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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
Beilstein/REAXYS Number:
2228563
EC Number:
201-034-0
MDL number:
MFCD00009621
UNSPSC Code:
85151701
PubChem Substance ID:
329747577
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.)

application(s)

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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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

11 - Combustible Solids

wgk_germany

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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Sigma-Aldrich

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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
Chong Zhao et al.
Autophagy, 9(2), 196-207 (2012-11-28)
Ursolic acid (UA) is a pentacyclic triterpenoid with promising cancer chemopreventive properties. A better understanding of the mechanisms underlying anticancer activity of UA is needed for further development as a clinically useful chemopreventive agent. Here, we found that both endoplasmic
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
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
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