74257-26-4

Basic information

• Product Name: 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester, (Z)-
• CAS NO: 74257-26-4
• Molecular Formula: C12H14O4
• Molecular Weight: 222.241
• Mol File: 74257-26-4.mol
• Article Data: 36

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester, (Z)-(74257-26-4)
• EPA Substance Registry System: 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester, (Z)-(74257-26-4)

Safety Data

• Hazardous Substances Data: 74257-26-4(Hazardous Substances Data)

Upstream product

• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 64-17-5 ethanol 
• 1071-46-1 hydrogen ethyl malonate 
• 121-33-5 vanillin 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 4421-08-3 3-methoxy-4-hydroxybenzonitrile 
• 1227148-49-3 C₁₈H₂₈O₄Si 
• 78-39-7 Triethyl orthoacetate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 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 
• 287382-72-3 1-feruloyl-2,3-dioleoyl glycerol 
• 95622-20-1 diethyl ester of 8-5-cyclic dehydrodiferulic acid 
• 80638-48-8 3-(3'-methoxy-4'-hydroxyphenyl)propionaldehyde 

Relevant articles and documents

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.

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.

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.