Synthesis Of Cinnamic Acids Research Articles

Synthesis of Cinnamic Acid and its Antimicrobial Activity: A Review

Cinnamic acid, a naturally occurring aromatic carboxylic acid, has garnered significant attention due to its diverse biological activities, including potent antimicrobial properties. This review delves into the synthesis of cinnamic acid, its structural elucidation, and its mechanism of action against various microorganisms. The synthesis methods, including traditional and modern approaches, are discussed in detail. Additionally, the review explores the antimicrobial activity of cinnamic acid and its derivatives, highlighting their potential applications in various fields such as pharmaceuticals and agriculture.

Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment

Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment

Transcriptomic and metabonomic insights into the biocontrol mechanism of Trichoderma asperellum M45a against watermelon Fusarium wilt.

Watermelon (Citrullus lanatus) is one of the most popular fruit crops. However, Fusarium wilt (FW) is a serious soil-borne disease caused by Fusarium oxysporum f. sp. niveum (FON) that severely limits the development of the watermelon industry. Trichoderma spp. is an important plant anti-pathogen biocontrol agent. The results of our previous study indicated that Trichoderma asperellum M45a (T. asperellum M45a) could control FW by enhancing the relative abundance of plant growth-promoting rhizobacteria (PGPR) in the rhizosphere of watermelon. However, there are few studies on its mechanism in the pathogen resistance of watermelon. Therefore, transcriptome sequencing of T. asperellum M45a-treated watermelon roots combined with metabolome sequencing of the rhizosphere soil was performed with greenhouse pot experiments. The results demonstrated that T. asperellum M45a could stably colonize roots and significantly increase the resistance-related enzymatic activities (e.g., lignin, cinnamic acid, peroxidase and peroxidase) of watermelon. Moreover, the expression of defense-related genes such as MYB and PAL in watermelon roots significantly improved with the inoculation of T. asperellum M45a. In addition, KEGG pathway analysis showed that a large number of differentially expressed genes were significantly enriched in phenylpropane metabolic pathways, which may be related to lignin and cinnamic acid synthesis, thus further inducing the immune response to resist FON. Furthermore, metabolic analysis indicated that four differential metabolic pathways were enriched in M45a-treated soil, including six upregulated compounds and one down-regulated compound. Among them, galactinol and urea were significantly positively correlated with Trichoderma. Hence, this study provides insight into the biocontrol mechanism of T. asperellum M45a to resist soil-borne diseases, which can guide its industrial application.

Facile synthesis of cinnamic acid sensitized rice husk biochar for removal of organic dyes from wastewaters: Batch experimental and theoretical studies

In this study, a novel adsorbent was prepared by modifying rice husk biochar (RHB) with cinnamic acid (CA). CA introduces the carboxylic group to biochar which is favorable for the adsorption of cationic methylene blue dye (MB) from the aqueous solution. The mechanism of adsorption and characteristics were investigated with the help of experimental and Density Functional Theory (DFT). The adsorption capacity of modified biochar for MB was enhanced (Langmuir Qmax of 277.8 mg g−1, for MB when Co = 200 mg/L, pH = 11, T = 25 °C) respectively. The adsorption kinetics plots were consistent with the pseudo-second-order model, indicating chemical adsorption through electrostatic interactions. The adsorption isotherm curves were well matched with the Langmuir model indicating the monolayer mechanism of adsorption. Based on DFT calculations the reactive sites were predicted by the ways of Molecular Electrostatic Potential (MEP). The material properties of CA-RHB were investigated by different characterization techniques (SEM, EDS, XRD, and FTIR). The investigation of various parameters indicates that the adsorption process increases with increasing pH, contact time, and dosage. The study suggests that modified rice husk biochar can be a promising sorbent for the adsorption of Methylene Blue (MB) from aqueous mediums.

β-Aminobutyric acid treatment accelerates the deposition of suberin polyphenolic and lignin at wound sites of potato tubers during healing

β-Aminobutyric acid (BABA) is a nonprotein amino acid that induces plant defense responses to numerous biotic and abiotic stresses. However, whether BABA treatment affects the wound healing process of potato tubers has yet to be reported. In this study, we examined the effects of BABA treatment on the weight loss and disease index of Solanum tuberosum L. cv. Atlantic potato tubers inoculated with Fusarium sulphureum and assessed the deposition of suberin polyphenolic (SPP) and lignin at the wound sites of these tubers during healing. We also investigated the indexes involved in phenylpropane metabolism, H2O2, and peroxidase in the underlying effect mechanism. BABA treatment effectively reduced the weight loss of wounded tubers (by 41.0 %) and the disease index of inoculated tubers (by 43.2 %) during healing (at 21 d and relative to the control). BABA treatment also accelerated the deposition of SPP and lignin at wound sites. SPP and lignin cell layers in the treated tubers were 58.45 % and 54.72 % thicker, respectively, than the equivalent cell layers in the controls at 7 d of healing. Additionally, BABA treatment significantly enhanced the activities of phenylalanine ammonia-lyase (PAL), 4-coumaryl coenzyme A ligase (4CL), cinnamic acid-4-hydroxylase (C4H), and cinnamyl alcohol dehydrogenase (CAD) while also promoting the synthesis of cinnamic acid, p-coumaric acid, caffeic acid, ferulic acid, sinapic acid, cinnamyl alcohol, coniferyl alcohol, and sinapyl alcohol, as well as increasing total phenolic and lignin content, at wound sites during healing. Furthermore, BABA treatment increased H2O2 content and peroxidase activity at the wounds. These results suggest that BABA treatment activates phenylpropanoid metabolism, increases H2O2 content and peroxidase activity, and accelerates the deposition of SPP and lignin in potato tuber wounds, all of which lead to reductions in the weight loss and disease index of tubers during healing.

Photosynthetic apparatus efficiency, phenolic acid profiling and pattern of chosen phytohormones in pseudometallophyte Alyssum montanum

The present study investigated the response of non-metallicolous (NM) and metallicolous (M) Alyssum montanum shoots cultured in vitro on a medium supplemented simultaneously with heavy metals (HMs) to identify mechanisms involved in alleviating metal-induced damage. Plant status in respect to photosynthetic apparatus efficiency was determined and linked with changes in biochemical composition of shoots, namely phenolic acids’ and stress-related phytohormones. Results showed the considerable inter-ecotype differences in (1) the photosynthetic pigments’ amount, (2) the functioning of membrane electron transporters as well as (3) the linear and alternative electron transport pathways, whose lower values were reported in NM than in M HM-treated culture. Photosynthetic apparatus protection in M specimens was assured by the activation of cinnamic acid synthesis (by phenylalanine ammonia lyase) and its further transformations to benzoic acid derivatives with high ability to counteract oxidative stress, that was accompanied by the overexpression of jasmonic acid stimulating antioxidant machinery. In turn, detrimental HM effects on NM shoots could result from the diminution of most phenolics’ accumulation, and only the content of coumarate (produced by bifunctional phenylalanine/tyrosine ammonia lyase) and rosmarinic acid increased. All these together with an enhanced concentration of abscisic acid might suggest that NM strategy to cope with HMs is based mostly on a restriction of metal movement with transpiration flow and their limited distribution in leaves. Summarizing, our findings for the first time point out the physiological and metabolic adaptation of pseudometallophyte A. montanum to adverse conditions.

Hemishell Zeolites Synthesized by Asymmetric Modification as Biphasic Nanoreactors with Tunable Amphiphilicity for Catalysis of Cascade Reactions.

It is strongly desired to design and synthesize amphiphilic nanoreactors with tunable compatibility, which are stable at the biphasic interface in both acidic and alkaline environments. Herein, a novel amphiphilic R1-ZSM-5-R2 nanoreactor with adjustable hydrophilic-lipophilic balance (solid) (HLB(S)) values has been successfully synthesized by hydrophilic/lipophilic asymmetric modification of the surface of hemishell zeolites. The hemishell zeolites obtained by alkali etching have different surfaces for this asymmetric modification. Owing to the unique hemishell structures and asymmetric modification, the R1-ZSM-5-R2 nanoreactors with an optimized type and amount of modified organosilanes show excellent stability and emulsifying properties under extreme environments, which is important for cascade reactions in a biphasic system. The modified amino groups on the surface of the nanoreactors not only enhance the hydrophilicity of the hemishell zeolites and stabilize ultrasmall Pt nanoparticles (1.90 nm) but also used for the catalytic synthesis of trans-cinnamaldehyde. The Pt@R1-ZSM-5-R2 amphiphilic catalysts fabricated through a one-step reduction of Pt nanoparticles present outstanding performances in the biphasic cascade synthesis of cinnamic acid, achieving a very high turnover frequency (TOF) of 978 h-1. The TOF values of the catalysts correspond well to the HLB(S) values of the R1-ZSM-5-R2 nanoreactors.

Synthesis of Cinnamic Acid Based on Perkin Reaction Using Sonochemical Method and Its Potential as Photoprotective Agent

<p>Cinnamic acid plays a vital role in the synthesis of other important compounds and as a precursor for the synthesis of commercial cinnamon esters used in perfumery, cosmetics, and pharmaceutical industries. The aim of this research is to synthesize cinnamic acid using sonochemical methods. Cinnamic acid was synthesized using Perkin reaction by reacting 0.05 mole of benzaldehyde with 0.073 mole of acetic acid anhydride and 0.03 mole of sodium acetate as a catalyst in the Erlenmeyer flask and then the mixture was put in a sonicator for 60 minutes at 70 <sup>o</sup>C. The synthesized compound was tested organoleptic properties, and the melting point was measured. The chemical structure was elucidated using FT-IR, H-NMR, and <sup>13</sup>C-NMR. The photoprotective activity was examined from its antioxidant and SPF values. The synthesized compound was found in the form of a shiny white fine crystal which had distinctive odor with a yield of 4.98% and the melting point was found at 133<sup> o</sup>C. In the structure elucidation using FT-IR (the aromatic ring absorption at the wave number 1580 cm<sup>-1</sup> -1600 cm<sup>-1</sup>. The wave number 1625 cm<sup>-1</sup>is an aromatic conjugated alkene group, while wave number 1689.4 cm<sup>-1 </sup>is a carbonyl group. The wave number 2500 cm<sup>-1 </sup>– 3250 cm<sup>-1 </sup>is an OH carboxylic acid group) , H-NMR (7.410 (<em>m</em>, 5H, Ar-H); 7.425(<em>t</em>, 1H); 7.572 (<em>d</em>, 1H); 8.057 (d, 1H,C=CH) and <sup>13</sup>C-NMR (129.309 ppm; 130.998 ppm; 134.58 ppm; 170.017 ppm) showed that when compared with the standard compound as the reference, the synthesized compound was confirmed to be cinnamic acid. The antioxidant activity test showed that at the concentration of 20 ppm the synthesized compound was able to reduce free radicals by 46.69%. This finding showed that the synthesized compound had antioxidant activity.</p>

Spatial Isolation of Carbon and Silica in a Single Janus Mesoporous Nanoparticle with Tunable Amphiphilicity.

Like surfactants with tunable hydrocarbon chain length, Janus nanoparticles also possess the ability to stabilize emulsions. The volume ratio between the hydrophilic and hydrophobic domains in a single Janus nanoparticle is very important for the stabilization of emulsions, which is still a great challenge. Herein, dual-mesoporous Fe3O4@mC&mSiO2 Janus nanoparticles with spatial isolation of hydrophobic carbon and hydrophilic silica at the single-particle level have successfully been synthesized for the first time by using a novel surface-charge-mediated selective encapsulation approach. The obtained dual-mesoporous Fe3O4@mC&mSiO2 Janus nanoparticles are made up of a pure one-dimensional mesoporous SiO2 nanorod with tunable length (50-400 nm), ∼100 nm wide and ∼2.7 nm mesopores and a closely connected mesoporous Fe3O4@mC magnetic nanosphere (∼150 nm diameter, ∼10 nm mesopores). As a magnetic "solid amphiphilic surfactant", the hydrophilic/hydrophobic ratio can be precisely adjusted by varying the volume ratio between silica and carbon domains, endowing the Janus nanoparticles surfactant-like emulsion stabilization ability and recyclability under a magnetic field. Owing to the total spatial separation of carbon and silica, the Janus nanoparticles with an optimized hydrophilic/hydrophobic ratio show spectacular emulsion stabilizing ability, which is crucial for improving the biphasic catalysis efficiency. By selectively anchoring catalytic active sites into different domains, the fabricated Janus nanoparticles show outstanding performances in biphasic reduction of 4-nitroanisole with 100% conversion efficiency and 700 h-1 high turnover frequency for biphasic cascade synthesis of cinnamic acid.

Electrosynthesis of cinnamic acid by electrocatalytic carboxylation of phenylacetylene in the presence of [NiII(Me4-NO2Bzo[15]tetraeneN4)] complex: An EC′CCC′C mechanism

A Ni(II) complex, [NiII(Me4-NO2Bzo[15]tetraeneN4)], was used for electrocatalytic reduction of CO2 in acetonitrile solvent. Then, the reduced form of CO2 (CO2−) was used for selective carboxylation of phenylacetylene to produce cinnamic acid at room temperature. The potential of the process is significantly less negative in comparison with those reported earlier. Using sacrificial magnesium electrode as anode, controlled potential coulometry was carried out in an undivided glass cell. The spectral characterizations of FTIR, 1H NMR, and 13C NMR demonstrated that cinnamic acid was the main product of the electrolysis. With respect to other catalysts, which have been previously reported in the literature, application of the Ni(II) complex in carboxylation of unsaturated compounds has three advantages: (1) the selectivity in the production of cinnamic acid; (2) more increase in the reduction current indicating that the carboxylation of phenylacetylene is fast; and (3) the potential shift of electrocatalytic reduction of CO2 to less negative values showing that the Ni(II) complex has an excellent electrocatalytic activity for CO2 reduction. According to the voltammetric and coulometric results, an EC′CCC′C mechanism was proposed for the electrocatalytic synthesis of cinnamic acid.

Engineering of Escherichia coli for the synthesis of N-hydroxycinnamoyl tryptamine and serotonin.

Plants synthesize various phenol amides. Among them, hydroxycinnamoyl (HC) tryptamines and serotonins exhibit antioxidant, anti-inflammatory, and anti-atherogenic activities. We synthesized HC-tryptamines and HC-serotonin from several HCs and either tryptamine or serotonin using Escherichia coli harboring the 4CL (4-coumaroyl CoA ligase) and CaHCTT [hydroxycinnamoyl-coenzyme A:serotonin N-(hydroxycinnamoyl)transferase] genes. E. coli was engineered to synthesize N-cinnamoyl tryptamine from glucose. TDC (tryptophan decarboxylase) and PAL (phenylalanine ammonia lyase) along with 4CL and CaHCTT were introduced into E. coli and the phenylalanine biosynthetic pathway of E. coli was engineered. Using this strategy, approximately 110.6mg/L of N-cinnamoyl tryptamine was synthesized. By feeding 100μM serotonin into the E. coli culture, which could induce the synthesis of cinnamic acid or p-coumaric acid, more than 99μM of N-cinnamoyl serotonin and N-(p-coumaroyl) serotonin were synthesized.

Microwave‐Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one‐pot microwave‐assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.

Polystyrene supported palladium nanoparticles catalyzed cinnamic acid synthesis using maleic anhydride as a substitute for acrylic acid

Maleic anhydride as a substitute for acrylic acid for cinnamic acid synthesis was explored elaborating the combined role of the support and the catalyst.

A Simple and Straightforward Synthesis of Cinnamic acids and Ylidene Malononitriles via Knoevenagel Condensation Employing DABCO as Catalyst

A Simple and Straightforward Synthesis of Cinnamic acids and Ylidene Malononitriles via Knoevenagel Condensation Employing DABCO as Catalyst

Protective effect of red light against blast disease caused by Magnaporthe oryzae in rice

In this study, the effect of light on the protection of rice against blast caused by Magnaporthe oryzae was investigated. When rice inoculated with M. oryzae was kept in the dark for 24 h and then exposed to various light conditions, the formation of a susceptible blast lesion was significantly inhibited under red light compared with natural or white light. Furthermore, there was greater formation of necrotic spots under red light compared to natural and white lights. The activity of phenylalanine ammonia-lyase (PAL) increased significantly after inoculation with M. oryzae spores in red light-treated rice, as compared with natural or white light-treated rice. This activity reached a maximum at 48 h after inoculation. The amount of cinnamic acid in M. oryzae-infected rice increased significantly after treatment with red light, as compared to treatment with natural light. These results suggested that increased PAL activity and cinnamic acid synthesis were involved in red light-induced resistance to M. oryzae infection. In conclusion, our results indicate that red light triggers the priming of the phenylpropanoid pathway for basal resistance following M. oryzae infection and protects rice plants against blast.

ChemInform Abstract: Sodium Tetraborate‐dibenzo‐18‐crown Ether‐6 Complex as Reagent in the Synthesis of Cinnamic Acids from Aromatic Aldehydes and Aliphatic Carboxylic Acids.

AbstractA new alternative to the classic Perkin synthesis of cinnamic acids is introduced.

