Study on the Synthesis of Phenylacetic Acid by Carbonylation of Benzyl Chloride under Normal Pressure

The influences of some factors on the yield of phenylacetic acid in thecarbonylation of benzyl chloride were studied in this paper. These factors included the variety andcontent of catalyst, and that of solvent, way of material feeding, reaction temperature, sodiumhydrate concentration, triphenylphosphine content, presence of surfactant, the ratio of organicphase volume to aqueous phase volume etc. The optimum reaction conditions were found to be: with aone-time pour of 0.15 g Pd(PPh_3)_2Cl_2, 0.24 g PPh_3, 75 ml NaOH of 3.5 mol/L, 20 ml benzylchloride and 55 ml n-butyl alcohol, and the reaction was carried out at 50℃ for about 3 hours. Theas-obtained yield of phenylacetic acid was as high as 97.6%. In addition, the influences of thepresence of phenylacetic acid and air in the reaction system were also studied. The results showedthat the presence of air in the system and the entrainment of phenylacetic acid in the circulatingorganic phase had great influence on the reaction rate, the stability and performance of catalystand the yield of phenylacetic acid.

Synthesis, Crystal Structure and Luminescence Property of a Cd(Ⅱ) Complex Assembled by 4-Carboxymethoxy Phenylacetic Acid

A new structure with the molecular formula [CdL]n was formed by CdSO4 with 4-carboxymethoxy phenylacetic acid （H2L） through the hydrothermal method. The complex was characterized by elemental analysis and infrared spectroscopy. The structure of the complex was determined by single-crystal X-ray diffraction, which is of monoclinic system, space group P21/c with a = 10.3887（2）, b = 7.10710（10）, c = 14.7212（2） , β = 120.6940（10）°, V = 934.65（3） 3, Dc = 2.278 g·cm-3, Z = 4, F（000） = 624, S = 1.022, the final R = 0.0187 and wR = 0.0487 for 2000 observer reflections （Ⅰ 〉 2σ（Ⅰ））. The center metal ion Cd（Ⅱ） in the complex is six-coordinated in a distorted octahedral geometry, and is connected with L ligands to form a 3D fishing net structure, which is a novel （3,6） network topology. The luminescence of the complex has been investigated, and the result reveals that it displays luminescent property in the voilet region.

Inhibitory Effects of Phenylacetic Acid on Proliferation of Human Pancreatic Carcinoma BXPC-3 Cells by the Regulation of Adenosine Deaminases Acting on RNA

The effect and mechanism of phenylacetic acid on the proliferation of pancreatic carcinoma cells were investigated in cultured pancreatic carcinoma BXPC-3 cells by means of 3-（4,5-dimethylthiazol-2-yl）-2,5-diphenyltetrazolium bromide assay and flow cytometry assay.The results show that the treatment of pancreatic carcinoma cells with phenylacetic acid significantly inhibited the cell proliferation in time-dependent and dose-dependent manners.The proliferation of BXPC-3 cells was inhibited at the stage of S phase,the cells at the end stage of S phase were accumulated abundantly,and thus DNA synthesis could not be accomplished entirely.In addition,the expression of adenosine deaminases acting on RNA（ADARs） mRNA in BXPC-3 cells and pancreatic carcinoma specimen were detected by RT-PCR.Having been treated with phenylacetic acid,ADAR2 mRNA in BXPC-3 cells was significantly decreased,the differences were of statistical significance（P0.01）.Taken together,these results suggest that phenylacetic acid may likely regulate the proliferation of pancreatic carcinoma cells through the regulation of ADAR2 mRNA expression.

ADSORPTION OF PHENYLACETIC ACID ON MACROPOROUS POLYMERIC ADSORBENTS

Several macroporous polymeric adsorbents (NDA-999, XAD-8, X-5 and XAD-2) were employed in the study to adsorb phenylacetic acid from aqueous solution. Effect of salt and ambient temperature on adsorption was studied using NDA-999 adsorbent and the adsorption process conforms to Freundlich抯 model reasonably. Adsorption dynamics were conducted in batch experiments in order to make clear the mechanism of adsorption process. It is proved that the squared driving force mass transfer model can be adopted to elucidate the process. The treatment process of industrial wastewater containing high strength of phenylacetic acid was proposed for cleaner production of phenylacetic acid.

Bacteroides fragilis Supernatant Extracts Enriched in Phenylacetic Acid Induce a Cytotoxic Effect in Mammalian Cells

Bacteroides species are nearly half of the fecal flora community and some are host symbionts crucial to host nutrition and systemic immunity. Among Bacteroides species B. fragilis strains are considered to be the opportunistic ones, being the most isolated anaerobic bacteria in clinical samples. Cell-free supernatants of 65 B. fragilis strains were assayed and they were capable of inducing vacuolating phenotype on Vero cells lineage. The supernatant of the Bacteroides fragilis ATCC 23745 strain was elicited to have the strongest vacuolating effect on Vero cells monolayers and peritoneal macrophages. Some drastic cell alterations were observed, such as a general disorganization of cytoplasm and chromatin condensation, evidencing cell death. By transmission electron microscopy it was confirmed that the vacuoles observed were, in fact, swollen mitochondria. An immunocytochemical assay, TUNEL, was used to confirm this hypothesis and showed that Vero cells and peritoneal macrophages were dying by apoptotic process after exposition of B. fragilis cell-free supernatant. Physical analysis of the apoptotic factor has revealed properties similar to short-chain fatty acids. After gas chromatography and mass spectrometry analysis, phenylacetic acid (PA) was characterized as the major compound present in the most purified active fraction. We believe that the PA is responsible for the pro-apoptotic effect elicited by the supernatant of B. fragilis cultures.

