Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

855022

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

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

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

Looking for similar products? Visit Product Comparison Guide

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Effects of 8-Hydroxyisocapnolactone-2-3-diol and friedelin on mast cell degranulation
Sahid MNA, et al.
Asian Pacific Journal of Tropical Medicine, 10(11), 1043-1046 (2017)
Microwave assisted one-pot synthesis of pyrazine derivatives of pentacyclic triterpenoids and their biological activity
Ghosh P, et al.
Indian J. Chem. B, 50B(11), 1519-1523 (2011)
Synthesis of friedelan triterpenoid analogs with DNA topoisomerase IIα inhibitory activity and their molecular docking studies
Mandal A, et al.
European Journal of Medicinal Chemistry, 54(11), 137-143 (2012)
Ricardo A Pires et al.
Natural product communications, 6(11), 1577-1579 (2012-01-10)
Black condensates (BC) are wastes of the insulation corkboard industry that contain several valuable chemicals, including friedelin, a terpene exhibiting biological activity. Herein, we report a straightforward procedure to extract friedelin from BC. Using this procedure, we were able to
V Duraipandiyan et al.
Folia histochemica et cytobiologica, 48(2), 311-313 (2010-08-03)
The present study was designed to evaluate the antifungal activity of Azima tetracantha extracts and isolated compound (friedelin) against fungi. Antifungal activity was carried out using broth microdilution method and fractions were collected using (silica gel) column chromatography. The antifungal
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service