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Xylitol /ˈzaɪlɪtɒl/ is a sugar alcohol used as a sweetener. The name derives from Greek: ξύλον, xyl[on], "wood" + suffix -itol, used to denote sugar alcohols. Xylitol is categorized as a polyalcohol or sugar alcohol (alditol). It has the formula CH₂OH(CHOH)₃CH₂OH and is an achiral^[3] isomer of pentane-1,2,3,4,5-pentol. Unlike other natural or synthetic sweeteners, xylitol is actively beneficial for dental health by reducing caries (cavities) to a third in regular use and helpful to remineralization.^[4] Multiple studies utilizing electron microscopy have indicated that xylitol is effective in inducing remineralization of deeper layers of demineralized enamel.^[5]^[6] Fair evidence was found that xylitol (as chewing gum, lozenges, nasal spray, etc.) reduced the incidence of acute middle ear infection in healthy children.^[7]

Xylitol is naturally found in low concentrations in the fibers of many fruits and vegetables, and can be extracted from various berries, oats, and mushrooms, as well as fibrous material such as corn husks and sugar cane bagasse.^[8]^[9]^[10] However, industrial production starts from xylan (a hemicellulose) extracted from hardwoods^[11] or corncobs, which is hydrolyzed into xylose and catalytically hydrogenated into xylitol. A study in rats found that xylitol had reduced or eliminated side effects compared to other artificial sweeteners, and lower caloric value and cariogenicity than sucrose.^[12]

Production

Xylitol is produced by hydrogenation of xylose, which converts the sugar (an aldehyde) into a primary alcohol. Another method of producing xylitol is through microbial processes, including fermentative and biocatalytic processes in bacteria, fungi, and yeast cells, that take advantage of the xylose-intermediate fermentations to produce high yield of xylitol.^[13] Common yeast cells used in effectly fermenting and producing xylitol are Candida tropicalis and Candida guilliermondii.^[14]

Properties

One gram of xylitol contains 2.4 kilocalories (kcal),^[15] as compared to one gram of sugar, which has 3.87 kcal.^[16] Xylitol has virtually no aftertaste, and is advertised as "safe for diabetics and individuals with hyperglycemia." This tolerance is attributed to the lower effect of xylitol on a person's blood sugar, compared to that of regular sugars as it has an extremely low glycemic index of 7 (glucose has a GI of 100).^[17]

Health benefits

Dental care

Xylitol is a "tooth-friendly", nonfermentable sugar alcohol.^[18]^[19] It appears to have more dental health benefits than other polyalcohols.^[20] The structure of xylitol contains a tridentate ligand, (H-C-OH)₃ that can rearrange with polyvalent cations like Ca²⁺. This interaction allows Ca²⁺ to be transported through the gut wall barrier and through saliva which may allow enamel to remineralize before dental cavities form.^[21]

Early studies from Finland in the 1970s found, compared with chewing sucrose-sweetened gum, xylitol resulted in nearly two fewer cavities or missing teeth.^[22] Cavity-causing bacteria prefer six-carbon sugars or disaccharides, while xylitol is non-fermentable and cannot be used as an energy source - while still being taken up into the cell (due to similar shape) and leaving no room for the six-carbon sugars, interfering with bacterial growth and reproduction. The harmful micro-organisms are starved in the presence of xylitol, allowing the mouth to remineralize damaged teeth with less interruption. This same property renders it unsuitable for making bread as it interferes with the ability of yeast to digest sugars.^[21] At least six grams of xylitol per day, in three to five chewing episodes, is thought to be needed for dental efficacy. A source of xylitol that releases it slowly, and a one- to three-minute initial pulse are thought to improve the dental effect.^[21]

Xylitol also inhibits the growth of Streptococcus pneumoniae, as well as the attachment of Haemophilus influenzae on the nasopharyngeal cells.^[21]

The perception of sweetness obtained from consuming xylitol causes the secretion of saliva which acts as a buffer against the acidic environment created by the microorganisms in dental plaque. Increase in salivation can raise the falling pH to a neutral range within few minutes of xylitol consumption.^[23]

