Introduction：Basic information about CAS 26791-73-1|Xanthatin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Xanthatin |
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| CAS Number | 26791-73-1 | Molecular Weight | 246.302 |
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| Density | 1.1±0.1 g/cm3 | Boiling Point | 444.3±45.0 °C at 760 mmHg |
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| Molecular Formula | C15H18O3 | Melting Point | 114.5-115° |
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| MSDS | / | Flash Point | 199.1±28.8 °C |
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Names
| Name | (3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one |
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| Synonym | More Synonyms |
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Xanthatin BiologicalActivity
| Description | Xanthatin is isolated from Xanthium strumarium leaves. Xanthatin exhibits strong antitumor activities against a variety of cancer cells through apoptosis persuasion and shows anti-inflammatory activities by inhibiting PGE2 synthesis and 5-lipoxygenase activity[1]. Xanthatin is a potent and orally active inhibitor of VEGFR2 kinase activity with an IC50 of 3.8 μM and prominently blocks the phosphorylation of VEGFR2 at Tyr951 site. Xanthatin inhibits angiogenesis and has the potential for the investigation of breast cancer[2]. |
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| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionResearch Areas >>Inflammation/ImmunologySignaling Pathways >>Metabolic Enzyme/Protease >>5-LipoxygenaseSignaling Pathways >>Protein Tyrosine Kinase/RTK >>VEGFRSignaling Pathways >>Anti-infection >>Bacterial |
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| Target | IC50: apoptosis; 3.8 μM (VEGFR2 kinase); 2.63 µg/mL (T. b. brucei)[1] |
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| In Vitro | Xanthatin is against T. b. brucei with an IC50 value of 2.63 µg/mL and exhibits weak irreversible inhibition of parasite specific trypanothione reductase[1]. Xanthatin (0-40 μM; 24 hours) has obscure inhibition effect on the proliferation of HUVEC in the absence of VEGF[2]. Xanthatin (5-40 μM; 24 hours) inhibits breast cancer cell proliferation in a dose responsive manner. Xanthatin inhibits HCC1937, MDA-MB-415, SK-BR-3, MCF-7 and MDA-MB-231 with IC50 values of 81 μM, 31 μM, 38 μM, 30 μM, and 17 μM, respectively[2]. Xanthatin (0-10 μM; 24 hours) dose dependently suppresses the phosphorylation of STAT3 (Ser727), at the same time, it also results in a rapid dephosphorylation of down-stream kinases of STAT3, including PI3K and Akt, including PI3K (p-PI3K p85 tyr458) and Akt[2]. Cell Proliferation Assay[2] Cell Line: HUVEC cells Concentration: 0 μM, 5 μM, 10 μM, 15 μM, 20 μM, 30 μM, 40 μM Incubation Time: 24 hours Result: Inhibited cell growth from dose 10 μM in the presence of vEGF. Cell Viability Assay[2] Cell Line: HCC1937, MDA-MB-415, SK-BR-3, MCF-7 and MDA-MB-231 cells Concentration: 5, 10, 15, 20, 30, and 40 μM Incubation Time: 24 hours Result: Inhibited breast cancer cell growth. Western Blot Analysis[2] Cell Line: HUVEC cells Concentration: 0, 3, and 10 μM Incubation Time: 24 hours Result: Inhibited VEGFR2 downstream signaling pathways and blocked VEGF-induced STAT3 activation in HUVEC. |
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| In Vivo | Xanthatin (intragastric administration; 20 mg/kg; once daily; 25 days) leads to significant inhibition of tumor volume. And this compound is well-tolerated and exhibits no significant difference in weight compares to the vehicle group[2]. Animal Model: Transplanted MDA-MB-231 cells into mice and constucted human breast cancer xenograft mouse model[2] Dosage: 20 mg/kg; once daily; 25 days Administration: Intragastric administration Result: Supressed tumor growth and tumor angiogenesis in vivo. |
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| References | [1]. Nibret E, et al. Biological activities of xanthatin from Xanthium strumarium leaves.Phytother Res. 2011 Dec;25(12):1883-90. [2]. Yu Y, et al. Xanthatin, a novel potent inhibitor of VEGFR2 signaling, inhibits angiogenesis and tumor growth in breast cancer cells.Int J Clin Exp Pathol. 2015 Sep 1;8(9):10355-64. |
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Chemical & Physical Properties
| Density | 1.1±0.1 g/cm3 |
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| Boiling Point | 444.3±45.0 °C at 760 mmHg |
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| Melting Point | 114.5-115° |
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| Molecular Formula | C15H18O3 |
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| Molecular Weight | 246.302 |
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| Flash Point | 199.1±28.8 °C |
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| Exact Mass | 246.125595 |
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| PSA | 43.37000 |
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| LogP | 1.58 |
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| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
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| Index of Refraction | 1.528 |
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| InChIKey | RBRPTFMVULVGIC-ZTIIIDENSA-N |
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| SMILES | C=C1C(=O)OC2CC(C)C(C=CC(C)=O)=CCC12 |
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| Storage condition | 2-8℃ |
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Safety Information
Synonyms
| (3aR,7S,8aS)-7-Methyl-3-methylene-6-[(1Z)-3-oxo-1-buten-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one |
| (3aR,7S,8aS)-7-Methyl-3-methylene-6-[(1Z)-3-oxobut-1-en-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one |
| [3aR-(3aa,7b,8ab)]-3,3a,4,7,8,8a-Hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-2H-cyclohepta[b]furan-2-one |
| (3aR,7S,8aS)-7-methyl-3-methylidene-6-[(1Z)-3-oxobut-1-en-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one |
| 8-epi-Xanthatin |
| Xanthatin |
| 2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-[(1Z)-3-oxo-1-buten-1-yl]-, (3aR,7S,8aS)- |
