| Identification | Back Directory | [Name]
RAPANONE | [CAS]
573-40-0 | [Synonyms]
RAPANONE
RAMATROBAN(RG)
2,5-dihydroxy-3-tridecyl-p-benzoquinone
2,5-DIHYDROXY-3-TRIDECYL-[1,4]BENZOQUINONE
2,5-dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione
2,5-Dihydroxy-3-tridecyl-2,5-cyclohexadiene-1,4-dione
2,5-dihydroxy-3-tridecyl-cyclohexa-2,5-diene-1,4-dione | [Molecular Formula]
C19H30O4 | [MDL Number]
MFCD00075883 | [MOL File]
573-40-0.mol | [Molecular Weight]
322.44 |
| Chemical Properties | Back Directory | [Melting point ]
142-145°C | [Boiling point ]
457.0±45.0 °C(Predicted) | [density ]
1.099±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [form ]
Solid | [pka]
2.84±0.50(Predicted) | [color ]
Light yellow to orange |
| Hazard Information | Back Directory | [Uses]
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]. | [Definition]
ChEBI: Rapanone is a member of dihydroxy-1,4-benzoquinones. | [in vivo]
Rapanone (2.5-10 mg/kg; i.p.) exhibits anti-inflammatory effects in the carrageenan paw oedema model in mice[4].
| [IC 50]
PLA2: 2.6 μM (IC50) | [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. DOI:10.1016/j.tiv.2019.104737
[2] Morais LS, et, al. Antileishmanial compounds from Connarus suberosus: Metabolomics, isolation and mechanism of action. PLoS One. 2020 Nov 6;15(11):e0241855. DOI:10.1371/journal.pone.0241855
[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. DOI:10.1016/j.jinorgbio.2017.02.019
[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. DOI:10.1055/s-2001-18839 |
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