Friedelin

Friedelin

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
CAS Number	559-74-0  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5171
ChEMBL	ChEMBL485998
ChemSpider	82597
ECHA InfoCard	100.008.369
EC Number	209-205-1
KEGG	C08626
PubChem CID	91472
UNII	AK21264UAD  Y
CompTox Dashboard (EPA)	DTXSID101015732
InChI 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
SMILES 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
Chemical formula	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). Infobox references

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 properties ^[4] 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

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.