Xylitol
Xylitol crystals
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Names | |
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Pronunciation | /ˈzaɪlɪtɒl/ |
IUPAC name
meso-Xylitol
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Systematic IUPAC name
(2R,3R,4S)-Pentane-1,2,3,4,5-pentol | |
Other names
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Identifiers | |
3D model (
JSmol ) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.001.626 |
E number | E967 (glazing agents, ...) |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C5H12O5 | |
Molar mass | 152.146 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[2] |
~100 g/L | |
Hazards | |
NFPA 704 (fire diamond) | |
Related compounds | |
Related alkanes
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Pentane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Xylitol is a
Xylitol is used as a
History
Structure, production, commerce
Xylitol is one of three 5-carbon sugar alcohols. The others are arabitol and ribitol. These three compounds differ in the stereochemistry of the three secondary alcohol groups.
Xylitol occurs naturally in small amounts in plums, strawberries, cauliflower, and pumpkin; humans and many other animals make trace amounts during metabolism of carbohydrates.[6] Unlike most sugar alcohols, xylitol is achiral.[8] Most other isomers of pentane-1,2,3,4,5-pentol are chiral, but xylitol has a plane of symmetry.
Industrial production starts with
Xylitol can also be obtained by industrial fermentation, but this methodology are not as economical as the acid hydrolysis/chromatography route described above. Fermentation is effected by bacteria, fungi, or yeast, especially Candida tropicalis.[6][10] According to the US Department of Energy, xylitol production by fermentation from discarded biomass is one of the most valuable renewable chemicals for commerce, forecast to be a US $1.4 billion industry by 2025.[11]
Uses
Xylitol is used as a
Xylitol is also found as an additive to saline solution for nasal irrigation and has been reported to be effective in improving symptoms of chronic sinusitis.[14]
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.[15]
Food properties
Nutrition, taste, and cooking
Humans absorb xylitol more slowly than sucrose, and xylitol supplies 40% fewer calories than an equal mass of sucrose.[12]
Xylitol has about the same sweetness as sucrose,[12] but is sweeter than similar compounds like sorbitol and mannitol.[6]
Xylitol is stable enough to be used in baking,[16] but because xylitol and other polyols are more heat-stable, they do not caramelise as sugars do. When used in foods, they lower the freezing point of the mixture.[17]
Food risks
No serious health risk exists in most humans for normal levels of consumption. The European Food Safety Authority has not set a limit on daily intake of xylitol. Due to the adverse laxative effect that all polyols have on the digestive system in high doses, xylitol is banned from soft drinks in the European Union. Similarly due to a 1985 report, by the E.U. Scientific Committee on Food, stating that "ingesting 50 g a day of xylitol can cause diarrhea", tabletop sweeteners, as well as other products containing xylitol are required to display the warning: "Excessive consumption may induce laxative effects".[18]
Metabolism
Xylitol has 2.4 kilocalories of
Primarily, the liver metabolizes absorbed xylitol. The main metabolic route in humans occurs in
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
Xylitol ingestion also increases motilin secretion, which may be related to xylitol's ability to cause diarrhea.[21] The less-digestible but fermentable nature of xylitol also contributes to constipation relieving effects.[22]
Health effects
Dental care
A 2015
Earache
In 2011
Diabetes
In 2011, EFSA approved a marketing claim that foods or beverages containing xylitol or similar sugar replacers cause lower blood glucose and lower insulin responses compared to sugar-containing foods or drinks.[16][30] Xylitol products are used as sucrose substitutes for weight control,[16][22] as xylitol has 40% fewer calories than sucrose (2.4 kcal/g compared to 4.0 kcal/g for sucrose).[16][31] The glycemic index (GI) of xylitol is only 7% of the GI for glucose.[32]
Adverse effects
Humans
When ingested at high doses, xylitol and other polyols may cause
Increased xylitol consumption can increase oxalate, calcium, and phosphate excretion to urine (termed
Dogs and other animals
Xylitol is poisonous to dogs.[36] Ingesting 100 milligrams of xylitol per kilogram of body weight (mg/kg bw) causes dogs to experience a dose-dependent insulin release; depending on the dose it can result in life-threatening hypoglycemia. Hypoglycemic symptoms of xylitol toxicity may arise as quickly as 30 to 60 minutes after ingestion. Vomiting is a common first symptom, which can be followed by tiredness and ataxia. At doses above 500 mg/kg bw, liver failure is likely and may result in coagulopathies like disseminated intravascular coagulation.[37]
Xylitol is safe for rhesus macaques, horses, and rats.[37]
A 2018 study suggests that xylitol is safe in cats in doses of up to 1000 mg/kg; however, this study was performed on only 6 cats, and should not be considered definitive.[38]
See also
References
- ^ Safety data sheet for xylitol Archived 3 March 2016 at the Wayback Machine from Fisher Scientific. Retrieved 2014-11-02.
