Methyl 2,4-dihydroxy-6-methylbenzoate

Base Information

• Chemical Name: Methyl 2,4-dihydroxy-6-methylbenzoate
• CAS No.: 3187-58-4
• Molecular Formula: C9H10 O4
• Molecular Weight: 182.176
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID2062901
• Nikkaji Number: J113.556B
• Wikidata: Q27136372
• Metabolomics Workbench ID: 135309
• ChEMBL ID: CHEMBL454431
• Mol file: 3187-58-4.mol

Synonyms:methyl orsellinate

Chemical Property of Methyl 2,4-dihydroxy-6-methylbenzoate

Chemical Property:

• Vapor Pressure: 4.8E-05mmHg at 25°C
• Melting Point: 141-142℃
• Boiling Point: 339.1°Cat760mmHg
• PKA: 8.27±0.23(Predicted)
• Flash Point: 138.1°C
• PSA: 66.76000
• Density: 1.296g/cm³
• LogP: 1.19280
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

97% ^*data from raw suppliers

Methyl2,4-Dihydroxy-6-methylbenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1C(=O)OC)O)O
• Uses: Methyl 2,4-Dihydroxy-6-methylbenzoate is a useful synthetic intermediate in the synthesis of Grifolic Acid (G786500); a selective partial GPR120 agonist. Grifolic Acid induces ERK and [Ca2+]i responses in cells expressing GPR120, but has no effects on those expressing GPR40.

Technology Process of Methyl 2,4-dihydroxy-6-methylbenzoate

There total 52 articles about Methyl 2,4-dihydroxy-6-methylbenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

methyl 2,4-dimethoxy-6-methylbenzoate (6110-37-8) → methyl orsellinate (3187-58-4)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo0624344

Reference yield: 90.0%

orsellinic acid (480-64-8) + methyl iodide (74-88-4) → methyl orsellinate (3187-58-4)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 25 ℃; for 12h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

Reference yield: 82.0%

methanol (67-56-1) + 1-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)pentane-2,4-dione (1213257-95-4) → methyl orsellinate (3187-58-4)

Guidance literature:

In dichloromethane; at 100 ℃; for 10h; Molecular sieve; Inert atmosphere; sealed tube;

DOI:10.1016/j.tetlet.2009.11.134

upstream raw materials:

diazomethane

diethyl ether

orsellinic acid

methanol

Downstream raw materials:

2-hydroxy-4-methoxy-6-methyl-benzoic acid methyl ester

methyl haematommate

methyl isohaematommate

methyl 2,4-dihydroxy-3,5-dibromo-6-methylbenzoate

Refernces

Total synthesis of cristatic acid.

10.1021/ol0061236

The research aims to achieve the first total synthesis of cristatic acid 1, a secondary metabolite with significant biological properties, including antibiotic activity against Gram-positive bacteria, hemolytic properties, and cytotoxicity. The synthesis is challenging due to the presence of a labile furan moiety, which restricts reaction conditions. The researchers successfully synthesized cristatic acid by employing palladium-catalyzed alkylation of vinylepoxide 10, derived from sulfonium salt 8, and using SEM ethers as protecting groups for phenolic OH functions. Key chemicals used in the process include methyl orsellinate, prenyl bromide, SEMCl, SeO2, tertBuOOH, mesyl chloride, LiBr, Pd(PPh3)4, dppe, and various other reagents for deprotection and functional group transformations. The successful synthesis of cristatic acid not only demonstrates a feasible route to this bioactive compound but also paves the way for further studies on the biological response to changes in functionality. The conclusions of the research confirm the structural integrity of the synthesized cristatic acid through X-ray analysis and other analytical and spectroscopic data, which are in full agreement with literature reports.