131086-98-1

Basic information

• Product Name: Urolithin D
• Synonyms: 3,4,8,9-Tetrahydroxy-6H-dibenzo[b,d]pyran-6-one;Urolithin D
• CAS NO: 131086-98-1
• Molecular Formula: C13H8O6
• Molecular Weight: 260.19902
• Mol File: 131086-98-1.mol

Chemical Properties

• Boiling Point: 634.1°Cat760mmHg
• Flash Point: 253°C
• Appearance: /
• Density: 1.766g/cm³
• Vapor Pressure: 1.13E-16mmHg at 25°C
• Refractive Index: 1.801
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: Urolithin D(CAS DataBase Reference)
• NIST Chemistry Reference: Urolithin D(131086-98-1)
• EPA Substance Registry System: Urolithin D(131086-98-1)

Safety Data

• Hazardous Substances Data: 131086-98-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Urolithin D is used as a research compound for evaluating the DNA gyrase inhibitory activity of ellagic acid derivatives. This application is significant because DNA gyrase is an essential enzyme in bacterial DNA replication, and its inhibition can lead to the development of new antibiotics and anti-cancer drugs.
Additionally, Urolithin D may have potential applications in other areas of the pharmaceutical industry, such as anti-inflammatory, anti-aging, and neuroprotective agents, due to its reported effects on various cellular pathways and processes. However, further research is needed to fully understand its potential and establish its efficacy in these areas.

InChI:InChI=1/C13H8O6/c14-8-2-1-5-6-3-9(15)10(16)4-7(6)13(18)19-12(5)11(8)17/h1-4,14-17H

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Relevant articles and documents

ENHANCING AUTOPHAGY OR INCREASING LONGEVITY BY ADMINISTRATION OF UROLITHINS OR PRECURSORS THEREOF

Disclosed are methods, compounds, and compositions useful for increasing autophagy and promoting longevity. The methods, compounds, and compositions relate to urolithins and urolithin precursors and use thereof. Certain urolithins are represented by Formula I, while certain urolithin precursors are represented by Formula IV. The urolithin may be urolithin A, urolithin B, urolithin C, or urolithin D. The urolithin precursor may be ellagic acid or an ellagitannin. The methods include in vivo, ex vivo, and in vitro uses of the compounds and compositions.

Urolithins, intestinal microbial metabolites of pomegranate ~ellagitannins, exhibit potent antioxidant activity in a cell-based assay

Many health benefits of pomegranate products have been attributed to the potent antioxidant action of their tannin components, mainly punicalagins and ellagic acid. While moving through the intestines, ellagitannins are metabolized by gut bacteria into urolithins that readily enter systemic circulation. In this study, the antioxidant properties of seven urolithin derivatives were evaluated in a cell-based assay. This method is biologically more relevant because it reflects bioavailability of the test compound to the cells, and the antioxidant action Is determined in the cellular environment. Our results showed that the antioxidant activity of urolithins was correlated with the number of hydroxy groups as well as the lipophilicity of the molecule. The most potent antioxidants are urolithins C and D with IC50 values of 0.16 and 0.33 μM, respectively, when compared to IC50 values of 1.1 and 1.4 μM of the parent ellagic acid and punicalagins, respectively. The dihydroxylated urolithin A showed weaker antioxidant activity, with an IC 50 value 13.6 μM, however, the potency was within the range of urolithin A plasma concentrations. Therefore, products of the intestinal microbial transformation of pomegranate ellagitannins may account for systemic antioxidant effects.

Tricyclic polyhydroxylic tyrosine kinase inhibitors

Certain tricyclic polyhydroxylic compounds, and their pharmaceutically-acceptable salts, are inhibitors of tyrosine kinase enzymes, and so are useful for the control of tyrosine kinase dependent diseases (e.g., cancer, atherosclerosis).

Dna gyrase inhibitory activity of ellagic acid derivatives

Ellagic acid was found to inhibit E. coli DNA gyrase supercoiling with approximately the same potency as nalidixic acid. Tricyclic analogs of ellagic acid, which vary in the number and position of the hydroxy soups as well as their replacement with haloge

Sequential Directed Ortho Metalation-Boronic Acid Cross-Coupling Reactions. A General Regiospecific Route to Oxygenated Dibenzopyran-6-ones Related to Ellagic Acid

A general regiospecific synthesis of dibenzopyran-6-one derivatives 1a,c and 8a-i related to ellagic acid is described (Scheme I, Table I).The sequence involves directed ortho metalation-boronation of benzamides 4 to give the arylboronic acids 5, which, upon palladium-catalyzed cross-coupling with alkoxybromobenzenes 6 leads to the biphenylamides 7.BBr3 demethylation followed by acid-catalyzed cyclization affords pyranone 8.In this manner, the naturally occurring dibenzopyranones 1a, autumnariol (1c), and the heterocyclic analogue 13 (Scheme III) were efficiently prepared.