Wikipedia

Sorbitol

Sorbitol(/ˈsɔː(r)bɪtɒl/), less commonly known asglucitol(/ˈɡluːsɪtɒl/), is asugar alcoholwith asweettastewhich the human body metabolizes slowly. It can be obtained byreductionofglucose,which changes the convertedaldehydegroup (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made frompotato starch,but it is also found in nature, for example in apples, pears, peaches, and prunes.[4]It is converted tofructosebysorbitol-6-phosphate 2-dehydrogenase.Sorbitol is anisomerofmannitol,another sugar alcohol; the two differ only in the orientation of thehydroxylgroup 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.056Edit this at Wikidata
E number E420(thickeners,...)
KEGG
MeSH Sorbitol
UNII
  • 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]
logP -4.67[3]
-107.80·10−6cm3/mol
Pharmacology
A06AD18(WHO)A06AG07(WHO)B05CX02(WHO)V04CC01(WHO)
Hazards
NFPA 704(fire diamond)
NFPA 704 four-colored diamondHealth 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 theirstandard state(at 25 °C [77 °F], 100 kPa).

As anover-the-counter drug,sorbitol is used as alaxativeto treatconstipation.[6]

Synthesis

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Sorbitol may be synthesised via a glucose reduction reaction[7]in which the convertedaldehydegroup is converted into ahydroxylgroup. The reaction requiresNADHand is catalyzed byaldose reductase.Glucose reduction is the first step of thepolyol pathwayofglucose metabolism,and is implicated in multiple diabetic complications.

The mechanism involves atyrosineresidue 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 majorglucose metabolismpathway in a normal human body, where theglucose levelis 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.

Uses

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Sweetener

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Sorbitol is asugar substitute,and when used in food it has theINS numberandE number420. Sorbitol is about 60% as sweet as sucrose (table sugar).[8]

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 producesshort-chain fatty acids,acetic acid,propionic acid,andbutyric acid,which are mostly absorbed and provide energy, but alsocarbon dioxide,methane,andhydrogenwhich do not provide energy. Even though theheat of combustionof sorbitol is higher than that of glucose (having two extra hydrogen atoms), the net energy contribution is between 2.5 and 3.4kilocaloriespergram,versus the approximately 4 kilocalories (17 kilojoules) for carbohydrates.[9]It is often used indiet foods(including diet drinks and ice cream), mints,cough syrups,and sugar-freechewing gum.[10]Most bacteria cannot use sorbitol for energy, but it can be slowly fermented in the mouth byStreptococcus mutans,a bacterium that causestooth decay.In contrast, many other sugar alcohols such asisomaltandxylitolare considered non-acidogenic.[11][12]

It also occurs naturally in manystone fruitsand berries from trees of the genusSorbus.[4][13]

Medical applications

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Laxative

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As is the case with othersugar alcohols,foods containing sorbitol can causegastrointestinal distress.Sorbitol can be used as alaxativewhen taken orally or as anenema.[6]Sorbitol works as a laxative by drawing water into thelarge intestine,stimulatingbowel movements.[6][14]Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a physician.[6][15]

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-timerectalenema.[6]

Other medical applications

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Sorbitol is used in bacterial culture media to distinguish the pathogenicEscherichia coliO157:H7from most other strains ofE. coli,because it is usually unable to ferment sorbitol, unlike 93% of knownE. colistrains.[16]

A treatment forhyperkalaemia(elevated bloodpotassium) uses sorbitol and theion-exchangeresinsodium polystyrene sulfonate(tradename Kayexalate).[17]The resin exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. In 2010, the U.S.FDAissued a warning of increased risk for gastrointestinal necrosis with this combination.[18]

Sorbitol is also used in the manufacture ofsoftgel capsulesto store single doses of liquid medicines.[19]

Health care, food, and cosmetic uses

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Sorbitol often is used in moderncosmeticsas ahumectantandthickener.[20]It is also used inmouthwashandtoothpaste.Some transparentgelscan be made only with sorbitol, because of its highrefractive index.

Sorbitol is used as acryoprotectantadditive (mixed withsucroseand sodium polyphosphates) in the manufacture ofsurimi,a processed fish paste.[21]It is also used as a humectant in somecigarettes.[22]

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.[23]In baking, it is also valuable because it acts as aplasticizer,and slows down thestalingprocess.[23]

Miscellaneous uses

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A mixture of sorbitol andpotassium nitratehas found some success as anamateursolidrocket fuel.It has similar performance to sucrose-basedrocket candy,but is easier to cast, less hygroscopic and does notcaramelize.[24]

Sorbitol is identified as a potential key chemical intermediate[25]for production of fuels frombiomassresources.Carbohydratefractions in biomass such ascelluloseundergo sequentialhydrolysisandhydrogenationin the presence of metal catalysts to produce sorbitol.[26]Complete reduction of sorbitol opens the way toalkanes,such ashexane,which can be used as abiofuel.Hydrogen required for this reaction can be produced by aqueous phasecatalytic reformingof sorbitol.[27]

19 C6H14O6→ 13 C6H14+ 36 CO2+ 42 H2O

The abovechemical reactionisexothermic,and 1.5molesof sorbitol generate approximately 1 mole ofhexane.When hydrogen is co-fed, nocarbon dioxideis produced.

