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It can be obtained by [[Redox|reduction]] of [[glucose]], which changes the converted [[aldehyde]] group (−CHO) to a primary alcohol group (−CH<sub>2</sub>OH). Most sorbitol is made from [[potato starch]], but it is also found in nature, for example in apples, pears, peaches, and prunes.<ref name=Teo>{{cite journal | pmid = 17132742 | year = 2006 | last1 = Teo | first1 = G | last2 = Suzuki | first2 = Y | last3 = Uratsu | first3 = SL | last4 = Lampinen | first4 = B | last5 = Ormonde | first5 = N | last6 = Hu | first6 = WK | last7 = Dejong | first7 = TM | last8 = Dandekar | first8 = AM | title = Silencing leaf sorbitol synthesis alters long-distance partitioning and apple fruit quality | volume = 103 | issue = 49 | pages = 18842–7 | doi = 10.1073/pnas.0605873103 | pmc = 1693749 | journal = Proceedings of the National Academy of Sciences of the United States of America| bibcode = 2006PNAS..10318842T | doi-access = free }}</ref> 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.<ref name="Kearsley, M. W. pp 249-249">Kearsley, M. W.; Deis, R. C. Sorbitol and Mannitol. In Sweeteners and Sugar Alternatives in Food Technology; Ames: Oxford, 2006; pp 249-249-261.</ref> While similar, the two sugar alcohols have very different sources in nature, [[melting point]]s, and uses. As an [[over-the-counter drug]], sorbitol is used as a [[laxative]] to treat [[constipation]].<ref name="drugs">{{cite web |title=Sorbitol |url=https://www.drugs.com/mtm/sorbitol.html |publisher=Drugs.com |access-date=8 July 2022 |date=23 November 2021}}</ref> ==Synthesis==  Sorbitol may be synthesised via a glucose reduction reaction<ref>{{cite web|title=Reduction of Glucose|url=http://butane.chem.uiuc.edu/pshapley/GenChem2/B8/1.html|website=butane.chem.uiuc.edu|access-date=2017-10-03|archive-date=2017-09-25|archive-url=https://web.archive.org/web/20170925133922/http://butane.chem.uiuc.edu/pshapley/GenChem2/B8/1.html|url-status=dead}}</ref> 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. <chem display="block">C6H12O6 + NADH + H+ -> C6H14O6 + NAD+</chem>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. [[File:Glucose reduction to sorbitol.svg|535x535px|Mechanism of glucose aldehyde reduction into sorbitol]] Glucose reduction is not the major [[glucose metabolism]] pathway in a normal human body, where the [[Blood sugar|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. ==Uses== ===Sweetener=== 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).<ref>[[Sugar substitute]]</ref> 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 acid]]s, [[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 [[kilocalorie]]s per [[gram]], versus the approximately 4 kilocalories (17 kilojoules) for carbohydrates.<ref>{{cite journal |last1=Tsuneyuki Oku and Sadako Nakamura |title=Digestion, absorption, fermentation, and metabolism of functional sugar substitutes and their available energy |journal=Pure Appl. Chem. |date=2002 |volume=74 |issue=7 |pages=1253–1261 |doi=10.1351/pac200274071253 |url=http://media.iupac.org/publications/pac/2002/pdf/7407x1253.pdf}}</ref> It is often used in [[diet food]]s (including diet drinks and ice cream), mints, [[cough syrup]]s, and sugar-free [[chewing gum]].<ref>{{cite book |last1=Campbell |last2=Farrell |title=Biochemistry |publisher=Brooks/Cole |edition=Seventh |year=2011 |isbn=978-1-111-42564-7 }}</ref> 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.<ref>{{cite journal|last=Hayes|first=C.|date=October 2001|title=The effect of non-cariogenic sweeteners on the prevention of dental caries: a review of the evidence|journal=Journal of Dental Education|volume=65|issue=10|pages=1106–1109|doi=10.1002/j.0022-0337.2001.65.10.tb03457.x|issn=0022-0337|pmid=11699985}}</ref><ref>{{cite journal|last1=Nicolas|first1=Guillaume G.|last2=Lavoie|first2=Marc C.