59044-29-0

Usage

Uses

Used in Pharmaceutical Industry:
Linolenoyl Chloride is used as a reagent for the synthesis of Quercetin fatty acid esters, which serve as antioxidants. These esters are valuable in the development of pharmaceuticals and nutraceuticals due to their potential health benefits, such as reducing oxidative stress and inflammation.
Used in Chemical Synthesis:
Linolenoyl Chloride is utilized in the synthesis of various organic compounds, particularly in the formation of esters. Its reactivity allows for the creation of new chemical entities with potential applications in different industries, such as pharmaceuticals, cosmetics, and materials science.

InChI:InChI=1/C18H29ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3/b4-3-,7-6-,10-9-

Upstream product

• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 104899-01-6 Linvanil 
• 57086-93-8 α-linolenoyl ethanolamide 
• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 2545-22-4 cholesterol all cis-9,12,15-octadecatrienoate 
• 1146533-07-4 5,5-dimethyl-3-oxocyclohex-1-en-1-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate 
• 1146532-71-9 3-oxocyclohex-1-en-1-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate 
• 1146532-85-5 methyl 6,6-dimethyl-4-oxo-2-(undec-10-enoyloxy)cyclohex-2-ene-1-carboxylate 
• 1146532-90-2 methyl 6,6-dimethyl-2-oxo-4-(undec-10-enoyloxy)cyclohex-3-ene-1-carboxylate 
• 504-40-5 1,3-distearoylglycerol 
• 224568-13-2 (9Z,12Z,15Z)-[1-13C]-octadeca-9,12,15-trienoic acid 

Relevant academic research and scientific papers

Enhancing the intestinal absorption of low molecular weight chondroitin sulfate by conjugation with α-linolenic acid and the transport mechanism of the conjugates

The purpose of this report was to demonstrate the effect of amphiphilic polysaccharides-based self-assembling micelles on enhancing the oral absorption of low molecular weight chondroitin sulfate (LMCS) in vitro and in vivo, and identify the transepithelial transport mechanism of LMCS micelles across the intestinal barrier. α-Linolenic acid-low molecular weight chondroitin sulfate polymers(α-LNA-LMCS) were successfully synthesized, and characterized by FTIR, 1HNMR, TGA/DSC, TEM, laser light scattering and zeta potential. The significant oral absorption enhancement and elimination half-life (t1/2) extension of LNA-LMCS2 in rats were evidenced by intragastric administration in comparison with CS and LMCS. Caco-2 transport studies demonstrated that the apparent permeability coefficient (P app) of LNA-LMCS2 was significantly higher than that of CS and LMCS (p 0.001), and no significant effects on the overall integrity of the monolayer were observed during the transport process. In addition, α-LNA-LMCS micelles accumulated around the cell membrane and intercellular space observed by confocal laser scanning microscope (CLSM). Furthermore, evident alterations in the F-actin cytoskeleton were detected by CLSM observation following the treatment of the cell monolayers with α-LNA-LMCS micelles, which further certified the capacity of α-LNA-LMCS micelles to open the intercellular tight junctions rather than disrupt the overall integrity of the monolayer. Therefore, LNA-LMCS2 with low cytotoxicity and high bioavailability might be a promising substitute for CS in clinical use, such as treating osteoarthritis, atherosclerosis, etc.

CATIONIC LIPIDS AND USES THEREOF

The present invention relates to novel cationic lipids of formula I, and more specifically formula IV. These are used, for example, in liposomes for the delivery of nucleic acids to cells.

Catalyst for synthesizing acyl chloride compounds and application thereof

The invention relates to a catalyst for synthesizing an acyl chloride compound and application of the catalyst. The structural formula is as shown in the specification, and in the formula, R is alkali of which the carbon atom number is 1-12. The catalyst is capable of effectively increasing the product yield, improving the production efficiency and lowering the production cost of acyl chloride, and has wide application prospects. The invention further provides a method for synthesizing acyl chloride with the catalyst.

Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids

A decarboxylative borylation of aliphatic acids for the synthesis of a variety of alkylboronates has been developed by mixing m-chloroperoxybenzoic acid (mCPBA)-activated fatty acids with bis(catecholato)diboron in N,N-dimethylformamide (DMF) at room temperature. A radical chain process is involved in the reaction which initiates from the B-B bond homolysis followed by the radical transfer from the boron atom to the carbon atom with subsequent decarboxylation and borylation.

Antiproliferative 3-deoxysphingomyelin analogs: Design, synthesis, biological evaluation and molecular docking of pyrrolidine-based 3-deoxysphingomyelin analogs as anticancer agents

Sphingomyelins and glycerophospholipids are structurally related phospholipids. Nevertheless, glycerophospholipids analogs are known as antitumor agents while sphingomyelin analogs were reported as cytoprotective agents. Herein, we have addressed the development of 3-deoxysphingomyelin analogs as cytotoxic agents possessing modified sphingobases. Thus, pyrrolidine-based 3-deoxysphingomyelin analogs were synthesized and evaluated against a panel of cell lines representing four major types of cancers. Compounds 3d, 4d and 6d elicited better GI50 values than the FDA approved drug miltefosine. Investigation of their impact on Akt phosphorylation as a possible mechanism for the antiproliferative activity of this class of compounds revealed that these compounds might elicit a concentration-dependent mechanism via inhibition of Akt phosphorylation at the lower concentration. Molecular docking predicted their binding modes to Akt to involve polar head binding to the Pleckstrin homology domain and hydrophobic tail extension into a hydrophobic pocket connecting the Pleckstrin homology domain and the kinase domain. As a whole, the described work suggests compounds 3d, 4d and 6d as promising pyrrolidine-based 3-deoxysphingomyelin analogs for development of novel cancer therapies.

GEMCITABINE AMPHIPHILE PRODRUGS

The present invention relates to improved prodrugs, and compositions thereof. In particular, it relates to amphiphilic gemcitabine prodrugs or amphiphilic prodrugs of other biologically active molecules with the capacity to make liquid crystalline nanostructured nanoparticles, and uses thereof to treat animals, including humans.

Amides of N-Deacetyllappaconitine and Unsaturated Fatty Acids

Amides were prepared from N-deacetyllappaconitine and unsaturated oleic, linoleic, α-linolenic, and γ-linolenic fatty acids.

Identification of in situ flower volatiles from kiwifruit (Actinidia chinensis var. deliciosa) cultivars and their male pollenisers in a New Zealand orchard

In situ flower volatiles from six kiwifruit cultivars (Actinidia chinensis var. deliciosa); ‘Hayward’, ‘Chieftain’, ‘M56’, ‘Zes007’ (Green11), ‘M36’, and ‘M43’ were collected by dynamic headspace sampling. Forty-five compounds were detected in the headspace of the flowers, with straight chain hydrocarbons and terpenes accounting for >98% of the volatiles emitted quantitatively across the six cultivars. Of these hydrocarbons, (3Z,6Z,9Z)-heptadecatriene is reported for the first time from a floral source while (8Z)-hexadecene and (9Z)-nonadecene are reported for the first time from kiwifruit flowers. All three hydrocarbons were verified by synthesis. Quantitative comparison of the six honey bee perceived compounds from the headspace of the cultivars showed that the males ‘M36’ and ‘M43’ closely matched the female cultivar Green11 that they are used to pollinate. Males ‘M56’ and ‘Chieftain’ were not as closely matched to the female cultivar ‘Hayward’ that they are used to pollinate. The male ‘M56’ in particular differed significantly from the female ‘Hayward’ in four of the six honey bee perceived compounds.

Preparation method of acyl chloride

The invention relates to a preparation method of acyl chloride. The method comprises the following steps that 1, carboxylic acid is added into a reactor, or carboxylic acid is dissolved in organic solvent, a device is connected, and the temperature is raised to 100 DGE C-250 DEG C; 2, phosgene is introduced into the reactor for a reaction, and then the temperature is decreased to room temperature; 3, nitrogen is introduced, residual phosgene and hydrogen chloride are cleaned away, reaction liquid which is reacted without solvent is subjected to decompression distillation and purification directly, and needed acyl chloride is obtained; reaction liquid which is reacted with the solvent is subjected to decompression distillation to remove the solvent, and needed acyl chloride is obtained. According to the preparation method of acyl chloride, no catalyst is added, the risks that in the synthesizing process, due to the fact that the catalyst is dissolved, color of the finial product of acyl chloride is increased, and the catalyst is remained in late products are avoided, after the reaction is finished, high-quality acyl chloride can be obtained through decompression distillation, and the technological process is simple; due to the fact that in the whole technological process, except for absorbable and available phosgene, hydrogen chloride and carbon dioxide, no other three waste is discharged, the preparation method of acyl chloride is environmentally friendly, and the good implement value is achieved.

Selective Modulation of Protein Kinase C α over Protein Kinase C by Curcumin and Its Derivatives in CHO-K1 Cells

Members of the protein kinase C (PKC) family of serine/threonine kinases regulate various cellular functions, including cell growth, differentiation, metabolism, and apoptosis. Modulation of isoform-selective activity of PKC by curcumin (1), the active constituent of Curcuma L., is poorly understood, and the literature data are inconsistent and obscure. The effect of curcumin (1) and its analogues, 4-[(2Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-2,6-dien-1-yl]-2-methoxyphenyl oleate (2), (9Z,12Z)-4-[(2Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-2,6-dien-1-yl]-2-methoxyphenyl octadeca-9,12-dienoate (3), (9Z,12Z,15Z)-4-[(2Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-2,6-dien-1-yl]-2-methoxyphenyl octadeca-9,12,15-trienoate (4), and (1E,6E)-1-[4-(hexadecyloxy)-3-methoxyphenyl]-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (5), and didemethylcurcumin (6) on the membrane translocation of PKCα, a conventional PKC, and PKC, a novel PKC, has been studied in CHO-K1 cells, in which these PKC isoforms are endogenously expressed. Translocation of PKC from the cytosol to the membrane was measured using immunoblotting and confocal microscopy. 1 and 6 inhibited the TPA-induced membrane translocation of PKCα but not of PKC. Modification of the hydroxyl group of curcumin with a long aliphatic chain containing unsaturated double bonds in 2-4 completely abolished this inhibition property. Instead, 2-4 showed significant translocation of PKCα but not of PKC to the membrane. No membrane translocation was observed with 1, 6, or the analogue 5 having a saturated long chain for either PKCα or PKC. 1 and 6 inhibited TPA-induced activation of ERK1/2, and 2-4 activated it. ERK1/2 is the downstream readout of PKC. These results show that the hydroxyl group of curcumin is important for PKC activity and the curcumin template can be useful in developing isoform specific PKC modulators for regulating a particular disease state.