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Phenylglyoxylic acid, Chinese name Benzoylformic acid, English name benzoylformate, phenyl-glyoxylicaci, phenyl-glyoxylicaci(phenyloxobutanoic acid), CAS No. 611-73-4, molecular formula c8h6o3, molecular weight 150.13. It is a white to grayish white powder with high melting point and low solubility in water, but high solubility in hot water and alcohols. It is a class of compounds containing carbonyl and carboxylic acid groups α- Keto acid (ester) compounds. Because it has multiple active groups and shows a variety of special properties, it can react with a variety of reagents to synthesize important pharmaceutical intermediates. In the field of biomedicine, acidobenzoico can be used to synthesize some compounds with biological activities, such as antibacterial agents, anti-inflammatory agents and anti-tumor drugs. In polymer chemistry, acidobenzoico can be used to synthesize polymers, such as nylon and polyester.
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Chemical Formula |
C8H6O3 |
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Exact Mass |
150 |
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Molecular Weight |
150 |
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m/z |
150 (100.0%), 151 (8.7%) |
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Elemental Analysis |
C, 64.00; H, 4.03; O, 31.97 |
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Phenylglyoxylic acid(C8H6O3), compound with both carbonyl (C=O) and carboxyl (-COOH) groups, has a unique molecular structure that endows it with a wide range of reactivity. In addition to the widely recognized fields of pharmaceutical intermediates, pesticide synthesis, and fluorescent materials, acidobenzoico has shown significant value in emerging areas such as biotechnology, environmental science, food industry, and energy materials.
1. Chiral drug synthesis: innovation in biocatalytic technology
The chemically synthesized kyselinamandlova is a racemic form, and traditional separation methods (such as chemical separation and chromatographic separation) have problems such as high cost and low efficiency. Benzoyl formic acid can be synthesized into high optical purity kyselinamandlova in one step through biocatalytic technology: under the catalysis of lipase (such as Candida Antarctica lipase B), benzoyl formic acid undergoes asymmetric reduction reaction with isopropanol to generate kyselinamandlova, which can reach a content of 98.5%. The process conditions are mild (30 ℃ pH 7.0), And the enzyme can be reused, significantly reducing production costs. kyselinamandlova is a key chiral intermediate for the synthesis of antibiotic cefaclor and antiviral drug oseltamivir, and its industrial production has achieved large-scale application.
2. Research on metabolic diseases: biomarkers and regulatory mechanisms
It is involved in the regulation of carbohydrate oxidation process in vivo, and its metabolites are closely related to metabolic syndrome such as diabetes and obesity. Studies have shown that the concentration of acidobenzoico in serum of diabetes patients is 2-3 times higher than that of healthy people, and the mechanism may be related to the increased oxidation of fatty acids caused by insulin resistance. In addition, it can reduce the rate of gluconeogenesis by inhibiting the activity of phosphoenolpyruvate carboxyl kinase (PEPCK), thus improving the blood glucose level of diabetes model mice (fasting blood glucose reduced by 35%). This discovery provides new drug targets for the treatment of metabolic diseases.
3. Enzyme catalyzed reactions: green synthesis technology
Reacting with heterocyclic compound derivatives (such as 2,2 '- bipyridine) and divalent iron salts (such as FeSO ₄) can generate ferrous protoporphyrinase mimetics, catalyzing olefin epoxidation reactions. For example, under the catalysis of the Fe (II) - bipyridine system, styrene is epoxidized to produce epoxyphenylethane with a yield of 92%, and the catalyst can be recycled more than 5 times without a significant decrease in activity. This catalyst can also be used for reactions such as alcohol oxidation and ketone reduction, with high selectivity (>95%) and low toxicity (LD50>5000mg/kg) advantages, in line with the principles of green chemistry.
Environmental Science Field: Innovation in Pollution Monitoring and Control
1. Environmental exposure biomarkers: Occupational health assessment
It is a specific metabolite of ethylbenzene/styrene exposure. The concentration of acidobenzoico in the urine of occupational exposure groups (such as chemical workers) is significantly positively correlated with the concentration of styrene in the air (r=0.85, p<0.01), with a detection limit of 0.1 μ g/L. This indicator has been used to evaluate the degree of environmental styrene pollution and human exposure risks, providing scientific basis for occupational health protection.
3. Organic pollutant degradation: photocatalytic technology
Composite with titanium dioxide (TiO ₂) can significantly improve the efficiency of photocatalytic degradation of organic pollutants. Under UV irradiation, the degradation rate of bisphenol A (BPA) by the phenyl-glyoxylicaci-TiO ₂ system is 40% higher than that of pure TiO ₂. The mechanism is that phenyl-glyoxylicaci acts as an electron donor, inhibiting photo generated electron hole recombination and prolonging carrier lifetime. This technology has been applied to industrial wastewater treatment, which can efficiently remove difficult to degrade pollutants such as endocrine disruptors and dyes.
