View source for Xylitol

{{Short description|Natural sweetener}}
{{short_description|Synthetic sweetener}}
{{use dmy dates|date=May 2021}}
{{chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 457481039
| Name           = Xylitol
| pronounce      = {{IPAc-en|ˈ|z|aɪ|l|ᵻ|t|ɒ|l}}
| Reference      = <ref>[[Safety data sheet]] for [http://ehsrms.uaa.alaska.edu/CMS/Laboratory/MSDS/MSDS%20by%20Vendor/Fisher/Xylitol.pdf xylitol] {{Webarchive|url=https://web.archive.org/web/20160303220707/http://ehsrms.uaa.alaska.edu/CMS/Laboratory/MSDS/MSDS%20by%20Vendor/Fisher/Xylitol.pdf |date=3 March 2016 }} from [[Fisher Scientific]]. {{Retrieved|access-date=2014-11-02}}</ref>
| ImageFile      = Xylitol.svg
| ImageSize      = 120 px
| ImageName      = Xylitol
| ImageFile1     = Xylitol crystals.jpg
| ImageSize1     = 250px
| ImageCaption1  = Xylitol crystals
| IUPACName      = ''meso''-Xylitol
| SystematicName = (2''R'',3''R'',4''S'')-Pentane-1,2,3,4,5-pentol
| OtherNames     = {{Unbulleted list|(2''R'',3''R'',4''S'')-Pentane-1,2,3,4,5-pentaol (not recommended)|(2''R'',3''R'',4''S'')-1,2,3,4,5-Pentahydroxypentane|Xylite}}
| Section1       = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 87-99-0
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VCQ006KQ1E
| ChEMBL = 96783
| KEGG = C00379
| PubChem = 6912
| ChemSpiderID = 6646
| SMILES = OC[C@@H](O)[C@H](O)[C@@H](O)CO
| InChI_Ref = {{ebicite|correct|EBI}}
| InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+
| InChIKey_Ref = {{ebicite|correct|EBI}}
| InChIKey = HEBKCHPVOIAQTA-SCDXWVJYSA-N
}}
| Section2 = {{Chembox Properties
  | C=5 | H=12 | O=5
  | Density = 1.52&nbsp;g/cm<sup>3</sup>
  | MeltingPtC = 92 to 96
  | MeltingPt_notes =
  | BoilingPtC = 345.39
  | BoilingPt_notes = Predicted value using Adapted Stein & Brown method<ref>
    {{cite web
      |title=Xylitol
      |series=Chemical Structure
      |website=Chemspider.com
      |url=http://www.chemspider.com/Chemical-Structure.6646.html
      |access-date=2015-05-13
     }}
</ref>
  | Solubility = 168 g/100 gref name=Ullmann/>
  }}
| Section3 = {{Chembox Hazards
  | NFPA-H = 1
  | NFPA-F = 1
  | NFPA-R = 0
  }}
| Section4 = 
| Section5 = 
| Section6 = 
| Section8 = {{Chembox Related
  | OtherFunction_label = [[alkane]]s
  | OtherFunction = [[Pentane]]
  }}
}}
'''Xylitol''' is a [[chemical compound]] with the formula {{chem|C|5|H|12|O|5}}, or HO(CH<sub>2</sub>)(CHOH)<sub>3</sub>(CH<sub>2</sub>)OH; specifically, one particular [[Stereoisomerism|stereoisomer]] with that structural formula. It is a colorless or white [[crystal]]line solid.  It is classified as a [[polyalcohol]]  and a [[sugar alcohol]], specifically an [[alditol]]. Of the common sugar alcohols, only sorbitol is more soluble in water.

The name derives from {{langx|grc|ξύλον}}, ''xyl[on]'' 'wood', with the suffix ''-itol'' used to denote it being a sugar alcohol.