Sorbitol based polyols are used in the production ofpolyurethanefoam for the construction industry.

It is also added afterelectroporationof yeasts in transformation protocols, allowing the cells to recover by raising theosmolarityof the medium.

Medical importance

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Aldose reductaseis the first enzyme in thesorbitol-aldose reductase pathway[28]responsible for the reduction of glucose to sorbitol, as well as the reduction ofgalactosetogalactitol.Too much sorbitol trapped in retinal cells, the cells of the lens, and theSchwann cellsthatmyelinateperipheral nerves, is a frequent result of long-term hyperglycemia that accompanies poorly controlleddiabetes.This can damage these cells, leading toretinopathy,cataractsand peripheralneuropathy,respectively.

Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health.[29]

Potential adverse effects

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Sorbitol may causeallergic reactionsin some people.[6]Common side effects from use as a laxative arestomach cramps,vomiting,diarrheaor rectal bleeding.[6]

Compendial status

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See also

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References

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  1. ^publications.iupac.org/pac/1996/pdf/6810x1919.pdf
  2. ^abcdeRecordin theGESTIS Substance Databaseof theInstitute for Occupational Safety and Health
  3. ^"Sorbitol_msds".
  4. ^abTeo 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.PMC1693749.PMID17132742.
  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. ^abcdefgh"Sorbitol".Drugs.com. 23 November 2021.Retrieved8 July2022.
  7. ^"Reduction of Glucose".butane.chem.uiuc.edu.Archived fromthe originalon 2017-09-25.Retrieved2017-10-03.
  8. ^Sugar substitute
  9. ^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.
  10. ^Campbell, Farrell (2011).Biochemistry(Seventh ed.). Brooks/Cole.ISBN978-1-111-42564-7.
  11. ^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.ISSN0022-0337.PMID11699985.
  12. ^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.ISSN1480-3275.PMID21217792.
  13. ^Nelson, Cox (2005).Lehninger Principles of Biochemistry(Fourth ed.). New York: W. H. Freeman.ISBN0-7167-4339-6.
  14. ^"sorbitol".Cancer Drug Guide.American Cancer Society. Archived fromthe originalon 2007-06-30.
  15. ^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.PMID7663066.S2CID43386314.
  16. ^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.PMC270845.PMID6355145.The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive
  17. ^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.PMID17377608.
  18. ^"Kayexalate (sodium polystyrene sulfonate) powder".fda.gov.Retrieved12 July2015.
  19. ^"Home – Catalent".catalent.com.Retrieved12 July2015.
  20. ^"Sorbitol 70%".bttcogroup.in.Archived fromthe originalon 10 July 2020.Retrieved12 July2015.
  21. ^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.ISSN0104-6632.
  22. ^"Gallaher Group".gallaher-group.com.Archived fromthe originalon 27 December 2008.Retrieved12 July2015.
  23. ^abChemical and functional properties of food saccharides.Tomasik, Piotr. Boca Raton: CRC Press. 2004.ISBN9780203495728.OCLC317752036.{{cite book}}:CS1 maint: others (link)
  24. ^Nakka R."KNSB Propellant".nakka-rocketry.net.Retrieved12 July2015.
  25. ^Metzger JO (2006). "Production of Liquid Hydrocarbons from Biomass".Angewandte Chemie International Edition.45(5): 696–698.doi:10.1002/anie.200502895.PMID16374789.
  26. ^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.
  27. ^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.Bibcode:2010RSERv..14..166T.doi:10.1016/j.rser.2009.08.010.
  28. ^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.PMID10783895.S2CID4426750.
  29. ^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.PMC4088045.PMID17171792.
  30. ^The United States Pharmacopeial Convention."Revisions to FCC, First Supplement".Archived fromthe originalon 5 July 2010.Retrieved6 July2009.
  31. ^Sigma Aldrich."D-Sorbitol".Retrieved15 February2022.
  32. ^European Pharmacopoeia."Index, Ph Eur"(PDF).Archived fromthe original(PDF)on 20 July 2011.Retrieved6 July2009.
  33. ^British Pharmacopoeia (2009)."Index, BP 2009"(PDF).Archived fromthe original(PDF)on 11 April 2009.Retrieved6 July2009.
  34. ^National Institute of Health Sciences (2016)."The Japanese Pharmacopoeia, Seventeenth Edition"(PDF).Archived fromthe original(PDF)on 4 March 2018.Retrieved17 August2018.
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  • Media related toSorbitolat Wikimedia Commons
  1. ^Beebe JA, Frey PA (1998-10-01)."Galactose Mutarotase: Purification, Characterization, and Investigations of Two Important Histidine Residues".Biochemistry.37(42): 14989–14997.doi:10.1021/bi9816047.ISSN0006-2960.
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