scholarly journals Influence of the pKa Value of Cinnamic Acid and P-Hydroxycinnamic Acid on the Solubility of a Lurasidone Hydrochloride-Based Coamorphous System

ACS Omega ◽  
2021 ◽  
Vol 6 (4) ◽  
pp. 3106-3119
Author(s):  
Yi Hu ◽  
Yujie Guo ◽  
Bin Li ◽  
Renjie Xu ◽  
Xiaoping Fang ◽  
...  
Keyword(s):  
Cinnamic Acid ◽  
Hydroxycinnamic Acid ◽  
Pka Value ◽  
Lurasidone Hydrochloride

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XIII. THE PHENYLPROPANOID SYSTEM IN LIGNIFICATION

1963 ◽  
Vol 41 (1) ◽  
pp. 621-628 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Amino Acids ◽  
Ferulic Acid ◽  
Cinnamic Acid ◽  
Biosynthetic Pathway ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Coniferyl Alcohol ◽  
Phenyllactic Acid ◽  
Phenylalanine Deaminase

Techniques of isotope competition and trapping were used to study the phenylpropanoid biosynthetic pathway in lignifying wheat plants. The results in general confirm earlier findings that phenyllactic acid (PLA), p-hydroxyphenyllactic acid (HPLA), phenylpyruvic, cinnamic, caffeic, ferulic, and sinapic acids can participate in lignification. L-Phenylalanine and L-tyrosine were converted to PLA and HPLA, respectively, but there was much less conversion of cinnamic acid to PLA, or p-hydroxycinnamic acid to HPLA. A pathway from phenylalanine to cinnamic acid via PLA, and an analogous pathway involving tyrosine thus remain as possible alternatives to the established routes involving deamination of these amino acids by phenylalanine deaminase or tyrase. Feeding of non-radioactive coniferyl alcohol with ferulic acid-C14 results in the formation of both coniferyl- and sinapyl-type lignin residues having lower specific radioactivities than were obtained after the feeding of ferulic acid-C14 alone. After a 5-hour metabolic period in the presence of ferulic acid-C14, both coniferyl aldehyde and coniferyl alcohol became labelled, and the radioactivity of the aldehyde was much higher than that of the alcohol. There was no evidence of coniferin formation. These findings indicate that coniferyl alcohol is formed from ferulic acid through coniferyl aldehyde, and that coniferin is probably unnecessary for lignification, at least in species other than conifers.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XIII. THE PHENYLPROPANOID SYSTEM IN LIGNIFICATION

1963 ◽  
Vol 41 (3) ◽  
pp. 621-628 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Amino Acids ◽  
Ferulic Acid ◽  
Cinnamic Acid ◽  
Biosynthetic Pathway ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Coniferyl Alcohol ◽  
Phenyllactic Acid ◽  
Phenylalanine Deaminase

Techniques of isotope competition and trapping were used to study the phenylpropanoid biosynthetic pathway in lignifying wheat plants. The results in general confirm earlier findings that phenyllactic acid (PLA), p-hydroxyphenyllactic acid (HPLA), phenylpyruvic, cinnamic, caffeic, ferulic, and sinapic acids can participate in lignification. L-Phenylalanine and L-tyrosine were converted to PLA and HPLA, respectively, but there was much less conversion of cinnamic acid to PLA, or p-hydroxycinnamic acid to HPLA. A pathway from phenylalanine to cinnamic acid via PLA, and an analogous pathway involving tyrosine thus remain as possible alternatives to the established routes involving deamination of these amino acids by phenylalanine deaminase or tyrase. Feeding of non-radioactive coniferyl alcohol with ferulic acid-C14 results in the formation of both coniferyl- and sinapyl-type lignin residues having lower specific radioactivities than were obtained after the feeding of ferulic acid-C14 alone. After a 5-hour metabolic period in the presence of ferulic acid-C14, both coniferyl aldehyde and coniferyl alcohol became labelled, and the radioactivity of the aldehyde was much higher than that of the alcohol. There was no evidence of coniferin formation. These findings indicate that coniferyl alcohol is formed from ferulic acid through coniferyl aldehyde, and that coniferin is probably unnecessary for lignification, at least in species other than conifers.

