97966-29-5

Basic information

• Product Name: 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid methyl ester
• Synonyms: 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid methyl ester;Methyl (E)-3'-hydroxy-4'-methoxycinnamate;(2E)-3-(3-Hydroxy-4-Methoxyphenyl)-2-propenoic Acid Methyl Ester
• CAS NO: 97966-29-5
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208
• Mol File: 97966-29-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 119-120℃
• Boiling Point: 370℃
• Flash Point: 145℃
• Appearance: /
• Density: 1.204
• Solubility: DCM, DMF, Ethyl Acetate, Methanol
• CAS DataBase Reference: 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid methyl ester(97966-29-5)
• EPA Substance Registry System: 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid methyl ester(97966-29-5)

Safety Data

• Hazardous Substances Data: 97966-29-5(Hazardous Substances Data)

Usage

Uses

(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic Acid Methyl Ester is an intermediate in the synthesis of Advantame (A307000), a high-intensity, low calorie sweetner.

Upstream product

• 67-56-1 methanol 
• 537-73-5 isoferulic acid 
• 331-39-5 caffeic acid 
• 74-88-4 methyl iodide 
• 125675-24-3 6-O-α-L-(3''-O-isoferuloyl)rhamnopyranosylcatalpol 
• 125697-69-0 6-O-α-L-(2''-O-isoferuloyl)rhamnopyranosylcatalpol 
• 93236-41-0 cistanoside 
• 75-36-5 acetyl chloride 
• 537-73-5 trans-3-hydroxy-4-methoxycinnamic acid 
• 621-59-0 isovanillin 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 36653-82-4 1-Hexadecanol 
• 1175860-42-0 iso-ferulic acid 

Downstream Products

• 537-73-5 isoferulic acid 
• 129150-61-4 3-(3-hydroxy-4-methoxyphenyl)-propionic acid methyl ester 
• 537-73-5 trans-3-hydroxy-4-methoxycinnamic acid 
• 731846-02-9 (E)-3-(3-Carboxymethoxy-4-methoxy-phenyl)-acrylic acid methyl ester 
• 143551-94-4 (Z)-3-<3-<4-(3-hydroxy-1-propenyl)phenoxy>-4-methoxyphenyl> propionic acid 
• 143551-93-3 methyl (Z)-3-<3-<4-(3-hydroxy-1-propenyl)phenoxy>-4-methoxyphenyl> propionate 
• 168135-09-9 methyl (Z)-3-<3-<4-(3-t-butyldimethylsilylether-1-propenyl)phenoxy>-4-methoxyphenyl> propionate 
• 168135-08-8 methyl-3-<3-<4-(3-t-butyldimethylsilylether-1-propynyl)phenoxy>-4-methoxyphenyl> propionate 
• 1135-15-5 dihydroisoferulic acid 
• 1459808-97-9 7,8-dihydroxy-N-(4-(phenyldiazenyl)phenethyl)-4,5-dihydro-1H-benzo[c]-azepine-2(3H)-carbothioamide 
• 1459809-07-4 7,8-dihydroxy-N-(4-((4-methoxyphenyl)diazenyl)phenethyl)-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide 
• 1459809-08-5 N-(4-((4-(diethylamino)phenyl)diazenyl)phenethyl)-7,8-di-hydroxy-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide 
• 1459809-09-6 7,8-dihydroxy-N-(4-((4-(trifluoromethyl)phenyl)diazenyl)phenethyl)-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide 

Relevant articles and documents

Triphenylphosphine-mediated serendipitous synthesis of alkyl cinnamates through the reaction of 3-hydroxy-4-methoxybenzaldehyde and dialkyl acetylenedicarboxylates

Alkyl cinnamates are formed in fairly good yields from the reaction of dialkyl acetylenedicarboxylates and 3-hydroxy-4-methoxybenzaldehyde in the presence of triphenylphosphine. Copyright Taylor & Francis Inc.

Search for novel histone deacetylase inhibitors. Part II: Design and synthesis of novel isoferulic acid derivatives

Previously, we described the discovery of potent ferulic acid-based histone deacetylase inhibitors (HDACIs) with halogeno-acetanilide as novel surface recognition moiety (SRM). In order to improve the affinity and activity of these HDACIs, twenty seven isoferulic acid derivatives were described herein. The majority of title compounds displayed potent HDAC inhibitory activity. In particular, IF5 and IF6 exhibited significant enzymatic inhibitory activities, with IC50 values of 0.73 ± 0.08 and 0.57 ± 0.16 μM, respectively. Furthermore, these compounds showed moderate antiproliferative activity against human cancer cells. Especially, IF6 displayed promising profile as an antitumor candidate with IC50 value of 3.91 ± 0.97 μM against HeLa cells. The results indicated that these isoferulic acid derivatives could serve as promising lead compounds for further optimization.

Inhibitory effects of substituted cinnamic acid esters on mushroom tyrosinase

A series of substituted cinnamic acid esters were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. Compound 8 was found to be the most potent inhibitor with IC 50 value of 5.60μM. Preliminary structure activity relationships (SARs) were concluded. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 8 was anti-competitive inhibitor.