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
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).
Infobox references

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.