Xylitol

 

Xylitol is a naturally occurring five-carbon sugar alcohol found in most plant material, including many fruits and vegetables. 

Xylitol-rich plant materials include birch and beechwood. 

Xylitol is colorless or white crystalline solid freely soluble in water that can be classified as a polyalcohol and a sugar alcohol, specifically an alditol.  

Synonyms: 

Xylitol

xylitol

Pre-Registration process

IUPAC names

(2R, 3R, 4S)-pentane-1,2,3,4,5-pentol

(2R,3r,4S)-Pentan-1,2,3,4,5-pentol

(2R,3r,4S)-pentane-1,2,3,4,5-pentol

(2S,3R,4R)-Pentane-1,2,3,4,5-pentaol

(2S,4R)-pentane-1,2,3,4,5-pentol

D-erythro-pentitol

pentane-1,2,3,4,5-pentol

Xylitol

xylitol

Xylitol, Xylit

Trade names

Xylitol T

EC / List no.: 201-788-0

CAS no.: 87-99-0

Mol. formula: C5H12O5

Xylitol is a chemical compound with the formula C5H12O5, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. 

The name derives from Ancient Greek: ξύλον, xyl[on] 'wood,' with the suffix -itol used to denote sugar alcohols.

Xylitol is used as a food additive and sugar substitute. 

Its European Union code number is E967.

Replacing sugar with xylitol in food products may promote better dental health, but evidence is lacking on whether xylitol itself prevents dental cavities.

Xylitol is a sugar alcohol that is commonly used as a sweetener.

 

Xylitol can be found naturally or artificially prepared mainly from plant materials chemically or by fermentation of hemicelluloses from agricultural biomass by yeast or bacteria strains. 

Xylitol has a significant antiplaque effect on teeth surface and can reduce gingival inflammation; it is being used as a preventive agent for dental caries due to decreasing the growth levels of pathogenic Streptococcus mutans and Streptococcus sangui at the very early stages. 

Xylitol can bind with calcium ions, consequently remineralizing teeth enamel and preventing osteoporosis. 

Due to its antibacterial and anti-inflammatory potential, xylitol can treat respiratory tract and middle ear diseases and prevent some diseases that cannot be cured through antibiotics or surgery. 

Xylitol can reduce constipation, diabetes, obesity, and other body syndromes or illnesses; it has also been revealed to stimulate digestion and the immune system. 

However, it can produce some side effects, such as irritable bowel syndrome, diarrhea, nephrolithiasis, etc., when consumed in excessive amounts. 

Different vehicles deliver xylitol to the human body, but chewing gums occupy a leading position. 

• Xylitol efficiently stimulates the immune system, digestion, lipid, and bone metabolism.

• Xylitol helps control glycemic and obesity and reduces ear and respiratory infections.

• Xylitol treats diseases that cannot be cured through antibiotics or surgery.

Xylitol is widely used as a sugar substitute and in "sugar-free" food products. 

Xylitol is added to chewing gum and other oral care products to prevent tooth decay and dry mouth. 

Xylitol is a non-fermentable sugar alcohol by most plaque bacteria, indicating that it cannot be fermented into cariogenic acid end-products. 

Xylitol works by inhibiting the growth of the plaque and saliva microorganisms after accumulating intracellularly into the microorganism. 

The recommended dose of xylitol for dental caries prevention is 6–10 g/day, and most adults can tolerate 40 g/day without adverse events.

IUPAC name: meso-Xylitol

Systematic IUPAC name: (2R,3R,4S)-Pentane-1,2,3,4,5-pentol

Other names

(2R,3R,4S)-Pentane-1,2,3,4,5-pentaol 

(2R,3R,4S)-1,2,3,4,5-Pentahydroxypentane

Xylite

Identifiers

CAS Number: 87-99-0 

History

Emil Fischer, a German chemistry professor, and his assistant Rudolf Stahel isolated a new compound from beech wood chips in September 1890 and named it Xylit, the German word for xylitol. 

The following year, the French chemist M.G. Bertrand isolated xylitol syrup by processing wheat and oat straw.

Sugar rationing during World War II led to an interest in sugar substitutes. 

Interest in xylitol and other polyols intensified, leading to their characterization and manufacturing methods.

Xylitol is one of three 5-carbon sugar alcohols.