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{{Short description|Natural sweetener}} |
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{{short_description|Synthetic sweetener}} |
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{{use dmy dates|date=May 2021}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 402759597 |
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| Name = Xylitol |
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| verifiedrevid = 457481039 |
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| Name = Xylitol |
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| Reference = <ref></ref> |
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| pronounce = {{IPAc-en|ˈ|z|aɪ|l|ᵻ|t|ɒ|l}} |
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| ImageFile = Xylitol-2D-structure.svg |
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| Reference = <ref>] for {{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 ]. {{Retrieved|access-date=2014-11-02}}</ref> |
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| ImageSize = 200px |
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| ImageName = Xylitol |
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| ImageFile = Xylitol.svg |
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| ImageFile1 = Xylitol crystals.jpg |
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| ImageSize = 120 px |
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| ImageSize1 = 250px |
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| ImageName = Xylitol |
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| ImageCaption1 = Xylitol crystals |
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| ImageFile1 = Xylitol crystals.jpg |
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| ImageSize1 = 250px |
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| IUPACName = (2''R'',3''r'',4''S'')-Pentane-1,2,3,4,5-pentol |
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| ImageCaption1 = Xylitol crystals |
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| OtherNames = 1,2,3,4,5-Pentahydroxypentane; <br>Xylite |
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| Section1 = {{Chembox Identifiers |
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| IUPACName = ''meso''-Xylitol |
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| SystematicName = (2''R'',3''R'',4''S'')-Pentane-1,2,3,4,5-pentol |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| 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}} |
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| CASNo = 87-99-0 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII = VCQ006KQ1E |
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| CASNo = 87-99-0 |
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| ChEMBL = <!-- blanked - oldvalue: 96783 --> |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = VCQ006KQ1E |
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| ChEMBL = 96783 |
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| KEGG = C00379 |
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| PubChem = 6912 |
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| ChemSpiderID = 6646 |
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| SMILES = OC(O)(O)(O)CO |
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| InChI_Ref = {{ebicite|correct|EBI}} |
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| InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ |
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| InChIKey_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = HEBKCHPVOIAQTA-SCDXWVJYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=5|H=12|O=5 |
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| C=5 | H=12 | O=5 |
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| Density = 1.52 g/cm³ |
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| Density = 1.52 g/cm<sup>3</sup> |
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| MeltingPt = 92-96 °C |
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| MeltingPtC = 92 to 96 |
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| MeltingPt_notes = |
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| BoilingPt = 216 °C |
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| Solubility = ~ 1.5 g/mL |
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| BoilingPtC = 345.39 |
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| BoilingPt_notes = Predicted value using Adapted Stein & Brown method<ref> |
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{{cite web |
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|title=Xylitol |
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|series=Chemical Structure |
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|website=Chemspider.com |
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|url=http://www.chemspider.com/Chemical-Structure.6646.html |
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|access-date=2015-05-13 |
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}} |
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</ref> |
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| Solubility = 168 g/100 g<ref name=Ullmann/> |
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}} |
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| Section3 = {{Chembox Hazards |
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| NFPA-H = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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}} |
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| Section4 = |
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| Section5 = |
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| Section6 = |
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| Section8 = {{Chembox Related |
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| OtherFunction_label = ]s |
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| OtherFunction = ] |
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}} |
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}} |
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}} |
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'''Xylitol''' is a ] 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 ] with that structural formula. It is a colorless or white ]line solid. It is classified as a ] and a ], specifically an ]. Of the common sugar alcohols, only sorbitol is more soluble in water. |
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| Section8 = {{Chembox Related |
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| Function = ]s |
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The name derives from {{langx|grc|ξύλον}}, ''xyl'' 'wood', with the suffix ''-itol'' used to denote it being a sugar alcohol. |
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| OtherFunctn = ] |
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Xylitol is used as a ] and ]. Its ] is '''E967'''.<ref name=EAPP-Food-legtn> |
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{{cite web |
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|title=Food legislation |
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|publisher=European Association of Polyol Producers |
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|website=polyols-eu.org |
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|date=22 March 2017 |
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|url=http://polyols-eu.org/legislation/food/ |
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|access-date=2019-02-07 |
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}} |
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}} |
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</ref> Replacing ] with xylitol in food products may promote better dental health, but evidence is lacking on whether xylitol itself prevents ].<ref name=Riley-etal-2015> |
