Friedelane

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Friedelane
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
PubChem CID
  • 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

  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.


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