Xylitol[1]
IUPAC name	(2R,3R,4S)-Pentane-1,2,3,4,5-pentanol
Other names	1,2,3,4,5-Pentahydroxypentane
Identifiers
CAS number	[87-99-0]
Properties
Molecular formula	C5H12O5
Molar mass	152.15 g/mol
Density	1.52 g/cm³
Melting point	92-96 °C Image File history File links Xylitol. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... This article is about the chemical element and its most stable form, or dioxygen. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	216 °C Italic text This article is about the boiling point of liquids. ...
Related compounds
Related alkanes	Pentane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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.^[2] It can be extracted from corn fibre,^[3] birch, raspberries, plums, and corn. Xylitol is roughly as sweet as sucrose but with only two-thirds the food energy. Chemical structure of methane, the simplest alkane Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon (C) and hydrogen (H) (i. ... Pentane (also known as amyl hydride or skellysolve) is an alkane hydrocarbon with the chemical formula CH3(CH2)3CH3. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... A sugar alcohol (also known as a polyol, polyhydric alcohol, or polyalcohol) is a hydrogenated form of carbohydrate, whose carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. ... Sugar free redirects here. ... Species Many species; see text and classification Birch is the name of any tree of the genus Betula, in the family Betulaceae, closely related to the beech/oak family, Fagaceae. ... Cultivated raspberries The raspberry (plural, raspberries) is the edible fruit of a number of species of the genus Rubus. ... Species See text. ... This article is about the maize plant. ... Flash point N/A Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ... Food energy is the amount of energy in food that is available through digestion. ...

Extraction of xylitol

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.^{[citation needed]} Image File history File links Xylitol_crystals. ... Image File history File links Xylitol_crystals. ... Species Many species; see text and classification Birch is the name of any tree of the genus Betula, in the family Betulaceae, closely related to the beech/oak family, Fagaceae. ... For other uses, see Europe (disambiguation). ... This article is about the disease that features high blood sugar. ... Not to be confused with inulin. ... This article is about the maize plant. ...

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,^{[citation needed]} 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.^[4] A calorie refers to a unit of energy. ... This article is about sugar as food and as an important and widely-traded commodity. ... Aftertaste is the persistence of a sensation of flavor after the stimulating substance has passed out of contact with the sensory end organs for taste. ... This article is about the disease that features high blood sugar. ... Hyperglycemia, hyperglycaemia, or high blood sugar is a condition in which an excessive amount of glucose circulates in the blood plasma. ... In medicine, blood sugar is a term used to refer to levels of glucose in the blood. ... This article deals with sugar as food and as an important, widely traded commodity; the word also has other uses; see Sugar (disambiguation) A sugar is a form of carbohydrate; the most commonly used sugar is a white crystalline solid, sucrose; used to alter the flavor and properties (mouthfeel, perservation...

Dietary use worldwide

Xylitol is widely used in Finland, its "home country". Many Finnish confectioneries employ xylitol, or have a xylitol version available. Virtually all chewing gum sold in Finland, and in the rest of Europe,^{[citation needed]} is sweetened with xylitol. It has been suggested that Candy be merged into this article or section. ... Chewing gum Chewing gum is a type of confectionery designed for fun and chewing. ...

The formerly Spanish company Chupa Chups, now Italian, makes a xylitol-based breath mint, Smint, that it markets worldwide. Note: This page or section contains IPA phonetic symbols in Unicode. ... Smint logo Smint is a breath mint made by Chupa Chups, which bills it as the first dental candy. ...

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 introduced xylitol-containing products to Hong Kong and Guangdong, the word "xylitol" is transcribed into Cantonese as "晒駱駝" (Jyutping: saai³ lok⁶ to⁴), which literally means "suntan camel", and the camel is used as a figurative icon in its advertisements.^[5] Packages of Extra Extra is the name of the second sugarfree gum launched by Wrigleys in the United States and was introduced in 1984 (the first being Orbit in 1977). ... Not to be confused with the former Kwantung Leased Territory in north-eastern China. ... Transcription is the conversion into written, typewritten or printed form, of a spoken language source, such as the proceedings of a court hearing. ... This article is about all of the Cantonese (Yue) dialects. ... Jyutping (sometimes spelled Jyutpin) is a romanization system for Standard Cantonese developed by the Linguistic Society of Hong Kong (LSHK) in 1993. ...

