62498-83-3

Basic information

• Product Name: 3-O-Acetyloleanderolide
• Synonyms: 3-O-Acetyloleanderolide
• CAS NO: 62498-83-3
• Molecular Formula: C32H50O5
• Molecular Weight: 514.74
• Mol File: 62498-83-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-O-Acetyloleanderolide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-Acetyloleanderolide(62498-83-3)
• EPA Substance Registry System: 3-O-Acetyloleanderolide(62498-83-3)

Safety Data

• Hazardous Substances Data: 62498-83-3(Hazardous Substances Data)

Usage

General Description

3-O-Acetyloleanderolide is a type of cardiac glycoside that is derived from the oleander plant. It has been found to possess potent insecticidal and anthelmintic properties, making it useful in agricultural and veterinary applications. In addition, research has shown that 3-O-Acetyloleanderolide exhibits potential anti-cancer activity, notably against breast cancer cells. Its mechanism of action involves inhibiting the Na+/K+-ATPase pump, leading to an increase in intracellular sodium and calcium ions, which can ultimately induce apoptosis in cancer cells. Despite its promising medicinal properties, the compound is highly toxic if ingested and should be handled with caution.

Upstream product

• 108-24-7 acetic anhydride 
• 19897-43-9 (3β,12α) 3,12-dihydroxy-18β-olean-28-oic acid 28,13-lactone 
• 508-02-1 Oleanolic acid 
• 85031-73-8 (3β,12α) 3,12-diacetoxy-olean-28-oic acid 28,13-lactone 
• 4339-72-4 oleanolic acid 3-acetate 
• 186581-53-3 diazomethane 

Downstream Products

• 35959-11-6 3β-acetoxy-13-hydroxy-12-oxo-oleanan-28-oic acid-lactone 
• 303114-51-4 oleanolic acid benzyl ester 
• 1724-17-0 oleanolic acid methyl ester 
• 25493-69-0 (4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 
• 508-02-1 Oleanolic acid 

Relevant articles and documents

Beckmann rearrangement within the ring C of oleanolic acid lactone: Synthesis, structural study and reaction mechanism analysis

Synthesis, spectral and X-ray analysis of three compounds, i.e. 3β-acetoxy-12-hydroxyimino-18β-oleanan-28,13β-olide (substrate) and 3β-acetoxy-12-nitrile-12,13-seco-15(14?→?13)-abeoolean-14(27)-en-28,13β-olide and 3β-acetoxy-12-oxo-12a-aza-C-homoolean-13(18)-en-28-oic acid (Beckmann rearrangement reaction products) are described. Structural analysis revealed that the oxime group in the ring C in substrate molecule had an E-configuration. The nitrile product with retained lactone group was a result of major transformations within rings C and D of oleanane skeleton. In lactam product free carboxyl group and a double bond in ring D instead of lactone system were formed in Beckmann rearrangement reaction.

Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP): A convenient 2-step procedure towards 12-oxo-28-carboxylic acid derivatives

A new straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding δ-hydroxy-γ- lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a two-step procedure for the preparation of oleanolic 12-oxo-28-carboxylic acid derivatives directly from Δ12-oleananes, without the need for an intermediary work-up, and keeping the same reaction solvent in both steps, is described as applied to the synthesis of 3,12-dioxoolean-28-oic acid.

Synthesis and α-glucosidase inhibitory activity of oleanolic acid derivatives

Glucosidations of oleanolic acid (1) and its dihydroxy-olide derivatives (2) were carried out to provide eight glycosides. All synthesized compounds were evaluated by in vitro α-glucosidase inhibitory activity assay. 3-Acetyl dihydroxy-olide oleanolic der