Rapanone
Chemical compound
From Wikipedia, the free encyclopedia
Rapanone is an organic compound and natural product. It is a tridecyl side chain derivative of 2,5-dihydroxy-1,4-benzoquinone with the chemical formula C19H30O4.
| |
| Names | |
|---|---|
| IUPAC name
2,5-Dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione | |
Other names
| |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.200.721 |
| EC Number |
|
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C19H30O4 | |
| Molar mass | 322.445 g·mol−1 |
| Melting point | 141 to 142 °C (286 to 288 °F; 414 to 415 K)[1] |
| Hazards | |
| GHS labelling:[2] | |
 | |
| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
| Related compounds | |
Related compounds |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Occurrence
It occurs in various plant species including Aconitum lamarckii, Aegiceras corniculatum, Embelia ribes, Heliotropium indicum, and several Ardisia species.[2][3] It also occurs in fungi including Irpex lacteus.[2]
Synthesis
Rapanone can be synthesized by the alkylation of 2,5-dihydroxy-1,4-benzoquinone with the peroxide of myristic acid.[1]
Pharmacology
Rapanone derivatives and related quinonoids are being researched for their potential anticancer properties, although their mechanism is unclear.[4][5][6][7] It is also classified as an antiparasitic agent.[8] Some studies claim iron chelating and free radical scavenging properties in rapanone and its derivatives.[9][10]