However, despite these promising conjectures two systematic reviews of clinical trials could not find conclusive evidence that xylitol was indeed superior to other polyols such as sorbitol^[24] or equal to that of topical fluoride in its anti-caries effect.^[25]

In the 33-month Xylitol for Adult Caries Trial, participants were given lozenges of either five grams of xylitol or a sucralose-sweetened placebo. While this study initially found no statistically significant reduction in 33-month caries increment among adults at an elevated risk of developing caries,^[26] a further examination of data from this study revealed a significant reduction in the incidence of root caries in the group that received xylitol.^[27]

In March, 2015, Cochrane published a review^[28] of the entire body of evidence surrounding xylitol's effects on dental caries. Their conclusion was that, while low-quality evidence suggests that over 2.5 to 3 years of use, a fluoride toothpaste containing xylitol may reduce caries when compared to a fluoride-only toothpaste, the remaining body of evidence is of low to very low quality and is insufficient to determine whether any other xylitol-containing products can prevent caries in infants, older children, or adults.

Xylitol is categorized by the U.S. Food and Drug Administration as a food additive.^[29] Like other sugar alcohol-sweetened products, xylitol-sweetened products are allowed to be labeled with the claim that they do not promote dental cavities.

Diabetes

Possessing approximately 33% fewer calories, xylitol is a lower-calorie alternative to table sugar. Absorbed more slowly than sugar, it does not contribute to high blood sugar levels or the resulting hyperglycemia caused by insufficient insulin response. This characteristic has also proven beneficial for people suffering from metabolic syndrome, a common disorder that includes insulin resistance, hypertension, hypercholesterolemia, and an increased risk for blood clots.^[30] Xylitol is used as a sweetener in medicines, chewing gum and pastilles.^[31]

Source of energy

In the human gut xylitol is not absorbed as well as glucose or fructose; the unabsorbed xylitol acts as a dietary soluble fiber in helping to maintain certain aspects of gut function. Bacterial fermentation, mainly in the large gut, partly converts xylitol to short-chain fatty acids that the gut can absorb as fuel for energy production in oxidative metabolic pathways. Xylitol also is useful in recovery after heavy exercise because the human body converts absorbed xylitol to glucose 6-phosphate and glycogen. The conversion is however slow, so that the xylitol amounts to a low-GI source of energy.^[32]^[33]

Ear infection

Xylitol chewing gum appears to decrease rates of acute otitis media in children going to daycare by 25%.^[34] Xylitol nasal sprays have also been shown to decrease incidence of acute otitis media as well as being a very effective way of both assisting and stimulating the body's own natural nasopharyngeal washing, and reducing both bacterial colonization and allergenic pollution, with their accompanying problems.^[35]

Osteoporosis

A feed containing Xylitol increased bone volume in rat studies conducted in 2001 and 2011, these results have generated interest in the sugar that would examine if it could be a human treatment for osteoporosis.^[36]^[37]^[38]

Safety

Xylitol has no known toxicity 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.^[39] Like most sugar alcohols, it has a laxative effect because sugar alcohols are not fully broken down during digestion. The effect depends upon the individual. In one study of 13 children, four experienced diarrhea when consuming over 65 grams per day.^[40] Studies have reported that adaptation occurs after several weeks of consumption.^[40]

As with other sugar alcohols, with the exception of erythritol, 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 bloating, flatulence, and diarrhea. 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 mannitol and sorbitol.^[40]^[41]

Xylitol toxicity in dogs

Xylitol is often fatal to dogs. According to the ASPCA Animal Poison Control Center, the number of cases of xylitol toxicosis in dogs has significantly increased since the first reports in 2002. Dogs that have ingested foods containing xylitol (greater than 100 milligrams of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar (hypoglycemia), which can be life-threatening.^[42] Low blood sugar can result in a loss of coordination, depression, collapse and seizures in as little as 30 minutes.^[43] Intake of doses of xylitol (greater than 500 – 1000 mg/kg bwt) has been implicated in liver failure in dogs, which can be fatal.^[44] Possible cause of hypoglycemia experienced by dogs is the fact that the xylitol in gum is released more slowly and absorbed over longer period than when it is consumed as a pure form.^[45]