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{{cite journal |
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|last1=Riley |first1=P. |last2=Moore |first2=D. |
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|last3=Ahmed |first3=F. |last4=Sharif |first4=M.O. |
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|last5=Worthington |first5=H.V. |
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|date=26 March 2015 |
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|title=Xylitol-containing products for preventing dental caries in children and adults |
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|journal=The Cochrane Database of Systematic Reviews |
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|volume=2015 |issue=3 |pages=CD010743 |
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|doi=10.1002/14651858.CD010743.pub2 |pmid=25809586 |
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|pmc=9345289 }}</ref><ref>{{cite journal |
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|title=Can xylitol – used in products like sweets, candy, chewing gum, and toothpaste – help prevent tooth decay in children and adults? |
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|series=Lay summary |
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|journal=The Cochrane Database of Systematic Reviews |
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|year=2015 |
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|doi=10.1002/14651858.CD010743.pub2 |
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|pmid=25809586 |
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|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 |
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|last1=Riley |
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|first1=P. |
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|last2=Moore |
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|first2=D. |
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|last3=Ahmed |
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|first3=F. |
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|last4=Sharif |
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|first4=M. O. |
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|last5=Worthington |
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|first5=H. V. |
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|volume=2015 |
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|issue=3 |
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|pages=CD010743 |
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|pmc=9345289 |
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}} {{open access}} |
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</ref> In the United States, xylitol is used as a common ], 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> |
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Xylitol can be toxic to ]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> |
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==History== |
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], a German chemist, and his assistant Rudolf Stahel isolated a new compound from ] wood chips in September 1890 and named it {{lang|de|Xylit}}, the German word for xylitol. The following year, the French chemist M. G. 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 ] led to an interest in ]. Interest in xylitol and other polyols became intense, leading to their ] and manufacturing methods.<ref name=Ur-Rehman-etal-2015/><ref name=Hicks-2010> |
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{{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> |
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==Structure, production, commerce== |
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Xylitol is one of three 5-carbon sugar alcohols. The others are ] and ]. These three compounds differ in the stereochemistry of the three secondary alcohol groups. |
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{{Gallery|title=5-carbon sugar alcohols|align= |
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|Arabitol.png |
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|Arabitol |
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|Ribitol structure.png |
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|Ribitol |
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| Xylitol-2D-structure.svg |
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|Xylitol |
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}} |
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}} |
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Xylitol occurs naturally in small amounts in plums, strawberries, cauliflower, and pumpkin; humans and many other animals make trace amounts during ] of ]s.<ref name=Ur-Rehman-etal-2015/> Unlike most sugar alcohols, xylitol is ].<ref name=Wrolstad-2012> |
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'''Xylitol''' ({{IPAc-en|icon|ˈ|z|aɪ|l|ɪ|t|ɒ|l}}; {{lang-el|ξύλον}}, ''xyl'', "wood" + suffix -''itol'', used to denote sugar alcohols) is a ] sweetener used as a naturally occurring ]. It is found in the ]s of many ]s and ]s, and can be extracted from various ], ]s, and ]s, as well as fibrous material such as ]s and ] ],<ref>{{cite book |last=Gare |first=Fran |title=The Sweet Miracle of Xylitol |url=http://books.google.com/?id=5tgZG6Sb2aAC |date=February 1, 2003 |publisher=Basic Health Publications, Inc. |isbn=1-59120-038-5 }}</ref><ref>{{cite journal | doi = 10.1016/j.biortech.2005.08.015 | author = Rao R Sreenivas, Ch , Prakasham RS, Sharma PN, Rao L Venkateswar | year = 2006 | title = Xylitol production from corn fibre and sugarcane bagasse hydrolysates by Candida tropicalis | url = | journal = Bioresource Technology | volume = 97 | issue = 15| pages = 1974–1978 | pmid = 16242318 }}</ref> and birch{{Citation needed|date=July 2011}}. Xylitol is roughly as sweet as ] with only two-thirds the ]. |
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{{cite book |
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|last=Wrolstad |first=Ronald E. |
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|year=2012 |
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|title=Food Carbohydrate Chemistry |
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|page=176 |
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|publisher=John Wiley & Sons |
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|isbn=9780813826653 |
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|url=https://books.google.com/books?id=gVB8l8ukYPYC&pg=PA176 |
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|access-date=2012-10-20 |via=Google Books |
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}} |
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</ref> Most other ]s of pentane-1,2,3,4,5-pentol are chiral, but xylitol has a plane of symmetry. |
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Industrial production starts with ] from which ] is extracted; raw biomass materials include ]s, ], and agricultural waste from processing maize, wheat, or rice. The mixture is hydrolyzed with acid to give ]. The xylose is purified by ]. Purified ] is catalytically ] into xylitol using a ] 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 ]) into the ], xylitol.<ref name=Ur-Rehman-etal-2015/> |
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As with other sugar alcohols, with the exception of ], consumption in excess of one's laxation threshold (the amount of sweetener that can be consumed before abdominal discomfort sets in) can result in temporary gastrointestinal side effects, such as ], ], and ]. Adaptation, an increase of the laxation threshold, occurs with regular intake. Xylitol has a lower laxation threshold than some sugar alcohols, but is more easily tolerated than others such as ] and ].<ref>, Canadian Diabetes Foundation, 2005.</ref><ref name=Wang1981>{{cite journal |author=Wang YM, van Eys J |title=Nutritional significance of fructose and sugar alcohols |journal=Annu. Rev. Nutr. |volume=1 |issue= |pages=437–75 |year=1981 |pmid=6821187 |doi=10.1146/annurev.nu.01.070181.002253 |url=}}</ref> |
