192211-41-9

Basic information

• Product Name: Benzyl ursolate
• Synonyms: (3beta)-3-Hydroxy-urs-12-en-28-oic acid phenylmethyl ester;Benzyl ursolate;(3β)-3-Hydroxy-urs-12-en-28-oic acid phenylmethyl ester
• CAS NO: 192211-41-9
• Molecular Formula: C₃₇H₅₄O₃
• Molecular Weight: 546.82
• Product Categories: Pentacyclic Triterpenes
• Mol File: 192211-41-9.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzyl ursolate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl ursolate(192211-41-9)
• EPA Substance Registry System: Benzyl ursolate(192211-41-9)

Safety Data

• Hazardous Substances Data: 192211-41-9(Hazardous Substances Data)

Usage

General Description

Benzyl ursolate is a chemical compound derived from ursolic acid, a natural triterpenoid found in many plants. Benzyl ursolate has been studied for its potential pharmaceutical and medicinal properties, including anti-inflammatory, anti-cancer, and anti-obesity effects. It has been shown to exhibit significant anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines and modulating signaling pathways involved in inflammation. Additionally, benzyl ursolate has been found to induce apoptosis and inhibit cell proliferation in various cancer cell lines, making it a potential candidate for anti-cancer drug development. Furthermore, it has also shown promising effects in preventing and treating obesity by reducing lipid accumulation and promoting fat metabolism. Overall, benzyl ursolate has shown potential in various pharmacological applications and continues to be a subject of ongoing research.

Upstream product

• 77-52-1 ursolic acid 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Relevant articles and documents

A hydrophilic conjugate approach toward the design and synthesis of ursolic acid derivatives as potential antidiabetic agent

In this study, a series of novel ursolic acid (UA) derivatives were designed and synthesized successfully via conjugation of hydrophilic and polar groups at 3-OH and/or 17-COOH position. Molecular docking studies were carried out with the binding of UA and acabose in the active site of α-glucosidase, in order to prove that the hydrophilic/polar moieties can interact with the hydrophobic group of the catalytic pocket and form hydrogen bonds. The bioactivities of these synthesized compounds against α-glucosidase were determined in vitro. Kinetic studies were performed to determine the mechanism of inhibition by compounds 3, 4, 10 and 11. The results indicated that most of the target compounds have significant inhibitory activity, and the compound 3, 4, 10 and 11 were potent inhibitors of α-glucosidase, with the IC50 values of 0.149 ± 0.007, 0.223 ± 0.023, 0.466 ± 0.016 and 0.298 ± 0.021 μM, respectively. These compounds were more potent than parent compound and acarbose. The kinetic inhibition studies revealed that compound 3 and 4 were mix-type inhibitors while compound 10 and 11 were non-competitive inhibitors. Furthermore, the molecular docking studies for these two kinds of compounds suggested that free carboxylic group at either C-3 or C-28 position could remarkably improve inhibitory activity. It is noteworthy that the exploration of relationship between hydrophilic and polar groups of these structures and the hydrophobic group in catalytic pocket is benefited from our rational design of potent α-glucosidase inhibitor.

Discovery and radiosensitization research of ursolic acid derivatives as SENP1 inhibitors

SUMOylation and deSUMOylation plays an important role in DNA damage response and the formation of radiotherapy resistance. SENP1 is the main specific isopeptidase to catalyze deSUMOylation modification. Inhibiting SENP1 upregulates cancer cell radiosensitivity and it becomes a promising target for radiosensitization. Herein, based on the structure of ursolic acid (UA), a total of 53 pentacyclic triterpene derivatives were designed and synthesized as SENP1 inhibitors. Ten derivatives exhibited better SENP1 inhibitory activities than UA and the preliminary structure-activity relationship was discussed. Most of the UA derivatives were low-cytotoxic, among which compound 36 showed the best radiosensitizing activity with the SER value of 1.45. It was the first study to develop small molecular SENP1 inhibitors as radiosensitizers.

Synthesis, biological evaluation and SAR studies of ursolic acid 3β-ester derivatives as novel CETP inhibitors

Cholesteryl ester transfer protein (CETP) is an attractive therapeutic target for the prevention and treatment of cardiovascular diseases by lowering low-density lipoprotein cholesterol levels as well as raising high-density lipoprotein cholesterol levels in human plasma. Herein, a series of ursolic acid 3β-ester derivatives were designed, synthesized and evaluated for the CETP inhibiting activities. Among these compounds, the most active compound is U12 with an IC50 value of 2.4 μM in enzymatic assay. The docking studies showed that the possible hydrogen bond interactions between the carboxyl groups at both ends of the molecule skeleton and several polar residues (such as Ser191, Cys13 and Ser230) in the active site region of CETP could significantly enhance the inhibition activity. This study provides structural insight of the interactions between these pentacyclic triterpenoid 3β-ester derivatives and CETP protein for the further modification and optimization.

Semisynthesis and biological evaluation of oleanolic acid 3-O-β-D-Glucuronopyranoside derivatives for protecting H9c2 cardiomyoblasts against H2O2-Induced injury

A series of novel oleanolic acid 3-O-β-D-glucuronopyranoside derivatives have been designed and synthesized. Biological evaluation has indicated that some of the synthesized compounds exhibit moderate to good activity against H2O2-in