|date=January 2011|title=[Streptococcus mutans and oral streptococci in dental plaque]|journal=Canadian Journal of Microbiology|volume=57|issue=1|pages=1–20|doi=10.1139/w10-095|issn=1480-3275|pmid=21217792}}</ref> It also occurs naturally in many [[drupe|stone fruit]]s and berries from trees of the genus ''[[Sorbus]]''.<ref name=Teo/><ref>{{cite book |last1=Nelson |last2=Cox |title=Lehninger Principles of Biochemistry |location=New York |publisher=W. H. Freeman |edition=Fourth |year=2005 |isbn=0-7167-4339-6 |url-access=registration |url=https://archive.org/details/lehningerprincip00lehn_0 }}</ref> ===Medical applications=== ====Laxative==== As is the case with other [[sugar alcohol]]s, foods containing sorbitol can cause [[Gastrointestinal disease|gastrointestinal distress]]. Sorbitol can be used as a [[laxative]] when taken orally or as an [[enema]].<ref name=drugs/> Sorbitol works as a laxative by drawing water into the [[large intestine]], stimulating [[bowel movements]].<ref name=drugs/><ref>{{cite web|url=http://www.cancer.org/docroot/CDG/content/CDG_sorbitol.asp |publisher=American Cancer Society |work= Cancer Drug Guide|title=sorbitol|archive-url=https://web.archive.org/web/20070630001051/http://www.cancer.org/docroot/CDG/content/CDG_sorbitol.asp |archive-date=2007-06-30 }}</ref> Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a physician.<ref name=drugs/><ref>{{cite journal | pmid= 7663066 | year= 1995 | last1= Lederle | first1= FA | title= Epidemiology of constipation in elderly patients. Drug utilisation and cost-containment strategies | volume= 6 | issue= 6 | pages= 465–9 | journal= Drugs & Aging | doi=10.2165/00002512-199506060-00006| s2cid= 43386314 }}</ref> Sorbitol is commonly used orally as a one-time dose of {{convert|30|-|150|ml}} 70% solution.<ref name=drugs/> It may also be used as a one-time [[rectum|rectal]] enema.<ref name=drugs/> ====Other medical applications==== Sorbitol is used in bacterial culture media to distinguish the pathogenic [[Escherichia coli O157:H7|''Escherichia coli'' O157:H7]] from most other strains of ''[[Escherichia coli|E. coli]]'', because it is usually unable to ferment sorbitol, unlike 93% of known ''E. coli'' strains.<ref name=wells_1983_101>{{cite journal |vauthors=Wells JG, Davis BR, Wachsmuth IK, etal |title=Laboratory investigation of hemorrhagic colitis outbreaks associated with a rare Escherichia coli serotype|journal=Journal of Clinical Microbiology|volume=18|issue=3|pages=512–20| date=September 1983 |pmid=6355145|pmc=270845|doi=10.1128/JCM.18.3.512-520.1983|quote=The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive}}</ref> A treatment for [[Hyperkalemia|hyperkalaemia]] (elevated blood [[potassium]]) uses sorbitol and the [[ion-exchange]] resin [[sodium polystyrene sulfonate]] (tradename Kayexalate).<ref>{{cite journal |vauthors=Rugolotto S, Gruber M, Solano PD, Chini L, Gobbo S, Pecori S |title=Necrotizing enterocolitis in a 850 gram infant receiving sorbitol-free sodium polystyrene sulfonate (Kayexalate): clinical and histopathologic findings |journal=J Perinatol |volume=27 |issue=4 |pages=247–9 | date=April 2007 |pmid=17377608 |doi=10.1038/sj.jp.7211677 |doi-access=free }}</ref> 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.<ref>{{cite web|url=https://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm186845.htm|title=Kayexalate (sodium polystyrene sulfonate) powder|work=fda.gov|access-date=12 July 2015}}</ref> Sorbitol is also used in the manufacture of [[softgel|softgel capsule]]s to store single doses of liquid medicines.<ref name="Catalent Softgel website">{{cite web|url=http://www.catalent.com/offerings/drug-delivery/drug-delivery-oral/softgel-technology|title=Home – Catalent|work=catalent.com|access-date=12 July 2015}}</ref> ===Health care, food, and cosmetic uses=== Sorbitol often is used in modern [[cosmetics]] as a [[humectant]] and [[thickener]].