Rapanone

Names

[ CAS No. ]:
573-40-0

[ Name ]:
Rapanone

[Synonym ]:
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

Biological Activity

[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].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

PLA2:2.6 μM (IC50)

[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].

[In Vivo]

Rapanone (2.5-10 mg/kg; i.p.) exhibits anti-inflammatory effects in the carrageenan paw oedema model in mice[4].

[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.

Chemical & Physical Properties

[ Density]:
1.099g/cm3

[ Boiling Point ]:
457ºC at 760mmHg

[ Melting Point ]:
142-145ºC

[ Molecular Formula ]:
C₁₉H₃₀O₄

[ Molecular Weight ]:
322.43900

[ Flash Point ]:
244.3ºC

[ Exact Mass ]:
322.21400

[ PSA ]:
74.60000

[ LogP ]:
5.09330

[ Index of Refraction ]:
1.53

Safety Information

[ HS Code ]:
2914690090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914690090

[ Summary ]:
2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Related Compounds

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