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855022 Sigma-Aldrich

Friedelin

technical grade

Synonym: (4β,5β,8α,9β,10α,13α,14β)-5,9,13-Trimethyl-24,25,26-trinoroleanan-3-one, DA-friedooleanan-3-one, Friedelan-3-one

  • CAS Number 559-74-0

  • Empirical Formula (Hill Notation) C30H50O

  • Molecular Weight 426.72

  •  Beilstein/REAXYS Number 1916451

  •  EC Number 209-205-1

  •  MDL number MFCD00017296

  •  PubChem Substance ID 24888367

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Complex Molecules
Quality Level   100
grade   technical grade
mp   262-265 °C (lit.)
SMILES string   C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]3[C@@]2(C)CC[C@@]4(C)[C@@H]5CC(C)(C)CC[C@]5(C)CC[C@]34C
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
InChI key   OFMXGFHWLZPCFL-SVRPQWSVSA-N

Description

General description

Friedelin, a pentacyclic triterpene, is found in several plants like Cissus quadrangularis, Celastrus vulcanicola, Terminalia avicennioides, and Alangium salvifolium. It is known to act as a histamine H1 receptor (H1R) antagonist, anti-microbial, anti-HIV, and anti-cancer agent.

Application

Friedelin can be used as a starting material in the synthesis of:
• Friedel-3-enol acetate, friedel-2-oxo-3-enol acetate, friedel-2-ene derivatives and friedelin ketoxime.
• Oxygenated friedelin derivatives as potent DNA topoisomerase IIα inhibitors.
• Its 1,4-pyrazine derivatives as potent antimicrobial agents.

Packaging

1 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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