24393-56-4 Usage
Description
Ethyl 4-methoxycinnamate, also known as Ethyl p-methoxycinnamate (EPMC), is a natural product derived from cinnamon, specifically found in K. galanga and C. zedoaria extracts. It is a white crystalline compound that is soluble in various organic solvents such as methanol, ethanol, and DMSO. EPMC exhibits a range of biological activities, including anti-inflammatory, antiangiogenic, antifungal, larvicidal, and analgesic properties. It also inhibits COX-1 and COX-2 in vitro and reduces the production of IL-1 and TNF-α in vivo.
Uses
Used in Pharmaceutical Industry:
Ethyl 4-methoxycinnamate is used as an antihyperglycemic/hypoglycemic agent for the development of potential therapeutic agents for type 2 diabetic patients. It works by stimulating insulin secretion from the pancreas, making it a promising candidate for the treatment of diabetes.
Used in Anti-inflammatory Applications:
Ethyl 4-methoxycinnamate is used as an anti-inflammatory agent due to its ability to inhibit COX-1 and COX-2 in vitro, as well as reduce the production of IL-1 and TNF-α in vivo. This makes it a potential candidate for the development of treatments for various inflammatory conditions.
Used in Antiangiogenic Applications:
Ethyl 4-methoxycinnamate is used as an antiangiogenic agent, as it inhibits blood vessel growth in rat aortic explants. This property makes it a potential candidate for the development of treatments aimed at preventing the formation of new blood vessels in diseases such as cancer.
Used in Antifungal Applications:
Ethyl 4-methoxycinnamate is used as an antifungal agent, as it demonstrates growth inhibition against various fungi, including T. rubrum, A. niger, S. cerevisiae, and E. floccosum. This makes it a potential candidate for the development of antifungal treatments.
Used in Larvicidal Applications:
Ethyl 4-methoxycinnamate is used as a larvicidal agent, as it is effective against Ae. aegypti, a mosquito species known to transmit diseases such as dengue, Zika, and yellow fever. This property makes it a potential candidate for the development of larvicides to control mosquito populations and reduce the spread of these diseases.
Preparation
Ethyl 4-methoxycinnamate synthesis: 4-Methoxycinnamic Acid (0.60 g, 3.36 mmol) was dissolved in 10 mL of dry N,N-dimethylformamide (DMF) in a 25-mL, roundbottomed flask. Cesium carbonate (1.65 g, 5.06 mmol) was added followed by iodoethane (1.0 mL, 12.5 mmol). The flask was capped (rubber septum) and the heterogeneous mixture stirred vigorously at 50 °C for one hour. After this time, HCl (1.0 M, 4.0 mL) was added to quench the reaction. The liquid was decanted from any remaining solid and extracted with 3 : 1 hexanes/ethyl acetate (2 x 10 mL). The organic layer was washed with brine (20 mL), dried with MgSO4, filtered, and solvent removed. The remaining oil solidified on standing to form colorless prisms.Synthesis of ethyl 4-methoxycinnamate
Check Digit Verification of cas no
The CAS Registry Mumber 24393-56-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,3,9 and 3 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 24393-56:
(7*2)+(6*4)+(5*3)+(4*9)+(3*3)+(2*5)+(1*6)=114
114 % 10 = 4
So 24393-56-4 is a valid CAS Registry Number.
InChI:InChI=1S/C12H14O3/c1-3-15-12(13)9-6-10-4-7-11(14-2)8-5-10/h4-9H,3H2,1-2H3/b9-6+
24393-56-4Relevant articles and documents
Tuning and enhancement of the Mizoroki-Heck reaction using polarized Pd nanocomposite carbon aerogels
Martín, Laura,Molins, Elies,Vallribera, Adelina
, p. 10208 - 10212 (2016)
The application of a positive electric field on a Pd(0)-carbon aerogel nanocomposite enhances the reaction rate of the Mizoroki-Heck reaction. By contrast, when a negative potential is employed the reaction is inhibited. On the other hand, chronoamperometry measurements have revealed the polarizing current intensity as an indirect measure of the reaction evolution. The cationic nature of the reaction intermediates was unambiguously confirmed and a polar mechanism has been finally proposed.
Barium Hydroxide as Catalyst in Organic Reactions; V. Application in the Horner Reaction under Solid-Liquid Phase-Transfer Conditions
Sinisterra, J. V.,Mouloungui, Z.,Delmas, M.,Gaset, A.
, p. 1097 - 1100 (1985)
A new application of a barium hydroxide catalyst for the Horner reaction is described.The scope of the synthetic method is shown; furthermore, the yields are higher and the reaction times shorter than those previously reported for similar experimental conditions (solid-liquid).Ethyl 3-(1'-pyrenyl)-acrylate and the 3-(1'-pyrenyl)-acrylonitrile are described for the first time.
Photoinduced Oxidative Alkoxycarbonylation of Alkenes with Alkyl Formates
Tang, Wan-Ying,Chen, Ling,Zheng, Ming,Zhan, Le-Wu,Hou, Jing,Li, Bin-Dong
supporting information, p. 3939 - 3943 (2021/05/26)
A photoinduced oxidative alkoxycarbonylation of alkenes initiated by intermolecular addition of alkoxycarbonyl radicals has been demonstrated. Employing alkyl formates as alkoxycarbonyl radical sources, a range of α,β-unsaturated esters were obtained with good regioselectivity and E selectivity under ambient conditions.
The Mizoroki-Heck reaction in mesoionic 1-butyl-3-methyltetrazolium-5-olate
Araki, Shuki,Hirashita, Tsunehisa,Kurabayashi, Hideaki
, (2021/10/12)
1-Butyl-3-methyltetrazolium-5-olate (1), a mesoionic compound, exists as a liquid at room temperature and can be used as a polar solvent for the Mizoroki-Heck reaction, wherein it has been proven to be a superior solvent to other solvents. The reaction of iodobenzene with ethyl acrylate in the presence of palladium acetate in mesoionic liquid 1 at 40 °C for 24 h gave ethyl cinnamate in 78% yield in the absence of ligands, while the use of other solvents, such as [bmim][BF4], [bmim][PF6], and DMF gave lower yields (43%, 37%, and 17%, respectively) under the same conditions. Heck-type coupling reactions of electron-deficient or electron-rich aryl iodides and bromobenzenes with olefins (15 examples, 7%–97%) were performed in 1. When a phosphine ligand was added to the reaction mixture, aryl bromides could be used, and the mesoionic liquid containing the catalysts could be reused at least five times.