3150-20-7 ,4-Methoxyphenyl b-D-galactopyranoside,
CAS:3150-20-7
C13H18O7 / 286.28
MFCD06797126
对甲氧基苯基-b-D-半乳糖苷, 4-甲氧基苯基-beta-D-半乳糖苷
4-Methoxyphenyl beta-D-Galactopyranoside (MeOPG) is a chemical compound derived from galactose, a simple sugar that is widely distributed in nature. MeOPG is commonly used as a substrate in enzymatic assays and as a starting material for the synthesis of other glycosides. Despite the many applications of MeOPG in scientific research and industry, there is still much to discover about its properties, synthesis, characterization, and biological activities. In this review, we provide an overview of the current state of research on MeOPG and highlight potential implications in various fields of research and industry.
Definition and Background:
MeOPG is a glycoside composed of a galactopyranoside (sugar) and a methoxyphenyl group. It is also known as p-Methoxyphenyl β-D-Galactopyranoside. MeOPG can be synthesized through the reaction of galactose and 4-methoxyphenol in the presence of a strong acid catalyst, such as sulfuric acid or hydrochloric acid. The resulting product is purified by crystallization or chromatography.
Physical and Chemical Properties:
MeOPG is a white crystalline powder that is sparingly soluble in water and soluble in organic solvents such as ethanol, methanol, and chloroform. Its melting point is 147-148°C. MeOPG is stable at room temperature and can be stored in a dry and cool environment for several years. The chemical formula of MeOPG is C14H20O8 and its molecular weight is 316.30 g/mol.
Synthesis and Characterization:
MeOPG can be synthesized through several methods, including acid-catalyzed reaction, enzymatic synthesis, and chemoenzymatic synthesis. The acid-catalyzed synthesis is the most common method and involves the reaction of galactose and 4-methoxyphenol in the presence of a strong acid catalyst. Enzymatic synthesis involves the use of glycosyltransferases or other enzymes that selectively transfer a sugar moiety to a phenolic acceptor. In chemoenzymatic synthesis, chemical reactions and enzymatic reactions are combined to achieve a specific glycoside product.
Analytical Methods:
Several analytical methods are available for the detection and quantitation of MeOPG, including high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), and mass spectrometry (MS). HPLC is the most commonly used method and allows for the separation, identification, and quantification of MeOPG in complex mixtures.
Biological Properties:
MeOPG has been reported to exhibit several biological activities, including antibacterial, antifungal, and anticancer properties. MeOPG has been shown to inhibit the growth of several bacterial species, including Escherichia coli, Streptococcus pneumoniae, and Staphylococcus aureus. MeOPG also exhibits antifungal activity against Candida albicans and Saccharomyces cerevisiae. In addition, MeOPG has been shown to induce apoptosis and inhibit cell proliferation in several cancer cell lines.
Toxicity and Safety in Scientific Experiments:
The acute toxicity of MeOPG is low and there are no reported cases of toxicity in scientific experiments. However, it is important to handle MeOPG with caution and follow proper safety protocols, as with any chemical compound.
Applications in Scientific Experiments:
MeOPG has several applications in scientific experiments, including as a substrate in enzymatic assays, as a model compound for the synthesis of other glycosides, and as a tool to study the biological activities of glycosides. MeOPG has also been used in the development of glycoside-based vaccines and therapeutics.
Current State of Research:
Research on MeOPG is ongoing and focuses on the synthesis of new glycosides with improved biological activities, the development of new analytical methods for the detection and quantification of MeOPG, and the study of the mechanisms underlying the biological activities of MeOPG.
Potential Implications in Various Fields of Research and Industry:
MeOPG has potential implications in several fields of research and industry, including pharmaceuticals, biotechnology, and food science. MeOPG can be used in the development of new antibacterial, antifungal, and anticancer drugs. MeOPG can also be used in the synthesis of glycoside-based therapeutics and vaccines.
Limitations and Future Directions:
Limitations of MeOPG include its low solubility in water and its limited biological activities. Future directions for research on MeOPG include the synthesis of new glycosides with improved biological activities, the development of new analytical methods for the detection and quantification of MeOPG, and the study of the mechanisms underlying the biological activities of MeOPG. In addition, further research is needed to determine the potential applications of MeOPG in various fields of research and industry.
Overall, the review shows that MeOPG is a useful and versatile compound in scientific research and industry. Its potential implications in various fields of research and industry make it an attractive compound for further study and development.
CAS Number | 3150-20-7 |
Product Name | 4-Methoxyphenyl beta-D-Galactopyranoside |
IUPAC Name | (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxane-3,4,5-triol |
Molecular Formula | C13H18O7 |
Molecular Weight | 286.28 g/mol |
InChI | InChI=1S/C13H18O7/c1-18-7-2-4-8(5-3-7)19-13-12(17)11(16)10(15)9(6-14)20-13/h2-5,9-17H,6H2,1H3/t9-,10+,11+,12-,13-/m1/s1 |
InChI Key | SIXFVXJMCGPTRB-KSSYENDESA-N |
SMILES | COC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O |
Canonical SMILES | COC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O |
Isomeric SMILES | COC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O |
CAS No: 3150-20-7 MDL No: MFCD06797126 Chemical Formula: C13H18O7 Molecular Weight: 286.28 |
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