Xylitol is used as a [[food additive]] and [[sugar substitute]].  Its [[E number|European Union code number]] is '''E967'''.<ref name=EAPP-Food-legtn>
{{cite web
 |title=Food legislation
 |publisher=European Association of Polyol Producers
 |website=polyols-eu.org
 |date=22 March 2017
 |url=http://polyols-eu.org/legislation/food/
 |access-date=2019-02-07
}}
</ref> Replacing [[sugar]] with xylitol in food products may promote better dental health, but evidence is lacking on whether xylitol itself prevents [[dental cavities]].<ref name=Riley-etal-2015>
{{cite journal
 |last1=Riley  |first1=P.      |last2=Moore  |first2=D.
 |last3=Ahmed  |first3=F.      |last4=Sharif |first4=M.O.
 |last5=Worthington  |first5=H.V.
 |date=26 March 2015
 |title=Xylitol-containing products for preventing dental caries in children and adults
 |journal=The Cochrane Database of Systematic Reviews
 |volume=2015 |issue=3  |pages=CD010743
 |doi=10.1002/14651858.CD010743.pub2  |pmid=25809586
|pmc=9345289 }}</ref><ref>{{cite journal
 |title=Can xylitol – used in products like sweets, candy, chewing gum, and toothpaste – help prevent tooth decay in children and adults?
 |series=Lay summary
 |journal=The Cochrane Database of Systematic Reviews 
 |year=2015
 |doi=10.1002/14651858.CD010743.pub2
 |pmid=25809586
 |url=https://www.cochrane.org/CD010743/ORAL_can-xylitol-used-in-products-like-sweets-candy-chewing-gum-and-toothpaste-help-prevent-tooth-decay-in-children-and-adults
|last1=Riley
 |first1=P.
 |last2=Moore
 |first2=D.
 |last3=Ahmed
 |first3=F.
 |last4=Sharif
 |first4=M. O.
 |last5=Worthington
 |first5=H. V.
 |volume=2015
 |issue=3
 |pages=CD010743
 |pmc=9345289
 }} {{open access}}
</ref> In the United States, xylitol is used as a common [[sugar substitute]], and is considered to be safe for humans.<ref name="fda">{{cite web |date=14 July 2023 |title=Aspartame and Other Sweeteners in Food |url=https://www.fda.gov/food/food-additives-petitions/aspartame-and-other-sweeteners-food |access-date=12 September 2024 |publisher=US Food and Drug Administration}}</ref>

Xylitol can be toxic to [[dog]]s.<ref name="dogs-fda">{{cite web |title=Paws off xylitol; It's dangerous for dogs |url=https://www.fda.gov/consumers/consumer-updates/paws-xylitol-its-dangerous-dogs |publisher=US Food and Drug Administration |access-date=9 September 2021 |date=7 July 2021}}</ref>

==History==
[[Emil Fischer]], a German chemistry professor, and his assistant Rudolf Stahel isolated a new compound from [[beech]] wood chips in September 1890 and named it {{lang|de|Xylit}}, the German word for xylitol. The following year, the French chemist M.&nbsp;G.&nbsp;Bertrand isolated xylitol syrup by processing wheat and oat straw.<ref name="pmid10890712">{{cite journal |vauthors=Mäkinen KK |title=The rocky road of xylitol to its clinical application |journal=Journal of Dental Research |volume=79 |issue=6 |pages=1352–5 |date=June 2000 |pmid=10890712 |doi=10.1177/00220345000790060101 |s2cid=31432699 |url=https://journals.sagepub.com/doi/10.1177/00220345000790060101?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed}}</ref> Sugar rationing during [[World War II|World War&nbsp;II]] led to an interest in [[sugar substitutes]]. Interest in xylitol and other polyols became intense, leading to their [[Characterization (materials science)|characterization]] and manufacturing methods.<ref name=Ur-Rehman-etal-2015/><ref name=Hicks-2010>
{{cite magazine |last=Hicks |first=Jesse |date=Spring 2010 |title=The pursuit of sweet |lang=en |magazine=Science History |url=https://www.sciencehistory.org/distillations/magazine/the-pursuit-of-sweet |publisher=Science History Institute}}</ref>

==Structure, production, commerce==
Xylitol is one of three 5-carbon sugar alcohols.  The others are [[arabitol]] and [[ribitol]].  These three compounds differ in the stereochemistry of the three secondary alcohol groups.
{{Gallery|title=5-carbon sugar alcohols|align=
|Arabitol.png
|Arabitol
|Ribitol structure.png
|Ribitol
| Xylitol-2D-structure.svg
|Xylitol
|
}}

Xylitol occurs naturally in small amounts in plums, strawberries, cauliflower, and pumpkin; humans and many other animals make trace amounts during [[metabolism]] of [[carbohydrate]]s.<ref name=Ur-Rehman-etal-2015/> Unlike most sugar alcohols, xylitol is [[Chirality (chemistry)|achiral]].<ref name=Wrolstad-2012>
{{cite book
 |last=Wrolstad  |first=Ronald E.
 |year=2012
 |title=Food Carbohydrate Chemistry
 |page=176
 |publisher=John Wiley & Sons
 |isbn=9780813826653
 |url=https://books.google.com/books?id=gVB8l8ukYPYC&pg=PA176
 |access-date=2012-10-20  |via=Google Books
}}
</ref> Most other [[isomer]]s of pentane-1,2,3,4,5-pentol are chiral, but xylitol has a plane of symmetry.