Xylitol toxicity in wild birds

A vet examined the bodies of 30 Cape sugarbirds that had died within 30 minutes of drinking a solution made with xylitol, from a feeder in a garden in Hermanus, South Africa.^[46]

Notes and references

^ Safety data sheet for xylitol from Fisher Scientific. Retrieved 2014-11-02.
^ "Xylitol". Chemspider. Retrieved 13 May 2015.
^ Wrolstad, Ronald E. (2012). Food Carbohydrate Chemistry. John Wiley & Sons. p. 176. ISBN 9780813826653. Retrieved October 20, 2012. Xylitol contains asymmetric carbon atoms, but it is not chiral because the molecule as a whole is symmetrical.
^ Steinberg, LM; Odusola, F; Mandel, ID (Sep–Oct 1992). "Remineralizing potential, antiplaque and antigingivitis effects of xylitol and sorbitol sweetened chewing gum.". Clinical preventive dentistry 14 (5): 31–4. PMID 1291185. Retrieved 13 November 2013.
^ Miake Y, et al. "Remineralization effects of xylitol on demineralized enamel.". nih.gov. Retrieved 12 July 2015.
^ http://www.drellie.com/pdfs/The-Remineralization-effects-of-XYLITOL.pdf
^ Azarpazhooh, A.; Limeback, H.; Lawrence, H. P.; Shah, P. S. (2011). Azarpazhooh, Amir, ed. "Xylitol for preventing acute otitis media in children up to 12 years of age". The Cochrane Library (11): CD007095. doi:10.1002/14651858.CD007095.pub2. PMID 22071833.
^ Gare, Fran (February 1, 2003). The Sweet Miracle of Xylitol. Basic Health Publications, Inc. ISBN 1-59120-038-5.
^ Rao, R. Sreenivas; Jyothi, Ch. Pavana; Prakasham, RS; Sharma, PN; Rao, L. Venkateswar (2006). "Xylitol production from corn fiber and sugarcane bagasse hydrolysates by Candida tropicalis". Bioresour. Technol. 97: 1974–8. doi:10.1016/j.biortech.2005.08.015. PMID 16242318. ^{[verification needed]}
^ "Xylitol production from corn fiber and sugarcane bagasse hydrolysates by Candida tropicalis". Bioresource Technology 97 (15): 1974–1978. October 2006. doi:10.1016/j.biortech.2005.08.015. PMID 16242318. |access-date= requires |url= (help)
^ Converti, Atillio; Parego, Patrizia; Dominguez, Jose Manuel (1999). "Xylitol Production from Hardwood Hemicellulose Hydrosylates" (PDF). Applied Biochemistry and Biotechnology 82: 141–151. doi:10.1385/abab:82:2:141.
^ Islam, Md. Shahidul; Indrajit, Mitesh (2012). "Effects of Xylitol on Blood Glucose, Glucose Tolerance, Serum Insulin and Lipid Profile in a Type 2 Diabetes Model of Rats". Annals of Nutrition and Metabolism 61 (1): 57–64. doi:10.1159/000338440. PMID 22832597.
^ Nigam, Poonam; Singh, D. (1995). "Processes for Fermentative Production of Xylitol--a Sugar Substitute". Process Biochemistry 30: 117–124. doi:10.1016/0032-9592(95)80001-8.
^ Barbosa,, M.F.S.; de Medeiros, M.B.; de Manchilha, I.M.; Schneider, H.; Lee, H. (1988). "Screening of yeasts for production of xylitol from D-xylose and some factors which affect xylitol yield in Candida guillermondii". J. Indust. Microbiol. 3: 241–251. doi:10.1007/bf01569582.
^ Walters, D. Eric. "Xylitol". All About Sweeteners. Retrieved March 14, 2012.
^ "Sugars, granulated (sucrose)". Self Nutrition Data. Retrieved March 14, 2012. With a serving size of 100 grams, there are 387 calories.
^ The American Journal of Clinical Nutrition, January 1, 2002: International table of glycemic index and glycemic load values Retrieved 2012-08-26
^ Edwardsson, Stig; Birkhed, Dowen; Mejàre, Bertil (1977). "Acid production from Lycasin, maltitol, sorbitol and xylitol by oral streptococci and lactobacilli". Acta Odontologica Scandinavica 35 (5): 257–263. doi:10.3109/00016357709019801. PMID 21508.
^ Drucker, D.B.; Verran, J. (1979). "Comparative effects of the substance-sweeteners glucose, sorbitol, sucrose, xylitol and trichlorosucrose on lowering of pH by two oral Streptococcus mutans strains in vitro". Archives of Oral Biology 24 (12): 965–970. doi:10.1016/0003-9969(79)90224-3. PMID 44996.
^ Maguire, A; Rugg-Gunn, A J (2003). "Xylitol and caries prevention — is it a magic bullet?". British Dental Journal 194 (8): 429–436. doi:10.1038/sj.bdj.4810022. PMID 12778091. Retrieved March 14, 2012.
^ ^a ^b ^c ^d Reusens, B. (2004). Remacle, Claude; Reusens, Brigitte, ed. Functional foods, ageing and degenerative disease. Cambridge, England: Woodhead Publishing. p. 202. ISBN 978-1-85573-725-9. Retrieved March 14, 2012.