First Bovine Serum Albumin‐Promoted Synthesis of Enones, Cinnamic Acids and Coumarins in Ionic Liquid: An Insight into the Role of Protein Impurities in Porcine Pancreas Lipase for Olefinic Bond Formation

AbstractDuring studies on exploiting the catalytic promiscuity of crude porcine pancreas lipase (PPL) in ionic liquid for CC bond formations, bovine serum albumin (BSA) was found to be competing for these reactions. After a detailed investigation, we establish that these transformations are possible by unspecific protein catalysis rather than catalytic promiscuity of “PPL” – a first insight into the role of protein impurities in crude enzyme. Thus, a novel and highly efficient, environmentally friendly approach involving synergistic catalysis by bovine serum albumin‐1‐butyl‐3‐methylimidazolium bromide (BSA‐[bmim]Br) has been developed for the synthesis of (E)‐α,β‐unsaturated compounds including a one‐pot cascade synthesis of cinnamic acids and coumarins via aldol, Knoevenagel and Knoevenagel–Doebner condensations.

The effect of methyl jasmonate vapors on content of phenolic compounds in seedlings of common buckwheat (Fagopyrum esculentum Moench)

The effect of methyl jasmonate (MJ) vapors on content of phenolic compounds: free phenolic acids, total quercetin, and total phenolics in etiolated buckwheat seedlings were studied. The data presented show that low concentration of MJ (10<sup>-8</sup> M) had no influence on <em>trans</em>-cinnamic acid (CA), but stimulated the accumulation of chlorogenic acid in hypocotyls and cotyledons of buckwheat seedlings. A moderate dose of MJ (10<sup>-6</sup> M) did not change the level of chlorogenic acid in the hypocotyls and cotyledons, but CA synthesis was promoted in cotyledons, whereas in hypocotyls no significant effect was found. Highest concentration of MJ (10<sup>-4</sup> M) caused small decline of CA in hypocotyls, but large stimulation of the acid production in cotyledons was noted. MJ had stimulatory effect on caffeic acid forming, but inhibited synthesis of vanillic acid in hypocotyls and cotyledons. Lowest concentration of MJ (10<sup>-8</sup> M) elicited accumulation of quercetin glycosides in both studied tissues of buckwheat seedlings, however at higher doses (10<sup>-8</sup> and 10<sup>-4</sup> M) did not affect the flavonol level. The obtained results suggest that nonequivalent influence of methyl jasmonate on the phenolics composition can be a result of various mechanisms of MJ uptake, transforming and/or its translocation in buckwheat hypocotyls and cotyledons. Decline of anthocyanins level in buckwheat hypocotyls caused by MJ cannot be explained by enhanced accumulation of quercetin glycosides or free phenolic acids, but probably by synthesis of other unknown phenolic compounds.

ChemInform Abstract: A Novel Direct Boron‐Mediated Synthesis of Cinnamic Acids from Aromatic Aldehydes and Aliphatic Carboxylic Acids.

AbstractLithium tetraborate, generated in situ from Na2B4O7 and LiCl, proves to be an unexpectedly efficient reagent for the direct synthesis of cinnamic acids (III) (8 examples) from aldehydes (II) and carboxylic acids (I).

SYNTHESIS OF SOME CINNAMIC ACID DERIVATIVES: EFFECT OF GROUPS ATTACHED ON AROMATIC RING TO THE REACTIVITY OF BENZALDEHYDE

Synthesis of cinnamic acid and its six derivatives has been done by employing Knoevenagel reaction. Benzaldehyde, 4-butylbenzaldehyde, 4-t-butylbenzaldehyde, 4-butoxybenzaldehyde, 4-phenylbenzaldehyde, 5-bromo-2,4-dimethoxybenzaldehyde, and 5-bromo-2,3-dimethoxybenzaldehyde were reacted with malonic acid in pyridine – piperidine to give cinnamic acid (85,3%), 4-butylcinnamic acid (69,3%), 4-t-butylcinnamic acid (77,7%), 4-butoxycinnamic acid (64,5%), 4-phenylcinnamic acid (65,5%), 5-bromo-2,4-dimethoxycinnamic acid (53,2%) and 5-bromo-2,4-dimethoxycinnamic acid (57,2%), respectively. It was disclosed that 4-alkyl, 4-alkoxy, 4-aryl, dan 2-alkoxy groups decrease the reactivity of carbonyl carbon of benzaldehyde. Keywords: cinnamic acid, cinnamic acid derivatives, Knoevenagel reaction