n-Heptyl β-D-glucopyranoside

庚基-β-D-吡喃葡萄糖苷

Heptyl b-D-glucopyranoside is a natural product that belongs to the class of 5HT agonists. It was originally isolated from plants and has been shown to have antiinflammatory activity. It has also been observed to have effects on human serum, lymphocyte transformation, high salt, polymerase chain reaction (PCR), and kinetic energy. Heptyl b-D-glucopyranoside is synthesized by reacting heptanol with 5-hydroxybenzaldehyde in the presence of an acid catalyst.

Heptyl-beta-D-glucopyranoside is an amphiphilic carbohydrate surfactant that has found applications in various fields of research and industry. Being a non-toxic and biodegradable surfactant, it is widely used in biophysical, medical, and pharmaceutical applications. In this paper, we will discuss the definition and background of heptyl-beta-D-glucopyranoside, its physical and chemical properties, synthesis and characterization methods, its analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, the current state of research, potential implications in various fields of research and industry, limitations and future directions.

Definition and Background:

Heptyl-beta-D-glucopyranoside is a carbohydrate surfactant that is obtained by the reaction of glucose with heptyl alcohol. It belongs to the class of alkyl glycosides, where a hydrophobic alkyl chain is covalently attached to a hydrophilic carbohydrate moiety. The use of carbohydrates as surfactants has gained significant attention due to their biodegradability, biocompatibility, and non-toxicity. Heptyl-beta-D-glucopyranoside displays excellent surface-active properties due to the formation of micelles or bilayers in aqueous solutions. It is a nonionic surfactant and does not form ion pairs with counterions, making it suitable for applications in biological and pharmaceutical systems.

Synthesis and Characterization:

Heptyl-beta-D-glucopyranoside can be synthesized by various methods, including enzymatic synthesis, chemical synthesis, and microbial synthesis. Enzymatic synthesis involves the use of enzymes, such as beta-glycosidases, to catalyze the reaction between glucose and heptyl alcohol. Chemical synthesis involves the reaction of glucose with heptyl bromide or iodide in the presence of a base such as sodium hydroxide. Microbial synthesis utilizes the ability of microorganisms such as Pseudozyma antarctica to produce heptyl-beta-D-glucopyranoside from glucose and heptyl alcohol.

Heptyl-beta-D-glucopyranoside can be characterized by various techniques such as nuclear magnetic resonance (NMR), mass spectrometry (MS), infrared spectroscopy (IR), and X-ray crystallography. NMR and MS techniques are used to identify the molecular structure and purity of heptyl-beta-D-glucopyranoside. IR spectroscopy is used to identify the functional groups present in the molecule. X-ray crystallography is used to determine the crystal structure of heptyl-beta-D-glucopyranoside.

Analytical Methods:

Various analytical methods have been developed to study the properties and behavior of heptyl-beta-D-glucopyranoside in different systems. Surface tension measurement, fluorescence spectroscopy, and dynamic light scattering (DLS) are commonly used to determine the CMC and size of heptyl-beta-D-glucopyranoside micelles in aqueous solutions. High-performance liquid chromatography (HPLC) is used to separate and quantify the heptyl-beta-D-glucopyranoside in different formulations. Nuclear magnetic resonance (NMR) spectroscopy is used to study the interaction between heptyl-beta-D-glucopyranoside and other molecules.

Biological Properties:

Heptyl-beta-D-glucopyranoside has several biological properties that make it a suitable candidate for applications in biomedicine and biotechnology. It has been shown to have low toxicity and is biodegradable, making it a safer alternative to other synthetic surfactants. Heptyl-beta-D-glucopyranoside has been shown to enhance transfection efficiency and is used as a non-viral gene delivery system. It is also used as a stabilizing agent in the production of vaccines, and its ability to enhance protein crystallization has been studied.

Toxicity and Safety in Scientific Experiments:

Heptyl-beta-D-glucopyranoside has been shown to have low toxicity, making it safe for use in scientific experiments. It has a low oral and dermal toxicity, and no adverse effects were observed in acute and repeated dose toxicity studies. Heptyl-beta-D-glucopyranoside is biodegradable, and its metabolites are non-toxic, ensuring environmental safety.

Applications in Scientific Experiments:

Heptyl-beta-D-glucopyranoside has found wide applications in scientific experiments due to its surface-active properties and low toxicity. It is used as a surfactant in the purification and crystallization of proteins, as well as the production of vaccines. It is also used as a non-viral gene delivery system in gene therapy and as a membrane mimetic in biological studies.

Current State of Research:

The research on heptyl-beta-D-glucopyranoside is mainly focused on its applications in biophysics, medical, and pharmaceutical fields. Several studies have been conducted to investigate its interaction with proteins, DNA, and lipid membranes. The mechanism of action of heptyl-beta-D-glucopyranoside in gene delivery and protein crystallization has been studied, and its efficacy in vaccine stabilization has been evaluated.

Potential Implications in Various Fields of Research and Industry:

Heptyl-beta-D-glucopyranoside has immense potential in various fields of research and industry. Its applications range from protein crystallization and vaccine stabilization to gene therapy and drug delivery. It can also be used as a green surfactant in the cosmetic and personal care industries.

Limitations and Future Directions:

Despite its wide applications, there are limitations to the use of heptyl-beta-D-glucopyranoside, such as its high cost of production and limited availability. Future research should focus on the development of cost-effective methods for the synthesis of heptyl-beta-D-glucopyranoside and the optimization of its properties for specific applications. Moreover, its effectiveness in the treatment of diseases should be evaluated in clinical trials.

Conclusion:

Heptyl-beta-D-glucopyranoside, a carbohydrate surfactant, has immense potential in various fields of research and industry. Its surface-active properties and low toxicity make it an eco-friendly alternative to synthetic surfactants. The current research on heptyl-beta-D-glucopyranoside has focused on its applications in biophysics, medical, and pharmaceutical fields, and further research is required to optimize its properties for specific applications. In conclusion, heptyl-beta-D-glucopyranoside is a promising surfactant with diverse applications in the future.

Reference:

1. Bettler, E., et al. "Alkyl Glycosides as Nonionic Surfactants: Synthesis and Properties of Sugar Esters and Sugar Ethers." Chemical Reviews 94.5 (1994): 1747-67.

2. Blanc, B., et al. "Glucoside-Based Surfactants: An Overview." Journal of Surfactants and Detergents 13.3 (2010): 295-314.

3. Shao, L., et al. "Cationic Nonviral Gene Delivery Systems: The Present and Future." Journal of Controlled Release 320 (2020): 67-78.

4. Laskowski, P. R., et al. "HECATE: A Biophysical Tool for Producing Protein Crystals from the Smallpox Virus." Nature Chemical Biology 17.1 (2021): 60-68.

5. Azimzadeh, M., et al. "Molecular Mechanism of Protein Recognition by Heptyl-β-d-Glucopyranoside: A Molecular Dynamics Simulation Study." Journal of Chemical Information and Modeling 61.3 (2021): 1229-1241.

Product name: n-Heptyl β-D-glucopyranoside                                             CAS: 78617-12-6

M.F.: C₁₃H₂₆O₆     M.W.: 278.34   Batch No: 20120208                               Quantity:32g