60415-65-8 ,D-吡喃葡萄糖 1-辛酸酯,
Octanoyl D-glucopyranoside,
Cas:60415-65-8
C14H26O7 / 306.35
MFCD00066997
D-吡喃葡萄糖 1-辛酸酯,
Octanoyl D-glucopyranoside is a potent inhibitor of histidine-mediated endocytosis and the activation of NF-κB signaling in human osteoarthritic chondrocytes. It has also been shown to inhibit viral replication by adenovirus. Octanoyl D-glucopyranoside inhibits the activity of several enzymes, including protein kinase C (PKC), nf-kappa B (NF-κB), and photolyase, which are all involved in inflammation. This compound also inhibits transcription, polymerization, and genotype expression. Octanoyl D-glucopyranoside has been shown to be effective against necrosis factor alpha (TNFα) and interleukin 1 beta (IL1β).
Octanoyl-D-glucopyranoside: A Comprehensive Review of Its Properties, Synthesis, Biological Activities, and Future Directions
Introduction
Octanoyl-D-glucopyranoside (OGlcOct) is a natural sugar surfactant that has attracted considerable attention in recent years due to its unique properties and potential applications. This compound is a glycolipid composed of a glucose molecule and an octanoic acid chain, which gives it both hydrophilic and hydrophobic properties. These properties make OGlcOct an ideal emulsifier and detergent in various industries, such as food, cosmetics, and pharmaceuticals. Moreover, OGlcOct has shown promising biological and therapeutic activities, which makes it a potential candidate for drug delivery and biomedical applications. In this article, we aim to provide a comprehensive review of OGlcOct's properties, synthesis, biological activities, and future directions.
Synthesis and Characterization
OGlcOct can be synthesized by different methods, including chemical synthesis, enzymatic synthesis, and microbial synthesis. Chemical synthesis involves the esterification of glucose with octanoic acid in the presence of a catalyst and solvent. Enzymatic synthesis utilizes enzymes such as lipases or glucosidases to catalyze the formation of OGlcOct from glucose and octanoic acid. Microbial synthesis uses microorganisms such as bacteria or fungi to produce OGlcOct from an appropriate carbon source. The synthesized OGlcOct can be characterized by various analytical techniques, such as high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), nuclear magnetic resonance (NMR) spectroscopy, and Fourier-transform infrared (FT-IR) spectroscopy.
Analytical Methods
The analysis of OGlcOct in various matrices is essential for quality control, safety assessment, and biomedical studies. HPLC and GC-MS are commonly used analytical methods for the determination of OGlcOct in various samples, including food, cosmetics, and biological fluids. NMR and FT-IR spectroscopy provide information on the structural and functional properties of OGlcOct and its interactions with other molecules. Other analytical techniques, such as mass spectrometry, capillary electrophoresis, and surface plasmon resonance, have also been used to study OGlcOct properties and applications.
Biological Properties
OGlcOct has shown promising biological activities, such as antimicrobial, antitumor, anti-inflammatory, antidiabetic, and immunomodulatory effects. The compound has been reported to inhibit the growth of Gram-positive and Gram-negative bacteria, fungi, and viruses. OGlcOct has also exhibited cytotoxicity against various cancer cell lines, such as breast cancer, colon cancer, and leukemia. The anti-inflammatory and antidiabetic activities of OGlcOct have been demonstrated in animal models, where the compound reduced the levels of proinflammatory cytokines and improved glucose metabolism. Moreover, OGlcOct has shown potential as an adjuvant in vaccine development, as it can enhance the immune response to antigens.
Toxicity and Safety in Scientific Experiments
The toxicity and safety of OGlcOct have been evaluated in various scientific experiments, including acute toxicity tests, Ames tests, and mammalian cell culture assays. OGlcOct has been shown to be relatively safe, with low acute toxicity and no genotoxicity or mutagenicity. However, some studies have reported cytotoxicity and adverse effects on cell viability and membrane integrity at high concentrations of OGlcOct. Therefore, further studies are needed to determine the safe and effective doses of OGlcOct in various applications.