Industrial production starts with [[lignocellulosic biomass]] from which [[xylan]] is extracted; raw biomass materials include [[hardwood]]s, [[softwoods]], and agricultural waste from processing maize, wheat, or rice. The mixture is hydrolyzed with acid to give [[xylose]].  The xylose is purified by [[chromatography]].  Purified [[xylose]] is catalytically [[hydrogenation|hydrogenated]] into xylitol using a [[Raney nickel]] catalyst.<ref name=Ullmann>{{cite book |doi=10.1002/14356007.a25_413.pub3 |chapter=Sugar Alcohols |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2012 |last1=Schiweck |first1=Hubert |last2=Bär |first2=Albert |last3=Vogel |first3=Roland |last4=Schwarz |first4=Eugen |last5=Kunz |first5=Markwart |last6=Dusautois |first6=Cécile |last7=Clement |first7=Alexandre |last8=Lefranc |first8=Caterine |last9=Lüssem |first9=Bernd |last10=Moser |first10=Matthias |last11=Peters |first11=Siegfried |isbn=9783527303854 }}</ref> The conversion changes the sugar (xylose, an [[aldehyde]]) into the [[primary alcohol]], xylitol.<ref name=Ur-Rehman-etal-2015/>

Xylitol can also be obtained by [[industrial fermentation]], but this methodology are not as economical as the acid hydrolysis/chromatography route described above. Fermentation is effected by bacteria, fungi, or yeast, especially ''[[Candida tropicalis]]''.<ref name=Ur-Rehman-etal-2015/><ref name=Jain-Mulay-2014>
{{cite journal
 |last1=Jain   |first1=H.
 |last2=Mulay  |first2=S.
 |date=March 2014
 |title=A review on different modes and methods for yielding a pentose sugar: Xylitol
 |journal=International Journal of Food Sciences and Nutrition
 |volume=65  |issue=2  |pages=135–143
 |doi=10.3109/09637486.2013.845651
 |pmid=24160912  |s2cid=39929588
}}
</ref> According to the US [[United States Department of Energy|Department of Energy]], xylitol production by [[fermentation]] from discarded [[biomass]] is one of the most valuable [[Renewable resource|renewable chemicals]] for commerce, forecast to be a US $1.4&nbsp;billion industry by 2025.<ref name=Felipe-H-P-etal-2019>
{{cite journal
 | last1=Felipe Hernández-Pérez  | first1=Andrés 
 | last2=de Arruda         | first2=Priscila Vaz
 | last3=Sene              | first3=Luciane
 | last4=da Silva          | first4=Silvio Silvério
 | last5=Kumar Chandel     | first5=Anuj
 | last6=de Almeida Felipe | first6=Maria das Graças
 | date=2019-07-16
 | title=Xylitol bioproduction: State-of-the-art, industrial paradigm shift, and opportunities for integrated biorefineries
 | journal=Critical Reviews in Biotechnology
 | volume=39  | issue=7  | pages=924–943
 | issn=0738-8551  | pmid=31311338  | s2cid=197421362 
 | doi=10.1080/07388551.2019.1640658
}}</ref>

==Uses==
Xylitol is used as a sugar substitute in such manufactured products as [[drug]]s, [[dietary supplement]]s, [[Confectionery|confections]], [[toothpaste]], and [[chewing gum]], but is not a common household sweetener.<ref name=Riley-etal-2015/><ref name=fda/><ref name=Drugs-2018>
{{cite web
 |title=Xylitol
 |year=2018
 |website=Drugs.com
 |url=https://www.drugs.com/npp/xylitol.html
 |access-date=12 October 2018
}}
</ref> Xylitol has negligible effects on [[blood sugar]] because its assimilation and metabolism are independent of [[insulin]].<ref name=Drugs-2018/> It is approved as a food additive and sugar substitute in the United States.<ref name=fda/> Xylitol is often marketed as "birch sugar".