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Xylitol can also be obtained by ], but this methodology are not as economical as the acid hydrolysis/chromatography route described above. Fermentation is effected by bacteria, fungi, or yeast, especially '']''.<ref name=Ur-Rehman-etal-2015/><ref name=Jain-Mulay-2014> |
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Xylitol is an ] with the formula (CHOH)<sub>3</sub>(CH<sub>2</sub>OH)<sub>2</sub>. This ] species is one of four ]s of 1,2,3,4,5-pentapentanol. |
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{{cite journal |
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|last1=Jain |first1=H. |
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|last2=Mulay |first2=S. |
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|date=March 2014 |
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|title=A review on different modes and methods for yielding a pentose sugar: Xylitol |
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|journal=International Journal of Food Sciences and Nutrition |
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|volume=65 |issue=2 |pages=135–143 |
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|doi=10.3109/09637486.2013.845651 |
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|pmid=24160912 |s2cid=39929588 |
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}} |
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</ref> According to the US ], xylitol production by ] from discarded ] is one of the most valuable ] for commerce, forecast to be a US $1.41 billion industry by 2025.<ref name=Felipe-H-P-etal-2019> |
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{{cite journal |
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| last1=Felipe Hernández-Pérez | first1=Andrés |
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| last2=de Arruda | first2=Priscila Vaz |
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| last3=Sene | first3=Luciane |
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| last4=da Silva | first4=Silvio Silvério |
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| last5=Kumar Chandel | first5=Anuj |
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| last6=de Almeida Felipe | first6=Maria das Graças |
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| date=2019-07-16 |
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| title=Xylitol bioproduction: State-of-the-art, industrial paradigm shift, and opportunities for integrated biorefineries |
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| journal=Critical Reviews in Biotechnology |
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| volume=39 | issue=7 | pages=924–943 |
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| issn=0738-8551 | pmid=31311338 | s2cid=197421362 |
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| doi=10.1080/07388551.2019.1640658 |
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}}</ref> |
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==Uses== |
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==Production of xylitol== |
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Xylitol is used as a sugar substitute in such manufactured products as ]s, ]s, ], ], and ], but is not a common household sweetener.<ref name=Riley-etal-2015/><ref name=fda/><ref name=Drugs-2018> |
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{{cite web |
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|title=Xylitol |
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|year=2018 |
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|website=Drugs.com |
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|url=https://www.drugs.com/npp/xylitol.html |
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|access-date=12 October 2018 |
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}} |
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</ref> Xylitol has negligible effects on ] because its assimilation and metabolism are independent of ].<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". |
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Xylitol is also found as an additive to ] solution for ] and has been reported to be effective in improving symptoms of chronic ].<ref name=Weissm-etal-2011> |
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Xylitol was discovered almost simultaneously by German and French chemists in the late 19th century, and was first popularized in ] as a safe sweetener for people with ] that would not impact ] levels.<ref name="xlear.com">http://xlear.com/xylitol-faq.aspx#4</ref> Its dental significance was researched in Finland in the early 1970s, when scientists at ] showed it had significant dental benefits.<ref name="xlear.com"/> Today, using ] or ] sources, the largest manufacturer globally is the Danish company ], with several other suppliers from ].<ref>http://www.ap-foodtechnology.com/Formulation/Danisco-ramps-up-xylitol-production-in-China-new-deal</ref> Xylitol is produced by ] of ], which converts the sugar (an ]) into a primary alcohol. |
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{{cite journal |
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|last1=Weissman |first1=Joshua D. |
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|last2=Fernandez |first2=Francisca |
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|last3=Hwang |first3=Peter H. |
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|date=November 2011 |
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|title=Xylitol nasal irrigation in the management of chronic rhinosinusitis: A pilot study |
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|journal=The Laryngoscope |
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|volume=121 |issue=11 |pages=2468–2472 |
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|doi=10.1002/lary.22176 |
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|issn=1531-4995 |pmid=21994147 |
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|s2cid=36572019 |
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|url=https://pubmed.ncbi.nlm.nih.gov/21994147/ |
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}} |
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</ref> |
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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> |
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==Properties== |
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100 ]s of xylitol contain 1405 ]s. One teaspoon (5 g) of xylitol contains 9.6{{Citation needed|date=July 2011}} <!-- this is too low; common cited food energy of xylitol is 2.4 -->] (Cal), as compared to one teaspoon of ], which has 15 Cal. Xylitol has virtually no ], and is advertised as "safe for ] and individuals with ]." This tolerance is attributed to the lower impact of xylitol on a person's ], compared to that of regular ]{{Citation needed|date=September 2011}} and also has a very low ] of 13 (glucose has a GI of 100).<ref>http://www.mendosa.com/netcarbs.htm</ref> |
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==Food properties== |
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==Dietary use worldwide== |
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Xylitol is used around the world, mainly as a sweetener in ]s and ]s. Other applications include oral hygiene products, such as ], fluoride tablets and ]es. The pharmaceutical industry uses xylitol as a sweetener in its products.<ref>-2008, Archived at ]</ref> |
