Xylitol 220432 225835981 2008-07-15T16:56:34Z Edgar181 491706 Reverted edits by [[Special:Contributions/149.152.60.107|149.152.60.107]] ([[User talk:149.152.60.107|talk]]) to last version by Qui1che {{Chembox new | Name = Xylitol | Reference =<ref>[http://www.sciencelab.com/msds.php?msdsId=9925453 MSDS for xylitol]</ref> | ImageFile = Xylitol.png | ImageSize = 200px | ImageName = Xylitol | IUPACName = (''2R,3R,4S'')-Pentane-1,2,3,4,5-pentanol | OtherNames = 1,2,3,4,5-Pentahydroxypentane | Section1 = {{Chembox Identifiers | CASNo = 87-99-0 }} | Section2 = {{Chembox Properties | Formula = [[carbon|C]]<sub>5</sub>[[hydrogen|H]]<sub>12</sub>[[oxygen|O]]<sub>5</sub> | MolarMass = 152.15 g/mol | Density = 1.52 g/cm³ | MeltingPt = 92-96 °C | BoilingPt = 216 °C }} | Section8 = {{Chembox Related | Function = [[alkane]]s | OtherFunctn = [[Pentane]] }} }} '''Xylitol''' is a five-carbon [[sugar alcohol]] that is used as a [[sugar substitute]]. Xylitol is a naturally occurring sweetener found in the fibers of many fruits and vegetables, including various berries, corn husks, oats, and mushrooms.<ref>{{cite book |last=Gare |first=Fran |title=The Sweet Miracle of Xylitol |url=http://books.google.com/books?id=5tgZG6Sb2aAC |date=February 1, 2003 |publisher=Basic Health Publications, Inc. |id=ISBN 1-59120-038-5 }}</ref> It can be extracted from corn fibre,<ref>R Sreenivas Rao, Ch. Pavanajyothi, RS Prakasham, PN Sharma, L Venkateswar Rao (2006) Xylitol production from corn fiber and sugarcane bagasse hydrolysates by Candida tropicalis ''Bioresource Technology'' 97:1974-1978.</ref> [[birch]], [[raspberry|raspberries]], [[plum]]s, and [[maize|corn]]. Xylitol is roughly as sweet as [[sucrose]] but with only two-thirds the [[food energy]]. ==Extraction of xylitol== [[Image:Xylitol crystals.jpg|thumb|right|Xylitol crystals]] Xylitol was first derived from [[Birch]] trees in [[Finland]] in the 19th century and was first popularized in [[Europe]] as a safe sweetener for [[diabetics]] that would not impact [[insulin]] levels. Today, using [[maize]] sources, most world supplies reportedly come from [[China]].{{Fact|date=February 2007}} ==Properties== One teaspoon (5 mL) of xylitol contains 9.6 [[calories]], as compared to one teaspoon of [[sugar]], which has 15 calories. Xylitol contains zero net effective carbohydrates,{{Fact|date=August 2007}} whereas sugar contains 4 grams per 5 mL. Xylitol has virtually no [[aftertaste]], and is advertised as "safe for [[diabetics]] and individuals with [[hyperglycemia]]". This is because sugar-alcohols have less impact on a person's [[blood sugar]] than regular [[sugars]].<ref>[http://fcs.tamu.edu/health/health_education_rural_outreach/Health_Hints/2006/april06/sugar-substitutes.php Sugar Substitutes: Are They Safe? - HealtHints Newsletter<!-- Bot generated title -->]</ref> ==Dietary use worldwide== Xylitol is widely used in [[Finland]], its "home country". Many Finnish [[confectionery|confectioneries]] employ xylitol, or have a xylitol version available. Virtually all [[chewing gum]] sold in Finland, and in the rest of Europe,{{Fact|date=March 2008}} is sweetened with xylitol. The formerly Spanish company [[Chupa Chups]], now Italian, makes a xylitol-based breath mint, [[Smint]], that it markets worldwide. In China, Japan, and South Korea, xylitol is found in wide assortment of chewing gums. There is brand of gum named "Xylitol" in all three countries; Japan also has a brand called "Xylish". In addition, when [[Extra (gum)|Extra]] introduced xylitol-containing products to [[Hong Kong]] and [[Guangdong]], the word "xylitol" is [[Transcription (linguistics)|transcribed]] into [[Cantonese (linguistics)|Cantonese]] as "晒駱駝" ([[Jyutping]]: saai<sup>3</sup> lok<sup>6</sup> to<sup>4</sup>), which literally means "suntan camel", and the camel is used as a figurative icon in its advertisements.<ref>[http://www.cnade.com/productdetail.php?pid=74177 Xylitol advertisement in Guangdong]</ref> In 2004, popular North American [[Trident gum]] was reformulated to include xylitol, but not as the main sweetener (which are still [[sorbitol]] and [[maltitol]]). It is also found in Smokey Mountain Snuff,<ref>[http://www.smokeysnuff.com/faq.cfm?cfid=540&cftoken=92393789 Smokey Mountain Snuff FAQ]</ref> and IceBreakers brand Ice Cubes Gum from [[The Hershey Company|Hershey]]. A discontinued sugarless gum, Carefree [[Koolerz]], was sweetened exclusively with xylitol. Xylichew, made in Finland (available in US), is also sweetened exclusively with xylitol. In 2006, William Wrigley Jr. Company reformulated their [[Orbit (gum)|Orbit]] gum to contain xylitol and released it under the name "Orbit Complete". Critics have noted that the amount of Xylitol in some chewing gums is small, and other sugar alcohols may be used in larger amounts. ==Medical applications== ===Dental care=== Xylitol is a "[[toothfriendly]]" sugar. In addition to not encouraging tooth decay (by replacing dietary sugars), xylitol may actively aid in repairing minor cavities caused by [[dental caries]].{{Fact|date=December 2007}} 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) [http://www.aapd.org/media/Policies_Guidelines/P_Xylitol.pdf Policy on the Use of Xylitol in Caries Prevention].</ref> In another study, researchers had mothers chew xylitol gum 3 months after delivery until their children were 2 years old. The researchers found that the xylitol group had "a 70% reduction in cavities (dmf)."<ref name="aapd"/> Recent research<ref>Tanzer, JM (1995). Xylitol chewing gum and dental caries. ''International dental journal'' 45 (1 Suppl 1):65-76. ([http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=7607747&query_hl=1&itool=pubmed_DocSum online abstract])</ref> confirms a [[Dental plaque|plaque]]-reducing effect and suggests that the compound, having some chemical properties similar to [[sucrose]], attracts and then "starves" harmful micro-organisms, allowing the mouth to remineralize damaged teeth with less interruption. (However, this same effect also interferes with [[yeast]] micro-organisms and others, so xylitol is inappropriate for making yeast-based [[bread]], for instance.) Xylitol based products are allowed by the [[Food and Drug Administration|U.S. Food and Drug Administration]] to make the medical claim that they do not promote dental cavities.<ref>[http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=101.80 U.S. FDA 21 CFR §101.80]</ref> A recent study demonstrated that a water additive for animals containing xylitol was effective in reducing plaque and [[Calculus (dental)|calculus]] accumulation in cats.<ref> Clarke, D.E. (2006) Drinking Water Additive Decreases Plaque and Calculus Accumulation in Cats. ''J Vet Dent''(23)2:79-82</ref> ===Diabetes=== Possessing approximately 40% less food energy,<ref>www.diabetes.org.nz/food/artificialsweeteners.html</ref> xylitol is a low-[[calorie]] alternative to table sugar. Absorbed more slowly than sugar, it doesn't contribute to high [[blood sugar]] levels or the resulting [[hyperglycemia]] caused by insufficient [[insulin]] response. ===Osteoporosis=== Xylitol also appears to have potential as a treatment for [[osteoporosis]]. A group of Finnish researchers has found that dietary xylitol prevents weakening of [[bone]]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. ([http://www.arclab.org/medlineupdates/abstract_11782878.html online abstract])</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. ([http://herkules.oulu.fi/isbn951425158X/ online])</ref> ===Ear and upper respiratory infections=== Studies have shown that xylitol chewing gum can help prevent ear infections<ref>Uhari M, et al. (1998). A novel use of xylitol sugar in preventing acute otitis media. Pediatrics, 102(4): 879&ndash;974.</ref> (acute [[otitis media]]); the act of chewing and swallowing assists with the disposal of [[earwax]] and clearing the [[middle ear]], whilst the presence of xylitol prevents the growth of bacteria in the [[eustachian tubes]] (auditory tubes or pharyngotympanic tubes) which connect the nose and ear.