206559-42-4

Basic information

• Product Name: 3-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID
• Synonyms: 3-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID;RARECHEM AL BO 1584;3-Bromo-5-(carboxymethyl)-2-hydroxyanisole, 6-Bromo-4-(carboxymethyl)-2-methoxyphenol
• CAS NO: 206559-42-4
• Molecular Formula: C₉H₉BrO₄
• Molecular Weight: 261.07
• Mol File: 206559-42-4.mol

Chemical Properties

• Melting Point: 183 °C
• Boiling Point: 379.2 °C at 760 mmHg
• Flash Point: 183.1 °C
• Appearance: /
• Density: 1.678 g/cm³
• Vapor Pressure: 2E-06mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.22±0.10(Predicted)
• CAS DataBase Reference: 3-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID(206559-42-4)
• EPA Substance Registry System: 3-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID(206559-42-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 206559-42-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID is used as a potential therapeutic agent for the treatment of oxidative stress-related diseases due to its antioxidant properties.
Used in Drug Development:
3-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID is used as a precursor in the development of new drugs, leveraging its chemical structure and properties for innovative pharmaceutical applications.
Used in Scientific Research:
3-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID is used as a research reagent in various scientific studies, contributing to the advancement of knowledge in biomedical and related fields.

InChI:InChI=1/C9H9BrO4/c1-14-7-3-5(4-8(11)12)2-6(10)9(7)13/h2-3,13H,4H2,1H3,(H,11,12)

Upstream product

• 1258845-38-3 (3-bromo-4-hydroxy-5-methoxyphenyl)acetic acid ethyl ester 
• 306-08-1 Homovanillic acid 
• 60563-13-5 ethyl homovanillate 

Downstream Products

• 1258845-51-0 N-(4-tert-butyl-benzyl)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)acetamide 
• 1258845-42-9 (4-acetoxy-3-bromo-5-methoxyphenyl)acetic acid 
• 1258845-74-7 3-[2-(3-bromo-4-hydroxy-5-methoxyphenyl)acetamido]-2-(3,4-dimethylbenzyl)propyl pivalate 
• 1258845-63-4 2-(4-tert-butylbenzyl)-3-[2-(3-bromo-4-hydroxy-5-methoxyphenyl)acetamido]propyl pivalate 
• 1258845-38-3 (3-bromo-4-hydroxy-5-methoxyphenyl)acetic acid ethyl ester 
• 1329991-29-8 C₁₈H₁₉BrO₄ 

Relevant articles and documents

Receptor activity and conformational analysis of 5′-halogenated resiniferatoxin analogs as TRPV1 ligands

A series of 5′-halogenated resiniferatoxin analogs have been investigated in order to examine the effect of halogenation in the A-region on their binding and the functional pattern of agonism/antagonism for rat TRPV1 heterologously expressed in Chinese hamster ovary cells. Halogenation at the 5-position in the A-region of RTX and of 4-amino RTX shifted the agonism of parent compounds toward antagonism. The extent of antagonism was greater as the size of the halogen increased (I > Br > Cl > F) while the binding affinities were similar, as previously observed for our potent agonists. In this series, 5-bromo-4-amino RTX (39) showed very potent antagonism with K i (ant) = 2.81 nM, which was thus 4.5-fold more potent than 5′-iodo RTX, previously reported as a potent TRPV1 antagonist. Molecular modeling analyses with selected agonists and the corresponding halogenated antagonists revealed a striking conformational difference. The 3-methoxy of the A-region in the agonists remained free to interact with the receptor whereas in the case of the antagonists, the compounds assumed a bent conformation, permitting the 3-methoxy to instead form an internal hydrogen bond with the C4-hydroxyl of the diterpene.

Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3- methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with Ki (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6′-iodononivamide.