6948-33-0

Basic information

• Product Name: 3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID
• Synonyms: RARECHEM AL BK 0099;3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID;3-(5-BROMO-4-HYDROXY-3-METHOXY)CINNAMIC ACID;3(5)-BROMOFERULIC ACID;5-BROMOFERULIC ACID;5-BROMO-4-HYDROXY-3-METHOXYCINNAMIC ACID;AKOS B004163;(2E)-3-(3-BROMO-4-HYDROXY-5-METHOXYPHENYL)ACRYLIC ACID
• CAS NO: 6948-33-0
• Molecular Formula: C₁₀H₉BrO₄
• Molecular Weight: 273.08
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives
• Mol File: 6948-33-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 255 °C
• Boiling Point: 381℃
• Flash Point: 184℃
• Appearance: /
• Density: 1.668
• Vapor Pressure: 1.72E-06mmHg at 25°C
• CAS DataBase Reference: 3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID(6948-33-0)
• EPA Substance Registry System: 3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID(6948-33-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 6948-33-0(Hazardous Substances Data)

Usage

General Description

3-Bromo-4-Hydroxy-5-Methoxycinnamic Acid, also known as ferulic acid and 3-(3-Hydroxy-4-Methoxyphenyl)-2-Propenoic Acid, is a naturally occurring organic compound that belongs to the hydroxycinnamic acid group. It is derived from certain plants and is commonly found in fruits, vegetables, and grains. 3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID has antioxidant properties and is often used in skincare and cosmetic products for its potential to protect against sun damage and aging. Additionally, 3-Bromo-4-Hydroxy-5-Methoxycinnamic Acid has been studied for its potential anti-inflammatory, anticancer, and neuroprotective properties, making it a subject of interest in the fields of medicine and pharmaceutical research.

InChI:InChI=1/C10H9BrO4/c1-15-8-5-6(2-3-9(12)13)4-7(11)10(8)14/h2-5,14H,1H3,(H,12,13)/p-1/b3-2+

Upstream product

• 141-82-2 malonic acid 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 108-24-7 acetic anhydride 

Downstream Products

• 144506-19-4 (±)-canabisin D 
• 4302-52-7 4-ethynylveratrole 
• 4302-33-4 3-chloro-3-(3,4-dimethoxy-phenyl)-propenal 
• 99187-34-5 3-Methoxy-4-hydroxy-5-brom-hydrozimtsaeure-hydrazid 
• 58335-57-2 3-Methoxy-4-hydroxy-5-brom-hydrozimtsaeuremethylester 
• 146072-13-1 methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate 
• 61222-88-6 methyl 3-methoxy-4-hydroxy-5-bromocinnamate 

Relevant articles and documents

Discovery of caffeic acid phenethyl ester derivatives as novel myeloid differentiation protein 2 inhibitors for treatment of acute lung injury

Myeloid differentiation protein 2 (MD2) is an essential molecule which recognizes lipopolysaccharide (LPS), leading to initiation of inflammation through the activation of Toll-like receptor 4 (TLR4) signaling. Caffeic acid phenethyl ester (CAPE) from propolis of honeybee hives could interfere interactions between LPS and the TLR4/MD2 complex, and thereby has promising anti-inflammatory properties. In this study, we designed and synthesized 48 CAPE derivatives and evaluated their anti-inflammatory activities in mouse primary peritoneal macrophages (MPMs) activated by LPS. The most active compound, 10s, was found to bind with MD2 with high affinity, which prevented formation of the LPS/MD2/TLR4 complex. The binding mode of 10s revealed that the major interactions with MD2 were established via two key hydrogen bonds and hydrophobic interactions. Furthermore, 10s showed remarkable protective effects against LPS-caused ALI (acute lung injury) in vivo. Taken together, this work provides new lead structures and candidates as MD2 inhibitors for the development of anti-inflammatory drugs.

Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines

Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 μM, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 μM for CAPE against BEL-7404.