86166-09-8

Basic information

• Product Name: 3-HYDROXY-(3BETA)-URS-12-EN-28-OIC ACID BUTYL ESTER
• Synonyms: 3-HYDROXY-(3BETA)-URS-12-EN-28-OIC ACID BUTYL ESTER
• CAS NO: 86166-09-8
• Molecular Formula: C34H56O3
• Molecular Weight: 512.81
• Mol File: 86166-09-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-HYDROXY-(3BETA)-URS-12-EN-28-OIC ACID BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-(3BETA)-URS-12-EN-28-OIC ACID BUTYL ESTER(86166-09-8)
• EPA Substance Registry System: 3-HYDROXY-(3BETA)-URS-12-EN-28-OIC ACID BUTYL ESTER(86166-09-8)

Safety Data

• Hazardous Substances Data: 86166-09-8(Hazardous Substances Data)

Upstream product

• 109-65-9 1-bromo-butane 
• 77-52-1 ursolic acid 

Relevant articles and documents

Synthesis and evaluation as potential antitumor agents of novel ursolic acid derivatives

Novel ursolic acid derivatives were synthesized, and their structures were confirmed by MS, IR, 1H NMR and 13C NMR spectral analysis. In vitro antitumor activities of these compounds against MGC-803 (gastric cancer cell) and Bcap-37 (breast cancer cell) human cancer cell lines were evaluated by MTT assay. The pharmacological screening results revealed that many derivatives exhibited moderate to high activities against the tested cell lines, and that most demonstrated more potent inhibitory activities than that of ursolic acid. Preliminarily mechanism study of representative compound 3h were carried out by acridine orange/ethidium bromide staining, Hoechst 33258 staining, terminal deoxynucleotidyl transferase biotin-dUTP nick end labeling assay, and flow cytometry which indicated that compound 3h can induce cell apoptosis of MGC-803 cells, and the apoptosis ratio reached 34.59 % after 36 h treatment at 10 μM.

In vitro and in vivo anticancer activity evaluation of ursolic acid derivatives

Twenty-three ursolic acid (1) derivatives 2-24 (ten novel compounds 8-10, 14-17 and 22-24) modified at the C-3 and the C-28 positions were synthesized, and their structures were confirmed by IR, 1H NMR, MS, and elemental analysis. The single crystals of compounds 15 and 17 were obtained. The cytotoxic activity of the derivatives was evaluated against HepG2, BGC-823, SH-SY5Y, HeLa and HELF cells by the MTT assay. The induction of apoptosis and affects on the cell cycle distribution with compound 14 were assessed by fluorescence microscopy, flow cytometry and the activity of caspase-3 in HepG2 cells. Compounds 14-17 had more significant antiproliferative ability against the four cancer cell lines and low cytotoxicity to human embryonic lung fibroblast cells (HELF). Compounds 11, 14-16, 21 and 23 were particularly active against HepG2 cell growth. Compound 14 was selected to investigate cell apoptosis and cell cycle distribution. Flow cytometric analysis and morphologic changes of the cell exhibited that treatment of HepG2 cells with compound 14 led to cell apoptosis accompanied by cell cycle arrest at the S phase in a dose-dependent manner. Furthermore, the activity of the caspase-3 enzyme was increased in the treated cells. In vivo studies using H22 xenografts in Kunming mice were conducted with compound 14 at doses of 50, 100 and 150 mg/kg body weight. The results revealed that the medium dosage group (100 mg/kg) showed significant anticancer activity (45.6 ± 4.3%) compared to the control group.

Esterification of two sterically hindered acids using ultrasound waves.

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