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===Nutrition, taste, and cooking=== |
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==Medical applications== |
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Humans absorb xylitol more slowly than sucrose, and xylitol supplies 40% fewer calories than an equal mass of sucrose.<ref name=Drugs-2018/> |
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<!-- Image with inadequate rationale removed: ] is marketed in part based on the claimed dental benefits of xylitol]] --> |
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Xylitol has about the same sweetness as ],<ref name=Drugs-2018/> but is sweeter than similar compounds like ] and ].<ref name=Ur-Rehman-etal-2015> |
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===Dental care=== |
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{{cite journal |
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Xylitol is a "tooth-friendly", nonfermentable sugar alcohol.<ref>{{cite | title = Acid production from Lycasin, maltitol, sorbitol and xylitol by oral streptococci and lactobacilli | authors = Edwardsson S, Birkhed D, Mejare B. | journal = Acta Odontol Scand 1977; 35: 257–263}}</ref><ref>{{cite | title = Comparative effects of the substance-sweeteners glucose, sorbitol, sucrose, xylitol and trichlorosucrose on lowering of pH by two oral Streptococcus mutans strains in vitro. | authors = Drucker D, Verran J. | journal = Arch Oral Biol 1980; 24: 965–970}}</ref> A systematic review study<ref>{{cite | title = Xylitol and caries prevention--is it a magic bullet? | url = http://www.nature.com/bdj/journal/v194/n8/abs/4810022a.html | authors = A Maguire & A J Rugg-Gunn | journal = British Dental Journal (2003) Apr 26;194(8):429-36}}</ref> on the efficacy of xylitol has indicated dental health benefits in ] prevention, showing superior performance to other ]s (polyalcohols). |
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|last1=Ur-Rehman |first1=S. |last2=Mushtaq |first2=Z. |
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This is because the structure of xylitol contains a tridentate ligand, (H-C-OH)3 that can rearrange with polyvalent cations like Ca (II). This interaction allows for Ca (II) to be transported through the gut wall barrier and through saliva may remineralize enamel before dental caries forms.<ref name="ReferenceA">{{cite | title = Functional Foods, ageing and degenerative disease | authors = C. Remacle and B. Reusens; 2004;1: 202}}</ref> |
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|last3=Zahoor |first3=T. |last4=Jamil |first4=A. |
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|last5=Murtaza |first5=M.A. |
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|date=2015 |
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|title=Xylitol: A review on bio-production, application, health benefits, and related safety issues |
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|journal=Critical Reviews in Food Science and Nutrition |
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|volume=55 |issue=11 |pages=1514–1528 |
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|doi=10.1080/10408398.2012.702288 |
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|pmid=24915309 |s2cid=20359589 |
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}} |
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</ref> |
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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 ] as sugars do. When used in foods, they lower the freezing point of the mixture.<ref name=leatherhead>{{cite web |
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Early studies from Finland in the 1970s found that a group chewing sucrose gum had 2.92 decayed, missing, or filled (dmf) teeth compared to 1.04 in the group chewing xylitol gums.<ref name="aapd">American Academy of Pediatric Dentistry. (2006) .</ref> Recent research<ref>Tanzer, JM (1995). Xylitol chewing gum and dental caries. ''International dental journal'' 45 (1 Suppl 1):65-76. ()</ref> confirms a ]-reducing effect and suggests the compound, having some chemical properties similar to ], attracts and then "starves" harmful micro-organisms, allowing the mouth to remineralize damaged teeth with less interruption. (However, this same effect also interferes with ] micro-organisms and others, so xylitol is inappropriate for making yeast-based ], for instance.) This is because cariogenic bacteria prefer fermentable six-carbon sugars, or disacharrides such as sucrose, as opposed to the nonfermentable xylitol, whose antimicrobial properties then "starve" the bacteria, reducing their growth and reproduction.<ref>{{cite | title = Functional Foods, ageing and degenerative disease | authors = C. Remacle and B. Reusens; 2004;1: 204}}</ref> Most of these studies suggest that at least 6 grams of xylitol per day is needed for dental efficacy; for most chewing gum or breath mints this would require 12 pieces per day (op cit). |
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|last1=Burgos |
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|first1=Karen |
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|last2=Subramaniam |
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|first2=Persis |
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|last3=Arthur |
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|first3=Jennifer |
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|date=21 November 2016 |
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|title=Reformulation guide for small to medium sized companies |
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|publisher=Leatherhead Food Research |
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|url=https://www.fdf.org.uk/corporate_pubs/Reformulation-Guide-Sugars-Aug2016.pdf |
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|via=The Food and Drink Federation |
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|access-date=28 October 2018 |
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|archive-date=27 September 2020 |
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|archive-url=https://web.archive.org/web/20200927023640/http://www.fdf.org.uk/corporate_pubs/Reformulation-Guide-Sugars-Aug2016.pdf |
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|url-status=dead |
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}}</ref> |
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===Food risks=== |
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Xylitol is specific in its inhibition of the ] group, ] that are significant contributors to tooth decay.<ref name="Milgrom">{{cite journal | author=Milgrom P, Ly KA, Roberts MC, Rothen M, Mueller G, Yamaguchi DK | title=Mutans streptococci dose response to xylitol chewing gum | journal=Journal of Dental Research | volume=85 | issue=2 | year=2006 | pages=177–181 | doi = 10.1177/154405910608500212 | pmc=2225984 | pmid=16434738 }}</ref> Xylitol inhibits mutans streptococci in the presence of other sugars, with the exception of ].<ref>{{cite journal | doi=10.1159/000073391 | author=Kakuta H, Iwami Y, Mayanagi H, Takahashi N | title=Xylitol inhibition of acid production and growth of mutans Streptococci in the presence of various dietary sugars under strictly anaerobic conditions | journal=Caries Research | volume=37 | issue=6 | year=2003 | pages=404–409 | pmid=14571117 }}</ref> |
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No serious health risk exists in most humans for normal levels of consumption. The ] has not set a limit on daily intake of xylitol. Due to the adverse ] effect that all polyols have on the digestive system in high doses, xylitol is banned from soft drinks in the ]. Similarly, due to a 1985 report by the E.U. ] which states that "ingesting 50 g a day of xylitol can cause ]", 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> |
