19272-90-3

Basic information

• Product Name: 4-HYDROXY-3-METHOXYCINNAMIDE
• Synonyms: 4-HYDROXY-3-METHOXYCINNAMIDE;FERULAMIDE;3-(4-hydroxy-3-methoxyphenyl)-2-propenamid;4-hydroxy-3-methoxy-cinnamamid;ferulamid;ferulicacidamide
• CAS NO: 19272-90-3
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 19272-90-3.mol

Chemical Properties

• Boiling Point: 435.3 °C at 760 mmHg
• Flash Point: 217 °C
• Appearance: /
• Density: 1.257 g/cm³
• Vapor Pressure: 3.48E-08mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 4-HYDROXY-3-METHOXYCINNAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-METHOXYCINNAMIDE(19272-90-3)
• EPA Substance Registry System: 4-HYDROXY-3-METHOXYCINNAMIDE(19272-90-3)

Safety Data

• Hazardous Substances Data: 19272-90-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-HYDROXY-3-METHOXYCINNAMIDE is used as a building block for the synthesis of other compounds, contributing to the development of new drugs and therapeutic agents.
Used in Anti-inflammatory Applications:
4-HYDROXY-3-METHOXYCINNAMIDE is utilized for its anti-inflammatory properties, potentially aiding in the treatment of conditions characterized by inflammation.
Used in Antioxidant Applications:
Leveraging its antioxidant properties, 4-HYDROXY-3-METHOXYCINNAMIDE is applied in scenarios where oxidative stress is a concern, helping to mitigate damage caused by reactive oxygen species.
Used in Cancer Treatment Research:
4-HYDROXY-3-METHOXYCINNAMIDE is studied for its potential role in the treatment of various types of cancer, due to its biological activities that may contribute to tumor suppression or inhibition of cancer progression.
Used in Neurodegenerative Disease Research:
4-HYDROXY-3-METHOXYCINNAMIDE is also being investigated for its potential applications in the treatment of neurodegenerative diseases, given its capacity to address oxidative stress and inflammation, which are often implicated in such conditions.
Overall, 4-HYDROXY-3-METHOXYCINNAMIDE is a versatile compound with a broad spectrum of potential applications in medicine and other fields, underscored by its unique structural features and biological activities.

InChI:InChI=1/C10H11NO3/c1-14-9-6-7(2-4-8(9)12)3-5-10(11)13/h2-6,12H,1H3,(H2,11,13)/b5-3+

Upstream product

• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 34749-55-8 3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid 
• 55882-65-0 4-acetoxyferuloyl chloride 
• 121-33-5 vanillin 
• 61012-31-5 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylamide 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 

Relevant articles and documents

A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives

A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, (Z) ketones may be obtained by the reaction of organometal compounds with an isomerized (Z) Weinreb amide.

Monoamine Oxidase Inhibitory Activity of Ferulic Acid Amides: Curcumin-Based Design and Synthesis

Ferulic acid has structural similarity with curcumin which is being reported for its monoamine oxidase (MAO) inhibitory activity. Based on this similarity, we designed a series of ferulic acid amides 6a-m and tested for their inhibitory activity on human MAO (hMAO) isoforms. All the compounds were found to inhibit the hMAO isoforms either selectively or non-selectively. Nine compounds (6a, 6b, 6g-m) were found to inhibit hMAO-B selectively, whereas the other four (6c-f) were found to be non-selective. There is a gradual shift from hMAO-B selectivity (6a,b) to non-selectivity (6c-f) as there is an increase in chain length at the amino terminus. In case of compounds having an aromatic nucleus at the amino terminus, increasing the carbon number between N and the aromatic ring increases the potency as well as selectivity toward hMAO-B. Compounds 6f, 6j, and 6k were subjected to membrane permeability and metabolic stability studies by in vitro assay methods. They were found to have a better pharmacokinetic profile than curcumin, ferulic acid, and selegiline. In order to understand the structural features responsible for the potency and selectivity of 6k, we carried out a molecular docking simulation study.