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70005-86-6 , Undecyl b-D-glucopyranoside

70005-86-6 , Undecyl b-D-glucopyranoside,
Cas:70005-86-6
C17H34O6 / 334.45
MFCD00083514

Undecyl b-D-glucopyranoside

正十一烷基 β-D-吡喃葡萄糖苷,

N-Undecyl beta-D-glucopyranoside is a surfactant, also called nonionic surfactant or neutral surfactant. Surfactants are substances that significantly reduce the surface tension of a liquid in which it is dissolved. The reduction in surface tension is useful in various applications, including emulsification, wetting, foaming, solubilization, and detergency. The n-Undecyl beta-D-glucopyranoside molecule consists of a long hydrophobic (water-repelling) alkyl chain (n-Undecyl, C11H23) and a hydrophilic (water-attracting) carbohydrate group (beta-D-glucopyranoside, C17H34O6).

Physical and Chemical Properties

N-Undecyl beta-D-glucopyranoside is a white or off-white crystalline powder with a faint sweet odor. It has a molecular weight of 334.45 g/mol and a melting point of 89-91 °C. The solubility of n-Undecyl beta-D-glucopyranoside in water is substantially high, and it can easily dissolve in other polar solvents such as methanol, ethanol, and isopropanol. The critical micelle concentration (CMC) of n-Undecyl beta-D-glucopyranoside is around 0.09-2.3 mM, and the surface tension at CMC is typically around 30-36 mN/m. The chemical structure of n-Undecyl beta-D-glucopyranoside is stable and resistant to various environmental factors, such as pH and temperature.

Synthesis and Characterization

N-Undecyl beta-D-glucopyranoside can be synthesized through various methods, including enzymatic methods, chemical methods, and chemical-enzymatic methods. In the chemical synthesis method, n-Undecyl-beta-D-glucopyranoside can be produced through the reaction of n-Undecyl alcohol with glucose in a suitable organic solvent in the presence of a suitable acid catalyst. The product is then purified through various techniques, such as crystallization, filtration, and chromatography. The characterization of n-Undecyl beta-D-glucopyranoside can be done using various techniques, including H-NMR (proton nuclear magnetic resonance), IR (infrared spectroscopy), mass spectrometry, and elemental analysis.

Analytical Methods

N-Undecyl beta-D-glucopyranoside can be analyzed using various analytical methods, including High-Performance Liquid Chromatography (HPLC), Capillary Electrophoresis (CE), and Gas Chromatography (GC). These analytical methods can be used to quantify the amount of n-Undecyl beta-D-glucopyranoside in a sample, determine its purity, and characterize its molecular structure.

Biological Properties

N-Undecyl beta-D-glucopyranoside has been shown to have various biological properties, including antimicrobial, antitumor, and cell-penetrating properties. Studies have shown that n-Undecyl beta-D-glucopyranoside can inhibit the growth of various bacterial strains, including Escherichia coli and Staphylococcus aureus. Additionally, it has been reported that n-Undecyl beta-D-glucopyranoside can induce apoptotic cell death in tumor cells, such as leukemia cells. Furthermore, n-Undecyl beta-D-glucopyranoside has been used to facilitate the delivery of drugs and genes into cells.

Toxicity and Safety in Scientific Experiments

Studies have shown that n-Undecyl beta-D-glucopyranoside is generally safe when used in scientific experiments at the recommended concentration range. However, like any other surfactant, excessive use of n-Undecyl beta-D-glucopyranoside can cause irritation to the skin and eyes. Therefore, it is essential to follow proper handling and safety procedures when using n-Undecyl beta-D-glucopyranoside in scientific experiments.

Applications in Scientific Experiments

N-Undecyl beta-D-glucopyranoside has various applications in scientific experiments, including protein solubilization, membrane protein stabilization, and cell lysis. Additionally, n-Undecyl beta-D-glucopyranoside is commonly used in the production of liposomes and emulsions. Furthermore, n-Undecyl beta-D-glucopyranoside is used as a detergent in various techniques, such as Western blotting, gel electrophoresis, and chromatography.

Current State of Research

Research on n-Undecyl beta-D-glucopyranoside is ongoing, with new discoveries and applications being identified continually. Studies are currently focused on the potential of n-Undecyl beta-D-glucopyranoside as a drug delivery agent, as well as its use in various biotechnological and pharmaceutical applications.

Potential Implications in Various Fields of Research and Industry

N-Undecyl beta-D-glucopyranoside has various potential implications in various fields of research and industry. Its use in drug delivery systems could lead to the development of new and more efficient drug delivery methods. Additionally, the use of n-Undecyl beta-D-glucopyranoside in various biotechnological and pharmaceutical applications, such as protein solubilization and membrane protein stabilization, could lead to the development of new and effective drugs.

Limitations and Future Directions

Despite its potential, there are still some limitations associated with n-Undecyl beta-D-glucopyranoside. For instance, its use in drug delivery systems is limited by its low molecular weight and water solubility. As such, more research is needed to overcome these limitations and fully exploit the potential of n-Undecyl beta-D-glucopyranoside. Possible future directions include the use of new and more efficient methods of synthesis, exploring its use in other applications beyond drug delivery, and further study to understand its interactions with biological systems.

In conclusion, n-Undecyl beta-D-glucopyranoside is a versatile surfactant that has gained widespread use in scientific experiments for its physical, chemical, and biological properties. Despite some limitations, research on n-Undecyl beta-D-glucopyranoside is ongoing, and its potential implications in various fields of research and industry make it an exciting area for future research.

CAS Number70005-86-6
Product Namen-Undecyl beta-D-glucopyranoside
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-undecoxyoxane-3,4,5-triol
Molecular FormulaC17H34O6
Molecular Weight334.45 g/mol
InChIInChI=1S/C17H34O6/c1-2-3-4-5-6-7-8-9-10-11-22-17-16(21)15(20)14(19)13(12-18)23-17/h13-21H,2-12H2,1H3/t13-,14-,15+,16-,17-/m1/s1
InChI KeyULDAPNVYSDTSFM-UHFFFAOYSA-N
SMILESCCCCCCCCCCCOC1C(C(C(C(O1)CO)O)O)O
Canonical SMILESCCCCCCCCCCCOC1C(C(C(C(O1)CO)O)O)O


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