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{{cite web |
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|title=Is xylitol good for your teeth? |
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|date=13 April 2016 |
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|series=Live well: Eat well |
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|publisher=U.K. ] |
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|url=https://www.nhs.uk/live-well/eat-well/is-xylitol-good-for-your-teeth/ |
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|access-date=28 October 2018 |
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}} |
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</ref> |
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===Metabolism=== |
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Xylitol also inhibits the growth of ''Streptococcus pneumoniae'', as well as the attachment of ''Haemophilus influenzae'' on the nasopharyngeal cells, making xylitol nose spray a very marketable product.<ref name="ReferenceA"/> Daily doses of xylitol below 3.44 grams are ineffective, and doses above 10.32 grams show no additional benefit.<ref name="Milgrom" /> |
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Xylitol has 2.4 kilocalories of ] per gram of xylitol (10 kilojoules per gram) according to ] and ] food-labeling regulations.<ref name=UN-FAO-y5022e04> |
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{{cite report |
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|chapter=Chapter 3: Energy Conversion Factors |
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|title=Calculation of the Energy Content of Foods |
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|department=Food and Agriculture Organization |
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|publisher=The United Nations |
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|chapter-url=http://www.fao.org/docrep/006/Y5022E/y5022e04.htm |
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|access-date=30 March 2017 |
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}} |
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</ref><ref name=EAPP-Food-legtn/> The real value can vary, depending on metabolic factors.<ref name="Livesey-2003" /> |
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Primarily, the liver metabolizes absorbed xylitol. The main metabolic route in humans occurs in ], via nonspecific ]-dependent dehydrogenase (polyol dehydrogenase), which transforms xylitol to ]. Specific ] phosphorylates it to ]. This then goes to ] for further processing.<ref name=Livesey-2003/> |
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Saliva containing xylitol is more ]ne than saliva which contains other sugar products. After taking xylitol products, the concentration of basic amino acids in saliva may rise. When saliva is alkaline (i.e., its ] is above 7), calcium and phosphate salts in saliva start to precipitate into those parts of enamel where they are lacking.<ref>http://xlear.com/xylitol-faq.aspx#9</ref> |
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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 ] into short-chain organic acids and gases, which may produce ]. The remnant unabsorbed xylitol that escapes fermentation is excreted unchanged, mostly in feces; less than 2 g of xylitol out of every 100 g ingested is excreted via urine.<ref name=Livesey-2003> |
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Xylitol-based products are allowed by the ] to make the medical claim that they do not promote dental cavities.<ref></ref> |
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{{cite journal |
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|last=Livesey |first=G. |
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|year=2003 |
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|title=Health potential of polyols as sugar replacers, with emphasis on low glycaemic properties |
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|journal=Nutrition Research Reviews |
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|volume=16 |issue=2 |pages=163–191 |
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|pmid=19087388 |issn=1475-2700 |
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|doi=10.1079/NRR200371 |doi-access=free |
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}} |
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</ref> |
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Xylitol ingestion also increases ] secretion, which may be related to xylitol's ability to cause diarrhea.<ref name=Wölnerhn-etal-2019> |
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A recent study demonstrated, as a water additive for cats, xylitol was effective in reducing plaque and ] accumulation.<ref>Clarke, D.E. (2006) Drinking Water Additive Decreases Plaque and Calculus Accumulation in Cats. ''J Vet Dent''(23)2:79-82</ref> However, there is evidence xylitol may be ]. |
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{{Cite journal |
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|author1=Wölnerhanssen, B. K. |author2=Meyer-Gerspach, A. C. |
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|author3=Beglinger, C. |author4=Islam, M. S. |
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|date=June 2019 |
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|title=Metabolic effects of the natural sweeteners xylitol and erythritol: A comprehensive review |
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|journal=Critical Reviews in Food Science and Nutrition |
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|volume=60 |issue=12 |pages=1986–1998 |
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|pmid=31204494 |doi=10.1080/10408398.2019.1623757 |
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|s2cid=189944738 |
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}} |
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</ref> The less-digestible but fermentable nature of xylitol also contributes to constipation relieving effects.<ref name=Salli-etal-2019/> |
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===Diabetes=== |
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==Health effects== |
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Possessing approximately 40% less food energy,<ref>www.diabetes.org.nz/food/artificialsweeteners.html</ref> xylitol is a low-] alternative to table sugar. Absorbed more slowly than sugar, it does not contribute to high ] levels or the resulting ] caused by insufficient ] response. This characteristic has also proven beneficial for people suffering from ], a common disorder that includes insulin resistance, hypertension, hypercholesterolemia, and an increased risk for blood clots.<ref>{{cite | title = An update on alternative sweeteners | authors = Marti N, Funes LL, Saura D, Micol V | Journal = International Sugar Journal; 2008; 110: 425}}</ref> |
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===Osteoporosis=== |
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===Dental care=== |
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A 2015 ] of ten studies between 1991 and 2014 suggested a positive effect in reducing ] of xylitol-containing ] 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=] | 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 ] in the mouth, thereby reducing dental caries and ], although there is concern that swallowed xylitol may cause ].<ref name="pmid32638045">{{cite journal | vauthors = Benahmed AG, Gasmi A, Bjørklund G | title=Health benefits of xylitol | journal=] | 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=] | volume=53 | issue=5 | pages=491–501 | year=2019 | doi= 10.1159/000499194 | pmid=31060040}}</ref> A 2022 review suggested that xylitol-containing ] 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> |