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,^[6] and IceBreakers brand Ice Cubes Gum from 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. Trident cum is a brand of sugarless chewing cum popular in the United States, Canada, Brazil and Mexico. ... Sorbitol, also known as glucitol, is a sugar alcohol the body metabolises slowly. ... Maltitol is a sugar alcohol (a polyol) used as a sugar substitute. ... The Hershey Company (NYSE: HSY), until April 2005 Hershey Foods Corporation,[5] commonly called Hersheys, is Americas largest chocolate company. ... Koolerz was a chewing gum produced by the The Hershey Company. ...

In 2006, William Wrigley Jr. Company reformulated their 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. Orbit is a brand of sugarless chewing gum from the Wrigley Company. ...

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.^{[citation needed]} 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.^[7] 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)."^[7] Recent research^[8] confirms a 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.) Toothfriendly products are safe for teeth. ... Improper removal of plaque caused a build up of calculus (dark yellow colour) near the gums on almost all the teeth. ... Flash point N/A Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ... Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic micro organisms classified in the kingdom Fungi, with about 1,500 species described;[1] they dominate fungal diversity in the oceans. ... For other uses, see Bread (disambiguation). ...

Xylitol based products are allowed by the U.S. Food and Drug Administration to make the medical claim that they do not promote dental cavities.^[9] FDA redirects here. ...

A recent study demonstrated that a water additive for animals containing xylitol was effective in reducing plaque and calculus accumulation in cats.^[10] Calculus (dark yellow colour) can be seen on almost all teeth near the gums In dentistry, calculus or tartar refers to hardened plaque on the teeth, formed by the presence of saliva, debris, and minerals. ...

Diabetes

Possessing approximately 40% less food energy,^[11] 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. The calorie is a unit of energy, in particular heat. ... In medicine, blood sugar is a term used to refer to levels of glucose in the blood. ... Hyperglycemia, hyperglycaemia, or high blood sugar is a condition in which an excessive amount of glucose circulates in the blood plasma. ... Not to be confused with inulin. ...

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 bones in laboratory rats, and actually improves bone density.^[12][13] Osteoporosis is a disease of bone that leads to an increased risk of fracture. ... This article is about the skeletal organs. ...

Ear and upper respiratory infections

Studies have shown that xylitol chewing gum can help prevent ear infections^[14] (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.^[15] 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.^[16] 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.^[17] Xylitol can be applied nasally through a saline solution containing xylitol. Otitis media is inflammation of the middle ear: the small space between the ear drum and the inner ear. ... Wet-type human earwax on a cotton swab. ... The middle ear is the portion of the ear internal to the eardrum, and external to the oval window of the cochlea. ... Anatomy of the human ear. ...

Candida yeast

A recent report suggests that consumption of xylitol may help control oral infections of Candida yeast; in contrast, galactose, glucose, and sucrose may increase proliferation.^[18] Species C. albicans C. dubliniensis C. glabrata C. guilliermondii C. kefyr C. krusei C. lusitaniae C. milleri C. oleophila C. parapsilosis C. tropicalis C. utilis Candida is a genus of yeasts. ... Galactose (also called brain sugar) is a type of sugar found in dairy products, in sugar beets and other gums and mucilages. ... Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. ... Flash point N/A Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ...

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%.^[19] Binomial name Streptococcus mutans Clarke 1924 Streptococcus mutans is a Gram-positive, facultatively anaerobic bacteria commonly found in the human oral cavity and is a significant contributor to tooth decay. ...

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 toxicity, and people have consumed as much as 400 grams daily for long periods with no apparent ill effects.^[20] Laxatives (or purgatives) are foods, compounds, or drugs taken to induce bowel movements or to loosen the stool, most often taken to treat constipation. ... Toxic redirects here, but this is also the name of a song by Britney Spears; see Toxic (song) Look up toxic and toxicity in Wiktionary, the free dictionary. ... BIC pen cap, about 1 gram. ...

