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xylitol

Product name xylitol
Synonyms xylit
(2S,3R,4R)-pentane-1,2,3,4,5-pentaol
GOST no data
CAS 87-99-0

Xylitol (E967) is a colorless, hygroscopic crystalline compound, a five-carbon sugar alcohol. It is soluble in water (169g/100ml at 20°C), methanol, ethanol, glycols, glycerol, pyridine, acetic acid and so on. Almost insoluble in dioxane, diethyl ether, esters, hydrocarbons, alkyl halides, propanol, butanol. Xylitol is an optically inactive compound. As a polyatomic alcohol it shows typical polyol chemical properties, thus it can form colored complexes with metals. Copper complex is used for xylitol quantitative and qualitative analysis by photometry.

It's sweetening property is twice as much of the sucrose. It also produces a perceived sensation of coolness in mouth as it comes in contact with the saliva for its negative heat of solution. Xylitol easily metabolizes (independently of insulin) in human body and produces small amount of energy (4.06 cal/g). Xylitol is found in nature in the fibers of many fruits and vegetables, including various berries (raspberries, strawberries, yellow plums), cauliflower, spinach, corn husks, oats, birch syrup, and mushrooms.

Recent investigations shows that xylitol may actively aid in repairing minor cavities caused by dental caries. It possess a weak laxative and choleretic action.

Production.

Xylitol produces on commercial scale by bagasse (rice and cotton seed hulls, corn stalks, coconut shells, sunflower peelings) processing. Pentosans occurring in many plants contain polysaccharide xylan, which can be hydrolized by action of mineral acids (sulfuric or hydrochloric) into D-xylose (pentose, which is also known as wood or birch sugar). Then D-xylose is hydrogenated on Raney nickel to produce xylitol. The process reactions can be summarized as under:

(C5H8O4)n (xylan) + HCl --> nC5H10O5 (D-xylose)

C5H10O5 + H2 --> C5H12O5 (xylitol)


Some manufacturers for making xylitol use microbiological or fermentative methods.

Uses.

  • Xylitol is a "toothfriendly" sugar. It is used as sugar-substitute in chewing gums and in toothpastes for oral hygiene and treatment of oral disease.
  • in food industries for making dietary products: beverages, cakes, gums and so on;
  • as a sugar alternative for diabetics;
  • as a treatment for osteoporosis, to penetrate the blood-brain barrier, for treatment of increased intraocular pressure;
  • as a component in making xyphthalic alkid resins, non-ionic surfactants, lacquers and adhesives;
  • to produce 1,4-xylitol anhydride - xylitane;
  • as a plasticizer and humidity stabilizer in production of cellophane, paper, perfumery and in cosmetics;

  • Manufacturer(s) State JSC Fergana chemical plant of furan compounds
    Chemical structure of xylitol

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