softgel capsules to store single doses of liquid medicines 20 Health care food and cosmetic uses edit Sorbitol often is used in modern cosmetics as a humectant and thickener 21 It is also used in mouthwash and toothpaste Some transparent gels can be made only with sorbitol because of its high refractive index Sorbitol is used as a cryoprotectant additive mixed with sucrose and sodium polyphosphates in the manufacture of surimi a processed fish paste 22 It is also used as a humectant in some cigarettes 23 Beyond its use as a sugar substitute in reduced sugar foods sorbitol is also used as a humectant in cookies and low moisture foods like peanut butter and fruit preserves 24 In baking it is also valuable because it acts as a plasticizer and slows down the staling process 24 Miscellaneous uses edit A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel 25 Sorbitol is identified as a potential key chemical intermediate 26 for production of fuels from biomass resources Carbohydrate fractions in biomass such as cellulose undergo sequential hydrolysis and hydrogenation in the presence of metal catalysts to produce sorbitol 27 Complete reduction of sorbitol opens the way to alkanes such as hexane which can be used as a biofuel Hydrogen required for this reaction can be produced by aqueous phase catalytic reforming of sorbitol 28 19 C6H14O6 13 C6H14 36 CO2 42 H2OThe above chemical reaction is exothermic and 1 5 moles of sorbitol generate approximately 1 mole of hexane When hydrogen is co fed no carbon dioxide is produced Sorbitol based polyols are used in the production of polyurethane foam for the construction industry It is also added after electroporation of yeasts in transformation protocols allowing the cells to recover by raising the osmolarity of the medium Medical importance editAldose reductase is the first enzyme in the sorbitol aldose reductase pathway 29 responsible for the reduction of glucose to sorbitol as well as the reduction of galactose to galactitol Too much sorbitol trapped in retinal cells the cells of the lens and the Schwann cells that myelinate peripheral nerves is a frequent result of long term hyperglycemia that accompanies poorly controlled diabetes This can damage these cells leading to retinopathy cataracts and peripheral neuropathy respectively Sorbitol is fermented in the colon and produces short chain fatty acids which are beneficial to overall colon health 30 Potential adverse effects editSorbitol may cause allergic reactions in some people 6 Common side effects from use as a laxative are stomach cramps vomiting diarrhea or rectal bleeding 6 Compendial status editFood Chemicals Codex 31 European Pharmacopoeia 32 6 1 33 British Pharmacopoeia 2009 34 Japanese Pharmacopoeia 17 35 See also editSorbitan IsosorbideReferences edit publications iupac org pac 1996 pdf 6810x1919 pdf a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health Sorbitol msds a b Teo G Suzuki Y Uratsu SL Lampinen B Ormonde N Hu WK Dejong TM Dandekar AM 2006 Silencing leaf sorbitol synthesis alters long distance partitioning and apple fruit quality Proceedings of the National Academy of Sciences of the United States of America 103 49 18842 7 Bibcode 2006PNAS 10318842T doi 10 1073 pnas 0605873103 PMC 1693749 PMID 17132742 Kearsley M W Deis R C Sorbitol and Mannitol In Sweeteners and Sugar Alternatives in Food Technology Ames Oxford 2006 pp 249 249 261 a b c d e f g h Sorbitol Drugs com 23 November 2021 Retrieved 8 July 2022 Reduction of Glucose butane chem uiuc edu SRINIVASAN K GUNDEKARI S India Patent WO2017 60922 April 13 2017 Sugar substitute Tsuneyuki Oku and Sadako Nakamura 2002 Digestion absorption fermentation and metabolism of functional sugar substitutes and their available energy PDF Pure Appl Chem 74 7 1253 1261 doi 10 1351 pac200274071253 Campbell Farrell 2011 Biochemistry Seventh ed Brooks Cole ISBN 978 1 111 42564 7 Hayes C October 2001 The effect of non cariogenic sweeteners on the prevention of dental caries a review of the evidence Journal of Dental Education 65 