DL-Arabinose
[CAS# 147-81-9]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: DL-Arabinose
• Synonyms: (+)-Xylose; 2,3,4,5-tetrahydroxypentanal
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• CAS Registry Number: 147-81-9
• EC Number: 205-699-8
• SMILES: C(C(C(C(C=O)O)O)O)O

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 375.4±42.0 ºC 760 mmHg (Calc.)^*
• Flash point: 180.8±27.9 ºC (Calc.)^*
• Solubility: soluble (water) (Expl.)
• Index of refraction: 1.612 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Safety Description: S24/25

Discovory and Applicatios

DL-Arabinose is a monosaccharide, specifically a pentose sugar, with the chemical formula C5H10O5. It is an isomeric form of arabinose that contains both the D- and L- forms of the sugar. This compound is a component of various polysaccharides and is commonly found in plant cell walls, especially in hemicellulose and pectins. It is also a naturally occurring sugar in some fruits and vegetables, as well as in certain microorganisms.

The discovery of arabinose dates back to the early 19th century, but its detailed structural characterization and significance in biochemistry and pharmacology were recognized later. The term "DL-Arabinose" refers to a mixture of both the D- and L-isomers of arabinose, which are mirror images of each other and can be interconverted under certain conditions. In its D-form, arabinose is commonly involved in various biochemical pathways, particularly in the synthesis of nucleotides and nucleic acids.

DL-Arabinose is of interest in biochemistry and biotechnology due to its role in metabolic pathways. It is used as a carbon source by some bacteria, especially those involved in the degradation of plant materials, and can be metabolized to form other sugars or compounds that contribute to cellular energy production. Additionally, arabinose is an important component in the study of sugar metabolism and the mechanisms of carbohydrate absorption in animals.

One of the most notable applications of DL-arabinose is in the field of biotechnology, particularly in genetic engineering. Arabinose is often used as an inducer in research involving bacterial transformation and gene expression systems. For example, in Escherichia coli (E. coli) and other bacteria, the arabinose operon system can be used to regulate the expression of inserted genes. By adding arabinose to the growth medium, researchers can activate or increase the expression of genes of interest, which is valuable in producing proteins for industrial or medical applications.

Furthermore, DL-arabinose has been studied for its potential health benefits. Some research suggests that it may have a role in reducing blood sugar levels, though this effect is still under investigation. The sugar is considered to have low glycemic properties, making it of interest in the development of food products for people with diabetes or those seeking to manage their blood sugar levels. However, more research is needed to confirm these health benefits and understand its metabolic effects fully.

In addition to its biological and pharmaceutical applications, DL-arabinose is also used in various industrial processes, including the production of sweeteners and food additives. It is sometimes used in the manufacturing of sugar alcohols and in the synthesis of other carbohydrate derivatives. As a sweetener, arabinose is considered to be less sweet than sucrose, but its use is gaining interest as a lower-calorie option in food products.

In conclusion, DL-arabinose is a versatile monosaccharide with applications in biotechnology, genetics, and potentially in the food industry. Its role in metabolic pathways, as well as its use in gene expression systems, underscores its importance in both scientific research and industrial applications. While further studies are needed to fully understand its health implications, DL-arabinose continues to be of interest for its potential as a functional ingredient in health-related food products and its utility in biotechnological processes.

References

1979. Xylose, Arabinose, and Rhamnose Fermentation by Bacteroides ruminicola. Applied and Environmental Microbiology, 38(1).
DOI: 10.1128/aem.38.1.7-12.1979