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| ImageFile1 = Sorbitol-3D-balls.png
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|IUPACName=<small>D</small>-Glucitol<ref>publications.iupac.org/pac/1996/pdf/6810x1919.pdf</ref>
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| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 506T60A25R
| KEGG = C00794
| 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
| InChIKey = FBPFZTCFMRRESA-JGWLITMVSA
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| MagSus = -107.80·10<sup>−6</sup> cm<sup>3</sup>/mol
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'''Sorbitol''' ({{IPAc-en|ˈ|s|ɔː|(|r|)|b|ᵻ|t|ɒ|l}}), less commonly known as '''glucitol''' ({{IPAc-en|ˈ|g|l|uː|s|ᵻ|t|ɒ|l}}), is a [[sugar alcohol]] with a [[sweet]] [[taste]] which the human body metabolizes slowly. 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==
<!-- linked from redirect [[Glucose reduction reaction]] -->
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]]
▲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.
==Uses==
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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 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
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====
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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">{{
===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>{{
Sorbitol is identified as a potential key chemical intermediate<ref>{{
| last1 = Metzger | first1 = Jürgen O.
| title = Production of Liquid Hydrocarbons from Biomass
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==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 }}</ref>▼
▲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>
==
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==
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