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855022

Sigma-Aldrich

Friedelin

technical grade

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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:
Molecular Weight:
426.72
Beilstein/REAXYS Number:
1916451
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

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

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1 of 4

This Item
F6886E9004P8629
Friedelin technical grade

855022

Friedelin

Forskolin from Coleus forskohlii, ≥98% (HPLC), powder

F6886

Forskolin

α-Ecdysone ≥90%

E9004

α-Ecdysone

5β-Pregnane-3α,17α,20α-triol

P8629

5β-Pregnane-3α,17α,20α-triol

form

solid

form

powder

form

powder

form

powder

grade

technical grade

grade

-

grade

-

grade

-

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Paulrayer Antonisamy et al.
The Journal of pharmacy and pharmacology, 63(8), 1070-1077 (2011-07-02)
Friedelin was isolated from Azima tetracantha Lam. leaves collected from Kallakurichi, Villuppuram district, Tamil Nadu, India. The anti-inflammatory, analgesic and antipyretic activities of friedelin have been investigated in Wistar rats and mice. Friedelin was isolated from the hexane extract of
Jacqueline Pereira Vistuba et al.
Journal of chromatography. A, 1274, 159-164 (2013-01-02)
The aim of this study was to develop a separation method using multiple injections in a single experimental run (MISER) employing gas chromatography with flame ionization detection (GC-FID) for the first time, without instrument modification, to increase the instrumental throughput.
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
Friedelane triterpenoids: transformations toward A-ring modifications including 2-homo derivatives
Das J, et al.
New. J. Chem., 42(9), 6673-6688 (2018)
A validated HPTLC method for the quantification of friedelin in Putranjiva roxburghii Wall extracts and in polyherbal formulations
Abhimanyu KK, et al.
Bulletin of Faculty of Pharmacy, Cairo University , 55(1), 79-84 (2017)

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