Xylitol

From Wikipedia, the free encyclopedia

Xylitol[1]
Chemical name	(2S,3R,4R)-Pentane-1,2,3,4,5-pentaol
Other names	1,2,3,4,5-Pentahydroxypentane
Chemical formula	C5H12O5
Molecular mass	152.15 g/mol
CAS number	[87-99-0]
Density	1.52 g/cm³
Melting point	92-96 °C
Boiling point	216 °C
SMILES	OC[C@H](O)[C@@H](O)[C@H](O)CO
Related alkanes	Pentane
E number	E967
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 contains 40% less food energy.

Contents 1 Extraction of xylitol 2 Properties 3 Dietary use worldwide 4 Medical applications 4.1 Dental care 4.2 Diabetes 4.3 Osteoporosis 4.4 Ear and upper respiratory infections 4.5 Candida yeast 5 Health concerns 6 Trivia 7 References 8 See also

[edit] Extraction of xylitol

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 primarily from China.^{[citation needed]}

As a food product it is not subject to drug regulations but xylitol based products have been certified by the American Food and Drug Administration as a suitable remedy for infantile dental caries.

[edit] 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, 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.[1]

[edit] 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, as well as 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. China and Korea even have a brand of gum named "Xylitol," while Japan has a brand called "Xylish."

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,^[4] 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."

[edit] Medical applications

[edit] 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^[5] 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 bread, for instance.)

[edit] Diabetes

Possessing approximately 40% less food energy,^[6] 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.

[edit] Osteoporosis

Xylitol also appears to have potential as a treatment for osteoporosis. A group of Finnish researchers have found that dietary xylitol prevents weakening of bones in laboratory rats, and actually improves bone density.^[7][8]

[edit] Ear and upper respiratory infections

Studies have shown that xylitol chewing gum can help prevent ear infections^[9] (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.^[10] 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.^[11] When bacteria enter the body they hold on to our 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.^[12] Xylitol can be applied nasally through a saline solution containing xylitol, such as Xlear Nasal Wash.

[edit] 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.^[13]

[edit] Health concerns

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

For dogs, xylitol can cause serious – possibly life-threatening – problems. Dogs which ingest products sweetened with xylitol may experience insulin-mediated low blood sugar hypoglycemia, possibly resulting in loss of coordination, depression, collapse and seizures as soon as 30 minutes after ingestion. It can also cause death in dogs. One case occurred in a standard poodle that ate five or six sweetened cookies. Xylitol can also cause liver failure and coagulopathy (failure of blood clotting) in dogs. Dogs that have eaten products sweetened with xylitol, including some sugar free gums, baked goods and tooth pastes, need immediate medical attention even if they are not showing illness. Sick dogs (vomiting, weak, seizuring, etc) are likely to need aggressive veterinary treatment and close monitoring of blood values.^[14][15][16]

[edit] Trivia

• When Extra introduced xylitol-containing products to Hong Kong and Guangdong, it translated the word "xylitol" phoenetically into Cantonese as saai³lok⁶to⁴ (晒駱駝), which literally meant "suntan camel", and used the camel as a figurative icon in its advertisements.^[17]
• 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.^[18]

[edit] References

[edit] See also

• Other sugar alcohols: mannitol, sorbitol, erythritol, maltitol, lactitol
• Herbal sweetener: stevia
• Artificial sweeteners: aspartame, sucralose
• Another birch-extracted treat: birch syrup