Euphol

Euphol
	source ↗
Names
	IUPAC name (3S,5R,10S,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
	Other names Euphadienol
Identifiers
CAS Number	514-47-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4940;
ChEMBL	ChEMBL465181;
ChemSpider	390292;
KEGG	C08624;
PubChem CID	441678;
CompTox Dashboard (EPA)	DTXSID201318412;
	InChI InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22+,25+,26+,28-,29+,30-/m1/s1 Key: CAHGCLMLTWQZNJ-WZLOIPHISA-N;
	SMILES C[C@H](CCC=C(C)C)[C@@H]1CC[C@]2([C@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C;
Properties
Chemical formula	C30H50O
Molar mass	426.729 g·mol−1
Density	g/cm3
Melting point	116 °C (241 °F; 389 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Euphol is a tetracyclic triterpene with the molecular formula C₃₀H₅₀O.¹

Natural occurrence

Euphol was isolated from cucumber and is an active principle of various plant species belonging to the Euphorbia genus.²

Uses

The compound is known for its potential hypotensive, anti-inflammatory, and antitumor activities.³⁴⁵

References

Shaban, Aya Fadle; Abd El Kawy, Mostafa A.; Hamed, Ahmed Ragab; Salama, Abeer; El Motayam, Amira Kamal (1 June 2025). "Euphol: chemical and biological aspects: A review". Egyptian Journal of Chemistry. 68 (6): 705–726. doi:10.21608/ejchem.2024.322067.10466. ISSN 0449-2285. Retrieved 22 July 2025.
Silva, Viviane A. O.; Rosa, Marcela N.; Miranda-Gonçalves, Vera; Costa, Angela M.; Tansini, Aline; Evangelista, Adriane F.; Martinho, Olga; Carloni, Adriana C.; Jones, Chris; Lima, João Paulo; Pianowski, Luiz F.; Reis, Rui Manuel (April 2019). "Euphol, a tetracyclic triterpene, from Euphorbia tirucalli induces autophagy and sensitizes temozolomide cytotoxicity on glioblastoma cells". Investigational New Drugs. 37 (2): 223–237. doi:10.1007/s10637-018-0620-y. hdl:1822/57883. ISSN 1573-0646. PMID 29931585.
Zhao, Maoyuan; Yang, Yi; Nian, Qing; Shen, Caifei; Xiao, Xiaolin; Liao, Wenhao; Zheng, Qiao; Zhang, Gang; Chen, Nianzhi; Gong, Daoyin; Tang, Jianyuan; Wen, Yueqiang; Zeng, Jinhao (1 February 2023). "Phytochemicals and mitochondria: Therapeutic allies against gastric cancer". Phytomedicine. 110 154608. doi:10.1016/j.phymed.2022.154608. ISSN 0944-7113. PMID 36586205. Retrieved 22 July 2025.
Singh, G. B.; Singh, Surjeet; Sharma, M. L.; Suri, O. P.; Chopra, C. L.; Ammon, H. P. T. (December 1989). "Hypotensive Activity of 8,24-Euphadien-3β-ol (Euphol)". Planta Medica. 55 (6): 498–500. Bibcode:1989PlMed..55..498S. doi:10.1055/s-2006-962079. ISSN 0032-0943. PMID 2616667. Retrieved 22 July 2025.
Cruz, L. S.; De Oliveira, T. L.; Kanunfre, C. C.; Paludo, K. S.; Minozzo, B. R.; Prestes, A. P.; Wang, M.; Fernandes, D.; Santos FAD; Manda, V. K.; Khan, S. I.; Ali, Z.; De Messias-Reason, I. J.; Avula, B.; Khan, I. A.; Beltrame, F. L. (2018). "Pharmacokinetics and cytotoxic study of euphol from Euphorbia umbellata (Bruyns) Pax latex". Phytomedicine. 47: 105–112. doi:10.1016/j.phymed.2018.04.055. PMID 30166094. S2CID 52132966.

[1] Shaban, Aya Fadle; Abd El Kawy, Mostafa A.; Hamed, Ahmed Ragab; Salama, Abeer; El Motayam, Amira Kamal (1 June 2025). "Euphol: chemical and biological aspects: A review". Egyptian Journal of Chemistry. 68 (6): 705–726. doi:10.21608/ejchem.2024.322067.10466. ISSN 0449-2285. Retrieved 22 July 2025.

[2] Silva, Viviane A. O.; Rosa, Marcela N.; Miranda-Gonçalves, Vera; Costa, Angela M.; Tansini, Aline; Evangelista, Adriane F.; Martinho, Olga; Carloni, Adriana C.; Jones, Chris; Lima, João Paulo; Pianowski, Luiz F.; Reis, Rui Manuel (April 2019). "Euphol, a tetracyclic triterpene, from Euphorbia tirucalli induces autophagy and sensitizes temozolomide cytotoxicity on glioblastoma cells". Investigational New Drugs. 37 (2): 223–237. doi:10.1007/s10637-018-0620-y. hdl:1822/57883. ISSN 1573-0646. PMID 29931585.

[3] Zhao, Maoyuan; Yang, Yi; Nian, Qing; Shen, Caifei; Xiao, Xiaolin; Liao, Wenhao; Zheng, Qiao; Zhang, Gang; Chen, Nianzhi; Gong, Daoyin; Tang, Jianyuan; Wen, Yueqiang; Zeng, Jinhao (1 February 2023). "Phytochemicals and mitochondria: Therapeutic allies against gastric cancer". Phytomedicine. 110 154608. doi:10.1016/j.phymed.2022.154608. ISSN 0944-7113. PMID 36586205. Retrieved 22 July 2025.

[4] Singh, G. B.; Singh, Surjeet; Sharma, M. L.; Suri, O. P.; Chopra, C. L.; Ammon, H. P. T. (December 1989). "Hypotensive Activity of 8,24-Euphadien-3β-ol (Euphol)". Planta Medica. 55 (6): 498–500. Bibcode:1989PlMed..55..498S. doi:10.1055/s-2006-962079. ISSN 0032-0943. PMID 2616667. Retrieved 22 July 2025.

[5] Cruz, L. S.; De Oliveira, T. L.; Kanunfre, C. C.; Paludo, K. S.; Minozzo, B. R.; Prestes, A. P.; Wang, M.; Fernandes, D.; Santos FAD; Manda, V. K.; Khan, S. I.; Ali, Z.; De Messias-Reason, I. J.; Avula, B.; Khan, I. A.; Beltrame, F. L. (2018). "Pharmacokinetics and cytotoxic study of euphol from Euphorbia umbellata (Bruyns) Pax latex". Phytomedicine. 47: 105–112. doi:10.1016/j.phymed.2018.04.055. PMID 30166094. S2CID 52132966.

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