^ "Policy on the Use of Xylitol in Caries Prevention" (PDF). Reference Manual (American Academy of Pediatric Dentistry) 33 (6): 42–44. 2010. Retrieved March 14, 2012.
^ Scheinin, Arje (1993). "Dental Caries, Sugars and Xylitol". Ann Med 25: 519–521.
^ Mickenautsch, Steffen; Yengopal, Veerasamy (2012). "Effect of xylitol versus sorbitol: A quantitative systematic review of clinical trials". International Dental Journal 62 (4): 175–88. doi:10.1111/j.1875-595X.2011.00113.x. PMID 23016999.
^ Mickenautsch, Steffen; Yengopal, Veerasamy (2012). "Anticariogenic effect of xylitol versus fluoride - a quantitative systematic review of clinical trials". International Dental Journal 62 (1): 6–20. doi:10.1111/j.1875-595X.2011.00086.x. PMID 22251032.
^ Bader, James D.; et al. (Jan 2013). "Results from the Xylitol for Adult Caries Trial (X-ACT)". The Journal of the American Dental Association 144 (1): 21–30. doi:10.14219/jada.archive.2013.0010.
^ Ritter, AV, Bader, JD, Leo, MC, Preisser, JS, Shugars, DA, Vollmer, WM, Amaechi, BT, Holland, JC (June 2013). "Tooth-surface-specific Effects of Xylitol: Randomized Trial Results". Journal of Dental Research 92 (6): 512–517. doi:10.1177/0022034513487211.
^ "Can xylitol used in products like sweets, candy, chewing gum and toothpaste help prevent tooth decay in children and adults?". Cochrane. 26 March 2015.
^ "CITE: 21CFR172.395". Code of Federal Regulations Title 21. United States Food and Drug Administration. 2012-04-01.
^ Martí, N.; Funes, L.L.; Saura, D.; Micol, V. (July 2008). "An update on alternative sweeteners". International sugar journal 110 (1315): 425–429. ISSN 0020-8841.
^ Savola, Päivikki. "Xylitol combats cavities". Advanced food development and functional foods from Finland. Finfood - Finnish Food Information. Archived from the original on April 18, 2008.
^ Vasilescu, Razvan; Ionescu, A.M.; Mihai, A.; Carniciu, S.; Ionescu-Tirgoviste, C. (2011). "Sweeteners and metabolic diseases: Xylitol as a new player". Proc. Rom. Acad. B 2: 125–128.
^ Xi Chen, Zi-Hua Jiang, Sanfeng Chen, and Wensheng Qin. Microbial and Bioconversion Production of D-xylitol and Its Detection and Application. Int J Biol Sci. 2010; 6(7): 834–844. Published online Dec 15, 2010. PMCID: PMC3005349
^ Azarpazhooh, A; Limeback, H; Lawrence, HP; Shah, PS (Nov 9, 2011). "Xylitol for preventing acute otitis media in children up to 12 years of age.". The Cochrane database of systematic reviews (11): CD007095. doi:10.1002/14651858.CD007095.pub2. PMID 22071833.
^ Jones, A (Summer 2001). "Intranasal Xylitol, Recurrent Otitis Media, and Asthma: Report of Three Cases.". Clinical Practice of Alternative Medicine (2): 112–117.
^ "Xylitol". drugs.com. Retrieved 12 July 2015.
^ Mattila PT, et al. "Increased bone volume and bone mineral content in xylitol-fed aged rats.". nih.gov. Retrieved 12 July 2015.
^ Sato H, et al. "The effects of oral xylitol administration on bone density in rat femur.". nih.gov. Retrieved 12 July 2015.
^ Mäkinen, KK (1976). "Long-term tolerance of healthy human subjects to high amounts of xylitol and fructose: general and biochemical findings". Internationale Zeitschrift fur Vitamin und Ernahrungsforschung Beiheft 15: 92–104. doi:10.1002/14651858.CD010743. PMID 783060.
^ ^a ^b ^c Wang, Yeu-Ming; van Eys, Jan (1981). "Nutritional significance of fructose and sugar alcohols". Annual Review of Nutrition 1: 437–75. doi:10.1146/annurev.nu.01.070181.002253. PMID 6821187.
^ "Sugar Alcohols" (PDF). Canadian Diabetes Association. May 2005. Retrieved March 14, 2012.
^ Dunayer, Eric K.; Gwaltney-Brant, Sharon M. (October 2006). "Acute hepatic failure and coagulopathy associated with xylitol ingestion in eight dogs". Journal of the American Veterinary Medical Association 229 (7): 1113–1117. doi:10.2460/javma.229.7.1113. PMID 17014359.
^ Dunayer, Erik K. (April 2004). "Hypoglycemia following canine ingestion of xylitol-containing gum". Veterinary and human toxicology 46 (2): 87–88. PMID 15080212.
^ Dunayer, Erik K. (December 2006). "New findings on the effects of xylitol ingestion in dogs" (PDF). Veterinary Medicine 101 (12): 791–797. Retrieved March 14, 2012.
^ Dunayer, Eric K (2004). "Hypoglycemia Following Canine Ingestion of Xylitol-Containing Gum". Vet. Human Toxicol. 46 (2): 87–88.
^ "Xylitol could kill sugarbirds - and pets". Independent Online. Retrieved 12 July 2015.

