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Urolithin B

Product NameUrolithin B
CAS1139-83-9
MFC13H8O3
MW212.2
EINECS
MOL File1139-83-9.mol

Chemical Properties

Melting point	247 °C
Boiling point	432.6±24.0 °C(Predicted)
Density	1.395±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: soluble5mg/mL, clear (warmed)
pka	9.03±0.20(Predicted)
form	powder
color	white to beige
Stability	Hygroscopic
InChI	InChI=1S/C13H8O3/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)16-12(10)7-8/h1-7,14H
InChIKey	WXUQMTRHPNOXBV-UHFFFAOYSA-N
SMILES	C12=CC(O)=CC=C1C1=CC=CC=C1C(=O)O2
LogP	2.947 (est)

Safety Information

Hazard Codes	Xn
Risk Statements	22
WGK Germany	3
HazardClass	IRRITANT
HS Code	2932209090
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2

Usage And Synthesis

Uses

Urolithin B is an intestinal microbial metabolite of ellagitannis and exhibits potent anti-oxidant and pro-oxidant activies depending on the assay system and conditions. Urolithin B can also display estrogenic and/or anti-estrogenic activity.

Definition

ChEBI: Urolithin B is a member of coumarins.

Biochem/physiol Actions

Urolithin B is a natural product with antiproliferative and antioxidant activity. Urolithin B is formed by metabolism from polyphenols found in some nuts and fruits, particularly pomegranates. Urolithin B has been shown to cross the blood brain barrier, and may have neuroprotective effects against Alzheimer′s Disease.

Synthesis

1143-62-0

1139-83-9

GENERAL METHODS: Urolithin A-C (30a-c, 1.0 eq.) was dissolved in methyl ether and cooled to 0 °C under argon protection. Boron tribromide (BBr3) was slowly added and the reaction progress was monitored by thin layer chromatography (TLC) until the starting material was completely consumed. Subsequently, the reaction mixture was acidified by the addition of 2N hydrochloric acid solution and extracted with ethyl acetate (EtOAc) to obtain the crude product. Finally, the crude product was purified by size exclusion chromatography to obtain the target compound 3-hydroxy-6H-benzo[c]benzopyran-6-one.

in vivo

Urolithin B (50 mg/kg; ip; once daily for 4 days) inhibits microglial activation in LPS-injected mouse brains, under neuroinflammatory condition^[1].
Urolithin B (10 μg/day; mini-osmotic pump delivery, 28 days) induces muscle hypertrophy and reduces muscle atrophy after sciatic nerve transection in mice^[2].

IC 50

Human Endogenous Metabolite

References

[1] Tetrahedron, 2013, vol. 69, # 44, p. 9277 - 9283
[2] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 433 - 444
[3] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5080 - 5095
[4] ChemMedChem, 2010, vol. 5, # 9, p. 1616 - 1630

Urolithin B

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