<ref>{{cite web|url=http://www.bttcogroup.in/sorbitol-70.html|title=Sorbitol 70%|work=bttcogroup.in|access-date=12 July 2015|archive-date=10 July 2020|archive-url=https://web.archive.org/web/20200710015140/http://www.bttcogroup.in/sorbitol-70.html|url-status=dead}}</ref> It is also used in [[mouthwash]] and [[toothpaste]]. Some transparent [[gel]]s can be made only with sorbitol, because of its high [[refractive index]]. Sorbitol is used as a [[cryoprotectant]] additive (mixed with [[sucrose]] and sodium poly[[phosphate]]s) in the manufacture of [[surimi]], a processed fish paste.<ref name="MedinaGarrote2002">{{cite journal|last1=Medina|first1=J.R.|last2=Garrote|first2=R.L.|title=The effect of two cryoprotectant mixtures on frozen surubí surimi|journal=Brazilian Journal of Chemical Engineering|volume=19|issue=4|year=2002|pages=419–424|issn=0104-6632|doi=10.1590/S0104-66322002000400010|doi-access=free}}</ref> It is also used as a humectant in some [[cigarette]]s.<ref>{{cite web|url=http://www.gallaher-group.com/products/table3_display.asp?brand_name=Benson+%26+Hedges+Gold&brand_family=Benson+%26+Hedges&product_type=CIGARETTE&country=UNITED+KINGDOM|title=Gallaher Group|work=gallaher-group.com|access-date=12 July 2015|archive-date=27 December 2008|archive-url=https://web.archive.org/web/20081227113352/http://www.gallaher-group.com/products/table3_display.asp?brand_name=Benson+%26+Hedges+Gold&brand_family=Benson+%26+Hedges&product_type=CIGARETTE&country=UNITED+KINGDOM|url-status=dead}}</ref> 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.<ref name=":0">{{cite book|title=Chemical and functional properties of food saccharides|date=2004|publisher=CRC Press|others=Tomasik, Piotr|isbn=9780203495728|location=Boca Raton|oclc=317752036}}</ref> In baking, it is also valuable because it acts as a [[plasticizer]], and slows down the [[staling]] process.<ref name=":0" /> ===Miscellaneous uses=== A mixture of sorbitol and [[potassium nitrate]] has found some success as an [[amateur rocketry|amateur]] solid [[rocket fuel]]. It has similar performance to sucrose-based [[rocket candy]], but is easier to cast, less hygroscopic and does not [[caramelization|caramelize]].<ref>{{Cite web |last=Nakka |first=Richard |title=KNSB Propellant |url=http://www.nakka-rocketry.net/sorb.html |access-date=12 July 2015 |website=nakka-rocketry.net}}</ref> Sorbitol is identified as a potential key chemical intermediate<ref>{{cite journal | last1 = Metzger | first1 = Jürgen O. | title = Production of Liquid Hydrocarbons from Biomass | doi = 10.1002/anie.200502895 | pmid = 16374789 | journal = Angewandte Chemie International Edition | volume = 45 | issue = 5 | pages = 696–698 | year = 2006 }}</ref> 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.<ref>{{cite journal|last=Shrotri|first=Abhijit|author2=Tanksale, Akshat |author3=Beltramini, Jorge Norberto |author4=Gurav, Hanmant |author5= Chilukuri, Satyanarayana V. |title=Conversion of cellulose to polyols over promoted nickel catalysts|journal=Catalysis Science & Technology|year=2012|volume=2|issue=9|pages=1852–1858|doi=10.1039/C2CY20119D}}</ref> Complete reduction of sorbitol opens the way to [[alkane]]s, 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.<ref>{{cite journal|last=Tanksale|first=Akshat|author2=Beltramini, Jorge Norberto |author3=Lu, GaoQing Max |title=A review of catalytic hydrogen production processes from biomass|journal=Renewable and Sustainable Energy Reviews|year=2010|volume=14|issue=1|pages=166–182|doi=10.1016/j.rser.2009.08.010|bibcode=2010RSERv..14..166T }}</ref> :19 C<sub>6</sub>H<sub>14</sub>O<sub>6</sub> → 13 C<sub>6</sub>H<sub>14</sub> + 36 CO<sub>2</sub> + 42 H<sub>2</sub>O The above [[chemical reaction]] is [[exothermic reaction|exothermic]], and 1.5 [[mole (unit)|mole]]s 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 [[Osmotic concentration|osmolarity]] of the medium. ==Medical importance== [[Aldose reductase]] is the first enzyme in the [[Polyol pathway|sorbitol-aldose reductase pathway]]<ref>{{cite journal | pmid = 10783895 | year = 2000 | last1 = Nishikawa | first1 = T | last2 = Edelstein | first2 = D | last3 = Du | first3 = XL | last4 = Yamagishi | first4 = S | last5 = Matsumura | first5 = T | last6 = Kaneda | first6 = Y | last7 = Yorek | first7 = MA | last8 = Beebe | first8 = D | last9 = Oates | first9 = PJ | last10 = Oates | first10 = Peter J. | last11 = Hammes | first11 = Hans-Peter | last12 = Giardino | first12 = Ida | title = Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage | volume = 404 | issue = 6779 | pages = 787–90 | doi = 10.1038/35008121 | journal = Nature | bibcode = 2000Natur.404..787N | s2cid = 4426750 | display-authors = 8 }}</ref> 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 [[myelin]]ate peripheral nerves, is a frequent result of long-term hyperglycemia that accompanies poorly controlled [[diabetes]]. This can damage these cells, leading to [[retinopathy]], [[cataract]]s and peripheral [[neuropathy]], respectively. Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health.<ref name=":2">{{cite journal | last1 = Islam | first1 = M. S. | last2 = Sakaguchi | first2 = E | year = 2006 | title = Sorbitol-based osmotic diarrhea: Possible causes and mechanism of prevention investigated in rats | journal = World Journal of Gastroenterology | volume = 12 | issue = 47| pages = 7635–7641 | doi=10.3748/wjg.v12.i47.7635| pmid = 17171792 | pmc = 4088045 | doi-access = free }}</ref> ==Potential adverse effects== Sorbitol may cause [[allergic reaction]]s in some people.<ref name=drugs/> Common side effects from use as a laxative are [[Cramp|stomach cramp]]s, vomiting, [[diarrhea]] or rectal bleeding.<ref name=drugs/> ==Compendial status== * [[Food Chemicals Codex]]<ref name=rffs>{{cite web |last = The United States Pharmacopeial Convention |title = Revisions to FCC, First Supplement |url = http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport04.html |access-date = 6 July 2009 |url-status = dead |archive-url = https://archive.today/20100705223317/http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport04.html |archive-date = 5 July 2010 }}</ref> * [[European Pharmacopoeia]]<ref name=dsbtl>{{cite web | last = Sigma Aldrich | author-link = Sigma Aldrich | title = D-Sorbitol | url = http://www.sigmaaldrich.com/US/en/product/sial/97336 | access-date = 15 February 2022 }}</ref> 6.1<ref name=ipe>{{cite web| last =European Pharmacopoeia| author-link =European Pharmacopoeia| title =Index, Ph Eur| url =https://www.edqm.eu/store/images/majbdd/200709201618250.6_1%20IndexE.pdf| access-date =6 July 2009| url-status =dead| archive-url =https://web.archive.org/web/20110720160054/https://www.edqm.eu/store/images/majbdd/200709201618250.6_1%20IndexE.pdf| archive-date =20 July 2011}}</ref> * [[British Pharmacopoeia]] 2009<ref name=ib29>{{cite web |last=British Pharmacopoeia |title=Index, BP 2009 |year=2009 |url=http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf |access-date=6 July 2009 |url-status=dead |archive-url=https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf |archive-date=11 April 2009 }}</ref> * [[Japanese Pharmacopoeia]] 17 <ref name=nihs>{{cite web |last=National Institute of Health Sciences |title=The Japanese Pharmacopoeia, Seventeenth Edition |year=2016 |url=http://jpdb.nihs.go.jp/jp17e/000217655.pdf |access-date=17 August 2018 |archive-date=4 March 2018 |archive-url=https://web.archive.org/web/20180304194003/http://jpdb.nihs.go.jp/jp17e/000217655.pdf |url-status=dead }}</ref> ==See also== *[[Sorbitan]] *[[Isosorbide]] ==References== {{Reflist|30em}} ==External links== *{{Commons category-inline}} {{Alcohols}} {{Blood substitutes and perfusion solutions}} {{Consumer Food Safety}} {{Diagnostic agents}} {{Fructose and galactose metabolism enzymes}} {{Laxatives}} [[Category:Commodity chemicals]] [[Category:E-number additives]] [[Category:Excipients]] [[Category:Laxatives]] [[Category:Osmotic diuretics]] [[Category:Sugar alcohols]] [[Category:Sugar substitutes]] </textarea><div class="templatesUsed"><div class="mw-templatesUsedExplanation"><p><span 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