Friedelin

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]

Friedelin
Names
Preferred 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)
ECHA InfoCard 100.008.369
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
  • 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 coloured powder
Density 0.693 g/cm3
Melting point 263°C
Boiling point 477.18°C
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

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. Advances in Pharmacology. Vol. 80. pp. 67–134. doi:10.1016/bs.apha.2017.03.004. ISBN 9780128112328. ISSN 1054-3589. PMID 28826544.
  • 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.


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