Xylitol

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Contents

Xylitol [1]
Xylitol.svg
Xylitol crystals.jpg
Xylitol crystals
Names
Pronunciation /ˈzaɪlɪtɒl/
IUPAC name
meso-Xylitol
Systematic IUPAC name
(2R,3R,4S)-Pentane-1,2,3,4,5-pentol
Other names
  • (2R,3R,4S)-Pentane-1,2,3,4,5-pentaol (not recommended)
  • (2R,3R,4S)-1,2,3,4,5-Pentahydroxypentane
  • Xylite
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.626 OOjs UI icon edit-ltr-progressive.svg
E number E967 (glazing agents, ...)
KEGG
PubChem CID
UNII
  • InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ Yes check.svgY
    Key: HEBKCHPVOIAQTA-SCDXWVJYSA-N Yes check.svgY
  • OC[C@@H](O)[C@H](O)[C@@H](O)CO
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)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Xylitol is a chemical compound with the formula C
5H
12O
5, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It is classified as a polyalcohol and a sugar alcohol, specifically an alditol. The name derives from Ancient Greek : ξύλον, xyl[on] 'wood', with the suffix -itol used to denote it being a sugar alcohol.

Xylitol is used as a food additive and sugar substitute. Its European Union code number is E967. [3] Replacing sugar with xylitol in food products may promote better dental health, but evidence is lacking on whether xylitol itself prevents dental cavities. [4]

History

Emil Fischer, a German chemistry professor, and his assistant Rudolf Stahel isolated a new compound from beech wood chips in September 1890 and named it Xylit, the German word for xylitol. The following year, the French chemist M.G. Bertrand isolated xylitol syrup by processing wheat and oat straw. [5] Sugar rationing during World War II led to an interest in sugar substitutes. Interest in xylitol and other polyols became intense, leading to their characterization and manufacturing methods. [6] [7]

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 lignocellulosic biomass from which xylan is extracted; raw biomass materials include hardwoods, softwoods, and agricultural waste from processing maize, wheat, or rice. The mixture is hydrolyzed with acid to give xylose. The xylose is purified by chromatography. Purified xylose is catalytically hydrogenated into xylitol using a Raney nickel catalyst. [9] The conversion changes the sugar (xylose, an aldehyde) into the primary alcohol, xylitol. [6]

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 sugar substitute in such manufactured products as drugs, dietary supplements, confections, toothpaste, and chewing gum, but is not a common household sweetener. [4] [12] Xylitol has negligible effects on blood sugar because its assimilation and metabolism are independent of insulin. [12] It is approved as a food additive in the United States [13] and elsewhere. Xylitol is often marketed as "birch sugar".

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 food energy per gram of xylitol (10 kilojoules per gram) according to U.S. and E.U. food-labeling regulations. [19] [3] The real value can vary, depending on metabolic factors. [20]

Primarily, the liver metabolizes absorbed xylitol. The main metabolic route in humans occurs in cytoplasm, via nonspecific NAD-dependent dehydrogenase (polyol dehydrogenase), which transforms xylitol to D-xylulose. Specific xylulokinase phosphorylates it to D-xylulose-5-phosphate. This then goes to pentose phosphate pathway for further processing. [20]

About 50% of eaten xylitol is absorbed via the intestines. Of the remaining 50% that is not absorbed by the intestines, in humans, 50–75% of the xylitol remaining in the gut is fermented by gut bacteria into short-chain organic acids and gases, which may produce flatulence. The remnant unabsorbed xylitol that escapes fermentation is excreted unchanged, mostly in feces; less than 2 g of xylitol out of every 100 g ingested is excreted via urine. [20]

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 Cochrane review of ten studies between 1991 and 2014 suggested a positive effect in reducing tooth decay of xylitol-containing fluoride toothpastes when compared to fluoride-only toothpaste, but there was insufficient evidence to determine whether other xylitol-containing products can prevent tooth decay in infants, children or adults. [23] Subsequent reviews support the belief that xylitol can suppress the growth of pathogenic Streptococcus in the mouth, thereby reducing dental caries and gingivitis, although there is concern that swallowed xylitol may cause intestinal dysbiosis. [24] [25] [26]