Xylitol is also found as an additive to [[Saline (medicine)|saline]] solution for [[nasal irrigation]] and has been reported to be effective in improving symptoms of chronic [[sinusitis]].<ref name=Weissm-etal-2011>
{{cite journal
 |last1=Weissman    |first1=Joshua D.
 |last2=Fernandez  |first2=Francisca
 |last3=Hwang      |first3=Peter H.
 |date=November 2011
 |title=Xylitol nasal irrigation in the management of chronic rhinosinusitis: A pilot study
 |journal=The Laryngoscope
 |volume=121  |issue=11  |pages=2468–2472
 |doi=10.1002/lary.22176
 |issn=1531-4995 |pmid=21994147
 |s2cid=36572019
 |url=https://pubmed.ncbi.nlm.nih.gov/21994147/
}}
</ref>

Xylitol can also be incorporated into fabrics to produce a cooling fabric. When moisture, such as sweat, comes into contact with the xylitol embedded in the fabric, it produces a cooling sensation.<ref>{{Cite journal |last1=Peng |first1=Yucan |last2=Cui |first2=Yi |date=2020-04-15 |title=Advanced Textiles for Personal Thermal Management and Energy |journal=Joule |language=en |volume=4 |issue=4 |pages=724–742 |doi=10.1016/j.joule.2020.02.011 |issn=2542-4351|doi-access=free |bibcode=2020Joule...4..724P }}</ref>

==Food properties==

===Nutrition, taste, and cooking===
Humans absorb xylitol more slowly than sucrose, and xylitol supplies 40% fewer calories than an equal mass of sucrose.<ref name=Drugs-2018/>

Xylitol has about the same sweetness as [[sucrose]],<ref name=Drugs-2018/> but is sweeter than similar compounds like [[sorbitol]] and [[mannitol]].<ref name=Ur-Rehman-etal-2015>
{{cite journal
 |last1=Ur-Rehman |first1=S.     |last2=Mushtaq |first2=Z.
 |last3=Zahoor    |first3=T.     |last4=Jamil   |first4=A.
 |last5=Murtaza   |first5=M.A.
 |date=2015
 |title=Xylitol: A review on bio-production, application, health benefits, and related safety issues
 |journal=Critical Reviews in Food Science and Nutrition
 |volume=55  |issue=11  |pages=1514–1528
 |doi=10.1080/10408398.2012.702288
 |pmid=24915309  |s2cid=20359589
}}
</ref>

Xylitol is stable enough to be used in baking,<ref name=UK-Diabetes-2018-10-28/> but because xylitol and other polyols are more heat-stable, they do not [[Caramelization|caramelise]] as sugars do. When used in foods, they lower the freezing point of the mixture.<ref name=leatherhead>{{cite web
 |last1=Burgos
 |first1=Karen
 |last2=Subramaniam
 |first2=Persis
 |last3=Arthur
 |first3=Jennifer
 |date=21 November 2016
 |title=Reformulation guide for small to medium sized companies
 |publisher=Leatherhead Food Research
 |url=https://www.fdf.org.uk/corporate_pubs/Reformulation-Guide-Sugars-Aug2016.pdf
 |via=The Food and Drink Federation
 |access-date=28 October 2018
 |archive-date=27 September 2020
 |archive-url=https://web.archive.org/web/20200927023640/http://www.fdf.org.uk/corporate_pubs/Reformulation-Guide-Sugars-Aug2016.pdf
 |url-status=dead
 }}</ref>

===Food risks===
No serious health risk exists in most humans for normal levels of consumption. The [[European Food Safety Authority]] has not set a limit on daily intake of xylitol. Due to the adverse [[laxative]] effect that all polyols have on the digestive system in high doses, xylitol is banned from soft drinks in the [[European Union]]. Similarly, due to a 1985 report by the E.U. [[Scientific Committee on Food]] which states that "ingesting 50&nbsp;g a day of xylitol can cause [[diarrhea]]", tabletop sweeteners (as well as other products containing xylitol) are required to display the warning "Excessive consumption may induce laxative effects".<ref name=UK-NHS-2016-04-13>
{{cite web
 |title=Is xylitol good for your teeth?
 |date=13 April 2016
 |series=Live well: Eat well
 |publisher=U.K. [[National Health Service]]
 |url=https://www.nhs.uk/live-well/eat-well/is-xylitol-good-for-your-teeth/
 |access-date=28 October 2018
}}
</ref>

