59044-29-0

Basic information

• Product Name: LINOLENOYL CHLORIDE
• Synonyms: LINOLENOYL CHLORIDE;CIS-LINOLENOYL CHLORIDE;DELTA 9-12-15 CIS-OCTADECATRIENOYL CHLORIDE;15-octadecatrienoylchloride,(z,z,z)-12;(9Z,12Z,15Z)-9,12,15-octadecatrienoyl chloride;Linolenoylchloridetech,70%;(9Z,12Z,15Z)-OCTADECA-9,12,15-TRIENOYL CHLORIDE;Linolenoyl chloride, tech., 70%
• CAS NO: 59044-29-0
• Molecular Formula: C₁₈H₂₉ClO
• Molecular Weight: 296.88
• EINECS: 261-572-7
• Mol File: 59044-29-0.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 382.9°C at 760 mmHg
• Flash Point: 184.8°C
• Appearance: /
• Density: 0.942g/cm³
• Vapor Pressure: 4.58E-06mmHg at 25°C
• Refractive Index: 1.478-1.48
• CAS DataBase Reference: LINOLENOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: LINOLENOYL CHLORIDE(59044-29-0)
• EPA Substance Registry System: LINOLENOYL CHLORIDE(59044-29-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26
• Hazardous Substances Data: 59044-29-0(Hazardous Substances Data)

Usage

Chemical Properties

dark brown liquid

Uses

Linolenoyl Chloride is a reagent used in the synthesis of Quercetin (Q509500) fatty acid esters as antioxidants.

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

• 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 
• 2423-13-4 (9Z,12Z,15Z)-9,12,15-Octadecatrien-1-al 
• 504-40-5 1,3-distearoylglycerol 
• 224568-13-2 (9Z,12Z,15Z)-[1-13C]-octadeca-9,12,15-trienoic acid 
• 94802-00-3 (3Z,6Z,9Z)-17-bromoheptadeca-3,6,9-triene 
• 57086-93-8 α-linolenoyl ethanolamide 

Relevant articles and documents

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.

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.

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.