2. Heavy metal pollution control: development of adsorption materials
Stable complexes can be formed with metal ions (such as Pb ² ⁺, Cd ² ⁺), and their carboxyl and carbonyl groups act as coordinating groups to efficiently adsorb heavy metal ions through chelation. For example, the modified magnetic nanoparticles (Fe ∝ O ₄ @ PGA) have a maximum adsorption capacity of 125mg/g for Pb ² ⁺ and can be quickly separated under an external magnetic field, making them suitable for the treatment of heavy metal pollution in water bodies. This material has passed the pilot test and has the potential for industrial application.
1. Food preservatives: development of natural alternatives
Methyl benzoate can be synthesized through esterification reaction, with a wide antibacterial spectrum and inhibitory effects on fungi (such as Aspergillus niger and Aspergillus flavus), yeast (such as brewing yeast), and bacteria (such as Escherichia coli and Staphylococcus aureus). The maximum allowable dosage in food is 0.2g/kg, commonly used for preserving jam, candied fruits, and beverages. Compared with traditional preservatives such as sodium benzoate, it has the advantages of low toxicity (ADI value 0-5mg/kg) and good solubility.
2. Flavor ingredients: natural essence synthesis
With elegant fruit and flower fragrance, it can be used to mix perfume, soap and cosmetics. Esters (such as ethyl benzoate) produced by its reaction with alcohols (such as ethanol and isopropanol) have a more lasting fragrance, and are commonly used as fixatives in high-end perfume (such as Chanel No.5 and Dior Ziego). In addition, natural flavors such as gamma decanolactone can be synthesized through enzymatic catalysis to meet consumers' demand for "clean label" products.
3. Food safety testing: development of biosensors
Can be used as an identification element for electrochemical sensors to detect harmful substances (such as nitrite and pesticide residues) in food. For example, based on its modified carbon nanotube electrode, the detection limit for nitrite is as low as 0.01 μ M, and phenylglyoxylic acid has strong anti-interference ability, making it suitable for rapid screening of nitrite in meat products. This technology has been validated through national standard methods and has the potential for on-site testing applications.
In the field of energy materials: breakthroughs in new energy and catalytic technology
1. Lithium ion batteries: electrolyte additives
It can be used as a film-forming additive for lithium-ion battery electrolytes, and its carbonyl and carboxyl groups can react with active substances on the electrode surface to form a stable solid electrolyte interface (SEI) film, which inhibits electrolyte decomposition and prolongs battery cycle life. Experiments have shown that adding 1% phenyl-glyoxylicaci to the electrolyte can increase the capacity retention rate of lithium-ion batteries to 85% after 500 cycles at 1C rate, which is 15% higher than the untreated system.
2. Fuel cell: catalyst carrier
Composite with carbon nanotubes (CNTs) can be used to prepare high-performance fuel cell catalyst carriers.
Its carboxyl group can covalently bond with platinum nanoparticles (Pt NPs) to improve the dispersion and stability of the catalyst. For example, the mass activity of Pt/PGA CNT catalyst in oxygen reduction reaction (ORR) reaches 0.32A/mg Pt, which is twice as high as commercial Pt/C catalyst, and the durability is significantly improved (activity decay<10% after 10000 cycles).
3. Solar cells: development of photosensitizers
The mixed system formed with ruthenium (Ru) complex can serve as a photosensitizer for dye-sensitized solar cells (DSSCs). Its absorption spectrum covers the visible light range (400-600nm), and its electron injection efficiency is high (>90%). The experiment showed that the photoelectric conversion efficiency of DSSC based on phenyl-glyoxylicaci Ru complex reached 8.2%, which was 15% higher than the traditional N719 dye system, and the cost was reduced by 30%.
Other fields: interdisciplinary innovation applications
1. Analytical Chemistry: Derivative Reagents
It can be used as a derivatization reagent for gas chromatography (GC) and liquid chromatography (HPLC) to analyze polar compounds such as amino acids and carboxylic acids. For example, the reaction with amino acids produces benzoyl amino acid derivatives, which have significantly increased volatility and are suitable for GC-MS analysis. This reagent has been used for the detection of amino acid composition in food, with a detection limit as low as 0.1 μ g/g.
2. Materials Science: Polymer Synthesis
Can be used as a comonomer to participate in the synthesis of functional polymer materials. For example, the hydrogel prepared by copolymerization with acrylic acid has high water absorption (water absorption>500%) and pH responsiveness, which can be used for drug controlled release and wound dressing.
In addition, polyurethane produced by reacting with isocyanates has excellent heat resistance (thermal decomposition temperature>300 ℃) and is suitable for aerospace materials.
3. Agricultural field: Plant growth regulators
And its derivatives can regulate plant growth and development. Research has shown that low concentrations of acidobenzoico (10 μ M) can promote rice seed germination and seedling growth by upregulating the expression of genes related to auxin (IAA) synthesis. In addition, phenylglyoxylic acidcan also induce plant disease resistance, such as improving tomato resistance to gray mold, with a control effect of up to 70%, and is environmentally friendly.
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