Xylitol

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Xylitol[1]
IUPAC name (2S,3R,4R)-Pentane-1,2,3,4,5-pentanol
Other names 1,2,3,4,5-Pentahydroxypentane
Identifiers
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Properties
C5H12O5
Molar mass 152.15 g/mol
Density 1.52 g/cm³
Melting point
Boiling point
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Xylitol, also called wood sugar or birch sugar, 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 fiber,[3] birch, raspberries, plums, and corn. Xylitol is roughly as sweet as sucrose but with two-thirds the food energy.

Extraction of xylitol

File:Xylitol crystals.jpg
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. In the late 20th century, xylitol in granular form began to be mass produced in the United States under the brand name "Ultimate Sweetener" using beet plants in California. Today, using maize sources, most world supplies reportedly come from China.[citation needed]

Properties

One teaspoon of xylitol contains 9.6 calories, as compared to one teaspoon of sugar, which has 15 calories. Xylitol also contains zero net effective carbohydrates,[citation needed] whereas sugar contains 4 grams per teaspoon. 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, and in the rest of Europe, is sweetened with xylitol.

The formerly Spanish company, now Italian, Chupa Chups 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 sorbitol and maltitol). Also sold in North America is Carefree Koolerz, which is a sugarless gum sweetened exclusively with xylitol. It is also found in Smokey Mountain Snuff,[6] and IceBreakers brand Ice Cubes Gum from Hershey.

In 2006, William Wrigley Jr. Company reformulated their Orbit gum to contain xylitol and released it under the name "Orbit Complete."

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. Recent research[7] 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.)

Xylitol based products are allowed by the U.S. Food and Drug Administration to make the medical claim that they do not promote dental caries.[8]

A recent study demonstrated that a water additive for animals containing xylitol was effective in reducing plaque and calculus accumulation in cats.[9]

Diabetes

Possessing approximately 40% less food energy,[10] 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.[11][12]

Ear and upper respiratory infections

Studies have shown that xylitol chewing gum can help prevent ear infections[13] (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 which connect the nose and ear.[14] 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.[15] 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.[16] Xylitol can be applied nasally through a saline solution containing xylitol, such as Xlear Nasal Wash.

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.[17]

Health concerns

Xylitol, like most sugar alcohols, can have a mild laxative effect at high doses. It has no known toxicity, and people have consumed as much as 400 grams daily for long periods with no apparent ill effects.[18]

Dogs ingesting foods containing high doses of xylitol (greater than 100mg xylitol consumed per kg bodyweight) have presented with low blood sugar (hypoglycaemia) which can be life-threatening.[19] Low blood sugar can manifest as loss of coordination, depression, collapse and seizures as soon as 30 minutes after ingestion.[20][21] 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.[22]

One reported death occurred in a standard poodle that ate five or six cookies sweetened with xylitol.[23]

As humans can tolerate much higher doses of xylitol, large amounts of xylitol can be found in even small quantities of food such as sugar-free gums, baked goods and tooth pastes.

Dogs that have eaten products containing high levels of xylitol might need immediate medical attention even if they are not yet showing illness. Sick dogs (vomiting, weak, seizuring, etc) are likely to need aggressive veterinary treatment and close monitoring of blood values.[24][25][26]

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.[27]

This application has also been used by YONEX to make shirts

References

  1. MSDS for xylitol
  2. Gare, Fran (Feb 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. http://fcs.tamu.edu/health/health_education_rural_outreach/Health_Hints/2006/april06/sugar-substitutes.php
  5. Xylitol advertisement in Guangdong
  6. Smokey Mountain Snuff FAQ
  7. Tanzer, JM (1995). Xylitol chewing gum and dental caries. International dental journal 45(1 Suppl 1):65-76. (online abstract)
  8. U.S. FDA 21 CFR §101.80
  9. Clarke, D.E. (2006) Drinking Water Additive Decreases Plaque and Calculus Accumulation in Cats. J Vet Dent(23)2:79-82
  10. www.diabetes.org.nz/food/artificialsweeteners.html
  11. 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)
  12. 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)
  13. Uhari M, et al. (1998). A novel use of xylitol sugar in preventing acute otitis media. Pediatrics, 102(4): 879–974.
  14. Drgreene.com
  15. Nasal-xylitol.com
  16. Besttreaments.co.uk
  17. 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
  18. [1] Mäkinen,longterm tolerance
  19. 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
  20. ASPCA article
  21. Dunayer, E.K (2004) Hypoglycemia following canine ingestion of xylitol-containing gum, Veterinary and Human Toxicology 46(2):87-88
  22. Dunayer, E.K (2006) New findings on the effects of xylitol ingestion in dogs Veterinary Medicine 101(12):791-797
  23. Dunayer, E.K (2006) New findings on the effects of xylitol ingestion in dogs Veterinary Medicine 101(12):791-797
  24. 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
  25. AVMA Press Release
  26. Dunayer, E.K (2006) New findings on the effects of xylitol ingestion in dogs Veterinary Medicine 101(12):791-797
  27. information from the Danisco website

See also

da:Xylitol de:Xylitol ko:자일리톨 it:Xilitolo nl:Xylitol no:Xylitol nn:Xylitol fi:Ksylitoli sv:Xylitol



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