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Merck
CN

Y0001523

Ursolic acid

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

3β-Hydroxy-12-ursen-28-ic acid

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About This Item

Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
77-52-1
Molecular Weight:
456.70
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329831473
MDL number:
MFCD00009621
Beilstein/REAXYS Number:
2228563

Key Documents

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Product Name

Ursolic acid, European Pharmacopoeia (EP) Reference Standard

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

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 key

WCGUUGGRBIKTOS-GPOJBZKASA-N

grade

pharmaceutical primary standard

API family

ursolic acid

manufacturer/tradename

EDQM

mp

292 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

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Application

Ursolic acid EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European 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.

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.

Other Notes

Sales restrictions may apply.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

wgk

WGK 3

Storage Class

11 - Combustible Solids

flash_point_f

580.5 °F

flash_point_c

304.7 °C

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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
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
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
L Novotný et al.
Neoplasma, 48(4), 241-246 (2001-11-20)
Ursolic acid, UA, as a pentacyclic triterpene is of interest to scientists in the area of oncology because of its cytotoxicity, induction of differentiation, anti-mutagenic, antiviral and anti-invasive activities. UA is capable of inducing apoptosis in tumor cells on one
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