This MedLibrary.org supplementary page on Xylitol is provided directly from the open source Wikipedia as a service to our readers. Please see the note below on authorship of this content, as well as the Wikipedia usage guidelines. To search for other content from our encyclopedia supplement, please use the form below:
Related Sponsors
| Xylitol[1] | |
|---|---|
 |
|
| IUPAC name | (2R,3R,4S)-Pentane-1,2,3,4,5-pentol |
| 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 |
| Boiling point |
216 °C |
| Related compounds | |
| Related alkanes | Pentane |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
|
Xylitol (from Greek ξύλον - xylon, "wood" + suffix -itol, used to denote sugar alcohols) is an organic compound with the formula (CHOH)3(CH2OH)2. This achiral species is one of three isomers of 1,2,3,4,5-pentapentanol. This sugar alcohol is used as a naturally occurring sugar substitute found in the fibres 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 with only two-thirds the food energy.
Contents |
Extraction of xylitol
Xylitol (Finnish ksylitoli) was first derived from Birch trees in Finland in the 20th century and was first popularised in Europe as a safe sweetener for people with diabetes that would not impact insulin levels. Today, using hardwood or maize sources, the largest manufacturer globally is the Danish company Danisco, with several other suppliers from China.citation needed
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]
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 is sweetened with xylitol.citation needed
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 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]
In 2004, popular North American Trident gum was reformulated to include xylitol, but not as the main sweetener (which are still aspartame, sorbitol and maltitol). The green apple flavor can be found without aspartame. 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.
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. Xylimax gum and mints have 1 gram of xylitol per piece, and xylitol is the only sweetener. (available in USA)
Spry brand chewing gum and mouthwash contain xylitol as their only sweetener.
Medical applications
Dental care
Xylitol is a "tooth friendly" sugar. 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 remineralise 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 U.S. Food and Drug Administration to make the medical claim that they do not promote dental cavities.[9]
A recent study demonstrated that a water additive for animals containing xylitol was effective in reducing plaque and calculus accumulation in cats.[10]
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.
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]
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 explained on the following referenced website about 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.
Infection
Xylitol has been found to increase the activity of neutrophils, the white blood involved in fighting many bacteria. This effect seems to be quite broad, acting even in cases such as general sepsis [18]
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.[19]
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%.[20]
Concerns
Xylitol, like most sugar alcohols, has 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.[21]
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.[22] Low blood sugar can manifest as loss of coordination, depression, collapse and seizures as soon as 30 minutes after ingestion.[23][24] Intake of very high doses of xylitol (greater than 500 - 1000 mg/kg bwt) has also been implicated in liver failure in dogs, which can be fatal.[25]
See also
- Other sugar alcohols: mannitol, sorbitol, erythritol, maltitol, lactitol
- Herbal sweetener: stevia
- Artificial sweeteners: aspartame, sucralose
- L-xylulose reductase
References
- ^ MSDS for xylitol
- ^ Gare, Fran (February 1, 2003). The Sweet Miracle of Xylitol. Basic Health Publications, Inc.. ISBN 1-59120-038-5.
- ^ R Sreenivas Rao, Ch. Pavanajyothi, RS Prakasham, PN Sharma, L Venkateswar Rao (2006) Xylitol production from corn fibre and sugarcane bagasse hydrolysates by Candida tropicalis Bioresource Technology 97:1974-1978.
- ^ Sugar Substitutes: Are They Safe? - HealtHints Newsletter
- ^ Xylitol advertisement in Guangdong
- ^ Smokey Mountain Snuff FAQ
- ^ a b American Academy of Pediatric Dentistry. (2006) Policy on the Use of Xylitol in Caries Prevention.
- ^ Tanzer, JM (1995). Xylitol chewing gum and dental caries. International dental journal 45 (1 Suppl 1):65-76. (online abstract)
- ^ U.S. FDA 21 CFR §101.80
- ^ Clarke, D.E. (2006) Drinking Water Additive Decreases Plaque and Calculus Accumulation in Cats. J Vet Dent(23)2:79-82
- ^ www.diabetes.org.nz/food/artificialsweeteners.html
- ^ 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)
- ^ 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)
- ^ Uhari M, et al. (1998). A novel use of xylitol sugar in preventing acute otitis media. Pediatrics, 102(4): 879–974.
- ^ Drgreene.com commercial site
- ^ Nasal-xylitol.com commercial site
- ^ Besttreaments.co.uk
- ^ Renko, Marjo; Valkonen P, Tapiainen T, Kontiokari T, Mattila P, Knuuttila M, Svanberg M, Leinonen M, Karttunen R, Uhari M (2008 Mar 11;8:45.). "Xylitol-supplemented nutrition enhances bacterial killing and prolongs survival of rats in experimental pneumococcal sepsis". BMC Microbiology. PMID 18334022. Retrieved on 2008-08-23.
- ^ 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
- ^ Maternal Xylitol Consumption to Prevent Mother-Child Transmission of Mutans Streptococci
- ^ [1] Mäkinen,longterm tolerance
- ^ Dunayer, E.K., Gwaltney-Brant, S.M. (2006) Acute hepatic failure and coagulopathy associated with xylitol ingestion in dogs, Journal of the American Veterinary Medical Association (229)7:1113-1117
- ^ ASPCA article
- ^ Dunayer, E.K (2004) Hypoglycemia following canine ingestion of xylitol-containing gum, Veterinary and Human Toxicology 46(2):87-88
- ^ Dunayer, E.K (2006) New findings on the effects of xylitol ingestion in dogs Veterinary Medicine 101(12):791-797
|
|||||
Wikipedia content modification information:
- This page was last modified on 5 October 2008, at 08:05.
Wikipedia Authorship and Review
Wikipedia content provided here is not reviewed directly by MedLibrary.org. Wikipedia content is authored by an open community of volunteers and is not produced by or in any way affiliated with MedLibrary.org.
Wikipedia Usage Guidelines
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article on "Xylitol".
The URL for this specific entry is:
All Wikipedia text is available under the terms of the GNU Free Documentation License. (See Copyrights for details). Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc.