Spectroscopy and Photochemistry of Phenylacetic Acid Esters and Related Substrates. The Stereoelectronic Dependence of the Aryl/Carboxyl Bichromophore Interaction

1994 ◽  
Vol 59 (10) ◽  
pp. 2792-2798 ◽  
Author(s):  
Annette M. Kasper ◽  
John J. Nash ◽  
Harry Morrison
Keyword(s):  
Phenylacetic Acid ◽  
Acid Esters

Directed Iridium‐Catalyzed Hydrogen Isotope Exchange Reactions of Phenylacetic Acid Esters and Amides

2019 ◽  
Vol 25 (26) ◽  
pp. 6517-6522 ◽  
Author(s):  
Mégane Valero ◽  
Daniel Becker ◽  
Kristof Jess ◽  
Remo Weck ◽  
Jens Atzrodt ◽  
...  
Keyword(s):  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Phenylacetic Acid ◽  
Exchange Reactions ◽  
Hydrogen Isotope Exchange ◽  
Acid Esters

Stereoselective Synthesis of 3-azabicyclo[3,3,1]Nonan-9α-yl α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate Hydrochloride

2005 ◽  
Vol 2005 (5) ◽  
pp. 322-323 ◽  
Author(s):  
He Liu ◽  
Xiang-Yu Han ◽  
Bo-Hua Zhong ◽  
Ke-Liang Liu
Keyword(s):  
Mandelic Acid ◽  
Phenylacetic Acid ◽  
Stereoselective Synthesis ◽  
Enantiomeric Excess ◽  
Starting Material ◽  
Sterically Hindered ◽  
Acid Esters

The isomers of α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetic acid esters derived from 3-azabicyclo[3,3,1]nonan-9α-ol ((R)-1 and (S)-1) were obtained in high enantiomeric excess by effective stereoselective synthesis from the chiral starting material, (S) or (R)-mandelic acid using pivaldehyde as a sterically hindered reagent

Mono- and bis(aminomethyl)phenylacetic acid esters as short-acting antiarrhythmic agents. 2

1993 ◽  
Vol 36 (17) ◽  
pp. 2494-2498 ◽  
Author(s):  
Robert J. Chorvat ◽  
Lawrence A. Black ◽  
Vasant V. Ranade ◽  
Cynthia Barcelon-Yang ◽  
David M. Stout ◽  
...  
Keyword(s):  
Phenylacetic Acid ◽  
Antiarrhythmic Agents ◽  
Short Acting ◽  
Acid Esters

scholarly journals Palladium-Catalyzed α-Arylation of Dimethyl Malonate and Ethyl Cyanoacetate with o-Alkoxybromobenzenes for the Synthesis of Phenylacetic Acid, Esters and Phenylacetonitriles

SynOpen ◽  
2017 ◽  
Vol 01 (01) ◽  
pp. 0091-0096
Author(s):  
José Cívicos ◽  
Paulo Costa ◽  
Jorge Domingos
Keyword(s):  
Bioactive Compounds ◽  
Phenylacetic Acid ◽  
Ethyl Cyanoacetate ◽  
Dimethyl Malonate ◽  
Palladium Catalyzed ◽  
Acid Esters

α-Aryl malonate and α-aryl cyano acetate moieties are found in the structures of many bioactive compounds. They are also key intermediates for the synthesis of many compounds such as isoflavonoids. In this work, we synthesized these compounds, with different patterns of substitution, starting with the palladium-catalyzed reaction of o-alkoxy-bromoarenes with dimethyl malonate or ethyl cyanoacetate. Under the conditions applied, moderate to good yields of arylmalonate mono­esters, phenylacetic esters or acids, and benzylnitrile derivatives were obtained.

scholarly journals Application of freeze-dried Yarrowia lipolytica biomass in the synthesis of lipophilic antioxidants

2020 ◽  
Author(s):  
Bartłomiej Zieniuk ◽  
Małgorzata Wołoszynowska ◽  
Ewa Białecka-Florjańczyk ◽  
Agata Fabiszewska
Keyword(s):  
Phenolic Acids ◽  
Phenylacetic Acid ◽  
Food Additives ◽  
Antioxidant Properties ◽  
Enzymatic Esterification ◽  
Butyl Esters ◽  
Chemical Structures ◽  
Freeze Dried ◽  
Food Matrices ◽  
Acid Esters

Abstract Objective The aim of the study was to evaluate the possibility of using Y. lipolytica biomass as a whole-cell catalyst in the synthesis of lipophilic antioxidants, with the example of esterification of five phenolic acids with 1-butanol. Results Freeze-dried Y. lipolytica biomass was successfully applied as a biocatalyst in the synthesis of esters of phenylpropanoic acid derivatives with 75–98% conversion. However, in the case of phenylacetic acid derivatives, results below 10% were obtained. The biological activity of phenolic acid esters was strongly associated with their chemical structures. Butyl 3-(4-hydroxyphenyl)propanoate showed an IC50 value of 19 mg/ml (95 mM) and TEAC value of 0.427. Among the compounds tested, butyl esters of 3-(4-hydroxyphenyl)propanoic and 4-hydroxyphenylacetic acids exhibited the highest antifungal activity. Conclusions Lipophilization of phenolic acids achieved by enzymatic esterification creates prospects for using these compounds as food additives with antioxidant properties in lipid-rich food matrices.

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