Friedelane

Friedelane
	Skeletal formula of
Names
	Preferred IUPAC name (4S,4aR,6aS,6aS,6bR,8aR,12aR,14aS,14bR)-4,4a,6a,6b,8a,11,11,14a-octamethyl-1,2,3,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-hexadecahydropicene
Identifiers
CAS Number	559-73-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:71575;
ChemSpider	20056444;
PubChem CID	15559345;
CompTox Dashboard (EPA)	DTXSID001165671 ;
	InChI InChI=1S/C30H52/c1-21-10-9-11-22-27(21,5)13-12-23-28(22,6)17-19-30(8)24-20-25(2,3)14-15-26(24,4)16-18-29(23,30)7/h21-24H,9-20H2,1-8H3/t21-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1 Key: KVSNMTUIMXZPLU-XOZXFAFYSA-N;
	SMILES C[C@H]1CCC[C@@H]2[C@@]1(CC[C@H]3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C)C)C)C)C;
Properties
Chemical formula	C30H52
Molar mass	412.746 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Friedelane is an aliphatic chemical compound and natural product. Its formula is C₃₀H₅₂.^[1] Friedelane is a triterpene, and it and similar compounds are found in several plants.^[2] One such compound found in the bark of cork oak, friedelin, is considered a "friedelane-like",^[3] and has noted antimicrobial properties.^[4] It is also a biological precursor of celastrol.^[5]

Occurrence

Friedelane is found in the wood of Calophyllum tomentosum,^[6] as well as the flowers of Pongamia pinnata.^[7]

References

↑ "Friedelane". PubChem. National Center for Biotechnology Information. Retrieved February 2, 2026.
↑ Chávez, H.; Estévez-Braun, A.; Ravelo, A. G.; González, A. G. (1998). "Friedelane Triterpenoids from Maytenus macrocarpa". Journal of Natural Products. 61 (1): 82–85. Bibcode:1998JNAtP..61...82C. doi:10.1021/np970232k. PMID 9461656.
↑ Yaghoobi Anzabi, Mohadese; Cmoch, Piotr; Luboradzki, Roman; Pakulski, Zbigniew (January 2024). "Selective transformations of friedelanes isolated from cork smoker wash solids". Steroids. 201 109333. doi:10.1016/j.steroids.2023.109333. PMID 37939981.
↑ Аrbаin, Dаyаr; Saputri, Gita Ayu; Syahputra, Ghalib Syukrilah; Widiyastuti, Yuli; Susanti, Deny; Taher, Muhammad (October 2021). "Genus Pterocarpus: A review of ethnopharmacology, phytochemistry, biological activities, and clinical evidence". Journal of Ethnopharmacology. 278 114316. doi:10.1016/j.jep.2021.114316. PMID 34116190.
↑ Lu, Yun; Luo, Yunfeng; Zhou, Jiawei; Hu, Tianyuan; Tu, Lichan; Tong, Yuru; Su, Ping; Liu, Yuan; Wang, Jiadian; Jiang, Zhouqian; Wu, Xiaoyi; Chen, Xiaochao; Huang, Luqi; Gao, Wei (February 2022). "Probing the functions of friedelane-type triterpene cyclases from four celastrol-producing plants". The Plant Journal. 109 (3): 555–567. Bibcode:2022PlJ...109..555L. doi:10.1111/tpj.15575. PMID 34750899.
↑ Karunanayake, Subadra; Sotheeswaran, Subramanian; Uvais, M.; Sultanbawa, S.; Balasubramaniam, Sinnathamby (January 1981). "Xanthones and triterpenes of Calophyllum tomentosum". Phytochemistry. 20 (6): 1303–1304. Bibcode:1981PChem..20.1303K. doi:10.1016/0031-9422(81)80026-X.
↑ Talapatra, Sunil K.; Mallik, Asok K.; Talapatra, Bani (1982). "Isopongaglabol and 6-methoxyisopongaglabol, two new hydroxyfuranoflavones from Pongamia glabra". Phytochemistry. 21 (3): 761–766. Bibcode:1982PChem..21..761T. doi:10.1016/0031-9422(82)83183-X.

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[1] "Friedelane". PubChem. National Center for Biotechnology Information. Retrieved February 2, 2026.

[2] Chávez, H.; Estévez-Braun, A.; Ravelo, A. G.; González, A. G. (1998). "Friedelane Triterpenoids from Maytenus macrocarpa". Journal of Natural Products. 61 (1): 82–85. Bibcode:1998JNAtP..61...82C. doi:10.1021/np970232k. PMID 9461656.

[3] Yaghoobi Anzabi, Mohadese; Cmoch, Piotr; Luboradzki, Roman; Pakulski, Zbigniew (January 2024). "Selective transformations of friedelanes isolated from cork smoker wash solids". Steroids. 201 109333. doi:10.1016/j.steroids.2023.109333. PMID 37939981.

[4] Аrbаin, Dаyаr; Saputri, Gita Ayu; Syahputra, Ghalib Syukrilah; Widiyastuti, Yuli; Susanti, Deny; Taher, Muhammad (October 2021). "Genus Pterocarpus: A review of ethnopharmacology, phytochemistry, biological activities, and clinical evidence". Journal of Ethnopharmacology. 278 114316. doi:10.1016/j.jep.2021.114316. PMID 34116190.

[5] Lu, Yun; Luo, Yunfeng; Zhou, Jiawei; Hu, Tianyuan; Tu, Lichan; Tong, Yuru; Su, Ping; Liu, Yuan; Wang, Jiadian; Jiang, Zhouqian; Wu, Xiaoyi; Chen, Xiaochao; Huang, Luqi; Gao, Wei (February 2022). "Probing the functions of friedelane-type triterpene cyclases from four celastrol-producing plants". The Plant Journal. 109 (3): 555–567. Bibcode:2022PlJ...109..555L. doi:10.1111/tpj.15575. PMID 34750899.

[6] Karunanayake, Subadra; Sotheeswaran, Subramanian; Uvais, M.; Sultanbawa, S.; Balasubramaniam, Sinnathamby (January 1981). "Xanthones and triterpenes of Calophyllum tomentosum". Phytochemistry. 20 (6): 1303–1304. Bibcode:1981PChem..20.1303K. doi:10.1016/0031-9422(81)80026-X.

[7] Talapatra, Sunil K.; Mallik, Asok K.; Talapatra, Bani (1982). "Isopongaglabol and 6-methoxyisopongaglabol, two new hydroxyfuranoflavones from Pongamia glabra". Phytochemistry. 21 (3): 761–766. Bibcode:1982PChem..21..761T. doi:10.1016/0031-9422(82)83183-X.

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