14473-89-3

Basic information

• Product Name: 3-METHYLCINNAMIC ACID
• Synonyms: RARECHEM BK HC T306;TIMTEC-BB SBB006620;3-M-TOLYL-ACRYLIC ACID;3-(3-METHYLPHENYL)-2-PROPENOIC ACID;3-Methylcinnamic acid,predominantly trans;3-METHYLCINNAMIC ACID, 97%, PREDOMINANTL;3-METHYLCINNAMIC ACID 97% PREDOMINANTLY TRANS;(E)-3-M-tolylacrylic acid
• CAS NO: 14473-89-3
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 221-199-2
• Product Categories: C10;Carbonyl Compounds;Carboxylic Acids
• Mol File: 14473-89-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 116-119 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-METHYLCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLCINNAMIC ACID(14473-89-3)
• EPA Substance Registry System: 3-METHYLCINNAMIC ACID(14473-89-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• Hazardous Substances Data: 14473-89-3(Hazardous Substances Data)

Usage

General Description

3-Methylcinnamic acid, also known as 3-methylphenylacrylic acid, is a organic compound that is classified as a cinnamic acid derivative. It is commonly found in natural sources such as cinnamon oil and is used in the production of various herbicides and insecticides. The compound exhibits anti-inflammatory and antioxidant properties, making it a potential candidate for pharmaceutical and cosmetic applications. With a molecular formula of C10H10O2, 3-methylcinnamic acid is a white crystalline solid with a melting point of 112-114°C and is sparingly soluble in water. It is primarily used as a flavoring agent in the food industry and as an intermediate in the synthesis of other chemicals.

Upstream product

• 141-82-2 malonic acid 
• 620-23-5 m-tolyl aldehyde 
• 2283-42-3 (S)-2-amino-3-(3-methylphenyl)propionic acid 
• 591-17-3 meta-bromotoluene 
• 79-10-7 acrylic acid 
• 108-31-6 maleic anhydride 
• 625-95-6 3-Iodotoluene 
• 124-38-9 carbon dioxide 
• 766-82-5 1-ethynyl-3-methyl-benzene 
• 201230-82-2 carbon monoxide 
• 64-18-6 formic acid 
• 68208-17-3 (R,S)-3-amino-3-(3-methylphenyl)propionic acid 
• 100-80-1 3-methylstyrene 
• 558-13-4 carbon tetrabromide 

Downstream Products

• 82444-40-4 (E)-methyl 3-methylcinnamate 
• 1041867-78-0 C₁₆H₁₃N₃O 
• 1361214-46-1 (R)-tert-butyl 3-((2R,3S)-2-((E)-3-methylstyryl)-4-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)azetidin-1-yl)-4-oxo-4-(((R)-1-phenylethyl)amino)butanoate 
• 1361214-49-4 (R)-3-((2R,3S)-2-((E)-3-methylstyryl)-4-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)azetidin-1-yl)-4-oxo-4-(((R)-1-phenylethyl)amino)butanoic acid 
• 1361214-51-8 (R)-4-([1,4'-bipiperidin]-1'-yl)-2-((2R,3S)-2-((E)-3-methylstyryl)-4-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)azetidin-1-yl)-4-oxo-N-((R)-1-phenylethyl)butanamide 
• 1361214-43-8 C₂₆H₃₂N₂O₃ 
• 1373283-61-4 (E)-N-methoxy-3-(3-methylphenyl)acrylamide 
• 1426659-96-2 (16α)-16-hydroxybeyeran-19-oic acid 16-O-3-methylcinnamate 
• 1426660-28-7 16α,19-dihydroxybeyerane 19-O-3-methycinnamate 
• 1426660-55-0 16α,19-dihydroxybeyerane di-O-3-methylcinnamate 
• 1426659-17-7 ent-kaur-16-ene-13,19-diol 19-O-3-methylcinnamate 
• 1584131-96-3 7-(4-nitrophenylsulfonyl)-10-m-tolyl-7-azaspiro[4.5]decane-1,6,8-trione 
• 1584132-12-6 (E)-3-(m-tolyl)acryloyl cyanide 
• 16619-29-7 3-(3-methylphenyl)-1-phenyl-2-propen-1-one 

