178600-68-5

Basic information

• Product Name: Oleoside
• Synonyms: Oleoside;(2S,3E,4S)-5-Carboxy-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-acetic acid
• CAS NO: 178600-68-5
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.33928
• Mol File: 178600-68-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 707.5±60.0 °C(Predicted)
• Appearance: /
• Density: 1.61±0.1 g/cm3(Predicted)
• PKA: 4.33±0.10(Predicted)
• CAS DataBase Reference: Oleoside(CAS DataBase Reference)
• NIST Chemistry Reference: Oleoside(178600-68-5)
• EPA Substance Registry System: Oleoside(178600-68-5)

Safety Data

• Hazardous Substances Data: 178600-68-5(Hazardous Substances Data)

Usage

General Description

Oleosides are a group of chemical compounds found in a variety of plants, including olive leaves and other Oleaceae family plants. These compounds are known for their potential therapeutic properties, including anti-inflammatory and antioxidant effects. Oleosides have been studied for their ability to reduce oxidative stress, protect against neurodegenerative diseases, and fight inflammation. They may also have potential as a natural alternative to traditional pharmaceuticals for treating conditions such as cancer, diabetes, and cardiovascular disease. Overall, oleosides are a promising group of compounds with diverse potential health benefits.

Upstream product

• 115547-25-6 sambacoside F 
• 30164-95-5 Oleoside dimethyl ester 
• 32619-42-4 oleuropeine 
• 1007558-31-7 ilicifolioside A 
• 1005197-22-7 ilicifolioside B 
• 60539-23-3 4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 

Downstream Products

• 52077-55-1 (4S,E)-4-(2-(3,4-dihydroxyphenethoxy)-2-oxoethyl)-3-ethylidene-2-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylic acid 
• 289030-99-5 Oleocanthal 

Relevant articles and documents

New semi-synthetic analogs of oleuropein show improved anticancer activity in?vitro and in?vivo

Oleuropein is a glucosylated seco-iridoid present in olive fruits and leaves. Due to its broad spectrum of biological activities, including anticancer properties, oleuropein has attracted scientific attention for the past 20 years. The promising antiproliferative activity of an olive leaf extract enriched in oleuropein against a series of human cancer cell lines, prompted us to proceed with the semi-synthesis of 51 analogs of oleuropein. Following their initial screening against the estrogen receptor negative breast cancer cell line SKBR3, 7 analogs were shown to display significant cytotoxicity and were further tested against 6 additional solid tumor-derived and leukemic cell lines. The analog with the most promising antitumor activity (24) was selected for more detailed studies. 24 was non-toxic to peripheral blood mononuclear cells derived from healthy blood donors when tested at concentrations close to its half maximal inhibitory concentration. In vivo administration of 24 in melanoma-bearing mice resulted in reducing tumor size in a dose-dependent manner and in inducing anti-melanoma-reactive immune responses. Our results suggest that analog 24, emerging from the initial structure of oleuropein, represents a promising lead structure for further optimization.

Oleuropein site selective hydrolysis by technomimetic nuclear magnetic resonance experiments

Technomimetic NMR experiments were performed in accordance with the lye treatment adopted during table olive industrial procedures for the debittering process causing oleuropein degradation. The site selective hydrolysis of the two ester groups, character

PROCESS FOR THE PRODUCTION OF OLEOCANTHAL, OLEACEIN AND THEIR ANALOGUES

A process for the production of a compound according to Formula (I), such as oleocanthal or oleacein, starting from oleuropein. The process provides the dialdehyde core of oleocanthal, oleacein and their analogues having the required stereochemistry. Furthermore, the process can be used for the production of a large number of structurally diverse products by varying the structure of the alcohol moiety in the esterification step.

Main antimicrobial compounds in table olives

The inhibitors involved in the lactic acid fermentation of table olives were investigated in aseptic olive brines of the Manzanilla and Gordal varieties. Phenolic and oleosidic compounds in these brines were identified by high-performance liquid chromatography with ultraviolet and electrospray ionization mass spectrometry detection, and several substances were also characterized by nuclear magnetic resonance. Among these compounds, the dialdehydic form of decarboxymethyl elenolic acid linked to hydroxytyrosol showed the strongest antilactic acid bacteria activity, and its presence in brines could explain the growth inhibition of these microorganisms during olive fermentation. However, it was found that the dialdehydic form of decarboxymethyl elenolic acid, identified for the first time in table olives, and an isomer of oleoside 11-methyl ester were also effective against Lactobacillus pentosus and can, therefore, contribute to the antimicrobial activity of olive brines. It must also be stressed that the three new inhibitors discovered in table olive brines exerted a more potent antibacterial activity than the well-studied oleuropein and hydroxytyrosol.