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.^[21] Low blood sugar can manifest as loss of coordination, depression, collapse and seizures as soon as 30 minutes after ingestion.^[22][23] 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.^[24] This article is about the domestic dog. ... Hypoglycemia is a medical term referring to a pathologic state produced and usually defined by a lower than normal amount of sugar (glucose) in the blood. ...

Other applications of xylitol

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.^[25] This application has also been used by Yonex to make shirts.^[26] Image File history File links No higher resolution available. ... For the digital circuits term, see Application-specific integrated circuit. ... Yonex Co. ...

See also

• Other sugar alcohols: mannitol, sorbitol, erythritol, maltitol, lactitol
• Herbal sweetener: stevia
• Artificial sweeteners: aspartame, sucralose
• L-xylulose reductase

Mannitol or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6) is an osmotic diuretic agent and a weak renal vasodilator. ... Sorbitol, also known as glucitol, is a sugar alcohol the body metabolises slowly. ... Erythritol ((2R,3S)-butane-1,2,3,4-tetraol) is a natural sugar alcohol (a type of sugar substitute) which has been approved for use in the United States[1] and throughout much of the world. ... Maltitol is a sugar alcohol (a polyol) used as a sugar substitute. ... Lactitol is a sugar alcohol used as a replacement sweetener for low calorie foods with approximately 40% of the sweetness of sugar. ... Species About 150 species, including: Stevia eupatoria Stevia ovata Stevia plummerae Stevia rebaudiana Stevia salicifolia Stevia serrata Stevia is a genus of about 150 species of herbs and shrubs in the sunflower family (Asteraceae), native to subtropical and tropical South America and Central America. ... Aspartame (or APM) (pronounced or ) is the name for an artificial, non-saccharide sweetener, aspartyl-phenylalanine-1-methyl ester; i. ... Sucralose is an artificial sweetener. ... L-xylulose reductase is an enzyme responsible for the metabolism of xylulose, converting it into xylitol. ...

References

1. ^ MSDS for xylitol
2. ^ Gare, Fran (February 1, 2003). The Sweet Miracle of Xylitol. Basic Health Publications, Inc.. ISBN 1-59120-038-5. 
3. ^ 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.
4. ^ Sugar Substitutes: Are They Safe? - HealtHints Newsletter
5. ^ Xylitol advertisement in Guangdong
6. ^ Smokey Mountain Snuff FAQ
7. ^ ^{a b} American Academy of Pediatric Dentistry. (2006) Policy on the Use of Xylitol in Caries Prevention.
8. ^ Tanzer, JM (1995). Xylitol chewing gum and dental caries. International dental journal 45 (1 Suppl 1):65-76. (online abstract)
9. ^ U.S. FDA 21 CFR §101.80
10. ^ Clarke, D.E. (2006) Drinking Water Additive Decreases Plaque and Calculus Accumulation in Cats. J Vet Dent(23)2:79-82
11. ^ www.diabetes.org.nz/food/artificialsweeteners.html
12. ^ Mattila PT, Svanberg MJ, Jämsä T, Knuuttila ML (2002). Improved bone biomechanical properties in xylitol-fed aged rats.Metabolism 51(1):92-6. (online abstract)
13. ^ 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. (online)
14. ^ Uhari M, et al. (1998). A novel use of xylitol sugar in preventing acute otitis media. Pediatrics, 102(4): 879–974.
15. ^ Drgreene.com commercial site
16. ^ Nasal-xylitol.com commercial site
17. ^ Besttreaments.co.uk
18. ^ 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
19. ^ Maternal Xylitol Consumption to Prevent Mother-Child Transmission of Mutans Streptococci
20. ^ [1] Mäkinen,longterm tolerance
21. ^ 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
22. ^ ASPCA article
23. ^ Dunayer, E.K (2004) Hypoglycemia following canine ingestion of xylitol-containing gum, Veterinary and Human Toxicology 46(2):87-88
24. ^ Dunayer, E.K (2006) New findings on the effects of xylitol ingestion in dogs Veterinary Medicine 101(12):791-797
25. ^ information from the Danisco website
26. ^ Yonex Mens Wimbledon Very Cool T-Shirt