CAS Number77-52-1
SynonymsMasterin; URSON; Merotaine; Neoage UR; EINECS 201-034-0; PRUNOL; MICROMEROL; Ursolicacid; Ursolic acid; MALOL; MFCD00009621; Ursolic
Molecular FormulaC30H48O3
Molecular Weight456.70
Purity≥90%
Density1.1±0.1 g/cm3
Boiling Point556.9±50.0 °C at 760 mmHg
Melting Point292 °C (dec.) (lit.)
Appearancegreen powder
EINECS201-034-0
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 77-52-1 |
| Catalog No. | 2A-9012894 |
| Chinese Name | 熊果酸 |
| Synonyms | Masterin; URSON; Merotaine; Neoage UR; EINECS 201-034-0; PRUNOL; MICROMEROL; Ursolicacid; Ursolic acid; MALOL; MFCD00009621; Ursolic |
| Molecular Formula | C30H48O3 |
| Molecular Weight | 456.70 |
| Purity | ≥90 |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 556.9±50.0 °C at 760 mmHg |
| Melting Point | 292 °C (dec.) (lit.) |
| Appearance | green powder |
| Water Solubility | insoluble |
| Storage Condition | This product is sealed and stored |
| Packaging | Foil bag |
| Application | Ursolic acid is a natural triterpene carboxylic acid compound with preventive and anti-cancer activities. |
| EINECS | 201-034-0 |
| HTC | 2942000000 |
| PubChem ID | 57654721 |
| MDL Number | MFCD00009621 |
| SMILES | [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 |
| Beilstein/REAXYS | 2228563 |
| NACRES Code | NA.22 |
| UNSPSC | 12352002 |
| Hazard Symbols | Transport |
| MSDS | msds/12894_1_77_52_1.pdf |
| Bioactivity | Ursolic acid(Bungeolic acid) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. IC50 value:Target:in vitro: UA induced phosphorylation of AMP-activated protein kinase alpha (AMPKα) and suppressed the protein expression of DNA methyltransferase 1 (DNMT1) in the dose-dependent manner [1]. The combination of ursolic acid (0.5 μM) and leucine (10 μM) proved to be the most effective in promoting myogenic differentiation. The combination of ursolic acid and leucine significantly increased CK activity than treatment with either agent alone. The level of myosin heavy chain, a myogenic differentiation marker protein, was also enhanced by the combination of ursolic acid and leucine [2]. Ursolic acid efficiently induced apoptosis, possibly via the downregulation of B-cell lymphoma 2 (Bcl-2), the upregulation of Bcl-2-associated X protein and the proteolytic activation of caspase-3. Furthermore, the activation of p38 mitogen-activated protein kinase and c-Jun N-terminal kinase was increased by the administration of ursolic acid. In addition, ursolic acid significantly suppressed the invasive phenotype of the SNU-484 cells and significantly decreased the expression of matrix metalloproteinase (MMP)-2 [3]. ursolic acid (UA) potently induces the apoptosis of gastric cancer SGC-7901 cells. Further mechanistic studies revealed that the ROCK1/PTEN signaling pathway plays a critical role in UA-mediated mitochondrial translocation of cofilin-1 and apoptosis [4].in vivo: UA treatment markedly improved the survival of septic rats, and attenuated CLP-induced lung injury, including reduction of lung wet/dry weight ratio, infiltration of leukocytes and proteins, myeloperoxidase activity, and malondialdehyde content. In addition, UA significantly decreased the serum levels of tumor necrosis factor-α, interleukin-6, and interleukin-1β, inhibited the expression of inducible nitric oxide synthase and cyclooxygenase-2 in the lung, which are involved in the productions of nitric oxide and prostaglandin E2 [5]. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer References [1]. Yie Y, et al. Ursolic acid inhibited growth of hepatocellular carcinoma HepG2 cells through AMPKα-mediated reduction of DNA methyltransferase 1. Mol Cell Biochem. 2014 Dec 30. [2]. Kim M, et al. The combination of ursolic acid and leucine potentiates the differentiation of C2C12 murine myoblasts through the mTOR signaling pathway. Int J Mol Med. 2015 Mar;35(3):755-62. [3]. Kim ES, et al. Ursolic acid inhibits the invasive phenotype of SNU-484 human gastric cancer cells. Oncol Lett. 2015 Feb;9(2):897-902. [4]. Li R, et al. Ursolic Acid Promotes Apoptosis of SGC-7901 Gastric Cancer Cells through ROCK/PTEN Mediated Mitochondrial Translocation of Cofilin-1. Asian Pac J Cancer Prev. 2014;15(22):9593-7. [5]. Hu Z, et al. Ursolic acid improves survival and attenuates lung injury in septic rats induced by cecal ligation and puncture. J Surg Res. 2014 Oct 22. pii: S0022-4804(14)00967-6. Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 556.9±50.0 °C at 760 mmHg Melting Point 292 °C (dec.)(lit.) Molecular Formula C30H48O3 Molecular Weight 456.700 Flash Point 304.7±26.6 °C Exact Mass 456.360352 PSA 57.53000 LogP 9.01 Vapour Pressure 0.0±3.4 mmHg at 25°C Index of Refraction 1.555 InChIKey WCGUUGGRBIKTOS-GPOJBZKASA-N SMILES CC1CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C2C1C Storage condition 2~8°C Water Solubility insoluble |
| Use of | Properties Articles132 Name ursolic acid Synonym More Synonyms Ursolic Acid Biological Activity Related Catalog Signaling Pathways >> Autophagy >> Autophagy Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer References [3]. Kim ES, et al. Ursolic acid inhibits the invasive phenotype of SNU-484 human gastric cancer cells. Oncol Lett. 2015 Feb;9(2):897-902. [4]. Li R, et al. Ursolic Acid Promotes Apoptosis of SGC-7901 Gastric Cancer Cells through ROCK/PTEN Mediated Mitochondrial Translocation of Cofilin-1. Asian Pac J Cancer Prev. 2014;15(22):9593-7. [5]. Hu Z, et al. Ursolic acid improves survival and attenuates lung injury in septic rats induced by cecal ligation and puncture. J Surg Res. 2014 Oct 22. pii: S0022-4804(14)00967-6. Chemical & Physical Properties Molecular Formula C30H48O3 Exact Mass 456.360352 PSA 57.53000 Index of Refraction 1.555 InChIKey WCGUUGGRBIKTOS-GPOJBZKASA-N Water Solubility insoluble |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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