Rapanone

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
ECHA InfoCard 100.200.721 Edit this at Wikidata
EC Number
  • 675-435-8
KEGG
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)
Hazards
GHS labelling:
GHS07: Exclamation mark
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.

Occurrence

It occurs in various plant species including Aconitum lamarckii, Aegiceras corniculatum, Embelia ribes, Heliotropium indicum, and several Ardisia species. It also occurs in fungi including Irpex lacteus.

Synthesis

Rapanone can be synthesized by the alkylation of 2,5-dihydroxy-1,4-benzoquinone with the peroxide of myristic acid.

Pharmacology

Rapanone derivatives and related quinonoids are being researched for their potential anticancer properties, although their mechanism is unclear. It is also classified as an antiparasitic agent. Some studies claim iron chelating and free radical scavenging properties in rapanone and its derivatives.

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. Bibcode:1948JAChS..70...71F. 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. Bibcode:2005JEthn..96..347K. 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. Bibcode:2020ToxVi..6304737P. doi:10.1016/j.tiv.2019.104737. ISSN 0887-2333. PMID 31756542.
  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. PMID 28237732.
  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. PMC 10880907. PMID 38389875.