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5. 緩和ケアにおける嚥下障害および誤嚥：評価およびマネージメント戦略 swallowing disorders and aspiration in palliative care assessment and strategies for management

English Journal

Construction and co-expression of plasmid encoding xylitol dehydrogenase and a cofactor regeneration enzyme for the production of xylitol from d-arabitol.

Zhou P, Li S, Xu H, Feng X, Ouyang P.SourceState Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing 210009, PR China; College of Food Science and Light Industry, Nanjing University of Technology, Nanjing 210009, PR China.
Enzyme and microbial technology.Enzyme Microb Technol.2012 Jul 15;51(2):119-24. Epub 2012 May 14.
The biotransformation of d-arabitol into xylitol was investigated with focus on the conversion of d-xylulose into xylitol. This critical conversion was accomplished using Escherichia coli to co-express a xylitol dehydrogenase gene from Gluconobacter oxydans and a cofactor regeneration enzyme gene wh
PMID 22664197

Removal of inhibitors from pre-hydrolysis liquor of kraft-based dissolving pulp production process using adsorption and flocculation processes.

Liu X, Fatehi P, Ni Y.SourceDepartment of Chemical Engineering and Limerick Pulp and Paper Centre, University of New Brunswick, Fredericton, NB, Canada E3B 5A3.
Bioresource technology.Bioresour Technol.2012 Jul;116:492-6. Epub 2012 Mar 29.
A process for removing inhibitors from pre-hydrolysis liquor (PHL) of a kraft-based dissolving pulp production process by adsorption and flocculation, and the characteristics of this process were studied. In this process, industrially produced PHL was treated with unmodified and oxidized activated c
PMID 22595100