- ^ "Xylitol". Chemspider.com. Chemical Structure. Retrieved 13 May 2015.
- ^ a b "Food legislation". polyols-eu.org. European Association of Polyol Producers. 22 March 2017. Retrieved 7 February 2019.
- ^ a b
Riley, P.; Moore, D.; Ahmed, F.; Sharif, M.O.; Worthington, H.V. (26 March 2015). "Xylitol-containing products for preventing dental caries in children and adults". The Cochrane Database of Systematic Reviews. 2015 (3): CD010743. PMID 25809586.
Riley, P.; Moore, D.; Ahmed, F.; Sharif, M. O.; Worthington, H. V. (2015). "Can xylitol – used in products like sweets, candy, chewing gum, and toothpaste – help prevent tooth decay in children and adults?". The Cochrane Database of Systematic Reviews. Lay summary. 2015 (3): CD010743.PMID 25809586. - S2CID 31432699.
- ^ a b c d e
Ur-Rehman, S.; Mushtaq, Z.; Zahoor, T.; Jamil, A.; Murtaza, M.A. (2015). "Xylitol: A review on bio-production, application, health benefits, and related safety issues". Critical Reviews in Food Science and Nutrition. 55 (11): 1514–1528. S2CID 20359589.
- ^ Hicks, Jesse (Spring 2010). "The pursuit of sweet". Science History. Science History Institute.
- ^
Wrolstad, Ronald E. (2012). Food Carbohydrate Chemistry. John Wiley & Sons. p. 176. ISBN 9780813826653. Retrieved 20 October 2012 – via Google Books.
- ISBN 9783527303854.
- ^
Jain, H.; Mulay, S. (March 2014). "A review on different modes and methods for yielding a pentose sugar: Xylitol". International Journal of Food Sciences and Nutrition. 65 (2): 135–143. S2CID 39929588.
- ^
Felipe Hernández-Pérez, Andrés; de Arruda, Priscila Vaz; Sene, Luciane; da Silva, Silvio Silvério; Kumar Chandel, Anuj; de Almeida Felipe, Maria das Graças (16 July 2019). "Xylitol bioproduction: State-of-the-art, industrial paradigm shift, and opportunities for integrated biorefineries". Critical Reviews in Biotechnology. 39 (7): 924–943. S2CID 197421362.
- ^ a b c d "Xylitol". Drugs.com. 2018. Retrieved 12 October 2018.
- ^ "Xylitol". United States Code of Federal Regulations. Food Additives Permitted for Direct Addition to Food for Human Consumption, Special Dietary and Nutritional Additives. U.S. Food and Drug Administration. 1 April 2012. CFR Title 21, Part 172, Section 172.395.
- ^
Weissman, Joshua D.; Fernandez, Francisca; Hwang, Peter H. (November 2011). "Xylitol nasal irrigation in the management of chronic rhinosinusitis: A pilot study". The Laryngoscope. 121 (11): 2468–2472. S2CID 36572019.
- ISSN 2542-4351.
- ^ a b c d "Xylitol". Diabetes.co.uk. Retrieved 28 October 2018.