Applications in Scientific Experiments
OGlcOct has been widely used in various scientific experiments, such as drug delivery, gene delivery, protein stabilization, and cell culture. OGlcOct can form stable complexes with drugs, proteins, and nucleic acids, which can enhance their stability, solubility, and bioavailability. The compound has also been used as a surfactant and stabilizer in various colloidal systems, such as liposomes, micelles, and emulsions. Moreover, OGlcOct has been used to improve the viability and differentiation of various cell types in culture, such as stem cells and primary cells.
Current State of Research
The current state of research on OGlcOct includes both basic and applied studies in various fields, such as food, cosmetics, pharmaceuticals, and biomedicine. The basic research on OGlcOct focuses on its physicochemical and biological properties, as well as its interactions with other molecules and systems. The applied research on OGlcOct includes its use as a surfactant, emulsifier, stabilizer, and drug delivery system in various industries. Moreover, the biomedical research on OGlcOct investigates its therapeutic and diagnostic potential in various diseases, such as cancer, diabetes, and infectious diseases.
Potential Implications in Various Fields of Research and Industry
OGlcOct has the potential to revolutionize various fields of research and industry, such as food, cosmetics, pharmaceuticals, and biomedicine. In the food industry, OGlcOct can be used as a natural emulsifier and stabilizer in various products, such as dairy, beverages, and baked goods. In the cosmetics industry, OGlcOct can be used as a natural surfactant and moisturizer in various personal care products, such as shampoos, lotions, and soaps. In the pharmaceutical industry, OGlcOct can be used as a drug delivery system and adjuvant in various formulations, such as oral, injectable, and topical. In the biomedicine field, OGlcOct can be used as a diagnostic agent and therapeutic agent in various diseases, such as cancer, diabetes, and infectious diseases.
Limitations and Future Directions
Despite the promising properties and applications of OGlcOct, some limitations and challenges need to be addressed in future research. First, the synthesis of OGlcOct is still expensive and not scalable, which limits its commercial applications. Therefore, new and efficient methods of synthesis need to be developed. Second, the biological activities of OGlcOct need to be further elucidated, as well as its mechanisms of action and toxicity in vivo. Third, the applications of OGlcOct in different industries need to be optimized and validated in large-scale studies. Fourth, the interactions of OGlcOct with other molecules and systems need to be better understood in order to predict its behavior in real-world applications. Finally, the future directions of OGlcOct research include the development and discovery of new analogs and derivatives with enhanced properties and applications.
Conclusion
OGlcOct is a natural sugar surfactant with unique properties and potential applications in various industries and fields of research. OGlcOct has been shown to possess promising biological and therapeutic activities, making it a potential candidate for drug delivery and biomedical applications. This comprehensive review of OGlcOct's properties, synthesis, biological activities, and future directions provides a foundation for further research on this compound and its applications.
CAS Number | 60415-65-8 |
Product Name | Octanoyl-D-glucopyranoside |
IUPAC Name | [(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] octanoate |
Molecular Formula | C14H26O7 |
Molecular Weight | 306.35 g/mol |
InChI | InChI=1S/C14H26O7/c1-2-3-4-5-6-7-10(16)21-14-13(19)12(18)11(17)9(8-15)20-14/h9,11-15,17-19H,2-8H2,1H3/t9-,11-,12+,13-,14?/m1/s1 |
InChI Key | MHQWMCFSLKPQTC-GQYPCLOQSA-N |
SMILES | CCCCCCCC(=O)OC1C(C(C(C(O1)CO)O)O)O |
Canonical SMILES | CCCCCCCC(=O)OC1C(C(C(C(O1)CO)O)O)O |
Isomeric SMILES | CCCCCCCC(=O)OC1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O |
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