Microbial Formation of Substituted Styrenes

1989 ◽  
Vol 44 (9-10) ◽  
pp. 765-770 ◽  
Author(s):  
Hans-Adolf Arfmann ◽  
Wolf-Rainer Abraham
Keyword(s):  
Carboxylic Acids ◽  
Benzene Ring ◽  
Cinnamic Acid ◽  
Methoxy Group ◽  
Methyl Chloride ◽  
Side Chains ◽  
Cinnamic Acids ◽  
Cinnamic Acid Derivatives ◽  
Aromatic Carboxylic Acids ◽  
High Yields

Various mono- and disubstituted cinnamic acid derivatives and aromatic carboxylic acids with saturated side chains were incubated mainly with Bacillus, Candida, Hansenula, and Saccharomyces strains. The cinnamic acids carrying a hydroxy- and/or a methoxy group at the 3- and/or 4-position of the benzene ring were decarboxylated with high yields. Most of the reactions were terminated within 24 to 48 h. Substitution at other ring positions afforded also decarboxylation, but at much lower yields. Derivatives with other residues like methyl, chloride, or bromide were not transform ed to the respective styrene. None of the saturated aromatic carboxylic acids could be decarboxylated by the strains used.

Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst

2021 ◽  
Author(s):  
Bin Zhao ◽  
Bo Xu
Keyword(s):  
Double Bond ◽  
Visible Light ◽  
Cinnamic Acid ◽  
Oxidative Cyclization ◽  
Coumarin Derivatives ◽  
Cinnamic Acids ◽  
Cinnamic Acid Derivatives ◽  
Double Bond Isomerization ◽  
Photocatalytic Synthesis

We have developed an efficient photocatalytic synthesis of coumarin derivatives via a tandem double bond isomerization/oxidative cyclization of cinnamic acids.

scholarly journals Efficient one-pot, four-component synthesis of N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives from the reaction of (isocyanoimino)triphenylphosphorane, dibenzylamine, an aromatic carboxylic acid and cyclobutanone

2012 ◽  
Vol 77 (9) ◽  
pp. 1175-1180 ◽  
Author(s):  
Nahid Shajari ◽  
Reza Kazemizadeh ◽  
Ali Ramazani
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Aromatic Carboxylic Acid ◽  
One Pot ◽  
Aromatic Carboxylic Acids ◽  
High Yields ◽  
Neutral Conditions

Four-component reaction of cyclobutanone, dibenzylamine and (Nisocyanimino) triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and under neutral conditions to afford N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives in high yields.

THE TRANSMISSION OF THE POLAR EFFECTS OF SUBSTITUENTS IN AROMATIC AND ARYLALIPHATIC CARBOXYLIC ACIDS: REACTIONS OF THE ACIDS WITH DIAZODIPHENYLMETHANE IN ETHANOL

1964 ◽  
Vol 42 (8) ◽  
pp. 1979-1983 ◽  
Author(s):  
K. Bowden ◽  
N. B. Chapman ◽  
J. Shorter
Keyword(s):  
Carboxylic Acids ◽  
Carbonyl Group ◽  
Cinnamic Acid ◽  
Field Effect ◽  
Rate Coefficients ◽  
Side Chain ◽  
Side Chains ◽  
Electronic Effects ◽  
Electron Effect

Rate coefficients have been determined for the reactions in ethanol at 30° of diazodiphenylmethane with several groups of carboxylic acids. Each group included the parent acid and three nuclear substituted acids. The parent acids were: benzoic, phenylacetic, β-phenylpropionic, phenoxyacetic, and trans-cinnamic acid. The reactions of 3-fluoro- (or chloro-) or 4-methyl-biphenyl-4′-carboxylic, and of 9-X-10-anthroic acids (X = Me, Cl, or Br) were also studied similarly. The Hammett polar susceptibility constant, ρ, has been calculated for each set of reactions. The values of ρ are discussed in terms of transmission of electronic effects through the side-chain by a field effect, and for side-chains conjugated with the ring, by a π-electron effect, both of which are inversely proportional to the first power of the distance of the carbonyl group from the ring.

Base catalyzed sustainable synthesis of phenyl esters from carboxylic acids using diphenyl carbonate

RSC Advances ◽  
2015 ◽  
Vol 5 (65) ◽  
pp. 53155-53160 ◽  
Author(s):  
Oliver Kreye ◽  
Michael A. R. Meier
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Elevated Temperatures ◽  
Diphenyl Carbonate ◽  
Aromatic Carboxylic Acids ◽  
High Yields

Phenyl esters were obtained in moderate to high yields by reaction of aliphatic and aromatic carboxylic acids with one equivalent of diphenyl carbonate in the presence of catalytic amounts of tertiary amine bases, under neat conditions at elevated temperatures (>100 °C).

scholarly journals Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of Z-cinnamic acid derivatives

