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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:
Molecular Weight:
456.70
Beilstein:
2228563
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

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

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.

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.

Packaging

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

Other Notes

Sales restrictions may apply.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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
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
Jaeyoung Chun et al.
Life sciences, 110(1), 23-34 (2014-07-06)
Ursolic acid (UA), a natural pentacyclic triterpenoid acid, has been reported to show immunomodulatory activity. This study investigated the effects of UA on nuclear factor-kappa B (NF-κB) signaling in cells and experimental murine colitis. Human intestinal epithelial cells (IECs) COLO
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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