<ref>[http://www.drgreene.com/21_837.html Drgreene.com commercial site]</ref> This action that xylitol has on bacteria in the back of the nose is best explained on the site dealing with the nasal application of xylitol.<ref>[http://www.nasal-xylitol.com Nasal-xylitol.com commercial site]</ref> When bacteria enter the body they hold on to the tissues by hanging on to 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>[http://www.besttreatments.co.uk/btuk/conditions/12828.html Besttreaments.co.uk]</ref> Xylitol can be applied nasally through a saline solution containing xylitol. ===Candida yeast=== A recent report suggests that consumption of xylitol may help control oral infections of ''[[candida (genus)|Candida]]'' yeast; in contrast, [[galactose]], [[glucose]], and [[sucrose]] 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> ===Benefits for pregnant or nursing women=== Xylitol is not only safe for pregnant and nursing women, but studies show that regular use significantly reduces the probability of transmitting the ''[[Streptococcus mutans]]'' bacteria, which is responsible for tooth decay, from mother to child during the first two years of life by as much as 80%.<ref>[http://iadr.confex.com/iadr/2006Brisb/techprogram/abstract_79780.htm Maternal Xylitol Consumption to Prevent Mother-Child Transmission of Mutans Streptococci<!-- Bot generated title -->]</ref> ==Concerns== Xylitol, like most sugar alcohols, can have a [[laxative]] effect, because sugar alcohols are not fully broken down during digestion. It has no known [[toxic]]ity, and people have consumed as much as 400 [[gram]]s daily for long periods with no apparent ill effects.<ref>[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=783060&dopt=Abstract] Mäkinen,longterm tolerance</ref> [[Dogs]] ingesting foods containing high doses of xylitol (greater than 100 milligram of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar ([[hypoglycaemia]]) which can be life-threatening.<ref>Dunayer, E.K., Gwaltney-Brant, S.M. (2006) Acute hepatic failure and coagulopathy associated with xylitol ingestion in eight dogs, ''Journal of the American Veterinary Medical Association'' (229)7:1113-1117</ref> Low blood sugar can manifest as loss of coordination, depression, collapse and seizures as soon as 30 minutes after ingestion.<ref>[http://www.aspca.org/site/PageServer?pagename=pro_apcc_dyk#21 ASPCA article]</ref><ref>Dunayer, E.K (2004) Hypoglycemia following canine ingestion of xylitol-containing gum, ''Veterinary and Human Toxicology'' 46(2):87-88</ref> Intake of very high doses of xylitol (greater than 500 - 1000 mg/kg bwt) has also been implicated in liver failure in 8 dogs, which can be fatal.<ref> Dunayer, E.K (2006) New findings on the effects of xylitol ingestion in dogs ''Veterinary Medicine'' 101(12):791-797</ref> ==Other applications of xylitol== {{Cleanup-section|date=November 2007}} [[ASICS]] Corp., a Japanese company, markets a line of women's t-shirts with xylitol infused into the fabric. Xylitol, like several other sugar alcohols, exhibits a cooling effect in the mouth. The t-shirts are intended to utilize this same property to keep a person cooler in warm weather.<ref>[http://danisco.mondosearch.com/cgi-bin/MsmGo.exe?grab_id=0&EXTRA_ARG=&host_id=42&page_id=3198&query=xylitol%20tshirts&hiword=tshirts%20xylitol%20XYLITOLS%20 information from the Danisco website]</ref> This application has also been used by [[Yonex]] to make shirts.<ref>[http://www.tennisnuts.com/ishop/677/shopscr5726.html Yonex Mens Wimbledon Very Cool T-Shirt<!-- Bot generated title -->]</ref> ==See also== * Other sugar alcohols: [[mannitol]], [[sorbitol]], [[erythritol]], [[maltitol]], [[lactitol]] * Herbal sweetener: [[stevia]] * Artificial sweeteners: [[aspartame]], [[sucralose]] * [[L-xylulose reductase]] ==References== {{reflist|2}} {{E number infobox 950-969}} [[Category:Sweeteners]] [[Category:Sugar alcohols]] [[da:Xylitol]] [[de:Xylitol]] [[es:Xilitol]] [[fr:Xylitol]] [[gl:Xilitol]] [[ko:자일리톨]] [[it:Xilitolo]] [[nl:Xylitol]] [[ja:キシリトール]] [[no:Xylitol]] [[nn:Xylitol]] [[pl:Ksylitol]] [[pt:Xilitol]] [[ru:Ксилит]] [[fi:Ksylitoli]] [[sv:Xylitol]] [[th:ไซลิทอล]] [[zh:木糖醇]]