Earache

In 2011 EFSA "concluded that there was not enough evidence to support" the claim that xylitol-sweetened gum could prevent middle-ear infections, also known as acute otitis media (AOM). [18] [27] A 2016 review indicated that xylitol in chewing gum or a syrup may have a moderate effect in preventing AOM in healthy children. [28] It may be an alternative to conventional therapies (such as antibiotics) to lower risk of earache in healthy children – reducing risk of occurrence by 25% [29]  – although there is no definitive proof that it could be used as a therapy for earache. [28]

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 gastrointestinal discomfort, including flatulence, diarrhea, and irritable bowel syndrome (see Metabolism above); some people experience the adverse effects at lower doses. [18] [33] Xylitol has a lower laxation threshold than some sugar alcohols but is more easily tolerated than mannitol and sorbitol. [34]

Increased xylitol consumption can increase oxalate, calcium, and phosphate excretion to urine (termed oxaluria , calciuria , and phosphaturia , respectively). These are known risk factors for kidney stone disease, but despite that, xylitol has not been linked to kidney disease in humans. [35]

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

Related Research Articles

<span class="mw-page-title-main">Aspartame</span> Artificial non-saccharide sweetener

Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel. Aspartame was approved by the US Food and Drug Administration (FDA) in 1974, and then again in 1981, after approval was revoked in 1980.

<span class="mw-page-title-main">Sucralose</span> Non-nutritive sweetener

Sucralose is an artificial sweetener and sugar substitute. As the majority of ingested sucralose is not metabolized by the body, it adds no calories. In the European Union, it is also known under the E number E955. It is produced by chlorination of sucrose, selectively replacing three of the hydroxy groups—in the C1 and C6 positions of the fructose portion and the C4 position of the glucose portion—to give a 1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactose disaccharide. Sucralose is about 600 times sweeter than sucrose, three times as sweet as both aspartame and acesulfame potassium, and twice as sweet as sodium saccharin.

<span class="mw-page-title-main">Sorbitol</span> Chemical compound

Sorbitol, less commonly known as glucitol, is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes. It is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. Sorbitol is an isomer of mannitol, another sugar alcohol; the two differ only in the orientation of the hydroxyl group on carbon 2. While similar, the two sugar alcohols have very different sources in nature, melting points, and uses.

<span class="mw-page-title-main">Sugar substitute</span> Sugarless food additive intended to provide a sweet taste

A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie or low-calorie sweetener. Artificial sweeteners may be derived through manufacturing of plant extracts or processed by chemical synthesis. Sugar substitute products are commercially available in various forms, such as small pills, powders, and packets.

<span class="mw-page-title-main">Toothpaste</span> Substance to clean and maintain teeth

Toothpaste is a paste or gel dentifrice used with a toothbrush to clean and maintain the aesthetics and health of teeth. Toothpaste is used to promote oral hygiene: it is an abrasive that aids in removing dental plaque and food from the teeth, assists in suppressing halitosis, and delivers active ingredients to help prevent tooth decay and gum disease (gingivitis). Owing to differences in composition and fluoride content, not all toothpastes are equally effective in maintaining oral health. The decline of tooth decay during the 20th century has been attributed to the introduction and regular use of fluoride-containing toothpastes worldwide. Large amounts of swallowed toothpaste can be poisonous. Common colors for toothpaste include white and blue.

<span class="mw-page-title-main">Tooth decay</span> Deformation of teeth due to acids produced by bacteria

Tooth decay, also known as cavities or caries, is the breakdown of teeth due to acids produced by bacteria. The cavities may be a number of different colors, from yellow to black. Symptoms may include pain and difficulty eating. Complications may include inflammation of the tissue around the tooth, tooth loss and infection or abscess formation. Tooth regeneration is an on-going stem cell based field of study that is trying to reverse the effects of decay, unlike most current methods which only try to make dealing with the effects easier.

