Xylitol
[CAS# 87-99-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Thiopyrimidine
• Name: Xylitol
• Molecular Formula: C₅H₁₂O₅
• Molecular Weight: 152.15
• CAS Registry Number: 87-99-0 (16277-71-7)
• EC Number: 201-788-0
• SMILES: C([C@H]([C@@H]([C@H](CO)O)O)O)O

Properties

• Solubility: Soluble 0.1 g/mL (water)
• Density: 1.515 g/mL
• Melting point: 92-96 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

The discovery of xylitol dates back to the late 19th century. In 1891, German chemist Emil Fischer and his colleague Rudolf Stahel first isolated xylitol from birch wood. They found a white crystalline substance that was comparable in sweetness to sucrose, but with unique metabolic properties. This polyol, or sugar alcohol, has the chemical formula C5H12O5 and features a molecular structure of five carbon atoms, including three secondary alcohol groups, which contribute to its stability and sweetness. Xylitol’s main properties are high water solubility, low glycemic index, and refreshing cooling effect when dissolved, making it a versatile ingredient in a variety of formulations.

Xylitol is widely used as a low-calorie sweetener in food and beverages. It provides about 2.4 calories per gram, significantly less than sucrose’s 4 calories per gram, making it an ideal sugar substitute for weight control and diabetes-friendly products. Its sweetness is roughly equivalent to sugar, allowing it to be substituted seamlessly in recipes.

Unlike traditional sugar, its non-fermentable nature prevents it from causing tooth decay. Xylitol is a common ingredient in sugar-free gum, candy, and mints because it inhibits the growth of Streptococcus mutans, a bacteria that causes tooth decay. This dental health benefit is one of the main reasons why it is widely used in oral care products.

In baking and confectionery, xylitol helps retain moisture and enhance texture without causing browning, making it suitable for products such as cookies, cakes, and frostings. Its stability at high temperatures also helps to maintain the flavor and consistency of baked goods.

The most important application of xylitol is in oral care. It is commonly used in toothpastes, mouthwashes, and dental chews due to its anti-caries properties. Xylitol reduces plaque formation and promotes the remineralization of tooth enamel, helping to prevent tooth decay and improve overall dental health. Regular use of products containing xylitol can reduce tooth decay and improve oral hygiene.

Xylitol also stimulates saliva production, helping to combat dry mouth (xerostomia). This is particularly beneficial for people who have dry mouth due to illness or as a side effect of medications, as increased saliva flow helps neutralize acids and reduces the risk of oral infections.

In pharmaceuticals, xylitol is used as an excipient in drug formulations. Its sweet taste and non-cariogenic properties make it suitable for use in chewable tablets, syrups, and lozenges, which can improve patient compliance, especially in pediatric formulations.

Emerging research suggests that xylitol may aid wound healing. Its antimicrobial properties help reduce the risk of wound infection and promote tissue regeneration, making it a potential ingredient in wound care products.

Due to its low glycemic index, xylitol is an excellent sugar substitute for diabetics. It does not cause a significant increase in blood sugar levels and is a safe sweetener that can be used to control blood sugar levels while enjoying a sweet taste.

In the industrial sector, xylitol is used to produce biodegradable polymers. Its chemical structure allows the synthesis of polyesters and other biocompatible materials, which helps develop environmentally friendly products in packaging and other applications.

Xylitol is also used as a fermentation substrate in biotechnology, supporting the growth of certain microorganisms and the production of bio-based chemicals. Its role in fermentation processes highlights its versatility as a raw material for industrial biotechnology.

References

1867. Die trockne Destillation des Holzes und die Producte derselben. Die trockene Destillation des Holzes und Verarbeitung der durch dieselbe erhaltenen Rohproducte auf feinere, wie auf Essigsaeure, essigsaure Salze, Terpentinoel, Wagenschmiere, Kienruss etc., 1.
DOI: 10.1007/978-3-662-33095-1_2

2024. Xylitol bioproduction by Candida tropicalis: effects of glucose/xylose ratio and pH on fermentation and gene expression. Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology], 55(4).
DOI: 10.1007/s42770-024-01564-y

2024. Production of sucrose-free and probiotic chocolate pudding using xylitol in combination with Lacticaseibacillus rhamnosus GG and Saccharomyces boulardii. Journal of Food Measurement and Characterization, 18(7).
DOI: 10.1007/s11694-024-03003-w