urolithin A

Base Information

• Chemical Name: urolithin A
• CAS No.: 1143-70-0
• Molecular Formula: C13H8O4
• Molecular Weight: 228.204
• Hs Code.: 2914400090
• European Community (EC) Number: 881-478-5
• UNII: ILJ8NEF6DT
• DSSTox Substance ID: DTXSID40150694
• Nikkaji Number: J12.496F
• Wikipedia: Urolithin_A
• Wikidata: Q15634120
• Metabolomics Workbench ID: 42482
• ChEMBL ID: CHEMBL1836264
• Mol file: 1143-70-0.mol

Synonyms:3,8-dihydroxy-6H-dibenzo(b,d)pyran-6-one;urolithin A

Chemical Property of urolithin A

Chemical Property:

• Vapor Pressure: 9.24E-12mmHg at 25°C
• Melting Point: 340-345 °C
• Refractive Index: 1.717
• Boiling Point: 527.9 °C at 760 mmHg
• PKA: 9.07±0.20(Predicted)
• Flash Point: 214.2 °C
• PSA: 70.67000
• Density: 1.516 g/cm³
• LogP: 2.35740
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 228.04225873
• Heavy Atom Count: 17
• Complexity: 317

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

Urolithin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)C(=O)OC3=C2C=CC(=C3)O
• Description: Urolithin A is a metabolite of ellagic acid. It is produced by the body after you ingest compounds found in particularly high concentration in pomegranates (particularly the bitter components such as the skin and seeds) and can help recycle defective mitochondria. Since it is a metabolite that results from the transformation of the tannins in pomegranate by gut bacteria, it can be classified as a postbiotic.It has been demonstrated to stimulate mitophagy and improve muscle health in old animals and in preclinical models of aging.
• Uses: Urolithin A is a major metabolite of ellagitannin and exhibits anti-inflammatory and antioxidant properties.

Technology Process of urolithin A

There total 39 articles about urolithin A 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: 99.0%

C27H20O4 → urolithin B (1143-70-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 10h;

Reference yield: 98.0%

3,8-bis-(tert-butyl-dimethyl-silanyloxy)-benzo[c]chromen-6-one → urolithin B (1143-70-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;

Reference yield: 85.0%

3-hydroxy-8-methoxy-6H-dibenzo-[b,d]pyran-6-one (35233-17-1) → urolithin B (1143-70-0)

Guidance literature:

With aluminum (III) chloride; In chlorobenzene; at 100 ℃;

DOI:10.1039/c7ra01548h

upstream raw materials:

2-bromo-5-hydroxybenzoic acid

recorcinol

N,N-Diethyl-2',4,4'-trimethoxy-2-biphenylcarboxamide

hydrogen iodide

Downstream raw materials:

3,8-di(t-butyldimethylsilyloxy)-6-[4-[2-(1-piperidino)ethoxy]-phenyl]dibenzo[b,d]pyran

3,8-di(t-butyldimethylsilyloxy)-6-[4-[2-(1-pyrrolidino)ethoxy]-phenyl]dibenzo[b,d]pyran

3,8-di(t-butyldimethylsilyloxy)-6-phenoxydibenzo[b,d]pyran

urolithin C

Refernces

• 1、 Yin, Peipei,Zhang, Jianwei,Yan, Linlin,Yang, Lingguang,Sun, Liwei,Shi, Lingling,Ma, Chao,Liu, Yujun. "Urolithin C, a gut metabolite of ellagic acid, induces apoptosis in PC12 cells through a mitochondria-mediated pathway". . p. 17254 - 17263. Retrieved 2017.
• 2、 Saha, Piu,Yeoh, Beng San,Singh, Rajbir,Chandrasekar, Bhargavi,Vemula, Praveen Kumar,Haribabu, Bodduluri,Vijay-Kumar, Matam,Jala, Venkatakrishna R.. "Gut Microbiota conversion of dietary ellagic acid into bioactive phytoceutical urolithin a inhibits heme peroxidases". . . Retrieved 2016.
• 3、 Noshadi, Bahareh,Ercetin, Tugba,Luise, Chiara,Yuksel, Mine Yarim,Sippl, Wolfgang,Sahin, Mustafa Fethi,Gazi, Mustafa,Gulcan, Hayrettin Ozan. "Synthesis, Characterization, Molecular Docking, and Biological Activities of Some Natural and Synthetic Urolithin Analogs". . . Retrieved 2020/07/24.
• 4、 -. "Synthetic method of urolithin A". Paragraph 0047-0050; 0056. . Retrieved 2020/12/08.