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(2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester, also known as oleanolic acid phenylmethyl ester, is a triterpenoid compound derived from the plant oleanolic acid. It is known for its diverse pharmacological activities, including anti-inflammatory, antioxidant, and anti-cancer properties. Oleanolic acid phenylmethyl ester has been studied for its potential in treating various diseases such as diabetes, liver disease, and cardiovascular disorders. It is of interest to the pharmaceutical and medical research industries for its promising therapeutic potential.

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  • 876723-81-8 Structure
  • Basic information

    1. Product Name: (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester
    2. Synonyms: (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester;(2alpha)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester
    3. CAS NO:876723-81-8
    4. Molecular Formula: C37H52O4
    5. Molecular Weight: 0
    6. EINECS: N/A
    7. Product Categories: Pentacyclic Triterpenes
    8. Mol File: 876723-81-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester(CAS DataBase Reference)
    10. NIST Chemistry Reference: (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester(876723-81-8)
    11. EPA Substance Registry System: (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester(876723-81-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 876723-81-8(Hazardous Substances Data)

876723-81-8 Usage

Uses

Used in Pharmaceutical Industry:
(2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester is used as a pharmaceutical agent for its anti-inflammatory, antioxidant, and anti-cancer properties. It has been studied for its potential in treating various diseases such as diabetes, liver disease, and cardiovascular disorders.
Used in Medical Research:
(2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester is used as a research compound in the development of new therapeutic agents. Its diverse pharmacological activities and potential in treating various diseases make it a promising candidate for further research and development in the medical field.

Check Digit Verification of cas no

The CAS Registry Mumber 876723-81-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,7,6,7,2 and 3 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 876723-81:
(8*8)+(7*7)+(6*6)+(5*7)+(4*2)+(3*3)+(2*8)+(1*1)=218
218 % 10 = 8
So 876723-81-8 is a valid CAS Registry Number.

876723-81-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2α-hydroxy-3-oxoolean-12-en-28-oic acid benzyl ester

1.2 Other means of identification

Product number -
Other names benzyl-2α-hydroxy-3-oxoolean-12-en-28-oic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:876723-81-8 SDS

876723-81-8Relevant articles and documents

Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties

Nelson, Andrew T.,Camelio, Andrew M.,Claussen, Karin R.,Cho, Jiyoon,Tremmel, Lisa,Digiovanni, John,Siegel, Dionicio

, p. 4342 - 4346 (2015/11/03)

The scalable syntheses of four oxygenated triterpenes have been implemented to access substantial quantities of maslinic acid, 3-epi-maslinic acid, corosolic acid, and 3-epi-corosolic acid. Semi-syntheses proceed starting from the natural products oleanolic acid and ursolic acid. Proceeding over five steps, each of the four compounds can be synthesized on the gram scale. Divergent diastereoselective reductions of α-hydroxy ketones provided access to the four targeted diol containing compounds from two precursors of the oleanane or ursane lineage. These compounds were subsequently evaluated for their ability to inhibit inflammatory gene expression in a mouse model of chemically induced skin inflammation. All compounds possessed the ability to inhibit the expression of one or more inflammatory genes induced by 12-O-tetradecanoylphorbol-13 acetate in mouse skin, however, three of the compounds, corosolic acid, 3-epi-corosolic acid and maslinic acid were more effective than the others. The availability of gram quantities will allow further testing of these compounds for potential anti-inflammatory activities as well as cancer chemopreventive activity.

Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B

Qian, Shan,Li, Haijiao,Chen, Yin,Zhang, Weiyu,Yang, Shengyong,Wu, Yong

, p. 1743 - 1750 (2011/03/18)

Protein tyrosine phosphatase 1B (PTP1B) is a negative regulator in the process of insulin signaling and a promising drug target for diabetes and obesity. Derivatives of oleanolic acid were synthesized and evaluated as PTP1B inhibitors. Several derivatives exhibited moderate to good inhibitory activities against PTP1B, with 25f displaying the most promising inhibition (IC 50 = 3.12 μM). Structure-activity relationship analyses of these derivatives demonstrated that the integrity of the A ring and 12-ene moieties was important in the retention of PTP1B enzyme inhibitory activities. In addition, hydrophilic and acidic groups as well as the distance between the oleanene and acid moieties were associated with PTP1B inhibitory activities. Possible binding modes of 25f were explored by molecular docking simulations.

Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B

Qiu, Wen-Wei,Shen, Qiang,Yang, Fan,Wang, Bo,Zou, Hui,Li, Jing-Ya,Li, Jia,Tang, Jie

scheme or table, p. 6618 - 6622 (2010/06/12)

A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 μM) and 29 (IC50 = 0.64 μM) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP.

Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: Synthesis, structure-activity relationships, and X-ray crystallographic studies

Wen, Xiaoan,Sun, Hongbin,Liu, Jun,Cheng, Keguang,Zhang, Pu,Zhang, Liying,Hao, Jia,Zhang, Luyong,Ni, Peizhou,Zographos, Spyros E.,Leonidas, Demettes D.,Alexacou, Kyra-Melinda,Gimisis, Thanasis,Hayes, Joseph M.,Oikonomakos, Nikos G.

experimental part, p. 3540 - 3554 (2009/04/07)

Twenty-five naturally occurring pentacyclic triterpenes, 15 of which were synthesized in this study, were biologically evaluated as inhibitors of rabbit muscle glycogen phosphorylase a (GPa). From SAR studies, the presence of a sugar moiety in triterpene saponins resulted in a markedly decreased activity (7, 18-20) or no activity (21, 22). These saponins, however, might find their value as potential natural prodrugs which are much more water-soluble than their corresponding aglycones. To elucidate the mechanism of GP inhibition, we have determined the crystal structures of the GPb-asiatic acid and GPb-maslinic acid complexes. The X-ray analysis indicates that the inhibitors bind at the allosteric activator site, where the physiological activator AMP binds. Pentacyclic triterpenes represent a promising class of multiple-target antidiabetic agents that exert hypoglycemic effects, at least in part, through GP inhibition.

Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors

Wen, Xiaoan,Zhang, Pu,Liu, Jun,Zhang, Luyong,Wu, Xiaoming,Ni, Peizhou,Sun, Hongbin

, p. 722 - 726 (2007/10/03)

The synthesis of a series of maslinic acid derivatives is described and their effect on rabbit muscle glycogen phosphorylase a evaluated. Within this series of compounds, 15 (IC50 = 7 μM) is the most potent GPa inhibitor. SAR of the maslinic acid derivatives are discussed.

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