Japanese Journal

がん患者の口腔乾燥に対するスプレー式保湿剤の開発と有用性評価

日本緩和医療薬学雑誌 8(3), 83-89, 2015-09
NAID 40020601890

Improvement of thermoelectric properties of composite films of PEDOT-PSS with xylitol by means of stretching and solvent treatment

Polymer journal 47(7), 522-526, 2015-07
NAID 40020510170

Improving xylitol production through recombinant expression of xylose reductase in the white-rot fungus Phanerochaete sordida YK-624(GENETICS, MOLECULAR BIOLOGY, AND GENE ENGINEERING)

Journal of bioscience and bioengineering 120(1), 6-8, 2015-07
NAID 110009973277

Related Pictures

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リンク元

「キシリトール」

Xylitol^[1]
	; Xylitol crystals
Names
	IUPAC name (2R,3r,4S)-Pentane-1,2,3,4,5-pentol
	Other names 1,2,3,4,5-Pentahydroxypentane;; Xylite
Identifiers
CAS Number	87-99-0
ChEMBL	ChEMBL96783
ChemSpider	6646
Jmol 3D model	Interactive image
PubChem	6912
UNII	VCQ006KQ1E
	InChI InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ Key: HEBKCHPVOIAQTA-SCDXWVJYSA-N ; InChI=1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ Key: HEBKCHPVOIAQTA-SCDXWVJYBA ;
	SMILES O[C@H](CO)[C@H](O)[C@@H](O)CO ;
Properties
Chemical formula	C5H12O5
Molar mass	152.15 g·mol−1
Density	1.52 g/cm3
Melting point	92 to 96 °C (198 to 205 °F; 365 to 369 K)
Boiling point	345.39 °C (653.70 °F; 618.54 K) Predicted value using Adapted Stein & Brown method
Solubility in water	~ 0.1 g/mL
Hazards
NFPA 704	1 1 0
Related compounds
Related alkanes	Pentane
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: xylitol
ラ: xylitolum
商: キシリット, Xylit、キリット、クリニット
関: キシリトール、

[1] Safety data sheet for xylitol from Fisher Scientific. Retrieved 2014-11-02.

[2] "Xylitol". Chemspider. Retrieved 13 May 2015.

[3] Wrolstad, Ronald E. (2012). Food Carbohydrate Chemistry. John Wiley & Sons. p. 176. ISBN 9780813826653. Retrieved October 20, 2012. Xylitol contains asymmetric carbon atoms, but it is not chiral because the molecule as a whole is symmetrical.

[4] Steinberg, LM; Odusola, F; Mandel, ID (Sep–Oct 1992). "Remineralizing potential, antiplaque and antigingivitis effects of xylitol and sorbitol sweetened chewing gum.". Clinical preventive dentistry 14 (5): 31–4. PMID 1291185. Retrieved 13 November 2013.

[5] Miake Y, et al. "Remineralization effects of xylitol on demineralized enamel.". nih.gov. Retrieved 12 July 2015.

[6] ttp://www.drellie.com/pdfs/The-Remineralization-effects-of-XYLITOL.pdf

[:21-7] Azarpazhooh, A.; Limeback, H.; Lawrence, H. P.; Shah, P. S. (2011). Azarpazhooh, Amir, ed. "Xylitol for preventing acute otitis media in children up to 12 years of age". The Cochrane Library (11): CD007095. doi:10.1002/14651858.CD007095.pub2. PMID 22071833.

[8] Gare, Fran (February 1, 2003). The Sweet Miracle of Xylitol. Basic Health Publications, Inc. ISBN 1-59120-038-5.

[9] Rao, R. Sreenivas; Jyothi, Ch. Pavana; Prakasham, RS; Sharma, PN; Rao, L. Venkateswar (2006). "Xylitol production from corn fiber and sugarcane bagasse hydrolysates by Candida tropicalis". Bioresour. Technol. 97: 1974–8. doi:10.1016/j.biortech.2005.08.015. PMID 16242318. ^{[verification needed]}

[10] "Xylitol production from corn fiber and sugarcane bagasse hydrolysates by Candida tropicalis". Bioresource Technology 97 (15): 1974–1978. October 2006. doi:10.1016/j.biortech.2005.08.015. PMID 16242318. |access-date= requires |url= (help)

[11] Converti, Atillio; Parego, Patrizia; Dominguez, Jose Manuel (1999). "Xylitol Production from Hardwood Hemicellulose Hydrosylates" (PDF). Applied Biochemistry and Biotechnology 82: 141–151. doi:10.1385/abab:82:2:141.

