40165-68-2

Basic information

• Product Name: Dioleylamine
• Synonyms: 9-Octadecen-1-amine, N-(9Z)-9-octadecen-1-yl-, (9Z)-; 9-Octadecen-1-amine, N-(9Z)-9-octadecenyl-, (9Z)-; 9-Octadecen-1-amine, N-9-octadecenyl-, (Z,Z)-; (9Z)-N-[(9E)-octadec-9-en-1-yl]octadec-9-en-1-amine; Dioleyl amine
• CAS NO: 40165-68-2
• Molecular Formula: C₃₆H₇₁N
• Molecular Weight: 517.9556
• EINECS: 254-819-5
• Mol File: 40165-68-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 590.6°C at 760 mmHg
• Flash Point: 205.8°C
• Density: 0.837g/cm³
• Vapor Pressure: 6.38E-14mmHg at 25°C
• Refractive Index: 1.469
• CAS DataBase Reference: Dioleylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Dioleylamine(40165-68-2)
• EPA Substance Registry System: Dioleylamine(40165-68-2)

Safety Data

• Hazardous Substances Data: 40165-68-2(Hazardous Substances Data)

Usage

General Description

Dioleylamine, also known as Oleylamine, is an organic compound that belongs to the class of amines. It is derived from oleic acid, which is a common fatty acid found in vegetable and animal fats. Dioleylamine has a long hydrophobic tail, making it an effective surfactant and emulsifier. It is often used in the production of various products such as pharmaceuticals, agrochemicals, and personal care products. It is also used as a corrosion inhibitor and as a precursor in the synthesis of other chemicals. Additionally, dioleylamine has been found to have antimicrobial and antifungal properties, making it useful in various industrial and agricultural applications.

Upstream product

• 143-28-2 oleoyl alcohol 
• 112-90-3 (Z)-9-octadecen-1-amine 
• 35709-09-2 oleyl methanesulfonate 
• 13044-38-7 (Z)-1-bromo-9-octadecene 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 72901-31-6 (9Z)-N-[(9Z)-9-octadecen-1-yl]-9-octadecenamide 
• 2423-10-1 Oleic aldehyde 

Relevant articles and documents

Simplifying the Chemical Structure of Cationic Lipids for siRNA-Lipid Nanoparticles

We report a potent cationic lipid, SST-02 ((3-hydroxylpropyl)dilinoleylamine), which possesses a simple chemical structure and is synthesized just in one step. Cationic lipids are key components of siRNA-lipid nanoparticles (LNP), which may serve as potential therapeutic agents for various diseases. For a decade, chemists have given enhanced potency and new functions to cationic lipids along with structural complexity. In this study, we conducted a medicinal chemistry campaign pursuing chemical simplicity and found that even dilinoleylmethylamine (SST-01) and methylpalmitoleylamine could be used for the in vitro and in vivo siRNA delivery. Further optimization revealed that a hydroxyl group boosted potency, and SST-02 showed an ID50 of 0.02 mg/kg in the factor VII (FVII) model. Rats administered with 3 mg/kg of SST-02 LNP did not show changes in body weight, blood chemistry, or hematological parameters, while the AST level decreased at a dose of 5 mg/kg. The use of SST-02 avoids a lengthy synthetic route and may thus decrease the future cost of nucleic acid therapeutics.

Design of Ionizable Lipids to Overcome the Limiting Step of Endosomal Escape: Application in the Intracellular Delivery of mRNA, DNA, and siRNA

The intracellular delivery of nucleic acid molecules is a complex process involving several distinct steps; among these the endosomal escape appeared to be of particular importance for an efficient protein production (or inhibition) into host cells. In the present study, a new series of ionizable vectors, derived from naturally occurring aminoglycoside tobramycin, was prepared using improved synthetic procedures that allow structural variations on the linker and hydrophobic domain levels. Complexes formed between the new ionizable lipids and mRNA, DNA, or siRNA were characterized by cryo-TEM experiments and their transfection potency was evaluated using different cell types. We demonstrated that lead molecule 30, bearing a biodegradable diester linker, formed small complexes with nucleic acids and provided very high transfection efficiency with all nucleic acids and cell types tested. The obtained results suggested that the improved and "universal" delivery properties of 30 resulted from an optimized endosomal escape, through the lipid-mixing mechanism.

RNAi PHARMACEUTICAL COMPOSITION FOR SUPPRESSING EXPRESSION OF KRAS GENE

The present invention provides a composition for suppressing the expression of a KRAS gene, comprising a lipid particle containing, as a drug, a double-stranded nucleic acid having an antisense strand having a sequence of bases complementary to the sequence of at least 19 continuous bases of any one KRAS gene's mRNA of sequence Nos. 1 to 3; and a cationic lipid represented by the following formula (I): wherein R1 and R2, which are the same or different, are each linear or branched alkyl, alkenyl or alkynyl having a carbon number of from 12 to 24; L1 and L2, which are the same or different, are each —CO—O— or —O—CO—; a and b, which are the same or different, are each 1 to 3; and R3 is a hydrogen atom, alkyl having a carbon number of from 1 to 6, or alkenyl having a carbon number of from 3 to 6, and the like.