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672315

Ursolic Acid

Name: Ursolic Acid
Brand: MM

A cell-permeable plant-derived pentacyclic triterpene acid that displays anti-inflammatory, immunomodulatory, and antitumor activities.

Synonym(s):

Ursolic Acid, 3β-Hydroxy-urs-12-en-28-oic acid, CG7, PTP1B Inhibitor VII, PTP Inhibitor XXVII, PTPN2/TCPTP Inhibitor II, SHP2 Inhibitor IV, 3β-Hydroxy-urs-12-en-28-oic acid, CG7, PTPN2/TCPTP Inhibitor II, SHP2 Inhibitor IV, PTP1B Inhibitor VII, PTP Inhibitor XXVII

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About This Item

Empirical Formula (Hill Notation):

C₃₀H₄₈O₃

CAS Number:

77-52-1

Molecular Weight:

456.70

UNSPSC Code:

12352211

NACRES:

NA.77

MDL number:

MFCD00009621

Assay:

≥90% (GC)

Form:

powder

Storage condition:

OK to freeze, protect from light

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Properties

Quality Segment

100

assay

≥90% (GC)

form

powder

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

white

solubility

DMF: 50 mg/mL, DMSO: 50 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

O[C@@H]1C([C@H]2[C@@]([C@@H]3[C@]([C@@]4(CC[C@@]5([C@@H]([C@H]([C@@H](CC5)C)C)C4=CC3)C(=O)O)C)(CC2)C)(CC1)C)(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

Description

General description

A cell-permeable plant-derived pentacyclic triterpene acid that displays anti-inflammatory, immunomodulatory, and antitumor activities. Shown to inhibit the phosphatase activity of SHP2, PTP1B, and TCPTP (IC₅₀ = 2.73, 3.08 and 3.33 µM, respectively) as well as induce IR autophosphorylation independent of its phosphatase inhibitory activity. Ursolic acid is also reported to inhibit NF-κB and STAT3 pathway activation in cancer cultures, resulting in enhanced sensitivity to chemotherapy agents and apoptotic cell death.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Li, Y., et al. 2010. Int. J. Cancer127, 462.
Pathak, A.K., et al. 2007. Mol. Cancer Res.5, 943.
Jung, S.H., et al. 2007. Biochem. J.403, 243.
Zhang, W., et al. 2006. Biochim. Biophys. Acta1760, 1505.
Shishodia, S., et al. 2003. Cancer Res.63, 4375.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

flash_point_f

580.5 °F

flash_point_c

304.7 °C

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