Rapanone

Rapanone
	source ↗
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
CAS Number	573-40-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8779;
ChEMBL	ChEMBL462801;
ChemSpider	90945;
ECHA InfoCard	100.200.721
EC Number	675-435-8;
KEGG	C10399;
PubChem CID	100659;
UNII	SH52PPU72X;
CompTox Dashboard (EPA)	DTXSID80205915 ;
	InChI 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;
	SMILES CCCCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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	Grevillol; Embelin;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.²³ 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.⁴⁵⁶⁷ It is also classified as an antiparasitic agent.⁸ Some studies claim iron chelating and free radical scavenging properties in rapanone and its derivatives.⁹¹⁰

External links

Natural Products Online

References

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.
PubChem. "Rapanone". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-26.
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.
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.
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.
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.
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.
"Rapanone MeSH Supplementary Concept Data 2026". meshb.nlm.nih.gov. Retrieved 2026-01-26.
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.
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.

[Fieser-1] 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.

[PubChem-2] 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] 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.

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