55268-58-1

Usage

Uses

Used in Pharmaceutical Applications:
9-[(Z)-2-[(1Z,3Z)-3-Hexenylidene]cyclopropylidene]nonanoic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester is used as an active pharmaceutical ingredient for its potential therapeutic properties. 9-[(Z)-2-[(1Z,3Z)-3-Hexenylidene]cyclopropylidene]nonanoic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester's unique structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Cosmetic Applications:
In the cosmetic industry, 9-[(Z)-2-[(1Z,3Z)-3-Hexenylidene]cyclopropylidene]nonanoic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester is used as an ingredient in various skincare and hair care products. Its emollient and moisturizing properties help improve the texture and appearance of the skin and hair, providing a smooth and healthy look.
Used in Food Industry:
9-[(Z)-2-[(1Z,3Z)-3-Hexenylidene]cyclopropylidene]nonanoic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester is used as an additive in the food industry, particularly in the formulation of edible oils and spreads. Its ability to improve the stability and texture of these products makes it a valuable component in the production of various food items.
Used in Research Applications:
In the field of scientific research, 9-[(Z)-2-[(1Z,3Z)-3-Hexenylidene]cyclopropylidene]nonanoic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester serves as a valuable tool for studying the properties and interactions of various biological systems. Its unique structure allows researchers to gain insights into the mechanisms of action of different molecules and their potential applications in various fields.

Upstream product

• 506-12-7 heptadecanoic acid 
• 1258782-46-5 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid cis-2-phenyl-[1,3]dioxan-5-yl ester 
• 95576-93-5 (Z,Z,Z)-octadeca-9,12,15-trienoic acid 2-((Z)-octadec-9-enoyloxy)-1-((Z)-octadec-9-enoyloxymethyl)ethyl ester 
• 14465-68-0 trilinolenin 

Downstream Products

• 18465-99-1 2,3-dihydroxypropyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate 

Relevant academic research and scientific papers

Influence of fatty acid desaturation on spontaneous acyl migration in 2-monoacylglycerols

The effect of desaturation from the C9 to the C15 carbon of 2-monoacylglycerol (2-MAG) fatty acids on spontaneous acyl migration is described. Three 2-MAG species, 2-monooleoylglycerol (C18:1 cis-Δ9), 2-monolinoleoylglycerol (C18:2 cis-Δ9,12), and 2-monolinolenoylglycerol (C18:3 cis-Δ9,12,15) were synthesized by lipase-catalyzed ethanolysis of their respective triacylglycerols and isolated in >60 % yield and at 2-MAG purities of >95 % relative to 1-monoacylglycerol (1-MAG). 1H-NMR spectroscopy was used to monitor the spontaneous acyl migration of the 2-MAG species over a temperature range from 20 to 80 °C. The relative energies of activation calculated from the Arrhenius relationships of the 2-MAG acyl migration rate constants were 73.3, 68.0, and 72.9 kJ mol-1 for the three 2-MAG species, respectively. Density functional calculations performed using the B3LYP functional at the 6-31+G* basis set on the three ketal ring intermediate of the three 2-MAG species followed a similar trend with a lack of relative energetic preference associated with the degree of desaturation. The kinetically determined relative activation energies were approximately twofold higher than the theoretical relative Gibbs free energies of the intermediates, suggesting that other factors influence acyl migration. In general, increasing desaturation after the C9 carbon of 2-MAG fatty acids had no appreciable effect on acyl migration rates. AOCS (outside the USA) 2012.

Rapid access to structured triacylglycerols acylated with n-3 polyunsaturated fatty acids for nutritional applications

In order to better understand the metabolic fate of n-3 polyunsaturated fatty acids (PUFAs), an efficient access to symmetrical and unsymmetrical triacylglycerols (TGs), esterified with PUFAs, with known high purity, is required. In this context, we optimized the esterification of a mixture of glycerols protected as dioxane and dioxolane with PUFAs. The kinetics of this reaction depends on various factors, such as the fatty acid chain length and the stereochemistry of the dioxane. Then, one-pot acetal hydrolysis and esterification of hydroxyl groups led to the desired structured TGs without either double bond isomerization or acyl migration (except when symmetrical TGs are acylated with long-chain saturated fatty acids in external positions). PUFAs location on the glycerol backbone was assayed by NMR, HPLC and pancreatic lipase hydrolysis.

Biologically active lipids binding membrane receptors

Neutral lipids are provided characterized by binding to phorboid and ingenoid receptors. These lipids are found in a wide variety of cellular sources as well as milk and may be isolated by specific extraction and chromatographic procedures. Depending upon the source, the glycerides may be mono- or di-glycerides, wherein the total number of carbon atoms of the fatty acids is in the range of 18 to 26, so that the monoglyceride has a fatty acid of at least 18 carbon atoms, while the di-glyceride has a fatty acid of at least 14 carbon atoms.