===Metabolism===
Xylitol has 2.4 kilocalories of [[food energy]] per gram of xylitol (10 kilojoules per gram) according to [[United States of America|U.S.]] and [[European Union|E.U.]] food-labeling regulations.<ref name=UN-FAO-y5022e04>
{{cite report
 |chapter=Chapter 3: Energy Conversion Factors
 |title=Calculation of the Energy Content of Foods
 |department=Food and Agriculture Organization
 |publisher=The United Nations
 |chapter-url=http://www.fao.org/docrep/006/Y5022E/y5022e04.htm
 |access-date=30 March 2017
}}
</ref><ref name=EAPP-Food-legtn/> The real value can vary, depending on metabolic factors.<ref name="Livesey-2003" />

Primarily, the liver metabolizes absorbed xylitol. The main metabolic route in humans occurs in [[cytoplasm]], via nonspecific [[NAD+|NAD]]-dependent dehydrogenase (polyol dehydrogenase), which transforms xylitol to [[D-xylulose|{{sc|D}}-xylulose]]. Specific [[xylulokinase]] phosphorylates it to [[D-xylulose-5-phosphate|{{sc|D}}-xylulose-5-phosphate]]. This then goes to [[pentose phosphate pathway]] for further processing.<ref name=Livesey-2003/>

About 50% of eaten xylitol is absorbed via the intestines. Of the remaining 50% that is not absorbed by the intestines, in humans, 50–75% of the xylitol remaining in the gut is fermented by [[gut bacteria]] into short-chain organic acids and gases, which may produce [[flatulence]]. The remnant unabsorbed xylitol that escapes fermentation is excreted unchanged, mostly in feces; less than 2&nbsp;g of xylitol out of every 100&nbsp;g ingested is excreted via urine.<ref name=Livesey-2003>
{{cite journal
 |last=Livesey  |first=G.
 |year=2003
 |title=Health potential of polyols as sugar replacers, with emphasis on low glycaemic properties
 |journal=Nutrition Research Reviews
 |volume=16  |issue=2  |pages=163–191
 |pmid=19087388  |issn=1475-2700
 |doi=10.1079/NRR200371  |doi-access=free
}}
</ref>

Xylitol ingestion also increases [[motilin]] secretion, which may be related to xylitol's ability to cause diarrhea.<ref name=Wölnerhn-etal-2019>
{{Cite journal
 |author1=Wölnerhanssen, B. K.  |author2=Meyer-Gerspach, A. C.
 |author3=Beglinger, C.         |author4=Islam, M. S.
 |date=June 2019
 |title=Metabolic effects of the natural sweeteners xylitol and erythritol: A comprehensive review
 |journal=Critical Reviews in Food Science and Nutrition
 |volume=60  |issue=12  |pages=1986–1998
 |pmid=31204494  |doi=10.1080/10408398.2019.1623757
|s2cid=189944738
 }}
</ref> The less-digestible but fermentable nature of xylitol also contributes to constipation relieving effects.<ref name=Salli-etal-2019/>

==Health effects==

===Dental care===
A 2015 [[Cochrane review]] of ten studies between 1991 and 2014 suggested a positive effect in reducing [[tooth decay]] of xylitol-containing [[fluoride]] toothpastes when compared to fluoride-only toothpaste, but there was insufficient evidence to determine whether other xylitol-containing products can prevent tooth decay in infants, children or adults.<ref name="pmid25809586">{{cite journal | vauthors = Riley P, Moore D, Ahmed F, Worthington HV | title=Xylitol-containing products for preventing dental caries in children and adults | journal=[[Cochrane Library#The_Cochrane Database of Systematic Reviews]] | volume=2015 | issue=3 | pages=CD010743 | year=2015 | doi= 10.1002/14651858.CD010743.pub2 | pmc=9345289 | pmid=25809586}}</ref> Subsequent reviews support the belief that xylitol can suppress the growth of pathogenic [[Streptococcus]] in the mouth, thereby reducing dental caries and [[gingivitis]], although there is concern that swallowed xylitol may cause [[Dysbiosis#Gut/intestinal dysbiosis|intestinal dysbiosis]].<ref name="pmid32638045">{{cite journal | vauthors = Benahmed AG, Gasmi A, Bjørklund G | title=Health benefits of xylitol | journal=[[Applied Microbiology and Biotechnology]] | volume=104 | issue=17 | pages=225–7237 | year=2020 | doi= 10.1007/s00253-020-10708-7 | pmid=32638045}}</ref><ref name="pmid35462747">{{cite journal | vauthors = ALHumaid J, Bamashmous M | title=Meta-analysis on the Effectiveness of Xylitol in Caries Prevention | journal=Journal of International Society of Preventive & Community Dentistry  | volume=12 | issue=2 | pages=133–138 | year=2022| doi= 10.4103/jispcd.JISPCD_164_21 | doi-access=free | pmc=9022379 | pmid=35462747}}</ref><ref name="pmid31060040">{{cite journal | vauthors = Janket S, Benwait J, Meurman JH | title=Oral and Systemic Effects of Xylitol Consumption | journal=[[Caries Research]] | volume=53 | issue=5 | pages=491–501 | year=2019 | doi= 10.1159/000499194 | pmid=31060040}}</ref> A 2022 review suggested that xylitol-containing [[chewing gum]] decreases plaque, but not xylitol-containing candy.<ref>{{Cite journal |last1=Söderling |first1=Eva |last2=Pienihäkkinen |first2=Kaisu |date=2022 |title=Effects of xylitol chewing gum and candies on the accumulation of dental plaque: a systematic review |journal=Clinical Oral Investigations |volume=26 |issue=1 |pages=119–129 |doi=10.1007/s00784-021-04225-8 |issn=1432-6981 |pmc=8791908 |pmid=34677696}}</ref>

