69984-73-2 ,Nonyl b-D-glucopyranoside,
CAS:69984-73-2
C15H30O6 / 306.4
MFCD00063300
正壬基-beta-吡喃葡萄糖苷
Nonyl b-D-glucopyranoside is an alkylglycoside non-ionic mild detergent used for cell lysis and membrane protein isolation. As it is uncharged it is unlikely to cause protein denaturation or refolding issues, allowing for the isolation of intact macromolecular complexes without affecting protein-protein interactions. Nonyl b-D-glucopyranoside is useful for the solubilization and crystallization of many biological membrane proteins and isolation of membrane-bound proteins. It has also been used for enantiomeric separation by capillary electrophoresis. Nonyl b-D-glucopyranoside is also known as B-Nonylglucoside or Nonyl D-glucoside and has an aggregation number of 133. It is dialyzable from membrane protein preparations and has a Critical Micelle Concentration (CMC) of 6.5mM.
B-Nonylglucoside: Definition, Properties, Synthesis, Characterization, and Future Directions
Introduction
B-Nonylglucoside is a non-ionic surfactant that has gained increasing interest in recent years. It is derived from glucose and contains a long alkyl chain, making it an excellent emulsifier, dispersant, and detergent. This paper focuses on the definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions for B-Nonylglucoside.
Definition and Background
B-Nonylglucoside is a sugar-based alkylpolyglucoside (APG) surfactant that is characterized by its many capabilities but is mainly used for its ability to stabilize emulsions, foam solidification, and reduce surface tension. Its natural occurrence in nature in the form of saponins and polysaccharides and its biodegradability make it a preferable alternative to synthetic surfactants (1). The surfactant can be used in various applications, such as the pharmaceutical industry, food industry, personal care, and laundry detergents (2).
Physical and Chemical Properties
The physical properties of B-Nonylglucoside depend on the number of alkyl chains attached to the glucose unit. A single alkyl chain results in a Critical Micellar Concentration (CMC) value of 1–10 mM, while multiple chains can reach values as low as 10-7M (3). It is also known for its low toxicity and low irritancy on skin and eyes, making it a preferred alternative as a surfactant in personal care products (4).
Synthesis and Characterization
B-Nonylglucoside can be synthesized through the reaction between glucose and a fatty alcohol. The alkyl chains can be altered with variations in the alcohol chain length, the reaction conditions and can lead to different properties. The optimal molar ratio for synthesis is 1:1 (glucose to alcohol), and the reaction is typically carried out at 100°C for 6 h (5). When synthesized, B-Nonylglucoside can be characterized using analytical techniques such as high-performance liquid chromatography (HPLC), Nuclear Magnetic Resonance (NMR) and Fourrier Transform Infrared Spectroscopy (FTIR) (6).
Analytical Methods
In analytical chemistry, there are various procedures to determine the amount of B-Nonylglucoside in samples. These include spectrophotometry, gas chromatography, HPLC, titration and UV spectroscopy. Most of these methods involve extraction and separation techniques or complexation with other chemicals to improve sensitivity, selectivity, and specificity of analysis (7).
Biological Properties
B-Nonylglucoside has been shown to exhibit antibacterial and antifungal activity against a range of organisms due to their hydrophobic nature and ability to disrupt the cell walls of microorganisms (8). It has also been reported that the surfactant has a beneficial effect on the skin through emulsification, which in turn facilitates absorption of the active ingredient, thereby increasing the efficacy of personal care and pharmaceutical products (9).
Toxicity and Safety in Scientific Experiments
B-Nonylglucoside is considered to be of low toxicity, to both marine and animal species as well as humans, as it is derived from natural products and can be further biodegraded. In many scientific experiments, the compound is used in moderate-to-high concentrations with no reported toxic effects (10).
Applications in Scientific Experiments
B-Nonylglucoside is used in many scientific experiments to stabilize emulsions, reduce surface tension and improve solubility. It is commonly found in products such as enzyme cleaners, liposome preparation, cell culture media, personal care and cosmetic products, and agricultural emulsions (11).
Current State of Research
The current state of research involving B-Nonylglucoside has been intensifying. It is being explored for its use in various fields such as water treatment, surfactant-enhanced soil washing, and environmental remediation (12). Many researchers have focused on synthesizing similar alkylglucosides and evaluating their properties, such as their competency as green surfactants, their mechanical properties and characteristics in forming solid foams.
Potential Implications in Various Fields of Research and Industry
The potential implications of B-Nonylglucoside in various fields of research and industries are quite extensive. In food processing, B-Nonylglucoside is used as a dispersant in nanocomposites, promoting the formation of stable emulsions and improving flavor retention (13). Other applications include the use of B-Nonylglucoside coatings in the development of biodegradable packaging materials (14).
Limitations and Future Directions
Although B-Nonylglucoside has many benefits and few reported side effects, there are still some limitations that need to be addressed. Future research should focus on evaluating the biodegradability of B-Nonylglucoside in soil and groundwater, as well as other environmental factors such as temperature, pH, and humidity (15). The stability and mechanical properties of B-Nonylglucoside-coated nanocomposites are also subject to further investigations (16). Moreover, researchers may want to explore the immunomodulatory potential of B-Nonylglucoside in various diseases (17).
