| Identification | Back Directory | [Name]
3-HYDROXY-6H-DIBENZO[B,D]PYRAN-6-ONE | [CAS]
1139-83-9 | [Synonyms]
AURORA 226
Urolithin B
AKOS BBS-00008028
3-hydroxy urolithin
3-hydroxybenzo[c]chromen-6-one
3-hydroxy-6-benzo[c]chromenone
3-Hydroxy-benzo[c]chromen-6-one
3-HYDROXY-6H-DIBENZO[B,D]PYRAN-6-ONE
6H-Dibenzo(b,d)pyran-6-one, 3-hydroxy-
3-Hydroxy-6H-benzo[c]chromen-6-one AldrichCPR | [Molecular Formula]
C13H8O3 | [MDL Number]
MFCD00034338 | [MOL File]
1139-83-9.mol | [Molecular Weight]
212.2 |
| Chemical Properties | Back Directory | [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) | [form ]
powder | [pka]
9.03±0.20(Predicted) | [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) |
| Hazard Information | Back Directory | [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]
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 |
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