STUDIES ON THE BIOSYNTHESIS OF VOLUCRISPORIN: II. METABOLISM OF SOME PHENYLPROPANOID COMPOUNDS BY VOLUCRISPORA AURANTIACA HASKINS

1966 ◽  
Vol 44 (4) ◽  
pp. 403-413 ◽  
Author(s):  
P. Chandra ◽  
G. Read ◽  
L. C. Vining
Keyword(s):  
Amino Acids ◽  
Cinnamic Acid ◽  
Biosynthetic Pathway ◽  
Shikimic Acid ◽  
Aromatic Amino Acids ◽  
Hydroxycinnamic Acid ◽  
Phenyllactic Acid ◽  
Radioactive Substrate

DL-Phenyllactic acid-α-14C, DL-phenylserine-α-14C, L-phenylalanine-carboxyl-14C, and shikimic acid-U-14C were incorporated into phenylalanine and tyrosine isolated from mycelial hydrolysates of Volucrispora aurantiaca as well as into volucrisporin. DL-m-Tyrosine-carboxyl-14C was incorporated into volucrisporin but not into the aromatic amino acids. L-Tyrosine-β-14C, cinnamic acid-α-14C, and m-hydroxycinnamic acid-α-14C were metabolized by the fungus but did not serve as precursors of volucrisporin or of mycelial phenylalanine. The results are consistent with the concept of a biosynthetic pathway to volucrisporin via phenylpyruvic and m-hydroxyphenylpyruvic acids. Substantial amounts of each radioactive substrate fed to V. aurantiaca PRL 1952 were incorporated into a brown melanoid pigment.

BIOSYNTHESIS OF QUERCETIN IN BUCKWHEAT: PART I

1957 ◽  
Vol 35 (3) ◽  
pp. 219-228 ◽  
Author(s):  
E. W. Underhill ◽  
J. E. Watkin ◽  
A. C. Neish
Keyword(s):  
Cinnamic Acid ◽  
Protocatechuic Acid ◽  
Shikimic Acid ◽  
Sinapic Acid ◽  
Hydroxycinnamic Acid ◽  
Fagopyrum Tataricum ◽  
Veratric Acid ◽  
Methoxycinnamic Acid ◽  
Hydrolysis Of ◽  
Ring Hydroxylation

Cuttings of Fagopyrum tataricum were allowed to metabolize various labelled compounds for 24 hours in the light. Quercetin was then isolated and degraded by alkaline hydrolysis of its pentamethyl ether into veratric acid (ring B plus carbon 2) and 2′-hydroxy-2,4′,6′-trimethoxyacetophenone (ring A plus carbons 3 and 4). Eleven amino acids, including tyrosine, were poor precursors of quercetin as were also protocatechuic acid and p-hydroxybenzoic acid. Shikimic acid, phenylalanine, p-hydroxycinnamic acid, and cinnamic acid were very good precursors followed by (in decreasing order of effectiveness) caffeic acid (fair), sinapic acid, m-methoxycinnamic acid, and ferulic acid (very poor). Quercetin formed from β- or ring-labelled cinnamic acid gave labelled veratric acid on degradation, and that from α- or carboxyl-labelled cinnamic acid gave labelled 2′-hydroxy-2,4′,6′-trimethoxyacetophenone. Two-ninths of the activity of quercetin formed from uniformly labelled phenylalanine was found in the acetophenone derivative and seven-ninths in the veratric acid. These results show that C6.C3 compounds are used with the carbon skeleton unchanged for the synthesis of ring B and carbons 2, 3, and 4 of quercetin and that the ring hydroxylation pattern of the compound used determines its effectiveness. None of the compounds were good precursors of ring A.

scholarly journals Studies on the application of the quinhydrone electrode in formamide. VII. The ionization constants and related thermodynamic quantities of (E)-cinnamic acid from E.M F. measurements at different temperatures

1976 ◽  
Vol 29 (7) ◽  
pp. 1609 ◽  
Author(s):  
UN Dash
Keyword(s):  
Cinnamic Acid ◽  
Ionization Constants ◽  
Thermodynamic Quantities ◽  
Temperature Range ◽  
Pka Value ◽  
Different Temperatures

The e.m.f. of the cell Ag-AgCl/NaCl(m3), NaA(m2), HA(m1) QH2-Q/Pt (where HA is cinnamic acid) in formamide has been measured at 5� intervals over the temperature range 5-45�C. The pKa value of (E)-cinnamic acid ranges from 7.02 � 0.03 at 5� to 6.78 � 0.05 at 45�.

