74257-25-3

Basic information

• Product Name: 2-Propenoicacid,3-(3,4-dihydroxyphenyl)-,ethylester,(2Z)-(9CI)
• Synonyms: 2-Propenoicacid,3-(3,4-dihydroxyphenyl)-,ethylester,(2Z)-(9CI)
• CAS NO: 74257-25-3
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 0
• Product Categories: ALCOHOL
• Mol File: 74257-25-3.mol
• Article Data: 48

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propenoicacid,3-(3,4-dihydroxyphenyl)-,ethylester,(2Z)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoicacid,3-(3,4-dihydroxyphenyl)-,ethylester,(2Z)-(9CI)(74257-25-3)
• EPA Substance Registry System: 2-Propenoicacid,3-(3,4-dihydroxyphenyl)-,ethylester,(2Z)-(9CI)(74257-25-3)

Safety Data

• Hazardous Substances Data: 74257-25-3(Hazardous Substances Data)

Upstream product

• 28028-62-8 ethyl ferulate 
• 1071-46-1 hydrogen ethyl malonate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 20583-78-2 3,4-dimethoxy-cinnamic acid ethyl ester 
• 64-17-5 ethanol 
• 331-39-5 caffeic acid 
• 621-59-0 isovanillin 
• 100976-84-9 ethyl 3,4-diacetoxycinnamate 
• 331-39-5 caffeic acid 
• 121-33-5 vanillin 

Downstream Products

• 123134-23-6 1-monoglyceryl caffeic acid ester 
• 2179-24-0 1-O-caffeoyl glyceride 
• 1609031-14-2 ethyl (E)-3-(3,4-Bis(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)acrylate 
• 1609030-89-8 (E)-3-(3,4-bis(2-hydroxyethoxy)phenyl)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)acrylamide 
• 1609030-87-6 (E)-3-(3,4-bis(2-hydroxyethoxy)phenyl)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide 
• 1609030-85-4 (E)-3-(3,4-bis(2-hydroxyethoxy)phenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide 
• 1609031-15-3 (E)-3-(3,4-bis(2-hydroxyethoxy)phenyl)acrylic Acid 
• 1300726-61-7 (E)-3-(3-hydroxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylic acid 
• 3598-22-9 methyl 3-(3,4-dihydroxyphenyl)propionate 
• 121701-63-1 Ethyl (E)-3-<(2R*,3S*)-3-(4-acetoxy-3-methoxyphenyl)-2-acetoxymethyl-1,4-benzodioxane-6-yl>propenoate 
• 121620-02-8 Ethyl (E)-3-<(2R*,3R*)-3-(4-acetoxy-3-methoxyphenyl)-2-acetoxymethyl-1,4-benzodioxane-6-yl>propenoate 
• 121701-65-3 Ethyl (E)-3-<(2R*,3S*)-2-(4-acetoxy-3-methoxyphenyl)-3-acetoxymethyl-1,4-benzodioxane-6-yl>propenoate 
• 121620-04-0 Ethyl (E)-3-<(2R*,3R*)-2-(4-acetoxy-3-methoxyphenyl)-3-acetoxymethyl-1,4-benzodioxane-6-yl>propenoate 

Relevant articles and documents

Solvent role in the lipase-catalysed esterification of cinnamic acid and derivatives. Optimisation of the biotransformation conditions

The esterification of cinnamic acid has been deeply investigated using ethanol as nucleophile and Candida antarctica lipase type B (CAL-B) as suitable biocatalyst. Special attention has been paid to the role that the solvent plays in the production of ethyl cinnamate. Therefore, volatile organic solvents and deep eutectic mixtures were employed in order to find optimal reaction conditions. Once that hexane was selected as the solvent of choice, other parameters that affect the enzyme activity were investigated in order to produce ethyl cinnamate with excellent yield. The CAL-B loading, nucleophile equivalents, temperature and reaction time have been identified as key parameters in the enzyme efficiency, and the potential of lipase-catalysed esterification has been finally exploited to produce a series of ethyl esters with different pattern substitutions on the aromatic ring.

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.