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481-74-3 (Chrysophanic acid)

1

Identification

Chrysophanic acid Chrysophanic acid
Name Chrysophanic acid
Formula C15H10O4
MW 254.24
CAS No. 481-74-3
EINECS 207-572-2
Smiles O=C(C1=C2C(O)=CC=C1)C3=CC(C)=CC(O)=C3C2=O
Synonyms Chrysophanol; 1,8-Dihydroxy-3-methylanthraquinone; 1,8-dihydroxy-3-methylanthracene-9,10-dione
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
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Introduction

Golden yellow plates or brown powder. Melting point 196°C. Slightly soluble in water. Pale yellow aqueous solutions turn red on addition of alkali. Solutions in concentrated sulfuric acid are red.

Background Information

Chrysophanol is an anthraquinone found in the root of Rheum wittrochii. It has been shown to increaseintracellular Ca2+ concentration and exhibit antifungal activities. An inducer of intracellular Ca2+ concentration and exhibit antifungal activities. ......by Affix Scientific
Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of <b>EGFR</b> and suppresses activation of <b>AKT</b> and <b>mTOR</b>/<b>p70S6K</b>. Target: EGFR<sup>[1]</sup> InVitro: Chrysophanol (Chrysophanic Acid) blocks proliferation of colon cancer cells by inhibiting EGFR/mTOR pathway. Chrysophanol, a natural anthraquinone, has anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanol treatment in SNU-C5 cells inhibits EGF-induced phosphorylation of EGFR and suppresses 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). Chrysophanol (80 and 120 μM) significantly blocks cell proliferation when combined with the mTOR inhibitor, Rapamycin. Chrysophanol inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K, and significantly blocks cell proliferation. Chrysophanol dose dependently decreases CCK-8 and the viability of EGFR-overexpressing SNU-C5 cells. Chrysophanol treatment dose-dependently decreases EGF induced phosphorylation of EGFR at Tyr1068. Chrysophanol (80 and 120 μM) reduces the phosphorylation levels of mTOR at Ser2448. Chrysophanol (80 and 120 μM) also decreases the phosphorylation levels of p70S6K at Thr389. Chrysophanol inhibits EGF-induced EGFR activation and suppresses activation of the downstream signaling molecules, AKT and mTOR/p70S6K<sup>[1]</sup>. Chrysophanol (CA) inhibits lipid accumulation in 3T3-L1 adipocytes. Chrysophanol down-regulates adipogenic factors in 3T3-L1 adipocytes. Chrysophanol induces thermogenic factors in primary cultured brown adipocytes. Chrysophanol suppresses adipogenesis and induces thermogenesis via activation of AMPK pathway<sup>[2]</sup>. InVivo: Chrysophanol (CA) improves HFD-induced obesity in C57BL/6 Mice. The in vivo performance of Chrysophanol is performed in male C57BL/6J mice to determine the efficacy of administered Chrysophanol. Mice fed the HFD gained significantly more weight than those fed the standard diet mice. On the other hand, weight gain of Chrysophanol group is significantly less than with the untreated HFD. Mice in the HFD-group gained 23.92 ± 1.74 g of weight, while those in the Chrysophanol group gained 16.72±2 g of weight after 16 weeks<sup>[2]</sup>. ......by MedChemexpress Co., Ltd.
Chrysophanic acid (Chrysophanol) is a a natural anthraquinone, has 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. (source: Phytother Res. 2011 Jun;25(6):833-7. ) Shelf life: >2 years if stored properly. Drug formulation: ......by MedKoo Biosciences, Inc.
Chrysophanic acid (Chrysophanol), a natural anthraquinone isolated from Dianella longifolia, is a EGFR/mTOR pathway inhibitor. ......by Selleck Chemicals LLC
Extracted from Rheum palmatum L.;Suitability:Boiling ethanol,benzene,chloroform,ether,acetic acid and acetone;Store the product in sealed,cool and dry condition ......by Target Molecule Corp.
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Protocol(Only for Reference)

Cell Experiment

Animal Experiment

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Physical and Chemical Properties

Appearance: EBNumber:EB000016521

Storage condition

Up to one week at 4°C or six months at -20°C. by Affix Scientific

Solubility

DMSO by CHEMSCENE, LLC
DMSO by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 5 mg/mL warming (19.66 mM); Water<1 mg/mL (<1 mM); Ethanol<1 mg/mL (<1 mM) by Selleck Chemicals LLC
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Mechanism and Indication

Signaling Pathways JAK/STAT Signaling Protein Tyrosine Kinase/RTK
Target EGFR
Research Area Cancer
Indications
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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Chrysophanic acid - No Development Reported
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Safety Data of Chrysophanic acid

Hazard Symbols : Xi
Risk Statements : R36/37/38
Safety Statements : S26;S37/39
RTECS : CB6725000
WGKGermany : 3
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Spectral Information

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Suppliers List

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Related Products

Other Forms of 481-74-3

Name CAS No Formula MW

Recommended Compounds in EGFR

Name CAS No Formula MW
Ginsenoside Rh2 78214-33-2 C36H62O8 622.87
Mutated EGFR-IN-1 1421372-66-8 C25H31N7O 445.56
AZD-9291 (mesylate) 1421373-66-1 C29H37N7O5S 595.71
Mutant EGFR inhibitor 1421373-62-7 C27H30ClN7O2 520.03
AZD-9291 1421373-65-0 C28H33N7O2 499.61
WHI-P180 (hydrochloride) 153437-55-9 C16H16ClN3O3 333.77
WHI-P180 211555-08-7 C16H15N3O3 297.31
Gefitinib (hydrochloride) 184475-55-6 C22H25Cl2FN4O3 483.36
Erlotinib (mesylate) 248594-19-6 C23H27N3O7S 489.54
BGB-102 807640-87-5 C22H25BrN4O2 457.36
Poziotinib 1092364-38-9 C23H21Cl2FN4O3 491.34
CO-1686 (hydrobromide) 1446700-26-0 C27H29BrF3N7O3 636.46
CO-1686 1374640-70-6 C27H28F3N7O3 555.55
CNX-2006 1375465-09-0 C26H27F4N7O2 545.53
PD 168393 194423-15-9 C17H13BrN4O 369.22
AG 18 118409-57-7 C10H6N2O2 186.17
Afatinib (dimaleate) 850140-73-7 C32H33ClFN5O11 718.08
AG-1478 153436-53-4 C16H14ClN3O2 315.75
Mubritinib 366017-09-6 C25H23F3N4O2 468.47
AST-1306 (TsOH) 1050500-29-2 C31H26ClFN4O5S 621.08

Recommended Compounds in Same Indication

Name CAS No Formula MW
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Route of Synthesis

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References

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More Information

Chrysophanic acid

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