40165-68-2

Usage

Uses

Used in Pharmaceutical Industry:
Dioleylamine is used as a surfactant and emulsifier for improving the solubility and stability of pharmaceutical formulations, facilitating the delivery of active ingredients and enhancing their therapeutic effects.
Used in Agrochemical Industry:
Dioleylamine is used as a surfactant and emulsifier in agrochemical formulations, enhancing the effectiveness of pesticides and other agricultural chemicals by improving their dispersion and absorption on plant surfaces.
Used in Personal Care Products:
Dioleylamine is used as a surfactant and emulsifier in personal care products, such as creams, lotions, and shampoos, to improve the texture, stability, and performance of these formulations.
Used as a Corrosion Inhibitor:
Dioleylamine is used as a corrosion inhibitor in various industrial applications, protecting metal surfaces from corrosion and extending the lifespan of equipment and structures.
Used as a Precursor in Chemical Synthesis:
Dioleylamine serves as a precursor in the synthesis of other chemicals, contributing to the production of a range of compounds for diverse applications.
Used in Industrial and Agricultural Applications:
Leveraging its antimicrobial and antifungal properties, Dioleylamine is used in industrial and agricultural settings to control microbial growth and protect materials and crops from spoilage and disease.

Upstream product

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

Relevant academic research and scientific papers

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.

Asymmetric cationic lipid based non-viral vectors for an efficient nucleic acid delivery

Cationic lipids have been extensively studied for their ability to complex with nucleic acids to condense and consequently deliver them into the cells. However, developing safe and efficient cationic lipids for delivering nucleic acids is still an unmet challenge. Prior structure-activity investigations led to the path to understanding the lipid structure and its transfection efficiency. The trend in the transfection profiles of linker-based lipids is different from linker-less lipids. Influence of unsaturation in the hydrophobic chains has been investigated in linker-based lipids. However, in linker-less lipids, it remains unexplored. Herein, we demonstrate that the designed cationic lipid Lipid S-U with an asymmetric hydrophobic core having one stearyl (18:0) and one oleyl chain (18:1) showed superior transfection efficiency compared to its symmetric counterparts, Lipid S-S (hydrophobic core comprising of two stearyl chains (18:0)), and Lipid U-U (two oleyl chains (18:1)), in vitro. Mechanistic studies involving membrane fusogenicity with FACS revealed that liposomes of Lipid S-U have higher fusogenicity (89%) with B16F10 cell membrane than saturated Lipid S-S (66%) and unsaturated Lipid U-U (70%). Endosomal escape studies with confocal microscopy in HEK 293 cells revealed that lipoplexes of Lipid S-U had a higher endosomal escape and released the genetic payload in cytoplasm more efficiently than saturated Lipid S-S and unsaturated Lipid U-U. These cumulative findings support the notion that higher cellular uptake and endosomal escape resulting from fusogenic liposomes of Lipid S-U play a pivotal role in the higher transfection efficiency of asymmetric Lipid S-U.

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.

LIPID NANO PARTICLES COMPRISING CATIONIC LIPID FOR DRUG DELIVERY SYSTEM

The present invention provides a lipid nano-particles, which allow nucleic acids to be easily introduced into cells, comprising a cationic lipid represented by formula (I) (wherein: R1 and R2 are, the same or different, alkenyl, etc, andX3 is absent or is alkyl, etc,X1 and X2 are hydrogen atoms, or are combined together to form a single bond or alkylene, andY1 is absent or anion,L1 is a single bond, etc,R3 is alkyl, etc), and the like.

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.

CATIONIC LIPID

The present invention provides a cationic lipid and the like. The cationic lipid is for delivering a medicament containing a cationic lipid which facilitates the introduction of a nucleic acid into a cell or the like, and is represented by formula (I). In the formula, R1 is linear or branched alkyl, alkenyl, or alkynyl, each having 8 to 24 carbon atoms, R2 is linear or branched alkyl, alkenyl, or alkynyl, each having 8 to 24 carbon atoms, or alkoxyethylene, alkoxypropylene, alkenyloxyethylene, alkenyloxypropylene, alkynyloxyethylene, or alkynyloxypropylene, R3 and R4 may be the same or different, and are each alkyl having 1 to 3 carbon atoms or are combined together to form alkylene having 2 to 6 carbon atoms, or R3 and R5 are combined together to form alkylene having 2 to 6 carbon atoms, R5 is a hydrogen atom, alkyl having 1 to 6 carbon atoms, alkenyl having 3 to 6 carbon atoms, amino, monoalkylamino, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, or the like, or is combined together with R3 to form alkylene having 2 to 6 carbon atoms, X is alkylene having 1 to 6 carbon atoms, and Y is a single bond, alkylene having 1 to 6 carbon atoms, or the like.

LIPID NANO PARTICLES COMPRISING COMBINATION OF CATIONIC LIPID

The present invention provides a lipid nano-particles, which allow nucleic acids to be easily introduced into cells, comprising a cationic lipid represented by formula (I) (wherein: R1 and R2 are, the same or different, alkenyl, etc, and X3 is absent or is alkyl, etc, X1 and X2 are hydrogen atoms, or are combined together to form a single bond or alkylene, and Y1 is absent or anion, L1 is a single bond, etc, R3 is alkyl, etc), and a cationic lipid represented by formula (II) (wherein: R4 and R5 are, the same or different, alkenyl, etc, and X4 and X5 are hydrogen atoms, or are combined together to form a single bond or alkylene, and X6 is absent or is alkyl, etc, Y2 is absent or anion, a and b are, the same or different, 0 to 3, and L4 is a single bond, etc, R6 is alkyl, etc, L2 and L3 are —O—, —CO—O— or —O—CO—), and the like.

Anchor dependency for non-glycerol based cationic lipofectins: Mixed bag of regular and anomalous transfection profiles

Although detailed structure-activity, physicochemical and biophysical investigations in probing the anchor influence in liposomal gene delivery have been reported for glycerol-based transfection lipids, the corresponding investigation for non-glycerol based simple monocationic transfection lipids have not yet been undertaken. Towards this end, herein, we delineate our structure-activity and physicochemical approach in deciphering the anchor dependency in liposomal gene delivery using fifteen new structural analogues (lipids 1-15) of recently reported non-glycerol based monocationic transfection lipids. The C14 analogues in both series 1 (lipids 1-6) and series 2 (lipids 7-15) showed maximum efficiency in transfecting COS-1 and CHO cells. However, the C12 analogue of the ether series (lipid 3) exhibited a seemingly anomalous behavior compared with its transfection efficient C10 and C14 analogues (lipids 2 and 4) in being completely inefficient to transfect both COS-1 and CHO cells. The present structure-activity investigation also convincingly demonstrates that enhancement of transfection efficiencies through incorporation of membrane re-organizing unsaturation elements in the hydrophobic anchor of cationic lipids is not universal but cell dependent. The strength of the interaction of lipids 1-15 with DNA was assessed by their ability to exclude ethidium bromide bound to the DNA. Cationic lipids with long hydrophobic tails were found, in general, to be efficient in excluding EtBr from DNA. Gel to liquid crystalline transition temperatures of the lipids was measured by fluorescence anisotropy measurement technique. In general (lipid 2 being an exception), transfection efficient lipids were found to have their mid transition temperatures at or below physiological temperatures (37°C).