Y0001523

Ursolic acid

European Pharmacopoeia (EP) Reference Standard

Synonym(s):
3β-Hydroxy-12-ursen-28-ic acid
Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
Molecular Weight:
456.70
Beilstein/REAXYS Number:
2228563
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

pharmaceutical primary standard

form

neat

manufacturer/tradename

EDQM

mp

292 °C (dec.) (lit.)

Featured Industry

Pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)CC[C@H](O)C2(C)C

InChI

1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

InChI key

WCGUUGGRBIKTOS-GPOJBZKASA-N

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Biochem/physiol Actions

Triterpenoid found in a variety of fruits, including apples. Cardioprotective and anti-tumor agent. Under study as a potential Alzheimer′s disease therapeutic due to its inhibitory effect on the interactions between amyloid-β and the CD36 receptor.

Packaging

Unit quantity: 25 mg. Subject to change. The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Caution

Other Notes

Sales restrictions may apply.

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

580.5 °F

Flash Point(C)

304.7 °C

Certificate of Analysis

Certificate of Origin

András Lőrincz et al.
Biochimica et biophysica acta, 1848(5), 1092-1098 (2015-01-27)
Effects of ursolic acid on the structural and morphological characteristics of dipalmitoyl lecithin(DPPC)-water system was studied by using differential scanning calorimetry (DSC), small- and wide-angle X-ray scattering (SWAXS), freeze-fracture method combined with transmission electron-microscopy (FF-TEM) and infrared spectroscopy (FT-IR). The...
Nighat Sultana
Journal of enzyme inhibition and medicinal chemistry, 26(5), 616-642 (2011-03-23)
Medicinal plants are becoming an important research area for novel and bioactive molecules for drug discovery. Novel therapeutic strategies and agents are urgently needed to treat different incurable diseases. Many plant derived active compounds are in human clinical trials. Currently...
Yasutaka Ikeda et al.
Molecular nutrition & food research, 52(1), 26-42 (2008-01-19)
There is growing interest in the elucidation of the biological functions of triterpenoids, ubiquitously distributed throughout the plant kingdom, some of which are used as anticancer and anti-inflammatory agents in Asian countries. Ursolic acid (UA), a natural pentacyclic triterpenoid carboxylic...
Ling Liu et al.
Molecular medicine reports, 9(6), 2505-2511 (2014-03-19)
Cyclooxygenase (COX)-2, a multi-functional molecule, is overexpressed in hepatocellular carcinomas. In order to understand cell proliferation and its association with COX-2 in HepG2 cells in the presence of ursolic acid (UA), viili exopolysaccharides (VEPS) and Astragalus polysaccharides (APS), the cell...
Kishor Mazumder et al.
Molecules (Basel, Switzerland), 18(8), 8929-8944 (2013-07-31)
Structure-activity relationships of ursane-type pentacyclic triterpenes obtained from natural sources and by chemical derivatization are reviewed. Ursolic acid, corosolic acid, and a new ursane-type pentacyclic triterpene, 7,24-dihydroxyursolic acid, were isolated from the methanolic extract of the leaves of the Bangladeshi...

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