===Earache===
In 2011 [[EFSA]] "concluded that there was not enough evidence to support" the claim that xylitol-sweetened gum could prevent middle-ear infections, also known as [[acute otitis media]] (AOM).<ref name=UK-NHS-2016-04-13/><ref>
{{cite journal
  |author=EFSA panel
  |date=June 2011
  |title=Scientific opinion on the substantiation of health claims related to sugar-free chewing gum sweetened with xylitol and plaque acid neutralisation (ID 485), maintenance of tooth mineralisation (ID 486, 562, 1181), reduction of dental plaque (ID 485, 3085)
 |journal=EFSA Journal
 |volume=9  |issue=6  |page=2266
 |doi=10.2903/j.efsa.2011.2266  |doi-access=free
}}
</ref> A 2016 review indicated that xylitol in chewing gum or a syrup may have a moderate effect in preventing AOM in healthy children.<ref name=Azarpazh-etal-2016>
{{cite journal
 |last1=Azarpazhooh |first1=A.
 |last2=Lawrence    |first2=H.P.
 |last3=Shah        |first3=P.S.
 |title=Xylitol for preventing acute otitis media in children up to 12&nbsp;years of age
 |journal=The Cochrane Database of Systematic Reviews
 |date=3 August 2016
 |volume=2016
 |issue=8 |page=CD007095
 |doi=10.1002/14651858.CD007095.pub3 |doi-access=free
 |pmid=27486835
|pmc=8485974
 }}
</ref> It may be an alternative to conventional therapies (such as [[antibiotic]]s) to lower risk of earache in healthy children&nbsp;– reducing risk of occurrence by 25%<ref name=Marom-etal-2016>
{{cite journal
 |last1=Marom   |first1=Tal            |last2=Marchisio |first2=Paola
 |last3=Tamir   |first3=Sharon Ovnat   |last4=Torretta  |first4=Sara
 |last5=Gavriel |first5=Haim           |last6=Esposito  |first6=Susanna
 |date=2016-02-12
 |title=Complementary and alternative medicine treatment options for otitis media
 |journal=Medicine
 |volume=95  |issue=6  |pages=e2695
 |doi=10.1097/MD.0000000000002695
 |issn=0025-7974  |pmc=4753897  |pmid=26871802
}}
</ref>&nbsp;– although there is no definitive proof that it could be used as a therapy for earache.<ref name=Azarpazh-etal-2016/>