Exploring cinnamic acid scaffold: development of promising neuroprotective lipophilic antioxidants

MedChemComm ◽  
2015 ◽  
Vol 6 (6) ◽  
pp. 1043-1053 ◽  
Author(s):  
Daniel Chavarria ◽  
Tiago Silva ◽  
Daniel Martins ◽  
Joana Bravo ◽  
Teresa Summavielle ◽  
...  
Keyword(s):  
Cinnamic Acid ◽  
Hydroxycinnamic Acid

New lipophilic hydroxycinnamic acid based derivatives were designed and synthesized and their antioxidant and neuroprotective activities evaluated.

Preparation of Water-Dispersible Nanoparticles by Self-Organization of Bio-Based Photo-Reactive Polymer

2011 ◽  
Vol 236-238 ◽  
pp. 2216-2220
Author(s):  
Dong Jian Shi ◽  
Ming Qing Chen ◽  
Mitsuru Akashi
Keyword(s):  
Cinnamic Acid ◽  
Potential Application ◽  
Hydroxycinnamic Acid ◽  
Pluronic F127 ◽  
Self Organization ◽  
Cinnamic Acid Derivatives ◽  
Reactive Polymer ◽  
Water Dispersible ◽  
Hyperbranched Polyesters

Hyperbranched polyesters, poly(4-hydroxycinnamic acid-co-3, 4-dihydroxycinnamic acid) [P(4HCA-co-DHCA)], were synthesized by the heat-transesterification of bio-based monomers 4HCA and DHCA. The P(4HCA-co-DHCA) nanoparticles were formed after two homogeneous copolymer solutions were mixed in DMF and TFA solutions, which are both good solvents for the copolymer P(4HCA-co-DHCA). For the potential application of the nanoparticles composed of cinnamic acid derivatives, water-dispersible nanoparticles were prepared by introduction of Pluronic F127 into the P(4HCA-co-DHCA) nanoparticles. The photo-reactivities of the nanoparticles were investigated.

BIOSYNTHESIS OF QUERCETIN IN BUCKWHEAT: PART I

1957 ◽  
Vol 35 (1) ◽  
pp. 219-228 ◽  
Author(s):  
E. W. Underhill ◽  
J. E. Watkin ◽  
A. C. Neish
Keyword(s):  
Cinnamic Acid ◽  
Protocatechuic Acid ◽  
Shikimic Acid ◽  
Sinapic Acid ◽  
Hydroxycinnamic Acid ◽  
Fagopyrum Tataricum ◽  
Veratric Acid ◽  
Methoxycinnamic Acid ◽  
Hydrolysis Of ◽  
Ring Hydroxylation

Cuttings of Fagopyrum tataricum were allowed to metabolize various labelled compounds for 24 hours in the light. Quercetin was then isolated and degraded by alkaline hydrolysis of its pentamethyl ether into veratric acid (ring B plus carbon 2) and 2′-hydroxy-2,4′,6′-trimethoxyacetophenone (ring A plus carbons 3 and 4). Eleven amino acids, including tyrosine, were poor precursors of quercetin as were also protocatechuic acid and p-hydroxybenzoic acid. Shikimic acid, phenylalanine, p-hydroxycinnamic acid, and cinnamic acid were very good precursors followed by (in decreasing order of effectiveness) caffeic acid (fair), sinapic acid, m-methoxycinnamic acid, and ferulic acid (very poor). Quercetin formed from β- or ring-labelled cinnamic acid gave labelled veratric acid on degradation, and that from α- or carboxyl-labelled cinnamic acid gave labelled 2′-hydroxy-2,4′,6′-trimethoxyacetophenone. Two-ninths of the activity of quercetin formed from uniformly labelled phenylalanine was found in the acetophenone derivative and seven-ninths in the veratric acid. These results show that C6.C3 compounds are used with the carbon skeleton unchanged for the synthesis of ring B and carbons 2, 3, and 4 of quercetin and that the ring hydroxylation pattern of the compound used determines its effectiveness. None of the compounds were good precursors of ring A.

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