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

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

Uses

Used in Skincare and Cosmetic Products:
3-Bromo-4-Hydroxy-5-Methoxycinnamic Acid is used as an antioxidant in skincare and cosmetic products for its potential to protect against sun damage and aging. Its presence in these products helps to reduce the harmful effects of free radicals and environmental stressors, promoting healthier and more youthful-looking skin.
Used in Pharmaceutical Research:
3-Bromo-4-Hydroxy-5-Methoxycinnamic Acid is used as a subject of interest in pharmaceutical research for its potential anti-inflammatory, anticancer, and neuroprotective properties. Its diverse range of biological activities makes it a promising candidate for the development of new drugs and therapies to treat various diseases and conditions.
Used in Food Industry:
3-Bromo-4-Hydroxy-5-Methoxycinnamic Acid is used as a natural preservative and antioxidant in the food industry. Its presence in fruits, vegetables, and grains contributes to the overall health benefits of these foods, as well as helps to extend their shelf life by protecting against oxidation and spoilage.
Used in Nutraceuticals:
3-Bromo-4-Hydroxy-5-Methoxycinnamic Acid is used as a nutraceutical ingredient for its potential health benefits. It can be found in dietary supplements and functional foods, where it may contribute to improved overall health and well-being by supporting the body's natural antioxidant defenses and promoting a healthy inflammatory response.

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

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

Downstream Products

• 144506-19-4 (±)-canabisin D 
• 146072-13-1 methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate 
• 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 
• 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.

New insights into the antioxidant activity of hydroxycinnamic acids: Synthesis and physicochemical characterization of novel halogenated derivatives

An interdisciplinary research project was developed combining the synthesis of a series of hydroxycinnamic acid derivatives and the evaluation of their physicochemical parameters (namely redox potentials and partition coefficients), along with the corresponding antioxidant activity. A structure-property-activity relationship (SPAR) approach was then applied aiming at establishing a putative relation between the physicochemical parameters of the compounds under study and their antioxidant activity. The results gathered allow concluding that the redox potentials could contribute to the understanding of the antioxidant activity and that the presence of an electron withdrawing group (EWG) of halogen type, namely a bromo atom, in an ortho position to a phenolic group of the cinnamic scaffold does not influence the antioxidant activity. On the other hand after the introduction of this type of substituent a significant increase on the lipophilicity of cinnamic derivatives was observed, which is a feature of extreme importance in the development of novel lipophilic antioxidants. The SPAR results revealed a relation between the redox potentials and the antioxidant activity of hydroxycinnamic acids and derivatives. The data obtained operate as a positive reinforce of the tendency to use redox properties as a guideline of the rational design of this type of compounds.

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.