===Diabetes===
In 2011, EFSA approved a marketing claim that foods or beverages containing xylitol or similar sugar replacers cause lower blood glucose and lower [[insulin]] responses compared to sugar-containing foods or drinks.<ref name=UK-Diabetes-2018-10-28>
{{cite web
 |title=Xylitol
 |url=https://www.diabetes.co.uk/sweeteners/xylitol.html
 |publisher=Diabetes.co.uk
 |access-date=28 October 2018
}}
</ref><ref name=EFSA-2011>
{{cite journal
 |author=EFSA panel
 |date=April 2011
 |title=Scientific opinion on the substantiation of health claims related to the sugar replacers xylitol, sorbitol, mannitol, maltitol, lactitol, isomalt, erythritol, D-tagatose, isomaltulose, sucralose and polydextrose and maintenance of tooth mineralisation by decreasing tooth demineralisation, and reduction of post-prandial glycaemic responses
 |journal=EFSA Journal
 |volume=9  |issue=4  |page=2076
 |doi=10.2903/j.efsa.2011.2076  |doi-access=free
}}
</ref> Xylitol products are used as [[sucrose]] substitutes for weight control,<ref name=UK-Diabetes-2018-10-28/><ref name=Salli-etal-2019>
{{Cite journal
 |last1=Salli    |first1=Krista     |last2=Lehtinen  |first2=Markus J.
 |last3=Tiihonen |first3=Kirsti     |last4=Ouwehand  |first4=Arthur C.
 |date=2019-08-06
 |title=Xylitol's health benefits beyond dental health: A comprehensive review
 |journal=Nutrients
 |volume=11  |issue=8  |pages=1813
 |doi=10.3390/nu11081813
 |issn=2072-6643  |pmc=6723878  |pmid=31390800
|doi-access=free }}
</ref> as xylitol has 40% fewer calories than sucrose (2.4&nbsp;kcal/g compared to 4.0&nbsp;kcal/g for sucrose).<ref name=UK-Diabetes-2018-10-28/><ref name=Tiefenbkr-2017>
{{cite book
 | last=Tiefenbacher  | first=Karl F.
 | year=2017
 | title=Wafer and Waffle
 | chapter=Technology of Main Ingredients – Sweeteners and Lipids
 | publisher=Elsevier
 | isbn=978-0-12-809438-9  | doi=10.1016/b978-0-12-809438-9.00003-x
 | pages=123–225
}}
</ref> The [[glycemic index]] (GI) of xylitol is only 7% of the GI for [[glucose]].<ref name=Foster-Powell-etal-2002>
{{cite journal
 |last1=Foster-Powell  |first1=K.
 |last2=Holt           |first2=S.H.
 |last3=Brand-Miller   |first3=J.C.
 |date=July 2002
 |title=International table of glycemic index and glycemic load values: 2002
 |journal=The American Journal of Clinical Nutrition
 |volume=76 |issue=1 |pages=5–56
 |doi=10.1093/ajcn/76.1.5 |pmid=12081815  |doi-access=free
}}
</ref>

==Adverse effects==

===Humans===
When ingested at high doses, xylitol and other polyols may cause [[gastrointestinal]] discomfort, including [[flatulence]], [[diarrhea]], and [[irritable bowel syndrome]] (see [[#Metabolism|Metabolism]] above); some people experience the adverse effects at lower doses.<ref name=UK-NHS-2016-04-13/><ref name=Mäkinen-2016>
{{cite journal
 |last=Mäkinen |first=Kauko
 |date=2016-10-20
 |title=Gastrointestinal disturbances associated with the consumption of sugar alcohols with special consideration of xylitol: Scientific review and instructions for dentists and other health-care professionals
 |journal=International Journal of Dentistry
 |volume=2016  |page=5967907
 |doi=10.1155/2016/5967907  |pmc=5093271  |pmid=27840639
|doi-access=free
 }}
</ref> Xylitol has a lower [[laxation]] threshold than some [[sugar alcohols]] but is more easily tolerated than [[mannitol]] and [[sorbitol]].<ref name=Can-Diabetes-2005-05-01>
{{cite report
 |title=Sugar Alcohols
 |date=2005-05-01
 |publisher=Canadian Diabetes Association
 |url=http://www.dm2nb.ca/pdf/patient_resources/diabetes/sugar_alcohols_cda.pdf
 |access-date=2012-03-14 |url-status=dead
 |archive-url=https://web.archive.org/web/20120425092501/http://www.dm2nb.ca/pdf/patient_resources/diabetes/sugar_alcohols_cda.pdf
 |archive-date= 2012-04-25
}}
</ref>