- ^ Burgos, Karen; Subramaniam, Persis; Arthur, Jennifer (21 November 2016). "Reformulation guide for small to medium sized companies" (PDF). Leatherhead Food Research. Archived from the original (PDF) on 27 September 2020. Retrieved 28 October 2018 – via The Food and Drink Federation.
- ^ a b c "Is xylitol good for your teeth?". Live well: Eat well. U.K. National Health Service. 13 April 2016. Retrieved 28 October 2018.
- ^ "Chapter 3: Energy Conversion Factors". Calculation of the Energy Content of Foods. Food and Agriculture Organization (Report). The United Nations. Retrieved 30 March 2017.
- ^ a b c
Livesey, G. (2003). "Health potential of polyols as sugar replacers, with emphasis on low glycaemic properties". Nutrition Research Reviews. 16 (2): 163–191. PMID 19087388.
- ^
Wölnerhanssen, B.K.; Meyer-Gerspach, A.C.; Beglinger, C.; Islam, M.S. (June 2019). "Metabolic effects of the natural sweeteners xylitol and erythritol: A comprehensive review". Critical Reviews in Food Science and Nutrition. 60 (12): 1986–1998. S2CID 189944738.
- ^ a b
Salli, Krista; Lehtinen, Markus J.; Tiihonen, Kirsti; Ouwehand, Arthur C. (6 August 2019). "Xylitol's health benefits beyond dental health: A comprehensive review". Nutrients. 11 (8): 1813. PMID 31390800.
- PMID 25809586.
- PMID 32638045.
- PMID 35462747.
- PMID 31060040.
- ^ EFSA pannel (June 2011). "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)". EFSA Journal. 9 (6): 2266. .
- ^ a b
Azarpazhooh, A.; Lawrence, H.P.; Shah, P.S. (3 August 2016). "Xylitol for preventing acute otitis media in children up to 12 years of age". The Cochrane Database of Systematic Reviews. 2016 (8): CD007095. PMID 27486835.
- ^
Marom, Tal; Marchisio, Paola; Tamir, Sharon Ovnat; Torretta, Sara; Gavriel, Haim; Esposito, Susanna (12 February 2016). "Complementary and alternative medicine treatment options for otitis media". Medicine. 95 (6): e2695. PMID 26871802.
- ^ EFSA panel (April 2011). "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". EFSA Journal. 9 (4): 2076. .
- ^
Tiefenbacher, Karl F. (2017). "Technology of Main Ingredients – Sweeteners and Lipids". Wafer and Waffle. Elsevier. pp. 123–225. ISBN 978-0-12-809438-9.
- ^
Foster-Powell, K.; Holt, S.H.; Brand-Miller, J.C. (July 2002). "International table of glycemic index and glycemic load values: 2002". The American Journal of Clinical Nutrition. 76 (1): 5–56. PMID 12081815.
- ^
Mäkinen, Kauko (20 October 2016). "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". International Journal of Dentistry. 2016: 5967907. PMID 27840639.
- ^ Sugar Alcohols (PDF) (Report). Canadian Diabetes Association. 1 May 2005. Archived from the original (PDF) on 25 April 2012. Retrieved 14 March 2012.
- ^
Janket, S.; Benwait, J.; Isaac, P.; Ackerson, L.K.; Meurman, J.H. (2019). "Oral and systemic effects of xylitol consumption". Caries Research. 53 (5): 491–501. S2CID 146811298.
- ^ "Paws off xylitol; It's dangerous for dogs". US Food and Drug Administration. 7 July 2021. Retrieved 9 September 2021.
- ^ a b
Schmid, R.D.; Hovda, L.R. (2016). "Acute hepatic failure in a dog after xylitol ingestion". Journal of Medical Toxicology. 12 (2): 201–205. PMID 26691320.
- ^
Jerzsele, A.; et al. (2018). "Effects of p.o. administered xylitol in cats". Journal of Veterinary Pharmacology and Therapeutics. 41 (3): 409–414. PMID 29430681.