[12] Islam, Md. Shahidul; Indrajit, Mitesh (2012). "Effects of Xylitol on Blood Glucose, Glucose Tolerance, Serum Insulin and Lipid Profile in a Type 2 Diabetes Model of Rats". Annals of Nutrition and Metabolism 61 (1): 57–64. doi:10.1159/000338440. PMID 22832597.

[13] Nigam, Poonam; Singh, D. (1995). "Processes for Fermentative Production of Xylitol--a Sugar Substitute". Process Biochemistry 30: 117–124. doi:10.1016/0032-9592(95)80001-8.

[14] Barbosa,, M.F.S.; de Medeiros, M.B.; de Manchilha, I.M.; Schneider, H.; Lee, H. (1988). "Screening of yeasts for production of xylitol from D-xylose and some factors which affect xylitol yield in Candida guillermondii". J. Indust. Microbiol. 3: 241–251. doi:10.1007/bf01569582.

[15] Walters, D. Eric. "Xylitol". All About Sweeteners. Retrieved March 14, 2012.

[16] "Sugars, granulated (sucrose)". Self Nutrition Data. Retrieved March 14, 2012. With a serving size of 100 grams, there are 387 calories.

[17] The American Journal of Clinical Nutrition, January 1, 2002: International table of glycemic index and glycemic load values Retrieved 2012-08-26

[18] Edwardsson, Stig; Birkhed, Dowen; Mejàre, Bertil (1977). "Acid production from Lycasin, maltitol, sorbitol and xylitol by oral streptococci and lactobacilli". Acta Odontologica Scandinavica 35 (5): 257–263. doi:10.3109/00016357709019801. PMID 21508.

[19] Drucker, D.B.; Verran, J. (1979). "Comparative effects of the substance-sweeteners glucose, sorbitol, sucrose, xylitol and trichlorosucrose on lowering of pH by two oral Streptococcus mutans strains in vitro". Archives of Oral Biology 24 (12): 965–970. doi:10.1016/0003-9969(79)90224-3. PMID 44996.

[20] Maguire, A; Rugg-Gunn, A J (2003). "Xylitol and caries prevention — is it a magic bullet?". British Dental Journal 194 (8): 429–436. doi:10.1038/sj.bdj.4810022. PMID 12778091. Retrieved March 14, 2012.

[ReferenceA-21] Reusens, B. (2004). Remacle, Claude; Reusens, Brigitte, ed. Functional foods, ageing and degenerative disease. Cambridge, England: Woodhead Publishing. p. 202. ISBN 978-1-85573-725-9. Retrieved March 14, 2012.

[aapd-22] "Policy on the Use of Xylitol in Caries Prevention" (PDF). Reference Manual (American Academy of Pediatric Dentistry) 33 (6): 42–44. 2010. Retrieved March 14, 2012.

[23] Scheinin, Arje (1993). "Dental Caries, Sugars and Xylitol". Ann Med 25: 519–521.

[24] Mickenautsch, Steffen; Yengopal, Veerasamy (2012). "Effect of xylitol versus sorbitol: A quantitative systematic review of clinical trials". International Dental Journal 62 (4): 175–88. doi:10.1111/j.1875-595X.2011.00113.x. PMID 23016999.

[25] Mickenautsch, Steffen; Yengopal, Veerasamy (2012). "Anticariogenic effect of xylitol versus fluoride - a quantitative systematic review of clinical trials". International Dental Journal 62 (1): 6–20. doi:10.1111/j.1875-595X.2011.00086.x. PMID 22251032.

[26] Bader, James D.; et al. (Jan 2013). "Results from the Xylitol for Adult Caries Trial (X-ACT)". The Journal of the American Dental Association 144 (1): 21–30. doi:10.14219/jada.archive.2013.0010.

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xylitol