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Xylitol also has potential as a treatment for ]. A group of Finnish researchers has found dietary xylitol prevents weakening of ]s in laboratory rats, and actually improves bone density.<ref>Mattila PT, Svanberg MJ, Jämsä T, Knuuttila ML (2002). Improved bone biomechanical properties in xylitol-fed aged rats.<cite>Metabolism</cite> 51(1):92-6. ()</ref><ref>Mattila, PT (1999). Dietary xylitol in the prevention of experimental osteoporosis: Beneficial effects on bone resorption, structure and biomechanics. Dissertation, Institute of Dentistry, University of Oulu. ()</ref> |
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===Earache=== |
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===Ear and upper respiratory infections=== |
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In 2011 ] "concluded that there was not enough evidence to support" the claim that xylitol-sweetened gum could prevent middle-ear infections, also known as ] (AOM).<ref name=UK-NHS-2016-04-13/><ref> |
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Studies have shown xylitol chewing gum can help prevent ear infections<ref>{{cite journal | doi = 10.1542/peds.102.4.879 | author = Uhari M ''et al.'' | year = 1998 | title = A novel use of xylitol sugar in preventing acute otitis media | url = | journal = Pediatrics | volume = 102 | issue = 4| pages = 879–974 }}</ref> (acute ]); the act of chewing and swallowing assists with the disposal of ] and clearing the ], while the presence of xylitol prevents the growth of bacteria in the ] (auditory or pharyngotympanic tubes) which connect the nose and ear.<ref></ref> When bacteria enter the body, they adhere to the tissues using a variety of sugar complexes. The open nature of xylitol and its ability to form many different sugar-like structures appears to interfere with the ability of many bacteria to adhere.<ref></ref> In a double-blind, randomized, controlled trial, saline solutions of xylitol significantly reduced the number of nasal coagulase-negative ''Staphylococcus'' bacteria. The researchers attributed the benefits to the increased effectiveness of ] (naturally present in the body) antimicrobial factors.<ref>{{cite journal |author=Zabner J, Seiler MP, Launspach JL, ''et al.'' |title=The osmolyte xylitol reduces the salt concentration of airway surface liquid and may enhance bacterial killing |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=97 |issue=21 |pages=11614–9 |year=2000 |month=October |pmid=11027360 |pmc=17249 |doi=10.1073/pnas.97.21.11614 |url=}}</ref> In a small clinical trial nasally administered xylitol reduced ear complaints in children previously having chronic complaints, on the order of almost one a month, by more than 92%. The author also reported beneficial effects on asthma with nasal administration. <ref>{{cite journal|author=Jones AH.|title=Intranasal xylitol, recurrent otitis media and asthma: Three case studies.|journal=Clinical Practice of Alternative Medicine.|volume=2|issue=2|pages=112-17.|year=2001. See more of the author's expansion on this topic in his book No More Allergies, Asthma, or Sinus Infections. Freedom Press. 2010}}</ref> |
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{{cite journal |
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|author=EFSA panel |
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|date=June 2011 |
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|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) |
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|journal=EFSA Journal |
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|volume=9 |issue=6 |page=2266 |
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|doi=10.2903/j.efsa.2011.2266 |doi-access=free |
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}} |
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</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> |
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{{cite journal |
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|last1=Azarpazhooh |first1=A. |
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|last2=Lawrence |first2=H.P. |
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|last3=Shah |first3=P.S. |
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|title=Xylitol for preventing acute otitis media in children up to 12 years of age |
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|journal=The Cochrane Database of Systematic Reviews |
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|date=3 August 2016 |
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|volume=2016 |
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|issue=8 |page=CD007095 |
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|doi=10.1002/14651858.CD007095.pub3 |doi-access=free |
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|pmid=27486835 |
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|pmc=8485974 |
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}} |
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</ref> It may be an alternative to conventional therapies (such as ]s) to lower risk of earache in healthy children – reducing risk of occurrence by 25%<ref name=Marom-etal-2016> |
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{{cite journal |
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|last1=Marom |first1=Tal |last2=Marchisio |first2=Paola |
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|last3=Tamir |first3=Sharon Ovnat |last4=Torretta |first4=Sara |
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|last5=Gavriel |first5=Haim |last6=Esposito |first6=Susanna |
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|date=2016-02-12 |
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|title=Complementary and alternative medicine treatment options for otitis media |
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|journal=Medicine |
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|volume=95 |issue=6 |pages=e2695 |
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|doi=10.1097/MD.0000000000002695 |
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|issn=0025-7974 |pmc=4753897 |pmid=26871802 |
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}} |
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</ref> – although there is no definitive proof that it could be used as a therapy for earache.<ref name=Azarpazh-etal-2016/> |
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===Infection=== |
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===Diabetes=== |
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In 2011, EFSA approved a marketing claim that foods or beverages containing xylitol or similar sugar replacers cause lower blood glucose and lower ] responses compared to sugar-containing foods or drinks.<ref name=UK-Diabetes-2018-10-28> |
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In rats, xylitol has been found to increase the activity of ], the white blood cells involved in fighting many bacteria. This effect seems to be quite broad, acting even in cases such as general ].<ref name='Renko'>{{cite journal|title=Xylitol-supplemented nutrition enhances bacterial killing and prolongs survival of rats in experimental pneumococcal sepsis|journal=BMC Microbiology|date=2008 March 11;8:45.|first=Marjo |last=Renko|coauthors=Valkonen P, Tapiainen T, Kontiokari T, Mattila P, Knuuttila M, Svanberg M, Leinonen M, Karttunen R, Uhari M|volume=8|issue=|pages=45|pmid=18334022 |format=|accessdate=2008-08-23|doi=10.1186/1471-2180-8-45|pmc=2294124 }}</ref> |
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{{cite web |
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|title=Xylitol |