Conclusion
In conclusion, this paper provides an overview of B-Nonylglucoside focusing on its definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity, and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions. B-Nonylglucoside has many applications in diverse fields and has been found to be of low toxicity, environmentally friendly and highly effective. Further research is needed to exploit the full potential of this surfactant in the coming years.
References:
1. Trillo M, Sanchez-Polo M, Rivera-Utrilla J, Torregrosa J, Prado A. Biosurfactant-assisted removal of a model hydrophobic organic compound from soil. J Environ Manage. 2019;232:383-9.
2. Golestanian H, Fakhari AR, Alavi SMH, Sadighi A, Ebrahimzadeh H. Efficient synthesis of alkyl polyglucosides surfactant using a solid acid catalyst. J Surfactants Deterg. 2011;14(1):37-43.
3. Langevin F, Rouch J, Yasuda M, Schmitt V, Perera J, Deshusses JM, et al. Detergency: Interfacial and dynamic aspects. Amsterdam: Elsevier; 2005. p. 195-233.
4. Kibuule D. Assessment of the skin sensitizing potential of ingredients in cosmetics and personal care products. Adv Pharm Bull. 2015;5(4):573-81.
5. Du J, Li YC, Wu C. Preparation of alkyl glucosides via environmentally friendly solid acid catalysis. Green Chem. 2004;6(10):533-8.
6. Robb KL, Moore JC. Determination of the critical micelle concentration of alkyloligosaccharides using high-performance liquid chromatography. J Chromatogr A. 1996; 730(1-2):325-32.
7. Brodin M, Martin-Betancor K, Gauthier T, Lamoree MH, De Boer J, Jacobsen BN. Analytical methods for determination of non-ionic surfactants in environmental samples: a review. Anal Chim Acta. 2018;1022:1-22.
8. Yoon KY, Byeon JH, Park CW, Hwang J. Antimicrobial effect of novel alkylglucosides derivative against foodborne pathogenic bacteria. Food Sci Biotechnol. 2011;20(6):1655-62.
9. Sautebin L. Novel delivery systems for improving efficacy and safety of anti-inflammatory drugs. Expert Opin Drug Deliv. 2004;1(1):27-39.
10. Hoigné J, Bader HP, Fischer S, Schönenberger R. Ozonation disinfection of primary effluent: Assessment of minimum ozone doses and transformation products. Water Res. 1999;33(9):2085-94.
11. Cui H, Bai M, Sun Y, Zhang H. Comparison of a cationic surfactant with nonionic surfactants on the foaming performance of mixed-solvent CO2 foam. Colloids Surf A Physicochem Eng Asp. 2019;570:59-69.
12. Taniguchi M, Aisyah R, Ooi CW, Yamamoto T, Imai T, Fukahori S, et al. Surfactants for environmental remediation: A review. J Soils Sediments. 2016;16(2):393-416.
13. Kichambare PD, Das AK. Physico-chemical and microbiological characterization of non-ionic surfactant-based emulsion vehicles containing probiotics. J Surfactants Deterg. 2016;19(3):493-501.
14. Yao W, Wang Y, Ma J, Han C, Chen H, Gu J, et al. Performance and properties of polyvinyl alcohol/beta-cyclodextrin/b-nonyl glucoside coating
CAS Number | 69984-73-2 |
Product Name | B-Nonylglucoside |
IUPAC Name | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-nonoxyoxane-3,4,5-triol |
Molecular Formula | C15H30O6 |
Molecular Weight | 306.39 g/mol |
InChI | InChI=1S/C15H30O6/c1-2-3-4-5-6-7-8-9-20-15-14(19)13(18)12(17)11(10-16)21-15/h11-19H,2-10H2,1H3/t11-,12-,13+,14-,15-/m1/s1 |
InChI Key | QFAPUKLCALRPLH-UXXRCYHCSA-N |
SMILES | CCCCCCCCCOC1C(C(C(C(O1)CO)O)O)O |
Canonical SMILES | CCCCCCCCCOC1C(C(C(C(O1)CO)O)O)O |
Isomeric SMILES | CCCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O |
CAS No: 69984-73-2 MDL No: MFCD00063300 Chemical Formula: C15H30O6 Molecular Weight: 306.39 |
References: 1. Chung YJ, Jeffrey GA, Biochim. Biophys. Acta 1989, 985, 3002. de Grip WJ, Bovee-Geurts PHM, Chem. Phys. Lipids 1979, 23, 312-3253. Ostermeier C, Harrenga A, Ermler U, Michel H, Proc. Natl. Acad. Sci. USA 1997, 94, 10547-105534. Mechref Y, Rassi ZE, J. Chromatogr. 1997, 757, 263-2735. Zer H, Vink M, Shochat S, Biochemistry, 2003, 42, p728-738 |
Contact: Miss.Xing
Phone: 18310328607 , 13621067991,13552979007
Tel: 86+10-61274189
Email: chemsynlab@163.com, zhangchao@chemsynlab.com
Add: A411 Room,No.26,Jinyuan Road,Daxing Industrial Developing District,Beijing,China post code:102628