855022

Friedelin

technical grade

• Synonym(s): (4β,5β,8α,9β,10α,13α,14β)-5,9,13-Trimethyl-24,25,26-trinoroleanan-3-one, DA-friedooleanan-3-one, Friedelan-3-one
• Empirical Formula (Hill Notation): C₃₀H₅₀O
• CAS Number: 559-74-0
• Molecular Weight: 426.72
• Beilstein: 1916451
• EC Number: 209-205-1
• MDL number: MFCD00017296
• UNSPSC Code: 12352115
• PubChem Substance ID: 24888367
• NACRES: NA.22

Properties

• grade: technical grade
• form: solid
• 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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves