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Merck

SML1791

Sigma-Aldrich

Urolithin A

≥97% (HPLC), powder, anti-inflammatory

Sinónimos:

3,8-Dihydroxy-6H-benzo[c]chromen-6-one

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About This Item

Fórmula empírica (notación de Hill):
C13H8O4
Número de CAS:
Peso molecular:
228.20
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Urolithin A, ≥97% (HPLC)

Quality Level

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

OC1=CC=C(C(C=CC(O)=C2)=C2C(O3)=O)C3=C1

InChI

1S/C13H8O4/c14-7-1-3-9-10-4-2-8(15)6-12(10)17-13(16)11(9)5-7/h1-6,14-15H

InChI key

RIUPLDUFZCXCHM-UHFFFAOYSA-N

Application

Urolithin A has been used:
  • to test its antileukemic activities on leukemic cell lines by in vitro cell proliferation assay
  • as a mitophagy activator to study the effect of phosphoglycerate mutase 5 (PGAM5) expression on mitophagic cell death during ischemia-reperfusion (I/R) injury
  • to study its inhibitory effect on epithelial-to-mesenchymal transition (EMT) in lung cancer cells via P53-Mdm2-Snail pathway
  • to study its effects on streptozotocin-induced diabetic cardiomyopathy in rats by activating sirtuin 1/silent mating type information regulation 2 homolog 1 (SIRT1) signaling

Biochem/physiol Actions

Urolithin A is a natural product with antiproliferative and antioxidant activity. Urolithin A is formed by metabolism from polyphenols found in some nuts and fruits, particularly pomegranates. Urolithin A has been shown to cross the blood brain barrier, and may have neuroprotective effects against Alzheimer′s Disease.
Urolithin A is the most studied urolithin with anti-inflammatory and anti-obesity properties. It may also prevent the progression of various cancer types including colon, prostate, and bladder cancer by downregulating several oncogenes such as the mammalian target of rapamycin (mTOR) and Kirsten rat sarcoma viral oncogene(K-Ras), upregulating tumor suppressor genes such as p53 and epidermal growth factor receptor (EGFR) in various tumor pathways.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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Yun Wang et al.
Toxicology in vitro : an international journal published in association with BIBRA, 29(5), 1107-1115 (2015-04-26)
The intestinal metabolites of ellagic acid (EA), urolithins are known to effectively inhibit cancer cell proliferation. This study investigates antiproliferative and antioxidant effects of urolithin A (UA) on cell survival of the HepG2 hepatic carcinomas cell line. The antiproliferative effects
Abdulaziz Musa Alzahrani et al.
International journal of molecular sciences, 22(11) (2021-06-03)
Leukemia is persistently a significant cause of illness and mortality worldwide. Urolithins, metabolites of ellagic acid and ellagitannins produced by gut microbiota, showed better bioactive compounds liable for the health benefits exerted by ellagic acid and ellagitannins containing pomegranate and
Tao Yuan et al.
ACS chemical neuroscience, 7(1), 26-33 (2015-11-13)
Pomegranate shows neuroprotective effects against Alzheimer's disease (AD) in several reported animal studies. However, whether its constituent ellagitannins and/or their physiologically relevant gut microbiota-derived metabolites, namely, urolithins (6H-dibenzo[b,d]pyran-6-one derivatives), are the responsible bioactive constituents is unknown. Therefore, from a pomegranate
Gadah Albasher et al.
Saudi journal of biological sciences, 29(2), 1210-1220 (2022-03-05)
This study examined the cardiac anti-cardiomyopathy (DC) protective effect of urolithin A in streptozotocin (STZ)-treated rats and investigated if this protection involves activation of SIRT1 signaling. Diabetes was induced first STZ (65 mg/kg, i.p.) before starting the experiments. Adult male rats
Sheng-Long Ding et al.
Journal of inflammation (London, England), 17, 13-13 (2020-03-27)
Osteoarthritis (OA) is characterized by inflammation and extracellular matrix (ECM) degradation and is one of the most common chronic degenerative joint diseases that causes pain and disability in adults. Urolithin A (UA) has been widely reported for its anti-inflammatory properties

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