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|url=https://www.diabetes.co.uk/sweeteners/xylitol.html |
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|publisher=Diabetes.co.uk |
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|access-date=28 October 2018 |
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}} |
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</ref><ref name=EFSA-2011> |
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{{cite journal |
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|author=EFSA panel |
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|date=April 2011 |
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|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 |
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|journal=EFSA Journal |
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|volume=9 |issue=4 |page=2076 |
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|doi=10.2903/j.efsa.2011.2076 |doi-access=free |
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}} |
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</ref> Xylitol products are used as ] substitutes for weight control,<ref name=UK-Diabetes-2018-10-28/><ref name=Salli-etal-2019> |
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{{Cite journal |
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|last1=Salli |first1=Krista |last2=Lehtinen |first2=Markus J. |
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|last3=Tiihonen |first3=Kirsti |last4=Ouwehand |first4=Arthur C. |
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|date=2019-08-06 |
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|title=Xylitol's health benefits beyond dental health: A comprehensive review |
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|journal=Nutrients |
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|volume=11 |issue=8 |pages=1813 |
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|doi=10.3390/nu11081813 |
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|issn=2072-6643 |pmc=6723878 |pmid=31390800 |
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|doi-access=free }} |
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</ref> as xylitol has 40% fewer calories than sucrose (2.4 kcal/g compared to 4.0 kcal/g for sucrose).<ref name=UK-Diabetes-2018-10-28/><ref name=Tiefenbkr-2017> |
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{{cite book |
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| last=Tiefenbacher | first=Karl F. |
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| year=2017 |
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| title=Wafer and Waffle |
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| chapter=Technology of Main Ingredients – Sweeteners and Lipids |
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| publisher=Elsevier |
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| isbn=978-0-12-809438-9 | doi=10.1016/b978-0-12-809438-9.00003-x |
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| pages=123–225 |
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}} |
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</ref> The ] (GI) of xylitol is only 7% of the GI for ].<ref name=Foster-Powell-etal-2002> |
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{{cite journal |
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|last1=Foster-Powell |first1=K. |
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|last2=Holt |first2=S.H. |
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|last3=Brand-Miller |first3=J.C. |
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|date=July 2002 |
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|title=International table of glycemic index and glycemic load values: 2002 |
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|journal=The American Journal of Clinical Nutrition |
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|volume=76 |issue=1 |pages=5–56 |
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|doi=10.1093/ajcn/76.1.5 |pmid=12081815 |doi-access=free |
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}} |
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</ref> |
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===''Candida'' yeast=== |
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==Adverse effects== |
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A recent report suggests consumption of xylitol may help control oral infections of '']'' yeast; in contrast, ], ], and ] may increase proliferation.<ref>Abu-Elteen, Khaled H. The influence of dietary carbohydrates on ''in vitro'' adherence of four Candida species to human buccal epithelial cells. ''Microbial Ecology in Health and Disease'' (2005), 17(3), 156-162</ref> |
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== Safety == |
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===Humans=== |
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When ingested at high doses, xylitol and other polyols may cause ] discomfort, including ], ], and ] (see ] above); some people experience the adverse effects at lower doses.<ref name=UK-NHS-2016-04-13/><ref name=Mäkinen-2016> |
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{{cite journal |
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|last=Mäkinen |first=Kauko |
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|date=2016-10-20 |
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|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 |
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|journal=International Journal of Dentistry |
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|volume=2016 |page=5967907 |
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|doi=10.1155/2016/5967907 |pmc=5093271 |pmid=27840639 |
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|doi-access=free |
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}} |
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</ref> Xylitol has a lower ] threshold than some ] but is more easily tolerated than ] and ].<ref name=Can-Diabetes-2005-05-01> |
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{{cite report |
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|title=Sugar Alcohols |
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|date=2005-05-01 |
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|publisher=Canadian Diabetes Association |
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|url=http://www.dm2nb.ca/pdf/patient_resources/diabetes/sugar_alcohols_cda.pdf |
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|access-date=2012-03-14 |url-status=dead |
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|archive-url=https://web.archive.org/web/20120425092501/http://www.dm2nb.ca/pdf/patient_resources/diabetes/sugar_alcohols_cda.pdf |
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|archive-date= 2012-04-25 |
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}} |
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</ref> |
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Increased xylitol consumption can increase oxalate, calcium, and phosphate excretion to urine (termed '']'', '']'', and '']'', respectively). These are known risk factors for ], but despite that, xylitol has not been linked to kidney disease in humans.<ref name=Janket-etal-2019> |
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Xylitol has no known ]ity in humans. In one study, the participants consumed a diet containing a monthly average of 1.5 kg of xylitol with a maximum daily intake of 430 g with no apparent ill effects.<ref name=Mäkinen_1976>{{cite journal |author=Mäkinen KK |title=Long-term tolerance of healthy human subjects to high amounts of xylitol and fructose: general and biochemical findings |journal=Int Z Vitam Ernahrungsforsch Beih |volume=15 |issue= |pages=92–104 |year=1976 |pmid=783060 |doi= |url=http://www.ncbi.nlm.nih.gov/pubmed/783060 }}</ref> Like most sugar alcohols, it has a ] effect because sugar alcohols are not fully broken down during digestion; albeit one-tenth the strength of ].{{Clarify|date=June 2011}} The effect depends upon the individual. In one study of 13 children, four experienced diarrhea when consuming over 65 grams per day.<ref name=Wang1981/> Studies have reported adaptation occurs after several weeks of consumption.<ref name="Wang1981"/> |
