Rapanone

Last updated
Rapanone
Names
IUPAC name
2,5-dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione
Other names
  • 2,5-dihydroxy-3-tridecyl-1,4-benzoquinone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 675-435-8
KEGG
PubChem CID
UNII
  • InChI=1S/C19H30O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(22)16(20)14-17(21)19(15)23/h14,20,23H,2-13H2,1H3
    Key: AMKNOBHCKRZHIO-UHFFFAOYSA-N
  • CCCCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O
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]
GHS-pictogram-exclam.svg
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).

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.

Contents

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]

References

  1. 1 2 Fieser, Louis F.; Chamberlin, Earl M. (1948-01-01). "Synthesis of Embelin, Rapanone and Related Quinones by Peroxide Alkylation1". Journal of the American Chemical Society. 70 (1): 71–75. doi:10.1021/ja01181a022. ISSN   0002-7863.
  2. 1 2 3 PubChem. "Rapanone". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-26.
  3. ↑ Kobayashi, Hideka; de Mejía, Elvira (2005-01-15). "The genus Ardisia: a novel source of health-promoting compounds and phytopharmaceuticals". Journal of Ethnopharmacology. 96 (3): 347–354. doi:10.1016/j.jep.2004.09.037. ISSN   0378-8741.
  4. ↑ Sarkar, Pritam; Ahnaf, Tasfiya Rufaidah; Rouf, Razina; Shilpi, Jamil Ahmad; Uddin, Shaikh Jamal (2024). "A Review on Bioactive Phytochemical Constituents and Pharmacological Activities of Aegiceras corniculatum: A Pharmaceutically Important Mangrove Plant". Journal of Chemistry. 2024 (1) 9992568. doi: 10.1155/2024/9992568 . ISSN   2090-9071.
  5. ↑ Ying, Hua-Zhong; Yu, Chen-Huan; Chen, Hao-Kun; Zhang, Huan-Huan; Fang, Jie; Wu, Fang; Yu, Wen-Ying (2020). "Quinonoids: Therapeutic Potential for Lung Cancer Treatment". BioMed Research International. 2020 (1) 2460565. doi: 10.1155/2020/2460565 . ISSN   2314-6141. PMC   7166295 . PMID   32337232.
  6. ↑ Sarkar, Chandan; Mondal, Milon; Khanom, Bilkis; Hossain, Md. Monir; Hossain, Md. Solayman; Sureda, Antoni; Islam, Muhammad Torequl; Martorell, Miquel; Kumar, Manoj; Sharifi-Rad, Javad; Al-Harrasi, Ahmed; Al-Rawahi, Ahmed (2021). "Heliotropium indicum L.: From Farm to a Source of Bioactive Compounds with Therapeutic Activity". Evidence-Based Complementary and Alternative Medicine. 2021 (1) 9965481. doi: 10.1155/2021/9965481 . ISSN   1741-4288. PMC   8187075 . PMID   34158818.
  7. ↑ Pardo Andreu, Gilberto L.; Reis, Felipe Zuccolotto Dos; González-Durruthy, Michael; Hernández, René Delgado; D'Vries, Richard F.; Vanden Berghe, Wim; Alberici, Luciane C. (2020-03-01). "Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death". Toxicology in Vitro. 63 104737. doi:10.1016/j.tiv.2019.104737. ISSN   0887-2333.
  8. ↑ "Rapanone MeSH Supplementary Concept Data 2026". meshb.nlm.nih.gov. Retrieved 2026-01-26.
  9. ↑ de la Vega-Hernández, Karen; Antuch, Manuel; Cuesta-Rubio, Osmany; Núñez-Figueredo, Yanier; Pardo-Andreu, Gilberto L (2017-05-01). "Discerning the antioxidant mechanism of rapanone: A naturally occurring benzoquinone with iron complexing and radical scavenging activities". Journal of Inorganic Biochemistry. 170: 134–147. doi:10.1016/j.jinorgbio.2017.02.019. ISSN   0162-0134.
  10. ↑ Mariyappan, Vaithiyalingam; Munuswamy-Ramanujam, Ganesh; Ramasamy, Mohankumar (2024-02-21). "Synthesis of novel rapanone derivatives via organocatalytic reductive C-alkylation: biological evaluation of antioxidant properties, in vivo zebrafish embryo toxicity, and docking studies". RSC Medicinal Chemistry. 15 (2): 623–635. doi:10.1039/D3MD00564J. ISSN   2632-8682.
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