Rapanone

Modify Date: 2024-01-09 12:42:25

Rapanone Structure
Rapanone structure
 Common Name Rapanone
CAS Number 573-40-0 Molecular Weight 322.43900
Density 1.099g/cm3 Boiling Point 457ºC at 760mmHg
Molecular Formula C19H30O4 Melting Point 142-145ºC
MSDS N/A Flash Point 244.3ºC

 Use of Rapanone


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].

 Names

Name 2,5-dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione
Synonym More Synonyms

 Rapanone 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
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

 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%

 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
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