Urolithin A 8-Methyl Ether

April 8, 2021

Urolithins are secondary metabolites of ellagic acid derived from ellagitannins. In humans ellagitannins are converted by the gut microflora into ellagic acid which is further transformed into urolithins A, urolithin B, urolithin C and urolithin D in the large intestines.

Urolithin A 8-Methyl Ether(35233-17-1)Specifications

Product Name Urolithin A 8-Methyl Ether powder
Chemical Name 3-hydroxy-8-methoxy-6H-benzo[c]chromen-6-one;

3-hydroxy-8-methoxybenzo[c]chromen-6-one;

35233-17-1;

MLS001049096;

SMR000386929;

ChemDiv3_002724;

Urolithin A 8-Methyl Ether;

CAS Number 35233-17-1
InChIKey IGJLBTGXYKPECW-UHFFFAOYSA-N
Molecular Formula C14H10O4
Molecular Weight 242.23
Monoisotopic Mass 242.057909 g/mol
Melting point 242 °C(Solv: acetic acid (64-19-7))
Boiling point  479.9±38.0 °C(Predicted)
Density 1.375±0.06 g/cm3(Predicted)
Biological Half-Life N/A
Color Light Beige to Very Dark Orange Solid
Solubility  Acetone (Slightly, Sonicated) DMSO (Slightly, Sonicated), Methanol (Slightly)
Storage Temperature  Hygroscopic, -20°C Freezer, Under inert atmosphere
Application Urolithin A 8-Methyl Ether is an intermediate in the synthesis of Urolithin A (U847000), a major metabolite of Ellagitannin and exhibits anti-inflammatory and antioxidant properties.

 

Reference

[1] Espín, Juan Carlos; Larrosa, Mar; García-Conesa, María Teresa; Tomás-Barberán, Francisco (2013). “Biological Significance of Urolithins, the Gut Microbial Ellagic Acid-Derived Metabolites: The Evidence So Far”. Evidence-Based Complementary and Alternative Medicine. 2013: 270418.  doi: 1155/2013/270418.  ISSN1741-427X.  PMC 3679724.  PMID 23781257.

[2] Ryu, Dongryeol; Mouchiroud, Laurent; Andreux, Pénélope A; Katsyuba, Elena; Moullan, Norman; Nicolet-dit-Félix, Amandine A; Williams, Evan G; Jha, Pooja; Sasso, Giuseppe Lo (2016). “Urolithin A induces mitophagy and prolongs lifespan in C. elegans and increases muscle function in rodents”. Nature Medicine. 22(8): 879–888. doi:1038/nm.4132. PMID 27400265.

[3] Ishimoto, Hidekazu; Shibata, Mari; Myojin, Yuki; Ito, Hideyuki; Sugimoto, Yukio; Tai, Akihiro; Hatano, Tsutomu (2011). “In vivo anti-inflammatory and antioxidant properties of ellagitannin metabolite urolithin A”(PDF). Bioorganic & Medicinal Chemistry Letters. 21(19): 5901–5904. doi:1016/j.bmcl.2011.07.086. PMID 21843938.

[4] Kasimsetty, S. G., et al.: J. Agri. Food. Chem., 58, 2180 (2010);

[5] Bialonska, D., et al.: J. Agri. Food. Chem., 57, 10181 (2009);