<span class="mw-page-title-main">Sugar alcohol</span> Organic compounds

Sugar alcohols are organic compounds, typically derived from sugars, containing one hydroxyl group (−OH) attached to each carbon atom. They are white, water-soluble solids that can occur naturally or be produced industrially by hydrogenating sugars. Since they contain multiple (−OH) groups, they are classified as polyols.

<span class="mw-page-title-main">Erythritol</span> Chemical compound

Erythritol (, ) is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L-erythrose and one of the two reduced forms of erythrulose. It is used as a food additive and sugar substitute. It is synthesized from corn using enzymes and fermentation. Its formula is C
4H
10O
4, or HO(CH2)(CHOH)2(CH2)OH.

<i>Streptococcus mutans</i> Species of bacterium

Streptococcus mutans is a facultatively anaerobic, gram-positive coccus commonly found in the human oral cavity and is a significant contributor to tooth decay. It is part of the "streptococci", an informal general name for all species in the genus Streptococcus. The microbe was first described by James Kilian Clarke in 1924.

<span class="mw-page-title-main">Dental fluorosis</span> Medical condition

Dental fluorosis is a common disorder, characterized by hypomineralization of tooth enamel caused by ingestion of excessive fluoride during enamel formation.

<span class="mw-page-title-main">Maltitol</span> Sugar alcohol used as a sweetener

Maltitol is a sugar alcohol used as a sugar substitute and laxative. It has 75–90% of the sweetness of sucrose and nearly identical properties, except for browning. It is used to replace table sugar because it is half as energetic, does not promote tooth decay, and has a somewhat lesser effect on blood glucose. In chemical terms, maltitol is known as 4-O-α-glucopyranosyl-D-sorbitol. It is used in commercial products under trade names such as Lesys, Maltisweet and SweetPearl.

The tooth-friendly label distinguishes products which are non-cariogenic and non-erosive, i.e. safe for teeth. To replace sugar, toothfriendly products often contain sweeteners that are not fermented by the microflora of the dental plaque. Products that are certified as toothfriendly also do not contain excessive amounts of food acids.

<span class="mw-page-title-main">Psicose</span> Chemical compound

D-Psicose (C6H12O6), also known as D-allulose, or simply allulose, is a low-calorie epimer of the monosaccharide sugar fructose, used by some major commercial food and beverage manufacturers as a low-calorie sweetener. First identified in wheat in the 1940s, allulose is naturally present in small quantities in certain foods.

<span class="mw-page-title-main">Early childhood caries</span> Dental disease of young children

Early childhood caries (ECC), formerly known as nursing bottle caries, baby bottle tooth decay, night bottle mouth and night bottle caries, is a disease that affects teeth in children aged between birth and 71 months. ECC is characterized by the presence of 1 or more decayed, missing, or filled tooth surfaces in any primary tooth. ECC has been shown to be a very common, transmissible bacterial infection, usually passed from the primary caregiver to the child. The main bacteria responsible for dental cavities are Streptococcus mutans (S.mutans) and Lactobacillus. There is also evidence that supports that those who are in lower socioeconomic populations are at greater risk of developing ECC.

<span class="mw-page-title-main">Isomaltulose</span> Chemical compound

Isomaltulose is a disaccharide carbohydrate composed of glucose and fructose. It is naturally present in honey and sugarcane extracts and is also produced industrially from table sugar (sucrose) and used as a sugar alternative.

Smint is a brand of sugar-free breath mints, known for their distinctive packaging that dispenses one mint at a time, and for their Reuleaux triangle shape. The name is a portmanteau of "sugarfree" and "mint", not of "small mint" as is commonly thought.

<span class="mw-page-title-main">Remineralisation of teeth</span>

Tooth remineralization is the natural repair process for non-cavitated tooth lesions, in which calcium, phosphate and sometimes fluoride ions are deposited into crystal voids in demineralised enamel. Remineralization can contribute towards restoring strength and function within tooth structure.

