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Merck
CN

03240595

Ursolic acid

primary 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:
85151701
NACRES:
NA.24
PubChem Substance ID:
329747577
EC Number:
201-034-0
Beilstein/REAXYS Number:
2228563
MDL number:
MFCD00009621

Key Documents

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Product Name

Ursolic acid, primary 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

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

mp

292 °C (dec.) (lit.)

application(s)

food and beverages

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Related Categories

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.

General description

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

580.5 °F

flash_point_c

304.7 °C

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Certificates of Analysis (COA)

Lot/Batch Number
HWI01537-2
HWI01537-1
HWI01570-2
HWI01570-1
HWI01570

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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
Yumiko Achiwa et al.
Bioscience, biotechnology, and biochemistry, 71(1), 31-37 (2007-01-11)
The phosphatidylinositol 3-kinase-Akt (PI3K-Akt) pathway and the mitogen activated protein kinase (MAPK) pathway are important in the development and proliferation of various human cancers. It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells.
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
Hao Zhang et al.
International journal of pharmaceutics, 441(1-2), 261-268 (2012-12-01)
It has been demonstrated that ursolic acid (UA) could effectively induces apoptosis of cancer cells by inhibiting the expression of cyclooxygenase 2 (COX-2), which constitutively expresses in gastric cancer. However, the hydrophobicity of UA increases the difficulty in its potential
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
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