Electrochemical response of MoS_(2) nanosheets/SiO_(2)-NH_(2) nanoparticles modified glassy carbon electrode to phenylacetic acid

Phenylacetic acid(PAA)is a primary raw material for illegal Methamphetamine(MATM)synthesis under the strong precursor chemicals supervisions of safrole and isosafrole.Therefore,trace detection of PAA at ultra-low concentration is a strategic technique and an urgent issue in the field of drug control.In this paper,trace determination of PAA at sub-nmol-L-1 concentration level is achieved by hydrogen bond adsorption and electrochemical catalysis through the prepared aminated SiO_(2)nanoparticles(SiO_(2)-NH_(2) NPs)and MoS_(2) nanosheets(NSs)modified glassy carbon electrode(GCE).The prepared MoS_(2) NS s/SiO_(2)-NH_(2) NPs modified electrode represents a detecting limit of 0.0989 nmol·L^(-1)and an obvious increasing linear range before the concentration increasement up to 60 nmol·L^(-1)in square wave voltammetry(SWV)responses of PAA.The SWV response of the modified electrode to PAA in the concentration range within 100 nmol·L^(-1)is higher than phenol,acetic acid(HOAc)and benzoic Acid(BEN).This electrochemical method for trace detection of PAA in aqueous solution with desired performance provides a feasible scheme for the detection of other drugs and aromatic precursor chemicals.

Amplification of an MFS Transporter Encoding Gene penT Significantly Stimulates Penicillin Production and Enhances the Sensitivity of Penicillium chrysogenum to Phenylacetic Acid

Penicillin is historically important as the first discovered drug against bacterial infections in human. Although the penicillin biosyn- thetic pathway and regulatory mechanism have been well studied in Penicillium chrysogenum, the compartmentation and molecular transport of penicillin or its precursors are still poorly understood. In search of the genomic database, more than 830 open reading frames （ORFs） were found to encode transmembrane proteins of P. chrysogenum. In order to investigate their roles on penicillin production, one of them （penT） was selected and cloned. The deduced protein ofpenTbelongs to the major facilitator superfamily （MFS） and contains 12 transmembrane spanning domains （TMS）. During fermentation, the transcription of penT was greatly induced by penicillin precursors phenylacetic acid （PAA） and phenoxyacetic acid （POA）. Knock-down of penT resulted in significant decrease of penicillin production, while over-expression of penT under the promoter of trpC enhanced the penicillin production. Introduction of an additional penT in the wild-type strain of P. chrysogenurn doubled the penicillin production and enhanced the sensitivity of P. chrysogenum to the penicillin precursors PAA or POA. These results indicate that penT stimulates penicillin production probably through enhancing the translocation of penicillin precursors across fungal cellular membrane. Penicillin is historically important as the first discovered drug against bacterial infections in human. Although the penicillin biosyn- thetic pathway and regulatory mechanism have been well studied in Penicillium chrysogenum, the compartmentation and molecular transport of penicillin or its precursors are still poorly understood. In search of the genomic database, more than 830 open reading frames （ORFs） were found to encode transmembrane proteins of P. chrysogenum. In order to investigate their roles on penicillin production, one of them （penT） was selected and cloned. The deduced protein ofpenTbelongs to the major facilitator superfamily （MFS） and contains 12 transmembrane spanning domains （TMS）. During fermentation, the transcription of penT was greatly induced by penicillin precursors phenylacetic acid （PAA） and phenoxyacetic acid （POA）. Knock-down of penT resulted in significant decrease of penicillin production, while over-expression of penT under the promoter of trpC enhanced the penicillin production. Introduction of an additional penT in the wild-type strain of P. chrysogenurn doubled the penicillin production and enhanced the sensitivity of P. chrysogenum to the penicillin precursors PAA or POA. These results indicate that penT stimulates penicillin production probably through enhancing the translocation of penicillin precursors across fungal cellular membrane.

Two new phenolic glycosides from the aerial parts of Androsace umbellata

Two new phenolic glycosides, 2-hydroxy-4-O-β-D-glucopyranosylphenylacetic acid methyl acetate （1） and 2-hydroxy-4-O-β-D- glucopyranosylphenylacetic acid （2） were isolated from the aerial parts ofAndrosace umbellata. Their structures were elucidated by spectral techniques. C 2009 Wen Cai Ye. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.