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{{cite journal |
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|last1=Janket |first1=S. |last2=Benwait |first2=J. |
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|last3=Isaac |first3=P. |last4=Ackerson |first4=L.K. |
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|last5=Meurman |first5=J.H. |
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|date=2019 |
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|title=Oral and systemic effects of xylitol consumption |
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|journal=Caries Research |
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|volume=53 |issue=5 |pages=491–501 |
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|doi=10.1159/000499194 |pmid=31060040 |s2cid=146811298 |
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|hdl=10138/305074 |hdl-access=free |
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}} |
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</ref> |
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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> |
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=== Dogs === |
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===Dogs and other animals=== |
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Xylitol is poisonous to ]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 milligrams of xylitol per kilogram of body weight (mg/kg bw) causes dogs to experience a dose-dependent ] release; depending on the dose it can result in life-threatening ]. Hypoglycemic symptoms of xylitol toxicity may arise as quickly as 30 to 60 minutes after ingestion. Vomiting is a common first symptom, which can be followed by tiredness and ]. At doses above 500 mg/kg bw, ] is likely and may result in ] like ].<ref name="Schmid-Hovda-2016"> |
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{{cite journal |
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|last1=Schmid |first1=R. D. |
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|last2=Hovda |first2=L. R. |
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|year=2016 |
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|title=Acute hepatic failure in a dog after xylitol ingestion |
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|journal=Journal of Medical Toxicology |
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|volume=12 |issue=2 |pages=201–205 |
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|doi=10.1007/s13181-015-0531-7 |pmc=4880608 |pmid=26691320 |
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}} |
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</ref> |
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Xylitol is safe for ]s, ]s, and ]s.<ref name="Schmid-Hovda-2016" /> |
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]s that have ingested foods containing high levels of xylitol (greater than 100 milligrams of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar (]), which can be life-threatening.<ref name=Dunayer_2006_acute>Dunayer, E.K., Gwaltney-Brant, S.M. (2006) Acute hepatic failure and coagulopathy associated with xylitol ingestion in dogs, ''Journal of the American Veterinary Medical Association'' (229)7:1113-1117</ref> Low blood sugar can result in a loss of coordination, depression, collapse and seizures in as soon as 30 minutes.<ref name=ASPCA></ref><ref name=Dunayer_2004>{{cite journal | author = Dunayer E.K | year = 2004 | title = Hypoglycemia following canine ingestion of xylitol-containing gum | url = | journal = Veterinary and Human Toxicology | volume = 46 | issue = 2| pages = 87–88 | pmid = 15080212 }}</ref> Intake of very high doses of xylitol (greater than 500 – 1000 mg/kg bwt) has also been implicated in liver failure in dogs, which can be fatal.<ref name=Dunayer_2006_new>{{cite journal | author = Dunayer E.K | year = 2006 | title = New findings on the effects of xylitol ingestion in dogs | url = | journal = Veterinary Medicine | volume = 101 | issue = 12| pages = 791–797 }}</ref> These are points of controversy, however, as earlier World Health Organization studies using much higher doses on dogs for long periods showed no ill effect.<ref> Xlear, Inc. Issues Response to JAVMA Report on Dogs and Xylitol</ref> A study published in the ''Journal of Veterinary Pharmacology and Therapeutics'' involved two groups of eight ] dogs fed either 1 or 4 g/kg of xylitol. In addition to developing hypoglycemia, all of the dogs developed elevated levels of liver enzymes associated with liver damage. The dogs also developed reduced serum phosphorus and potassium, and increased serum calcium.<ref name=Xia_2009>{{cite journal |author=Xia, Z, He, Y, Yu, J |title=Experimental acute toxicity of xylitol in dogs |journal=Journal of Veterinary Pharmacology and Therapeutics |volume=5 |issue=32 |pages=465–469 |year=2009 |pmid=19754913 |doi= 10.1111/j.1365-2885.2009.01065.x|url=http://www.ncbi.nlm.nih.gov/pubmed/19754913 }}</ref> |
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A 2018 study suggests that xylitol is safe for ]s in doses of up to 1000 mg/kg; however, this study was performed on only 6 cats and should not be considered definitive.<ref name="Jerzsele-etal-2018"> |
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{{cite journal |
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|last1=Jerzsele |first1=A. |
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|display-authors=etal |
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|date=2018 |
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|title=Effects of p.o. administered xylitol in cats |
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|journal=Journal of Veterinary Pharmacology and Therapeutics |
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|volume=41 |issue=3 |pages=409–414 |
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|pmid=29430681 |doi=10.1111/jvp.12479 |doi-access=free |
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}} |
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</ref> |
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==See also== |
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==See also== |
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{{Portal|Food|Medicine}} |
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* Other sugar alcohols: ], ], ], ], ], ] |
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<!-- Please keep entries in alphabetical order & add a short description ] --> |
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* Herbal sweetener: ] |
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* Artificial sweeteners: ], ] |
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==References== |
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{{reflist}} |
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==External links== |
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==Notes and references== |
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* {{Commons category inline}} |
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{{reflist|2}} |
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{{Alcohols}} |
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{{E number infobox 950-969}} |
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{{E number infobox 950-969}} |
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