Introduction：Basic information about CAS 573-40-0|Rapanone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Rapanone |
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| CAS Number | 573-40-0 | Molecular Weight | 322.43900 |
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| Density | 1.099g/cm3 | Boiling Point | 457ºC at 760mmHg |
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| Molecular Formula | C19H30O4 | Melting Point | 142-145ºC |
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| MSDS | / | Flash Point | 244.3ºC |
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Names
| Name | 2,5-dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione |
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| Synonym | More Synonyms |
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Rapanone BiologicalActivity
| Description | Rapanone is a natural benzoquinone. Rapanone exhibits a broad spectrum of biological actions, including anti-tumor, antioxidant, anti-inflammatory, antibacterial and antiparasitic. Rapanone also is a potent and selective human synovial PLA2 inhibitor, with an IC50 of 2.6 μM[1][2][3][4]. |
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| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Metabolic Enzyme/Protease >>PhospholipaseResearch Areas >>Inflammation/ImmunologySignaling Pathways >>Anti-infection >>Bacterial |
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| Target | PLA2:2.6 μM (IC50) |
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| In Vitro | Rapanone (10-40 μM; 24 h) inhibits the cell viability, with IC50s of 35.58 μM and 27.89 μM for primary rats hepatocytes and HepG2 cells, respectively[1]. Rapanone (10-40 μM; 24 h) induces a concentration-dependent mitochondrial membrane potential dissipation, ATP depletion, hydrogen peroxide generation and, phosphatidyl serine externalization in HepG2 cells[1]. Rapanone inhibits electron transport at Complex III and promotes mitochondrial dysfunction[1]. |
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| In Vivo | Rapanone (2.5-10 mg/kg; i.p.) exhibits anti-inflammatory effects in the carrageenan paw oedema model in mice[4]. |
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| References | [1]. Andreu GLP, et, al. Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death. Toxicol In Vitro. 2020 Mar;63:104737. [2]. Morais LS, et, al. Antileishmanial compounds from Connarus suberosus: Metabolomics, isolation and mechanism of action. PLoS One. 2020 Nov 6;15(11):e0241855. [3]. Vega-Hernández K, et, al. Discerning the antioxidant mechanism of rapanone: A naturally occurring benzoquinone with iron complexing and radical scavenging activities. J Inorg Biochem. 2017 May;170:134-147. [4]. Ospina LF, et, al. Inhibition of acute and chronic inflammatory responses by the hydroxybenzoquinonic derivative rapanone. Planta Med. 2001 Dec;67(9):791-5. |
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Chemical & Physical Properties
| Density | 1.099g/cm3 |
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| Boiling Point | 457ºC at 760mmHg |
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| Melting Point | 142-145ºC |
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| Molecular Formula | C19H30O4 |
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| Molecular Weight | 322.43900 |
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| Flash Point | 244.3ºC |
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| Exact Mass | 322.21400 |
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| PSA | 74.60000 |
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| LogP | 5.09330 |
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| Index of Refraction | 1.53 |
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| InChIKey | AMKNOBHCKRZHIO-UHFFFAOYSA-N |
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| SMILES | CCCCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O |
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Safety Information
Customs
| HS Code | 2914690090 |
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| Summary | 2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0% |
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Synonyms
| Rapanone |
| 2,4-DIHYDRO-4-PHENYL-3H-1,2,4-TRIAZOL-3-ONE |
| 2,5-dihydroxy-3-tridecyl-1,4-benzoquinone |
| 2,5-Dihydroxy-3-tridecyl-benzo<1,4>chinon |
