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Merck
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855022

Sigma-Aldrich

Friedelin

technical grade

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C30H50O
Número de CAS:
559-74-0
Peso molecular:
426.72
Beilstein/REAXYS Number:
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

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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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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
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
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