10 1106 1109 doi 10 1002 j 0022 0337 2001 65 10 tb03457 x ISSN 0022 0337 PMID 11699985 Nicolas GG Lavoie MC January 2011 Streptococcus mutans and oral streptococci in dental plaque Canadian Journal of Microbiology 57 1 1 20 doi 10 1139 w10 095 ISSN 1480 3275 PMID 21217792 Nelson Cox 2005 Lehninger Principles of Biochemistry Fourth ed New York W H Freeman ISBN 0 7167 4339 6 sorbitol Cancer Drug Guide American Cancer Society Archived from the original on 2007 06 30 Lederle FA 1995 Epidemiology of constipation in elderly patients Drug utilisation and cost containment strategies Drugs amp Aging 6 6 465 9 doi 10 2165 00002512 199506060 00006 PMID 7663066 S2CID 43386314 Wells JG Davis BR Wachsmuth IK et al September 1983 Laboratory investigation of hemorrhagic colitis outbreaks associated with a rare Escherichia coli serotype Journal of Clinical Microbiology 18 3 512 20 doi 10 1128 JCM 18 3 512 520 1983 PMC 270845 PMID 6355145 The organism does not ferment sorbitol whereas 93 of E coli of human origin are sorbitol positive Rugolotto S Gruber M Solano PD Chini L Gobbo S Pecori S April 2007 Necrotizing enterocolitis in a 850 gram infant receiving sorbitol free sodium polystyrene sulfonate Kayexalate clinical and histopathologic findings J Perinatol 27 4 247 9 doi 10 1038 sj jp 7211677 PMID 17377608 Kayexalate sodium polystyrene sulfonate powder fda gov Retrieved 12 July 2015 Home Catalent catalent com Retrieved 12 July 2015 Sorbitol 70 bttcogroup in Archived from the original on 10 July 2020 Retrieved 12 July 2015 Medina J Garrote R 2002 The effect of two cryoprotectant mixtures on frozen surubi surimi Brazilian Journal of Chemical Engineering 19 4 419 424 doi 10 1590 S0104 66322002000400010 ISSN 0104 6632 Gallaher Group gallaher group com Archived from the original on 27 December 2008 Retrieved 12 July 2015 a b Chemical and functional properties of food saccharides Tomasik Piotr Boca Raton CRC Press 2004 ISBN 9780203495728 OCLC 317752036 a href Template Cite book html title Template Cite book cite book a CS1 maint others link Richard Nakka s Experimental Rocketry Web Site nakka rocketry net Retrieved 12 July 2015 Metzger JO 2006 Production of Liquid Hydrocarbons from Biomass Angewandte Chemie International Edition 45 5 696 698 doi 10 1002 anie 200502895 PMID 16374789 Shrotri A Tanksale Akshat Beltramini Jorge Norberto Gurav Hanmant Chilukuri Satyanarayana V 2012 Conversion of cellulose to polyols over promoted nickel catalysts Catalysis Science amp Technology 2 9 1852 1858 doi 10 1039 C2CY20119D Tanksale A Beltramini Jorge Norberto Lu GaoQing Max 2010 A review of catalytic hydrogen production processes from biomass Renewable and Sustainable Energy Reviews 14 1 166 182 doi 10 1016 j rser 2009 08 010 Nishikawa T Edelstein D Du XL Yamagishi S Matsumura T Kaneda Y Yorek MA Beebe D et al 2000 Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage Nature 404 6779 787 90 Bibcode 2000Natur 404 787N doi 10 1038 35008121 PMID 10783895 S2CID 4426750 Islam MS Sakaguchi E 2006 Sorbitol based osmotic diarrhea Possible causes and mechanism of prevention investigated in rats World Journal of Gastroenterology 12 47 7635 7641 doi 10 3748 wjg v12 i47 7635 PMC 4088045 PMID 17171792 The United States Pharmacopeial Convention Revisions to FCC First Supplement Archived from the original on 5 July 2010 Retrieved 6 July 2009 Sigma Aldrich D Sorbitol Retrieved 15 February 2022 European Pharmacopoeia Index Ph Eur PDF Archived from the original PDF on 20 July 2011 Retrieved 6 July 2009 British Pharmacopoeia 2009 Index BP 2009 PDF Archived from the original PDF on 11 April 2009 Retrieved 6 July 2009 National Institute of Health Sciences 2016 The Japanese Pharmacopoeia Seventeenth Edition PDF Archived from the original PDF on 4 March 2018 Retrieved 17 August 2018 External links edit nbsp Media related to Sorbitol at Wikimedia Commons Retrieved from https en wikipedia org w index php title Sorbitol amp oldid 1199691799, wikipedia, wiki, book, books, library,

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