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Y0001523

Ursolic acid

European Pharmacopoeia (EP) Reference Standard

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Synonym(s):
3β-Hydroxy-12-ursen-28-ic acid
Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
77-52-1
Molecular Weight:
456.70
Beilstein:
2228563
MDL number:
MFCD00009621
UNSPSC Code:
41116107
PubChem Substance ID:
329831473
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.

WGK

WGK 3

Flash Point(F)

580.5 °F

Flash Point(C)

304.7 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Zi-Ming Chen et al.
Steroids, 87, 21-25 (2014-06-01)
Three novel degraded steroids, named albocisterols A-C (1-3), have been isolated from cultures of Antrodiella albocinnamomea. Their structures were defined by comprehensive spectroscopic analysis and single crystal X-ray crystallography. The mixture of compounds 2 and 3 exhibited significant inhibitory activities
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
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
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