Increased xylitol consumption can increase oxalate, calcium, and phosphate excretion to urine (termed ''[[oxaluria]]'', ''[[calciuria]]'', and ''[[phosphaturia]]'', respectively). These are known risk factors for [[kidney stone disease]], but despite that, xylitol has not been linked to kidney disease in humans.<ref name=Janket-etal-2019>
{{cite journal
 |last1=Janket  |first1=S.        |last2=Benwait   |first2=J.
 |last3=Isaac   |first3=P.        |last4=Ackerson  |first4=L.K.
 |last5=Meurman |first5=J.H.
 |date=2019
 |title=Oral and systemic effects of xylitol consumption
 |journal=Caries Research
 |volume=53  |issue=5  |pages=491–501
 |doi=10.1159/000499194  |pmid=31060040  |s2cid=146811298
 |hdl=10138/305074  |hdl-access=free
}}
</ref> 
A 2024 study suggests that xylitol is prothrombotic (increases clotting) and is associated with cardiovascular risk when consumed at "typical dietary amounts".<ref>{{cite journal | url=https://doi.org/10.1093/eurheartj/ehae244 | doi=10.1093/eurheartj/ehae244 | title=Xylitol is prothrombotic and associated with cardiovascular risk | date=2024 | last1=Witkowski | first1=Marco | last2=Nemet | first2=Ina | last3=Li | first3=Xinmin S. | last4=Wilcox | first4=Jennifer | last5=Ferrell | first5=Marc | last6=Alamri | first6=Hassan | last7=Gupta | first7=Nilaksh | last8=Wang | first8=Zeneng | last9=Tang | first9=Wai Hong Wilson | last10=Hazen | first10=Stanley L. | journal=European Heart Journal | volume=45 | issue=27 | pages=2439–2452 | pmid=38842092 | pmc=11492277 | pmc-embargo-date=June 6, 2025 }}</ref>

===Dogs and other animals===
Xylitol is poisonous to [[dog]]s.<ref name="dogs-fda">{{cite web |title=Paws off xylitol; It's dangerous for dogs |url=https://www.fda.gov/consumers/consumer-updates/paws-xylitol-its-dangerous-dogs |publisher=US Food and Drug Administration |access-date=9 September 2021 |date=7 July 2021}}</ref> Ingesting 100&nbsp;milligrams of xylitol per kilogram of body weight (mg/kg&nbsp;bw) causes dogs to experience a dose-dependent [[insulin]] release; depending on the dose it can result in life-threatening [[hypoglycemia]]. Hypoglycemic symptoms of xylitol toxicity may arise as quickly as 30 to 60&nbsp;minutes after ingestion. Vomiting is a common first symptom, which can be followed by tiredness and [[ataxia]]. At doses above 500&nbsp;mg/kg&nbsp;bw, [[liver failure]] is likely and may result in [[Coagulopathy|coagulopathies]] like [[disseminated intravascular coagulation]].<ref name="Schmid-Hovda-2016">
{{cite journal
 |last1=Schmid  |first1=R. D.
 |last2=Hovda   |first2=L. R.
 |year=2016
 |title=Acute hepatic failure in a dog after xylitol ingestion
 |journal=Journal of Medical Toxicology
 |volume=12  |issue=2  |pages=201–205
 |doi=10.1007/s13181-015-0531-7  |pmc=4880608  |pmid=26691320
}}
</ref> 

Xylitol is safe for [[rhesus macaque]]s, [[horse]]s, and [[rat]]s.<ref name="Schmid-Hovda-2016" /> 

A 2018 study suggests that xylitol is safe for [[cat]]s in doses of up to 1000&nbsp;mg/kg; however, this study was performed on only 6 cats and should not be considered definitive.<ref name="Jerzsele-etal-2018">
{{cite journal
 |last1=Jerzsele  |first1=A.
 |display-authors=etal
 |date=2018
 |title=Effects of p.o. administered xylitol in cats
 |journal=Journal of Veterinary Pharmacology and Therapeutics
 |volume=41 |issue=3 |pages=409–414
 |pmid=29430681  |doi=10.1111/jvp.12479  |doi-access=free
}}
</ref>

==See also==
{{Portal|Food|Medicine}}
<!-- Please keep entries in alphabetical order & add a short description [[WP:SEEALSO]] -->
{{div col|colwidth=20em}}
* [[Aspartame]]
* [[Birch sap]]
* [[L-xylulose reductase|{{sc|L}}-Xylulose reductase]]
* [[Xylonic acid]]
{{div col end}}
<!-- please keep entries in alphabetical order -->

==References==
{{reflist}}

==External links==
* {{Commons category inline}}

{{Alcohols}}
{{E number infobox 950-969}}
{{Authority control}}

[[Category:Chewing gum]]
[[Category:E-number additives]]
[[Category:Excipients]]
[[Category:Sugar alcohols]]
[[Category:Sugar substitutes]]
[[Category:Veterinary toxicology]]