117570-93-1

Basic information

• Product Name: 2-(2-CARBOXYMETHYL-PHENOXY)-3,4-DIMETHYL-BENZOIC ACID
• Synonyms: 2-(2-CARBOXYMETHYL-PHENOXY)-3,4-DIMETHYL-BENZOIC ACID
• CAS NO: 117570-93-1
• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.31
• Mol File: 117570-93-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Vapor Pressure: 0Pa at 20℃
• Refractive Index: 1.607
• CAS DataBase Reference: 2-(2-CARBOXYMETHYL-PHENOXY)-3,4-DIMETHYL-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-CARBOXYMETHYL-PHENOXY)-3,4-DIMETHYL-BENZOIC ACID(117570-93-1)
• EPA Substance Registry System: 2-(2-CARBOXYMETHYL-PHENOXY)-3,4-DIMETHYL-BENZOIC ACID(117570-93-1)

Safety Data

• Hazardous Substances Data: 117570-93-1(Hazardous Substances Data)

Usage

Chemical classification

2-(2-Carboxymethyl-phenoxy)-3,4-dimethyl-benzoic acid is a chemical compound and a derivative of benzoic acid.

Molecular structure

The compound features two methyl groups at the 3 and 4 positions on the benzene ring and a carboxymethyl-phenoxy group attached to the second carbon of the benzoic acid.

Potential pharmaceutical applications

It has potential use as a drug due to its structural features and ability to interact with biological systems.

Research focus

The compound is likely to be researched for its pharmacological properties and potential therapeutic applications.

InChI:InChI=1/C17H16O5/c1-10-7-8-13(17(20)21)16(11(10)2)22-14-6-4-3-5-12(14)9-15(18)19/h3-8H,9H2,1-2H3,(H,18,19)(H,20,21)

Upstream product

• 1021381-67-8 C₁₇H₁₅BrO₅ 
• 1202661-54-8 sodium 2-iodo-3,4-dimethyl-benzoate 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 87-59-2 2,3-Dimethylaniline 
• 50419-58-4 2-amino-3,4-dimethylbenzoic acid 
• 6579-44-8 2,3-dimethyl-α-isonitrosoacetanilide 
• 20205-43-0 6,7-dimethylisatin 
• 117571-22-9 (2-hydroxyphenyl)acetic acid disodium salt 
• 129833-31-4 3,4-dimethyl-2-iodobenzoic acid 

Downstream Products

• 117570-53-3 vadimezan 

Relevant articles and documents

Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists

STING (Stimulator of Interferon Genes) has become a focal point in immunology research and a target in drug discovery. The discovery of a potent human-STING agonist is expected to revolutionize current anti-virus or cancer immunotherapy. Inspired by the structure and function of murine STING-specific agonists (DMXAA and CMA), we rationally designed and synthesized four series of novel compounds for the enhancement of human sensitivity. In the cell-based assay, we identified six compounds from all the synthetic small molecules: 2g, 9g, and 12b are STING agonists that are efficacious across species, and all have the skeleton of acridone; 1b, 1c, and 12c just function in the murine STING pathway. Notably, 12b exhibits the best activity among the six agonists, and its inductions of both human and murine STING-dependent signalling are similar to that of 2′3′-cGAMP, which is a well-known STING inducer. While a protein assay indicated that 2 g, 9 g, and 12b could activate the pathway by directly binding human STING, 12b also displayed the strongest binding affinity. Additionally, our studies show that 12b can induce faster, more powerful, and more durable responses of assorted cytokines in a native system than 2′3′-cGAMP. Consequently, our team is the first to successfully modify murine STING agonists to obtain human sensitivity, and these results suggest that 12b is a potent direct-human-STING agonist. Additionally, the acridone analogues demonstrate tremendous potential in the treatment of tumours or viral infections.

ORGANIC COMPOUNDS

The present invention provides an improved process for the synthesis of 5,6-dimethyl-9-oxo-9H-xanthen 4-yl-acetic acid (DMXAA). The process yields pure and colorless product, and is suitable for large scale production.

An improved synthesis of 5,6-dimethylxanthenone-4-acetic acid (DMXAA)

5,6-Dimethylxanthenone-4-acetic acid (DMXAA) is a novel anticancer agent with a number of unique activities, and is in clinical trial. The current synthesis of DMXAA involves six steps, beginning with a heterogeneous reaction to form an isonitrosoacetanilide, and gives an overall yield of 11% from 2,3-dimethylaniline. We report an alternative synthesis of the key intermediate 3,4-dimethylanthranilic acid via nitration of 3,4-dimethylbenzoic acid and separation of the key desired isomer by ready crystallisation. This, together with improvements in the rest of the synthesis, provide a shorter and higher-yielding route to DMXAA (22% overall from 3,4-dimethylbenzoic acid).