ChemicalBook CAS DataBase List Urolithin A

Urolithin A synthesis

11synthesis methods

Product Name:Urolithin A
CAS Number:1143-70-0
Molecular formula:C13H8O4
Molecular Weight:228.2

2-bromo-5-methoxybenzoic acid is coupled with resorcinol to yield the intermediate “methoxy” product (Intermediate A), which is then isolated via filtration and dried for use in step 2. The solvent methanol is utilized in this step.
the intermediate product, "Intermediate A", is treated with the Lewis acid, AlCl3, in order to obtain a crude urolithin A. The ether cleavage of Intermediate A is accomplished by activation of the methyl ether through the addition of the Lewis acid, AlCl3, in toluene. The activated species is then hydrolyzed by the addition of water. Following hydrolysis, the crude product is filtered and dried.
crude urolithin A is dissolved in dimethyl sulfoxide (DMSO) for a polish filtration and subsequently precipitated from this DMSO solution by the addition of water. The filter cake is rinsed by water, followed by methanol. The raw urolithin A is then triturated with acetic acid (HOAc) to further purify the product and then collected by filtration. Following filtration, the purified product is rinsed with HOAc followed by tert-butyl-methyl ether (TBME), then dried to yield the final product, urolithin A.

Synthesis of Urolithin A

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Yield:1143-70-0 64%

Reaction Conditions:

with boron tribromide in dichloromethane at 0;Inert atmosphere;

Steps:

1 4.7 General procedure for the preparation of urolithins A-C (2a-c)

General procedure: A solution of methyl ether of urolithins A-C 30a-c (1.0equiv) was cooled at 0°C under Ar atmosphere and was added BBr₃ slowly. Once the stating material was completely consumed by TLC, a solution of 2N HCl was added to acidify and partitioned with EtOAc to give the crude product. The crude product was purified by size exclusion chromatography to obtain the product.

References:

Nealmongkol, Prattya;Tangdenpaisal, Kassrin;Sitthimonchai, Somkid;Ruchirawat, Somsak;Thasana, Nopporn [Tetrahedron,2013,vol. 69,# 44,p. 9277 - 9283]

35450-36-3 Synthesis