03240595

Ursolic acid

primary 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
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

mp

292 °C (dec.) (lit.)

Featured Industry

Food and Beverages

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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Related Categories

General description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Application

Reference Standard in the analysis of herbal medicinal products

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.

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

Ming-Chuan Liu et al.
European journal of medicinal chemistry, 58, 128-135 (2012-11-06)
This study designed and synthesized a series of novel ursolic acid derivatives in an attempt to develop potent antitumor agents. Their structures were confirmed using MS, IR, (1)H NMR and (13)C NMR. The inhibitory activities of the title compounds against...
Qing-you Zheng et al.
Cellular signalling, 25(1), 206-213 (2012-09-25)
Here we studied the cellular mechanisms of ursolic acid's anti-bladder cancer ability by focusing on endoplasmic reticulum stress (ER stress) signaling. We show that ursolic acid induces a significant ER stress response in cultured human bladder cancer T24 cells. ER...
Zhongling Zhu et al.
International journal of nanomedicine, 8, 129-136 (2013-01-16)
Ursolic acid is a promising anticancer agent. The current study aims to evaluate the single- and multiple-dose pharmacokinetics (PK) as well as the safety of ursolic acid nanoliposomes (UANL) in healthy volunteers and in patients with advanced solid tumors. Twenty-four...
Seung-Hyung Kim et al.
European journal of pharmacology, 701(1-3), 131-143 (2012-12-04)
Allergic asthma is a chronic airway disorder characterized by airway hyperresponsiveness to allergens, chronic airway inflammation, airway edema, increased mucus secretion, excess production of Th2 cytokines, and eosinophil accumulation in the lungs. Ursolic acid is known for its pharmacological effects...
Shuilong Leng et al.
International journal of cancer, 133(12), 2781-2790 (2013-06-06)
Ursolic acid (UA) has been reported to possess anticancer activities. Although some of the anticancer activities of UA have been explained by its apoptosis-inducing properties, the mechanisms underlying its anticancer actions are largely unknown. We have found that UA-activated autophagy...

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