Friedelane

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Friedelane
Skeletal formula of
Skeletal formula of
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
  • 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).
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Occurrence

Friedelane is found in the wood of Calophyllum tomentosum,[6] as well as the flowers of Pongamia pinnata.[7]

References

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