Article · Wikipedia archive · Last revised Jul 20, 2026

Friedelane

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

Last revised
Jul 20, 2026
Read time
≈ 2 min
Length
346 w
Citations
7
Source
Wikipedia ↗

Friedelane
Skeletal formula of
Skeletal formula of source ↗
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
3D model (JSmol)
ChEBI
ChemSpider
  • 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
  • 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
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).

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

References

  1. "Friedelane". PubChem. National Center for Biotechnology Information. Retrieved February 2, 2026.
  2. Chávez, H.; Estévez-Braun, A.; Ravelo, A. G.; González, A. G. (January 1, 1998). "Friedelane Triterpenoids from Maytenus macrocarpa". Journal of Natural Products. 61 (1): 82–85. doi:10.1021/np970232k. ISSN 0163-3864.
  3. Yaghoobi Anzabi, Mohadese; Cmoch, Piotr; Luboradzki, Roman; Pakulski, Zbigniew (January 1, 2024). "Selective transformations of friedelanes isolated from cork smoker wash solids". Steroids. 201 109333. doi:10.1016/j.steroids.2023.109333. ISSN 0039-128X.
  4. Аrbаin, Dаyаr; Saputri, Gita Ayu; Syahputra, Ghalib Syukrilah; Widiyastuti, Yuli; Susanti, Deny; Taher, Muhammad (October 5, 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. ISSN 0378-8741.
  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 (2022). "Probing the functions of friedelane‐type triterpene cyclases from four celastrol‐producing plants". The Plant Journal. 109 (3): 555–567. doi:10.1111/tpj.15575. ISSN 0960-7412.
  6. Karunanayake, Subadra; Sotheeswaran, Subramanian; Uvais, M.; Sultanbawa, S.; Balasubramaniam, Sinnathamby (January 1, 1981). "Xanthones and triterpenes of Calophyllum tomentosum". Phytochemistry. 20 (6): 1303–1304. doi:10.1016/0031-9422(81)80026-X. ISSN 0031-9422.
  7. Talapatra, Sunil K.; Mallik, Asok K.; Talapatra, Bani (January 1, 1982). "Isopongaglabol and 6-methoxyisopongaglabol, two new hydroxyfuranoflavones from Pongamia glabra". Phytochemistry. 21 (3): 761–766. doi:10.1016/0031-9422(82)83183-X. ISSN 0031-9422.