Relevant articles and documents

Method for preparing alpha, beta-unsaturated carboxylic acid compound

The invention discloses a method for preparing an alpha, beta-unsaturated carboxylic acid compound, which comprises the following steps: 1) in an atmosphere containing carbon dioxide, heating and reacting a mixture containing hydrosilane and a copper catalyst to obtain a system I; and 2) adding a raw material containing alkyne and a nickel catalyst into the system I in the step 1), and heating to react. The method has the advantages of simple, easily available, cheap and stable raw materials, common, easily available and stable catalyst, mild reaction conditions, simple post-treatment, high yield and the like.

Design, synthesis, and evaluation of novel cinnamic acid-tryptamine hybrid for inhibition of acetylcholinesterase and butyrylcholinesterase

Background: Acetylcholine deficiencies in hippocampus and cortex, aggregation of β-amyloid, and β-secretase over activity have been introduced as main reasons in pathogenesis of Alzheimer’s disease. Methods: Colorimetric Ellman’s method was used for determination of IC50 value in AChE and BChE inhibitory activity. The kinetic studies, neuroprotective and β-secretase inhibitory activities, evaluation of inhibitory potency on β-amyloid (Aβ) aggregations induced by AChE, and docking study were performed for prediction of the mechanism of action. Result and discussion: A new series of cinnamic acids-tryptamine hybrid was designed, synthesized, and evaluated as dual cholinesterase inhibitors. These compounds demonstrated in-vitro inhibitory activities against acetyl cholinesterase (AChE) and butyryl cholinesterase (BChE). Among of these synthesized compounds, (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)acrylamide (5q) demonstrated the most potent AChE inhibitory activity (IC50 = 11.51?μM) and (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(2-chlorophenyl)acrylamide (5b) were the best anti-BChE (IC50 = 1.95?μM) compounds. In addition, the molecular modeling and kinetic studies depicted 5q and 5b were mixed type inhibitor and bound with both the peripheral anionic site (PAS) and catalytic sites (CAS) of AChE and BChE. Moreover, compound 5q showed mild neuroprotective in PC12 cell line and weak β-secretase inhibitory activities. This compound also inhibited aggregation of β-amyloid (Aβ) in self-induced peptide aggregation test at concentration of 10?μM. Conclusion: It is worth noting that both the kinetic study and the molecular modeling of 5q and 5b depicted that these compounds simultaneously interacted with both the catalytic active site and the peripheral anionic site of AChE and BChE. These findings match with those resulted data from the enzyme inhibition assay. [Figure not available: see fulltext.]

Trans-cinnamic acid compound preparation method

The invention relates to a trans-cinnamic acid compound preparation method, which comprises: adding aromatic aldehyde 1, malonic acid and [bmim] PF6 to a 50 mL round bottom flask, and adding piperidine under stirring; carrying out oil bath heating to a temperature of 80-90 DEG C, and carrying out a reaction for 4-8 h; after completing a thin layer chromatography analysis detection reaction, cooling the reaction solution to a room temperature; extracting the reaction solution three times with a 10% NaOH aqueous solution; combining the three extracted NaOH aqueous solutions, and adding 10% HCl under stirring to adjust the pH value to 5; and precipitating a solid product, filtering, carrying out water washing to achieve a neutral pH value, filtering, and carrying out pressure reducing dryingto obtain a white solid. According to the present invention, cinnamic acid and the derivative thereof are prepared by using piperidine as the catalyst, and the product is extracted and separated withthe alkaline aqueous solution, such that the operation is simple; the ionic liquid [bmim]PF6 is recycled after the pressure reducing drying; the method has advantages of easily-available raw materials, simple operation, mild reaction conditions and the like; and the separating and purifying step of the product is simple, the use of organic solvents is avoided, and the effects of environmental protection and emission reduction are achieved.