79355-89-8

Basic information

• Product Name: 2α,3β,19α-Trihydroxyolean-12-ene-24,28-dioic acid
• Synonyms: 2α,3β,19α-Trihydroxyolean-12-ene-24,28-dioic acid;Bartogenic acid
• CAS NO: 79355-89-8
• Molecular Formula: C₃₀H₄₆O₇
• Molecular Weight: 518.68204
• Mol File: 79355-89-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2α,3β,19α-Trihydroxyolean-12-ene-24,28-dioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2α,3β,19α-Trihydroxyolean-12-ene-24,28-dioic acid(79355-89-8)
• EPA Substance Registry System: 2α,3β,19α-Trihydroxyolean-12-ene-24,28-dioic acid(79355-89-8)

Safety Data

• Hazardous Substances Data: 79355-89-8(Hazardous Substances Data)

Usage

General Description

2α,3β,19α-Trihydroxyolean-12-ene-24,28-dioic acid is a natural triterpenoid compound found in the Chinese herb Ardisia japonica. It exhibits a range of pharmacological activities, including anti-inflammatory, anti-carcinogenic, and anti-diabetic effects. Its structure consists of a pentacyclic triterpene skeleton with three hydroxyl groups at positions 2, 3, and 19, as well as two carboxylic acid groups at positions 24 and 28. 2α,3β,19α-Trihydroxyolean-12-ene-24,28-dioic acid has shown potential as a therapeutic agent in the treatment of various diseases and may serve as a lead compound for the development of new drugs. Its diverse biological activities make it a subject of interest in medicinal chemistry and natural product research.

Synthetic route

dimethyl bartogenate (79355-86-5) → 2α,3β,19α-trihydroxyolean-12-ene-24,28-dioic acid (79355-89-8)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 60℃; for 12h;

2α,3β,19α-trihydroxyolean-12-en-24,28-dioic acid 28-β-D glucopyranoside ester → 2α,3β,19α-trihydroxyolean-12-ene-24,28-dioic acid (79355-89-8)

Conditions	Yield
With sodium hydroxide for 0.166667h; Heating;	20 mg

diazomethane (186581-53-3, 908094-01-9) + 2α,3β,19α-trihydroxyolean-12-ene-24,28-dioic acid (79355-89-8) → dimethyl bartogenate (79355-86-5)

Conditions	Yield
In methanol; diethyl ether at 0℃; for 1h;	2 g

2α,3β,19α-trihydroxyolean-12-ene-24,28-dioic acid (79355-89-8) → dimethyl-12,13-epoxybartogenate (103763-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 g / diethyl ether; methanol / 1 h / 0 °C 2: 0.034 g / m-chloroperbenzoic acid / CHCl3 / 48 h / 0 - 10 °C View Scheme

Upstream product

• 79355-86-5 dimethyl bartogenate 

Relevant articles and documents

Constituents of fagaceae (Cupuliferae). XIX: Triterpene saponins and acylated flavonoids from Quercus robur L. var. stenocarpa Beck.

In addition to four known glycosides from leaves of Quercus robur L. var. stenocarpa Beck. a new triterpene saponin has been isolated and identified as 28-β-D-glucopyranosyl ester of the 2α,3β,19α-trihydroxy-olean-12-ene-24,28-dioic acid (1).