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| IUPAC Name: | 1,8-dihydroxy-3-methylanthracene-9,10-dione |
| Description: | Chrysophanic acid (Chrysophanol) is a natural anthraquinone with anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid preferentially blocked proliferation in SNU-C5 cells but not in other cell lines (HT7, HT29, KM12C, SW480, HCT116 and SNU-C4) with low levels of EGFR expression. Chrysophanic acid treatment in SNU-C5 cells inhibited EGF-induced phosphorylation of EGFR and suppressed activation of downstream signaling molecules, such as AKT, extracellular signal-regulated kinase (ERK) and the mammalian target of rapamycin (mTOR)/ribosomal protein S6 kinase (p70S6K). Chrysophanic acid (80 and 120 µm) significantly blocked cell proliferation when combined with the mTOR inhibitor, rapamycin. These findings offer the first evidence of anticancer activity for chrysophanic acid via EGFR/mTOR mediated signaling transduction pathway. Chrysophanol is a natural compound found in the roots and rhizomes of Rheum palmatum L. It can be used in cosmetics material. |
| Molecular Weight: | 254.24 |
| Molecular Formula: | C15H10O4 |
| Canonical SMILES: | CC1=CC(=C2C(=C1)C(=O)C3=C(C2=O)C(=CC=C3)O)O |
| InChI: | InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3 |
| InChI Key: | LQGUBLBATBMXHT-UHFFFAOYSA-N |
| Boiling Point: | Sublimes |
| Melting Point: | 194-197 °C |
| Purity: | ≥ 98 % |
| Density: | 0.92 g/cm cu at 25 °C |
| Solubility: | less than 1 mg/mL at 64 °F |
| Appearance: | Orange solid |
| Decomposition: | Hazardous decomposition products formed under fire conditions. - carbon oxides |
| MDL: | MFCD00001208 |
| LogP: | 2.18160 |
| Quality Standard: | Enterprise Standard |
| Stability: | Stable under recommended storage conditions |
| Vapor Pressure: | 3.69X10-10 mm Hg at 25 °C (est) |
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