Canadian health claims by Health Canada, the department of the Government of Canada responsible for national health, has allowed five scientifically verified disease risk reduction claims to be used on food labels and on food advertising. Other countries, including the United States and Great Britain, have approved similar health claims on food labels.

<span class="mw-page-title-main">Added sugar</span> Caloric sweeteners added to food and beverages

Added sugars or free sugars are sugar carbohydrates added to food and beverages at some point before their consumption. These include added carbohydrates, and more broadly, sugars naturally present in honey, syrup, fruit juices and fruit juice concentrates. They can take multiple chemical forms, including sucrose, glucose (dextrose), and fructose.

<span class="mw-page-title-main">Sweetened beverage</span> Type of beverage

Sugar-sweetened beverages (SSB) are any beverage with added sugar. They have been described as "liquid candy". Consumption of sugar-sweetened beverages have been linked to weight gain and an increased risk of cardiovascular disease mortality. According to the CDC, consumption of sweetened beverages is also associated with unhealthy behaviors like smoking, not getting enough sleep and exercise, and eating fast food often and not enough fruits regularly.

References

  1. ↑ Safety data sheet for xylitol Archived 3 March 2016 at the Wayback Machine from Fisher Scientific. Retrieved2014-11-02.
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  3. 1 2 "Food legislation". polyols-eu.org. European Association of Polyol Producers. 22 March 2017. Retrieved 7 February 2019.
  4. 1 2 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. doi:10.1002/14651858.CD010743.pub2. PMC   9345289 . 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. doi:10.1002/14651858.CD010743.pub2. PMC   9345289 . PMID   25809586. Open Access logo PLoS transparent.svg
  5. ↑ Mäkinen KK (June 2000). "The rocky road of xylitol to its clinical application". Journal of Dental Research. 79 (6): 1352–5. doi:10.1177/00220345000790060101. PMID   10890712. S2CID   31432699.
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  21. ↑ 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. doi:10.1080/10408398.2019.1623757. PMID   31204494. S2CID   189944738.
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  27. ↑ 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. doi: 10.2903/j.efsa.2011.2266 .
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  29. ↑ 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. doi:10.1097/MD.0000000000002695. ISSN   0025-7974. PMC   4753897 . PMID   26871802.
  30. ↑ 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. doi: 10.2903/j.efsa.2011.2076 .
  31. ↑ Tiefenbacher, Karl F. (2017). "Technology of Main Ingredients – Sweeteners and Lipids". Wafer and Waffle. Elsevier. pp. 123–225. doi:10.1016/b978-0-12-809438-9.00003-x. ISBN   978-0-12-809438-9.
  32. ↑ 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. doi: 10.1093/ajcn/76.1.5 . PMID   12081815.
  33. ↑ 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. doi: 10.1155/2016/5967907 . PMC   5093271 . PMID   27840639.
  34. ↑ Sugar Alcohols (PDF) (Report). Canadian Diabetes Association. 1 May 2005. Archived from the original (PDF) on 25 April 2012. Retrieved 14 March 2012.
  35. ↑ 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. doi:10.1159/000499194. hdl: 10138/305074 . PMID   31060040. S2CID   146811298.
  36. ↑ "Paws off xylitol; It's dangerous for dogs". US Food and Drug Administration. 7 July 2021. Retrieved 9 September 2021.
  37. 1 2 Schmid, R.D.; Hovda, L.R. (2016). "Acute hepatic failure in a dog after xylitol ingestion". Journal of Medical Toxicology. 12 (2): 201–205. doi:10.1007/s13181-015-0531-7. PMC   4880608 . PMID   26691320.
  38. ↑ Jerzsele, A.; et al. (2018). "Effects of p.o. administered xylitol in cats". Journal of Veterinary Pharmacology and Therapeutics. 41 (3): 409–414. doi: 10.1111/jvp.12479 . PMID   29430681.
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