D(+)-Xylose
[CAS# 58-86-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: D(+)-Xylose
• Synonyms: Wood sugar
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• CAS Registry Number: 58-86-6
• EC Number: 200-400-7
• SMILES: C([C@H]([C@@H]([C@H](C=O)O)O)O)O

Properties

• Melting point: 148-158 °C
• alpha: 20 ° (c=10, H2O)
• Water solubility: soluble

Safety Data

• Safety Statements: S24/25

Discovery and Applications

D(+)-Xylose is a naturally occurring sugar with significant applications in various fields, including biochemistry, medicine, and food science. It was first isolated in the early 20th century during studies on plant polysaccharides. D(+)-Xylose is a pentose sugar, which means it has five carbon atoms, and it is commonly found in plant materials, especially in hemicellulose, which is a major component of plant cell walls.

The discovery of D(+)-Xylose is attributed to the work of early carbohydrate chemists who were investigating the structure and properties of complex carbohydrates. The sugar was identified through the hydrolysis of xylan, a polysaccharide found in wood and plant fibers. This process revealed D(+)-Xylose as a key component of the resulting sugar mixture, contributing to the understanding of plant cell wall composition and the chemistry of pentose sugars.

In the field of biochemistry, D(+)-Xylose plays a crucial role as a marker in diagnostic tests. One of its primary applications is in the D-xylose absorption test, which is used to assess the absorption capabilities of the small intestine. This test helps diagnose malabsorption conditions and gastrointestinal disorders. The patient consumes a dose of D(+)-Xylose, and its levels in the blood and urine are measured to evaluate the digestive system's function.

In the food industry, D(+)-Xylose is utilized as a sweetener and as a component in the production of various sugar substitutes. Its sweetness is less intense than that of sucrose, but it can be used to modify the sweetness profile of products and to provide functional benefits in certain food formulations. Additionally, D(+)-Xylose is used in the production of xylitol, a sugar alcohol derived from xylose, which is commonly used as a sugar substitute in products such as chewing gum and dental care items.

The chemical properties of D(+)-Xylose also make it valuable in research on carbohydrate chemistry and enzymology. Its interactions with enzymes and other carbohydrates provide insights into the mechanisms of carbohydrate metabolism and the synthesis of complex polysaccharides.

Despite its beneficial applications, the extraction and purification of D(+)-Xylose from natural sources can be challenging due to its presence in complex mixtures. Advances in extraction and analytical techniques have improved the efficiency and purity of D(+)-Xylose obtained for various applications.

References

2024. Regulatory potential of a xylated rhamnoglycan from Ulva reticulata on inflammatory cytokines. Journal of Applied Phycology.
DOI: 10.1007/s10811-024-03352-5

2024. Assessment of Lignin Residues from Bioethanol Production of Olive Stones as Green Chemical Thickener of Epoxidized Linseed Oil. Journal of Polymers and the Environment.
DOI: 10.1007/s10924-024-03216-6

2003. Contribution to the study of Himatanthus sucuuba: latex macromolecule, microelements and carbohydrates. Acta Amazonica.
DOI: 10.1590/1809-4392200331110