Sorbitol: Difference between revisions

| IUPACNameSystematicName = (2''S'',3''R'',4''R'',5''R'')-Hexane-1,2,3,4,5,6-hexol

| OtherNames = <small>D</small>-glucitol; <small>D</small>-Sorbitol; Sorbogem; Sorbo

| LogP =-4.67<ref name="chemsrc">{{Citecite web|url=https://www.chemsrc.com/en/cas/50-70-4_904692.html|title=Sorbitol_msds}}</ref>

'''Sorbitol''' ({{IPAc-en|ˈ|s|ɔːrɔː|(|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 (−C(OH)H−CH₂OH). 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. It has a pKa of 13.14 +/- .2<ref>SciFinderWeb</ref>

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.

:[[File:Mechanism of glucose reduction reaction.png|center]]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.

Sorbitol is referred to as a nutritive sweetener because it provides some dietary energy:. 2It is partly absorbed from the small intestine and metabolized in the body, and partly fermented in the large intestine.6 The fermentation produces [[kilocalorieshort-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 (11having two extra hydrogen atoms), the net energy contribution is between 2.5 and 3.4 [[kilojoulekilocalorie]]s) per [[gram]], versus the averageapproximately 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>{{Citecite 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>{{Citecite 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>

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 doctorphysician.<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 found in some dried fruits and may contribute to the laxative effects of prunes.<ref>{{Cite journal | pmid = 11401245 | year = 2001 | last1 = Stacewicz-Sapuntzakis | first1 = M | last2 = Bowen | first2 = PE | last3 = Hussain | first3 = EA | last4 = Damayanti-Wood | first4 = BI | last5 = Farnsworth | first5 = NR | title = Chemical composition and potential health effects of prunes: a functional food? | volume = 41 | issue = 4 | pages = 251–86 | doi = 10.1080/20014091091814 | journal = Critical Reviews in Food Science and Nutrition| s2cid = 31159565 }}</ref> Sorbitol was first discovered in the fresh juice of mountain ash ([[Sorbus aucuparia]]) berries in 1872.<ref>{{cite book|last=Panda|first=H.|title=The Complete Book on Sugarcane Processing and By-Products of Molasses (with Analysis of Sugar, Syrup and Molasses)|year=2011|publisher=ASIA PACIFIC BUSINESS PRESS Inc|isbn=978-8178331447|page=416|url=https://books.google.com/books?id=2UM4AQAAQBAJ&pg=PA416}}</ref> It is also found in the fruits of apples, plums, pears, cherries, dates, peaches and apricots.

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|accessdateaccess-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|accessdateaccess-date=12 July 2015}}</ref>

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|accessdateaccess-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|accessdateaccess-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, Sorbitolsorbitol is also used as a humectant in cookies and low-moisture foods like peanut butter and fruit preserves.<ref name=":0">{{Citecite 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" />

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>{{citeCite web |last=Nakka |first=Richard |title=KNSB Propellant |url=http://www.nakka-rocketry.net/sorb.html |titleaccess-date=Richard12 Nakka'sJuly Experimental Rocketry2015 Web Site|workwebsite=nakka-rocketry.net|accessdate=12 July 2015}}</ref>

Sorbitol is identified as a potential key chemical intermediate<ref>{{Citecite journal

[[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. Aldose reductase inhibitors, which are substances that prevent or slow the action of aldose reductase, are currently being investigated as a way to prevent or delay these complications.<ref>{{cite web|url=http://findarticles.com/p/articles/mi_m0876/is_n67/ai_14676055 |archive-url=https://archive.is/20120710070620/http://findarticles.com/p/articles/mi_m0876/is_n67/ai_14676055 |url-status=dead |archive-date=2012-07-10 |title=Sorbitol: a hazard for diabetics? }}</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>

==AdversePotential medicaladverse effects==

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|archive-url = https://archive.istoday/20100705223317/http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport04.html

| last = [[Sigma Aldrich]]

| url = http://www.sigmaaldrich.com/catalogUS/ProductDetail.do?lang=en&N4=/product/sial/97336

| accessdateaccess-date = 615 JulyFebruary 20092022

}}</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| accessdateaccess-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>

|accessdateaccess-date=6 July 2009

* [[Japanese Pharmacopoeia]] 17 <ref name=nihs>{{cite web

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