Article · Wikipedia archive · Last revised Jul 20, 2026

Friedelin

Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant. It is noted as having antimicrobial properties and has been recovered from the byproducts of corkboard manufacturing. The compound is also a biological precursor of celastrol. It is considered a friedelane-type compound, appearing structurally similar with the addition of a ketone group.

Last revised
Jul 20, 2026
Read time
≈ 2 min
Length
407 w
Citations
7
Source
Wikipedia ↗
Friedelin
source ↗
Names
Systematic IUPAC name
(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-Octamethylicosahydropicen-3(2H)-one
Other names
Friedeline; Friedelan-3-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.369
EC Number
  • 209-205-1
KEGG
UNII
  • InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1
    Key: OFMXGFHWLZPCFL-SVRPQWSVSA-N
  • C[C@H]1C(=O)CC[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
C30H50O
Molar mass 426.729 g·mol−1
Appearance white powder
Density 0.693 g/cm3
Melting point 263 °C (505 °F; 536 K)
Boiling point 477.18 °C (890.92 °F; 750.33 K)
Hazards
Flash point 233.9 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica,1 and Quercus stenophylla.2 Friedelin is also found in the roots of the Cannabis plant.3 It is noted as having antimicrobial properties4 and has been recovered from the byproducts of corkboard manufacturing.5 The compound is also a biological precursor of celastrol.6 It is considered a friedelane-type compound, appearing structurally similar with the addition of a ketone group.5

References

References

  1. Medicinal Plants In the Republic of Korea. Natural Products research institute (Seoul National University). p. 187.
  2. Onishi, Y; Hanaoka, M (1968). "Studies on the chemical components of Quercus stenophylla Makino. I. Isolation of friedelin from the leaves of Quercus stenophylla Makino". Yakugaku Zasshi (in Japanese). 88 (9): 1244–1245. doi:10.1248/yakushi1947.88.9_1244. PMID 5751298.
  3. Russo, Ethan B; Marcu, Jahan (2017). "Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads". Cannabinoid Pharmacology. Advances in Pharmacology. Vol. 80. pp. 67–134. doi:10.1016/bs.apha.2017.03.004. ISBN 978-0-12-811232-8. ISSN 1054-3589. PMID 28826544.
  4. Аrbаin, Dаyаr; Saputri, Gita Ayu; Syahputra, Ghalib Syukrilah; Widiyastuti, Yuli; Susanti, Deny; Taher, Muhammad (2021-10-05). "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. Yaghoobi Anzabi, Mohadese; Cmoch, Piotr; Luboradzki, Roman; Pakulski, Zbigniew (2024-01-01). "Selective transformations of friedelanes isolated from cork smoker wash solids". Steroids. 201 109333. doi:10.1016/j.steroids.2023.109333. ISSN 0039-128X.
  6. 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.
External links
  • Sunil, C; Duraipandiyan, V; Ignacimuthu, S; Al-Dhabi, N. A (2013). "Antioxidant, free radical scavenging and liver protective effects of friedelin isolated from Azima tetracantha Lam. Leaves". Food Chemistry. 139 (1–4): 860–5. doi:10.1016/j.foodchem.2012.12.041. PMID 23561182.