1519-55-7

Basic information

• Product Name: ALPHA-CYANO-4-METHOXYCINNAMIC ACID
• Synonyms: 4-METHOXYBENZYLIDENECYANOACETIC ACID;ALPHA-CYANO-4-METHOXYCINNAMIC ACID;(E)-2-CYANO-3-(4-METHOXYPHENYL)ACRYLIC ACID;LABOTEST-BB LT00455210;a-Cyano-4-methoxycinnamic acid;à-cyano-4-methoxycinnamic acid;α-cyano-4-methoxycinnamic acid;2-Cyano-3-(4-methoxy-phenyl)-acrylic acid
• CAS NO: 1519-55-7
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• Product Categories: C11 to C12;Carbonyl Compounds;Carboxylic Acids
• Mol File: 1519-55-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 230-234 °C(lit.)
• Boiling Point: 392.8°C at 760 mmHg
• Flash Point: 191.4°C
• Appearance: /solid
• Density: 1.28g/cm³
• Vapor Pressure: 7.09E-07mmHg at 25°C
• Refractive Index: 1.606
• BRN: 2110241
• CAS DataBase Reference: ALPHA-CYANO-4-METHOXYCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-CYANO-4-METHOXYCINNAMIC ACID(1519-55-7)
• EPA Substance Registry System: ALPHA-CYANO-4-METHOXYCINNAMIC ACID(1519-55-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1519-55-7(Hazardous Substances Data)

Usage

General Description

Alpha-Cyano-4-Methoxycinnamic Acid (ACMC) is a chemical compound commonly used in matrix-assisted laser desorption/ionization (MALDI) technique for mass spectrometry (an analytical technique that measures the mass-to-charge ratio of ions) due to its crystallization properties. ALPHA-CYANO-4-METHOXYCINNAMIC ACID belongs to the family of Phenylpropanoids and Polyketides. It tends to ionize nucleic acids as it exhibits strong proton affinity. It is also used in the analysis of low molecular-weight proteins, peptides, and oligosaccharides. The compound is often sold in its crystalline form which is white to off-white in color. Its chemical formula is C11H9NO3.

InChI:InChI=1/C11H9NO3/c1-15-10-4-2-8(3-5-10)6-9(7-12)11(13)14/h2-6H,1H3,(H,13,14)/b9-6-

Upstream product

• 110-89-4 piperidine 
• 123-11-5 4-methoxy-benzaldehyde 
• 372-09-8 cyanoacetic acid 
• 107-85-7 1-amino-3-methylbutane 
• 2286-29-5 ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate 
• 151-50-8 potassium cyanide 

Downstream Products

• 13565-23-6 2-(4-methoxyphenyl)succinic acid 
• 21405-62-9 2-(4-methoxybenzyl)malonic acid 
• 286848-35-9 2-(imino-{N'-[(3-oxo-5,6-diphenyl-3H-[1,2,4]triazin-2-yl)-acetyl]-hydrazino}-methyl)-3-(4-methoxy-phenyl)-acrylic acid 
• 23795-66-6 (Z)-2-Cyano-N-cyclohexyl-3-(4-methoxy-phenyl)-acrylamide 
• 141736-03-0 (Z)-2-Cyano-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-3-(4-methoxy-phenyl)-acrylamide 
• 141736-04-1 (Z)-3-(4-Methoxy-phenyl)-2-(morpholine-4-carbonyl)-acrylonitrile 
• 36397-19-0 α-Cyano-β-(4-methoxyphenyl)propionic acid 
• 104-01-8 4-Methoxyphenylacetic acid 
• 2286-29-5 ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate 

Relevant articles and documents

NOVEL CATHODE BUFFER LAYER MATERIAL AND ORGANIC OR ORGANIC/INORGANIC HYBRID PHOTOELECTRIC DEVICE COMPRISING SAME

The present invention relates to a novel cathode buffer layer material, and an organic or organic/inorganic hybrid photoelectric device comprising same, and, if a novel compound of the present invention is applied to a cathode buffer layer of an organic photoelectric device such as organic solar cells, organic photodiode, colloidal quantum dot solar cell, and perovskite solar cell, a surface property of an electron transfer layer is improved via a high dipole moment of the novel compound, an electron can be easily extracted from a photoactive layer to a cathode electrode, and series resistance and leakage current can be reduced, thereby having a useful industrial effect, as performance of the organic or organic/inorganic hybrid photoelectric device being manufactured, such as an organic solar cell, organic photodiode, colloidal quantum dot solar cell, and perovskite solar cell, can be significantly improved.

Monocarboxylate transporter 1 inhibitors as potential anticancer agents

Potent monocarboxylate transporter 1 inhibitors (MCT1) have been developed based on α-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCT1 inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.

Synthesis of 2-cyano-3-(methoxy-substituted-phenyl)acrylamides as herbicides

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