Urolithin A
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| Category | Others |
| Catalog number | BBF-04125 |
| CAS | 1143-70-0 |
| Molecular Weight | 228.20 |
| Molecular Formula | C13H8O4 |
| Purity | ≥98% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04125 | 1 g | $439 | In stock |
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Add to cartDescription
Urolithin A is a secondary metabolite of ellagitannins by the gut bacteria. It exhibits anti-inflammatory, antioxidant and antiproliferative effects. Urolithin A can cross the blood brain barrier thus has the potential therapeutic effect against Alzheimer's Disease.
Specification
| Synonyms | 3,8-dihydroxy-6H-benzo[c]chromen-6-one; 3,8-Dihydroxy-6H-dibenzo(b,d)pyran-6-one; 6H-Dibenzo[b,d]pyran-6-one, 3,8-dihydroxy- |
| Storage | Keep in a dry and well-ventilated place. |
| IUPAC Name | 3,8-dihydroxybenzo[c]chromen-6-one |
| Canonical SMILES | C1=CC2=C(C=C1O)C(=O)OC3=C2C=CC(=C3)O |
| InChI | 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 |
Properties
| Appearance | Solid |
| Boiling Point | 527.9°C at 760 mmHg |
| Melting Point | >300°C (dec.) |
| Flash Point | 214.2ºC |
| Density | 1.516 g/cm3 |
| Solubility | Soluble in DMSO (20 mg/mL) |
| LogP | 2.35740 |
Reference Reading
1.Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic.
Cerdá B1, Cerón JJ, Tomás-Barberán FA, Espín JC. J Agric Food Chem. 2003 May 21;51(11):3493-501.
The water-soluble ellagitanin punicalagin has been reported to be toxic to cattle. Taking into account that this antioxidant polyphenol is very abundant in pomegranate juice (> or =2 g/L), the present study evaluated the possible toxic effect of punicalagin in Sprague-Dawley rats upon repeated oral administration of a 6% punicalagin-containing diet for 37 days. Punicalagin and related metabolites were identified by HPLC-DAD-MS-MS in plasma, liver, and kidney. Five punicalagin-related metabolites were detected in liver and kidney, that is, two ellagic acid derivatives, gallagic acid, 3,8-dihydroxy-6H-dibenzo[b,d]pyran-6-one glucuronide, and 3,8,10-trihydroxy-6H-dibenzo[b,d]pyran-6-one. Feedstuff intake, food utility index, and growth rate were lower in treated rats during the first 15 days without significant adverse effects, which could be due to the lower nutritional value of the punicalagin-enriched diet together with a decrease in its palatability (lower food intake).
2.Dissimilar in vitro and in vivo effects of ellagic acid and its microbiota-derived metabolites, urolithins, on the cytochrome P450 1A1.
González-Sarrías A1, Azorín-Ortuño M, Yáñez-Gascón MJ, Tomás-Barberán FA, García-Conesa MT, Espín JC. J Agric Food Chem. 2009 Jun 24;57(12):5623-32. doi: 10.1021/jf900725e.
This research shows that the dietary polyphenol ellagic acid (EA) and its colonic metabolites, urolithin-A (3,8-dihydroxy-6H-dibenzo[b,d]pyran-6-one, Uro-A) and urolithin-B (3-hydroxy-6H-dibenzo[b,d]pyran-6-one, Uro-B), modulate phase I and phase II detoxifying enzymes in colon cancer Caco-2 cells. EA and the urolithins, at micromolar concentrations achievable in the colon from the diet, induced the expression and activity of CYP1A1 and UGT1A10 and inhibited several sulfotransferases. As a result, the synthesis of glucuronides was favored over sulfated conjugates in the treated cells. In situ exposure to these compounds dissolved in buffer also led to the induction of CYP1A1 in the rat colon. However, in situ exposure to the compounds dissolved in oil or oral supplementation of the single compounds or pomegranate extract (PE) added to the feed failed to induce CYP1A1 in the colon mucosa. These results suggest that EA and urolithins may exert some blocking chemopreventive effects in the colon but that this effect is critically affected by interfering factors, such as the food matrix nature.
3.Pomegranate ellagitannin-derived compounds exhibit antiproliferative and antiaromatase activity in breast cancer cells in vitro.
Adams LS1, Zhang Y, Seeram NP, Heber D, Chen S. Cancer Prev Res (Phila). 2010 Jan;3(1):108-13. doi: 10.1158/1940-6207.CAPR-08-0225.
Estrogen stimulates the proliferation of breast cancer cells and the growth of estrogen-responsive tumors. The aromatase enzyme, which converts androgen to estrogen, plays a key role in breast carcinogenesis. The pomegranate fruit, a rich source of ellagitannins (ET), has attracted recent attention due to its anticancer and antiatherosclerotic properties. On consumption, pomegranate ETs hydrolyze, releasing ellagic acid, which is then converted to 3,8-dihydroxy-6H-dibenzo[b,d]pyran-6-one ("urolithin") derivatives by gut microflora. The purpose of this study was to investigate the antiaromatase activity and inhibition of testosterone-induced breast cancer cell proliferation by ET-derived compounds isolated from pomegranates. A panel of 10 ET-derived compounds including ellagic acid, gallagic acid, and urolithins A and B (and their acetylated, methylated, and sulfated analogues prepared in our laboratory) were examined for their ability to inhibit aromatase activity and testosterone-induced breast cancer cell proliferation.
4.The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans.
Cerdá B1, Espín JC, Parra S, Martínez P, Tomás-Barberán FA. Eur J Nutr. 2004 Aug;43(4):205-20. Epub 2004 Jan 6.
BACKGROUND: The antiatherogenic activity of pomegranate juice has been attributed to its antioxidant polyphenols. The most potent in vitro antioxidant polyphenol from this juice is the ellagitannin punicalagin. However, the bioavailability of ellagitannins, including punicalagin, has not been previously described in humans.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