2020 ◽  
Vol 19 (6) ◽  
pp. 819-830 ◽  
Author(s):  
Rocío B. Rodríguez ◽  
Ramiro L. Zapata ◽  
María L. Salum ◽  
Rosa Erra-Balsells
Keyword(s):  
Ionic Liquids ◽  
Cinnamic Acid ◽  
Substituent Effect ◽  
Pure Acid ◽  
Protic Ionic Liquids ◽  
Cinnamic Acids ◽  
Cinnamic Acid Derivatives

Cinnamic acids in their PIL form are more reactive than in their pure acid forms toward photoisomerization. This knowledge is successfully used for establishing an efficient and practical synthetic protocol for synthesizing Z-cinnamic derivatives.

scholarly journals Aroma Profile of Galangal Composed of Cinnamic Acid Derivatives and Their Structure-Odor Relationships

2016 ◽  
Vol 11 (10) ◽  
pp. 1934578X1601101 ◽  
Author(s):  
Toshio Hasegawa ◽  
Momohiro Hashimoto ◽  
Takashi Fujihara ◽  
Hideo Yamada
Keyword(s):  
Cinnamic Acid ◽  
Methoxy Group ◽  
Steam Distillation ◽  
Linear Chain ◽  
Hexane Extract ◽  
Hexane Extraction ◽  
Cinnamic Acid Derivatives ◽  
Aroma Profile ◽  
Main Component ◽  
Fruity Odor

Cinnamic acid derivatives are important odorants due to their characteristic scent. Some fragrance materials, such as cinnamon bark, matsutake mushrooms, and Kaempferia galanga L. rhizome (galangal), contain several cinnamic acid derivatives as important odor constituents. The main odor constituent of galangal is ( E)-ethyl 4-methoxycinnamate, but the odor of this compound is different from that of galangal. We investigated the aroma profile of galangal using our previously described method that considers the intermolecular interactions of the odorant compounds with their receptors. Odorant compounds in galangal were extracted by hexane extraction, steam distillation, and headspace sampling. The odor of the hexane extract was different from that of the steam distillate and similar to that of galangal; therefore, we searched for the key compounds contributing to the aroma profile of galangal by separating the constituents of the hexane extract. A fraction with a galangal-like odor was obtained by bulb-to-bulb distillation of the hexane extract. The main component of this fraction was not ( E)-ethyl 4-methoxycinnamate, but rather ethyl cinnamate. These results indicate that ethyl cinnamate is more important in the aroma profile of galangal than ( E)-ethyl 4-methoxycinnamate. GC-MS analysis revealed that this fraction contained aromatic compounds, cyclic terpenes, and linear chain compounds in addition to ethyl cinnamate. We synthesized cinnamic acid derivatives and examined the importance of the odor expression of these cinnamic acid derivatives. Cinnamic acid derivatives lacking a p-methoxy group had a strong fruity odor. Replacement of the hydrogen atom at the para position with a methoxy group altered and weakened the odor. We found that a p-methoxy group in cinnamic acid derivatives plays an important role in the aroma profile of galangal.

scholarly journals The efficient and selective catalytic oxidation of para-substituted cinnamic acid derivatives by the cytochrome P450 monooxygenase, CYP199A4

RSC Advances ◽  
2016 ◽  
Vol 6 (60) ◽  
pp. 55286-55297 ◽  
Author(s):  
Rebecca R. Chao ◽  
James J. De Voss ◽  
Stephen G. Bell
Keyword(s):  
Cytochrome P450 ◽  
Catalytic Oxidation ◽  
Cinnamic Acid ◽  
Product Formation ◽  
Cytochrome P450 Enzyme ◽  
Cinnamic Acids ◽  
P450 Monooxygenase ◽  
Cinnamic Acid Derivatives ◽  
Selective Catalytic Oxidation ◽  
P450 Enzyme

The cytochrome P450 enzyme, CYP199A4 oxidised para substituted alkyloxy- and alkyl-cinnamic acids, with high product formation activity.

Coupling of carboxylic acids with internal alkynes by supported ruthenium catalysts: direct and selective syntheses of multi-substituted phthalide derivatives

2015 ◽  
Vol 51 (9) ◽  
pp. 1654-1657 ◽  
Author(s):  
Hiroki Miura ◽  
Kentaro Tsutsui ◽  
Kenji Wada ◽  
Tetsuya Shishido
Keyword(s):  
Carboxylic Acids ◽  
Ruthenium Catalysts ◽  
Aromatic Carboxylic Acids ◽  
Ru Catalyst ◽  
Internal Alkynes ◽  
High Yields

Supported ruthenium catalysts promote coupling of various kinds of aromatic carboxylic acids with internal alkynes, giving the corresponding multi-substituted phthalide derivatives in high yields. The supported Ru catalyst can be recycled at least five times with no loss of activity.

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