28028-62-8

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 121-33-5 vanillin 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 64-17-5 ethanol 
• 78-39-7 Triethyl orthoacetate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 1227148-49-3 C₁₈H₂₈O₄Si 
• 1071-46-1 hydrogen ethyl malonate 
• 4421-08-3 3-methoxy-4-hydroxybenzonitrile 

Downstream Products

• 61292-90-8 ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate 
• 458-35-5 coniferol 
• 515835-74-2 ethyl 3-[4-(3,4,5-triacetyloxybenzoyloxy)-3-methoxyphenyl]-2-propenoate 
• 475147-21-8 bis-4,4'-(2-ethoxycarbonyl-1-ethenyl)-2,2'-methoxyphenoxymethane 
• 1071421-86-7 1⁽³⁾-feruloyl monobutyryl-glycerol 
• 1075207-65-6 1⁽³⁾-feruloyl dibutyryl glyceride 
• 4657-33-4 4-hydroxy-3-methoxy butyl cinnamate 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 34749-55-8 3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid 
• 81766-26-9 4-O-acetyl-coniferyl alcohol 
• 287382-72-3 1-feruloyl-2,3-dioleoyl glycerol 
• 864960-95-2 3-(4-fluoro-3-methoxyphenyl)-2-propenoic acid ethyl ester 
• 64-17-5 ethanol 

Relevant academic research and scientific papers

On the origin of the methyl radical loss from deprotonated ferulic and isoferulic acids: Electronic excitation of a transient structure

Formation of radical fragments from even-electron ions is an exception to the "even-electron rule". In this work, ferulic acid (FA) and isoferulic acid (IFA) were used as the model compounds to probe the fragmentation mechanisms and the isomeric effects o

Structure property relationships of biobased: N -alkyl bisferulate epoxy resins

In this work, a series of bio-based chemically recyclable epoxy resins were synthesized from n-alkyl bisferulate esters that do not activate human estrogen receptor alpha (ERα). Viscosities of corresponding glycidyl ether n-alkyl bisferulate resins, determined by steady shear rheology, range from 12-9.4 Pa s. Activation energies of flow range from 83-96 kJ mol-1 and are similar to the diglycidyl ether bisphenol A (DGEBA). Thermomechanical properties of diglycidyl ether n-alkyl bisferulate resins cured with isophorone diamine were governed by the length of α,ω-diols that link glycidyl ether ferulate units. That is, the glassy phase modulus and alpha transition temperatures range from 3400-2400 MPa (at 25 °C) and 40-53 °C (peak of E′′), respectively. Furthermore, the onset of thermal degradation (Td5%) varied from 331-300 °C. Chemical recycling of cured epoxy resins was performed by static immersion in 10 w/w sodium hydroxide aqueous solutions at 60 °C. Times required for complete conversion of cured resins to water-soluble degradation products was also α,ω-diol length dependent and varied from 5 to 65 h. Thus, diglycidyl ether of n-alkyl bisferulate resins provides a viable biobased alternative to BPA epoxy resins as well as the option of chemical degradability and recovery of fillers in composite applications.

Lipase-catalyzed synthesis of ferulate esters

Four commercially available esterases were screened for their ability to esterify ferulic acid (4-hydroxy-3-methoxy cinnamate). Novozym 435 was found to be the only one of those screened to convert ferulic acid to ethyl and octyl ferulate at 20 and 14% yields, respectively. The highest percentage conversion was obtained using a 1:1 mole ratio of alcohol to ferulic acid in stirred batch reactions in anhydrous 2-methyl-2-propanol at 60 °C using one equivalent (wt/wt based on ferulic acid) of Novozym 435. Increased water content and a higher alcohol/ethyl ferulate ratio had adverse effects on the lipase-catalyzed esterification. The Novozym 435 activity was tested in less polar solvents (anhydrous toluene and hexane) by monitoring the alcoholysis of ethyl ferulate with 1-octanol, which resulted in a 50% yield of octyl ferulate. The alcoholysis was improved to 83% by applying a 16 mm Hg vacuum for 5 min every 24 h to remove the ethanol co-product. The optimal alcoholysis parameters were applied to the alcoholysis of ethyl ferulate with monoolein and the transesterification with triolein. The transesterification of ethyl ferulate with triolein in anhydrous toluene produced a combined 44% yield of ferulyl monoolein and ferulyl diolein, a 20% greater yield than that obtained for alcoholysis using monoolein. The highest yield, 77%, of ferulyl monoolein and ferulyl diolein was achieved using a threefold excess of neat triolein. The lipase-catalyzed transesterification of ethyl ferulate with triolein appears to be a technically feasible route to ferulyl-substituted acylglycerols, which are potentially useful sunscreen ingredients.

Characterization of the chemical composition of a byproduct from Siam benzoin gum

The mixture of bark and gum obtained after size-grading of Siam benzoin gum was studied to establish its potential application as a valuable new grade of the balsamic resin. An analysis of its volatile constituents by means of static headspace and SPME led to the identification of 26 and 50 compounds, respectively. Significant differences were observed in both the headspace composition and olfactory properties of the byproduct as compared to those of Siam benzoin gum. This prompted the further analysis of its volatile extract and its resinoid by GC techniques, resulting in the identification of 60 (99.5%) and 16 (89.1%) components, respectively. To examine the influence of bark pieces, different extracts obtained from the raw material and from a sorted sample were analyzed by GC and HPLC techniques. The chemical compositions and the yields determined for the two resinoids lead to the conclusion that this harvesting byproduct is a new grade of Siam benzoin gum, providing interesting olfactory notes that differ from those of other grades.

Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions

To develop novel antiviral agents, some novel conjugates between ferulic acid and eugenol or isoeugenol were designed and synthesized by the link reaction. The antiviral activities of compounds were evaluated using the half leaf dead spot method. Bioassay results showed acceptable antiviral activities of some conjugates against the tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Compounds A9, A10, E1, and E4 showed remarkable curative, protective, and inactivating effects on TMV and CMV at 500 μg mL-1. Notably, these compounds exhibited excellent protective effects on TMV and CMV. The EC50 values of compounds A9, A10, E1, and E4 against TMV were 180.5, 169.5, 211.4, and 135.5 μg mL-1, respectively, and those against CMV were 210.5, 239.1, 218.4, and 178.6 μg mL-1, respectively, which were superior to those of ferulic acid (471.5 and 489.2 μg mL-1), eugenol (456.3 and 463.2 μg mL-1), isoeugenol (478.4 and 487.5 μg mL-1), and ningnanmycin (246.5 and 286.6 μg mL-1). Then, the antiviral mechanisms of compound E4 were investigated by determining defensive enzyme activities and multi-omics analysis. The results indicated that compound E4 resisted the virus infection by enhancing defensive responses via inducing the accumulation of secondary metabolites from the phenylpropanoid biosynthesis pathway in tobacco.

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

METHOD FOR PRODUCING CINNAMIC ACID ESTER COMPOUND

A method for producing a cinnamic acid ester derivative includes reacting a cinnamic acid derivative compound represented by the formula (1), wherein the symbols are as defined in the description, with an alcohol compound represented by the formula: R6OH, wherein the symbol is as defined in the description, in the presence of a strong acid resin catalyst without using a solvent. As the cinnamic acid derivative compound, cinnamic acid, ferulic acid, and caffeic acid are preferred, and as the alcohol compound, methanol, ethanol, propanol, butanol, pentanol, hexanol, ethylene glycol, glycerol, phenethyl alcohol, and a monosaccharide are preferred.

Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents

Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.

Study on the formation of antihypertensive twin drugs by caffeic acid and ferulic acid with telmisartan

Purpose: This study aimed to synthesize twin drugs from cinnamic acid compounds, caffeic acid (CFA) and ferulic acid (FLA), which can antagonize endothelin-1 (ET-1) with telmisartan through ester bonds. Moreover, the antihypertensive effect of telmisartan and its influence on blood pressure variability (BPV) were enhanced, and the bioavailability of caffeic acid and ferulic acid was improved. Methods: Six twin drugs, which were the target compounds, were synthesized. Hypertensive rats (SHR) and conscious sinoaortic-denervated (SAD) rats were spontaneously used as models for pharmacodynamic research to study the antihypertensive efficacy of these twin drugs. Wistar rats were employed as pharmacokinetic research models to investigate the pharmacokinetics of the target compounds via intragastric administration. Cellular pharmacodynamic research was also conducted on the antagonistic action on Ang II-AT1, ETA and ETB receptor. Results: Compound 1a was determined as the best antihypertensive twin drug and thus was further studied for its effect on BPV. Compared with that of telmisartan, the antihypertensive effect of compound 1a was improved (p50 of Lps-2 was still two orders of magnitude higher than that of the positive drug telmisartan. Hence, the twin drugs worked by metabolizing and regenerating telmisartan and caffeic acid or ferulic acid in the body. Conclusion: The synthesized twin drugs improved telmisartan’s antihypertensive effects, significantly decreased BPV in SAD rats and increased the bioavailability of caffeic acid and ferulic acid. This study serves as a basis for the development of new angiotensin receptor blocker (ARB) in the future and a reference for the development of new drugs to antagonize ET-1.

Grafting Nature-Inspired and Bio-Based Phenolic Esters onto Cellulose Nanocrystals Gives Biomaterials with Photostable Anti-UV Properties

New nature-inspired and plant-derived p-hydroxycinnamate esters and p-hydroxycinnamate diesters provide excellent protection against UV radiation when incorporated into a matrix. Herein, an efficient and sustainable pathway is reported to graft these phenolic compounds onto cellulose nanocrystals (CNCs) via click-type copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction. The successful grafting of the phenolic esters on CNC surface was evidenced by a range of chemical analyses, and the degrees of substitution (DS) of the CNC were found to depend on the structure of the phenolic ester grafted. Moreover, aqueous suspensions of the phenolic ester-grafted CNCs not only strongly absorb in both the UVA and UVB regions, but they also exhibit average to very high photostability. Their wide spectrum UV-absorbing properties and their stability upon exposure to UV are highly influenced by the structure of the phenolic ester, particularly by the extra ester group in p-hydroxycinnamate diesters. These findings demonstrate that cellulose nanocrystals decorated with such plant-derived and nature-inspired phenolic esters are promising sustainable nanomaterials for anti-UV applications.