35709-09-2

Usage

Uses

Used in Cosmetic Industry:
CIS-9-OCTADECENYL METHANESULFONATE is used as a nonionic surfactant for its emulsifying, emollient, and thickening properties in skin creams, lotions, and other cosmetic products. It helps to create stable emulsions and improve the texture and feel of these products, providing a smooth and moisturizing experience for the user.
Used in Pharmaceutical Industry:
CIS-9-OCTADECENYL METHANESULFONATE is used as a starting material in the synthesis of lipidic alcohols and amines, which are essential components in the development of various pharmaceutical products. These synthesized compounds can be used in drug delivery systems, enhancing the bioavailability and efficacy of medications.

InChI:InChI=1/C19H38O3S/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-23(2,20)21/h10-11H,3-9,12-19H2,1-2H3/b11-10+

Upstream product

• 143-28-2 oleoyl alcohol 
• 124-63-0 methanesulfonyl chloride 
• 60-29-7 diethyl ether 
• 19788-74-0 cis-10-nonadecenoic acid methyl ester 
• 112-62-9 Methyl oleate 

Downstream Products

• 593-31-7 rac-1-(Z-9-octadecenyl)glycerol 
• 84696-69-5 N-oleylmorpholine 
• 150844-25-0 1-O-(4-methoxybenzyl)-2-O-methyl-3-O-(cis-9-octadecenyl)-sn-glycerol 
• 150844-23-8 1,6-di-O-(cis-9-octadecenyl)-2,5-di-O-methyl-3,4-bis-O-(4-methoxybenzyl)-D-mannitol 
• 13044-38-7 (Z)-1-bromo-9-octadecene 
• 22297-32-1 1-[(triphenylcarbinyl)oxy]-2,3-bis[(Z)-octadec-9-enyloxy]propane 
• 291312-49-7 2-(9-octadecenyl)-1,3-benzylideneglycerol 
• 104162-47-2 DODMA 
• 66-27-3 Methyl methanesulfonate 
• 926652-61-1 dioleyloxybenzaldehyde 
• 1189331-85-8 (5R)-4-benzyl-5-oleyloxymethyl-[1,3,4]-oxathiazinane-3,3-dioxide 
• 1189332-05-5 (5S)-4-benzyl-5-oleyloxymethyl-[1,3,4]-oxathiazinane-3,3-dioxide 
• 1346224-29-0 (3R,4R)-1-benzyl-3,4-bis((Z)-octadec-9-enyloxy)pyrrolidine 
• 40165-68-2 di((Z)-octadec-9-enyl)amine 

Relevant academic research and scientific papers

Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities

Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.

Nucleic acid medicine delivery system and application thereof

The invention discloses a nucleic acid medicine delivery system and application thereof. The system consists of a neutral base lipid carrier and metal salt, wherein the structure of the neutral base lipid carrier is shown as a formula I. In addition, the delivery system provided by the invention also comprises metal salt. The experiment proves that through the existence of metal ion, the silent activity of the nucleic acid medicine can be effectively improved; the effective transportation of the nucleic acid medicine in the cells and in the body can be realized. The chemical modification methods such as D,L-isonucleoside modification, deoxyinosine modification, peptide conjugation modification and phosphorylation modification are jointly used for nucleic acid delivery system study; the advantages and rules of the nucleic acid delivery in a composite modification mode are sufficiently explored; the modification strategies are used in the nucleic acid medicine study. Study proves that the products obtained through chemical modification are more applicable to the system; in addition, the advantages of stable physicochemical properties, good bioactivity and good membrane permeability and the like are realized. The nucleic acid medicine delivery system provided by the invention has wide application prospects in the gene treatment field. The formula is shown in the description.

COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF AGENTS

The disclosure features amino lipids and compositions involving the same. Nanoparticle compositions include an amino lipid as well as additional lipids such as phospholipids, structural lipids, PEG lipids, or a combination thereof. Nanoparticle compositions further including therapeutic and/or prophylactic agents such as RNA are useful in the delivery of therapeutic and/or prophylactic agents to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.

COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF AGENTS

The disclosure features amino lipids and compositions involving the same. Nanoparticle compositions include an amino lipid as well as additional lipids such as phospholipids, structural lipids, PEG lipids, or a combination thereof. Nanoparticle compositions further including therapeutic and/or prophylactic agents such as RNA are useful in the delivery of therapeutic and/or prophylactic agents to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.

MANUFACTURING METHOD OF CATIONIC LIPID

PROBLEM TO BE SOLVED: To provide a manufacturing method of industrial cationic lipid capable of efficiently providing high purity cationic lipid without needs for special facility. SOLUTION: A cationic lipid represented by the formula (2) is obtained by mixing cationic lipid represented by the formula (1) and a tetraalkylammonium salt having X- in an organic solvent, filtering deposited tetraalkylammonium iodide to obtain a filtrate and concentrating the filtrate to deposit tetraalkylammonium iodide. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Supramolecular assemblies of novel aminonucleoside phospholipids and their bonding to nucleic acids

A novel class of aminonucleoside phospholipids has been developed. These molecules could spontaneously assemble into supramolecular structures including multilamellar organization, hydrogels, superhelical strands, and vesicles. Their ability to bind to DNA by hydrogen bonding and π-π stacking interactions was investigated by many means. This journal is

Synthesis of antimitotic thioglycosides: In vitro and in vivo evaluation of their anticancer activity

The synthesis and biological activity of oleylN-acetyl-α- and β-d-glucosaminides (1 and 2, respectively) and their thioglycosyl analogues (3 and 4, respectively) are reported. The compounds exhibited antimitotic activity on rat glioma (C6) and human lung carcinoma (A549) cell cultures in the micromolar range. Analysis of cell extracts using ultra performance liquid chromatography-mass spectrometry showed that the synthetic glycosides produce alterations in glycosphingolipid metabolism, with variable effect on the level of glucosylceramide depending on the configuration of the antimitotic used. In vivo experiments in nude mice bearing an implanted C6 glioma showed that the α-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides.

Alkyl sulfonyl derivatized PAMAM-G2 dendrimers as nonviral gene delivery vectors with improved transfection efficiencies

Amphiphilic dendrimer-based gene delivery vectors bearing peripheral alkyl sulfonyl hydrophobic tails were constructed using low-generation PAMAM-G2 as the core and functionalized by means of the aza-Michael type addition of its primary amino groups to vinylsulfone derivatives as an efficient tool for surface engineering. While the unmodified PAMAM-G2 was unable to efficiently transfect eukaryotic cells, functionalized PAMAM-G2 dendrimers were able to bind DNA at low N/P ratios, protect DNA from digestion with DNase I and showed high transfection efficiencies and low cytotoxicity. Dendrimers with a C18 alkyl chain produced transfection efficiencies up to 3.1 fold higher than LipofectAMINE 2000 in CHO-k1 cells. The dendriplexes based in functionalized PAMAM-G2 also showed the ability to retain their transfection properties in the presence of serum and the ability to transfect different eukaryotic cell lines such as Neuro-2A and RAW 264.7. Taking advantage of the vinylsulfone chemistry, fluorescent PAMAM-G2 derivatives of these vectors were prepared as molecular probes to determine cellular uptake and internalization through a clathrin-independent mechanism.

Versatile site-specific conjugation of small molecules to siRNA using click chemistry

We have previously demonstrated that conjugation of small molecule ligands to small interfering RNAs (siRNAs) and anti-microRNAs results in functional siRNAs and antagomirs in vivo. Here we report on the development of an efficient chemical strategy to make oligoribonucleotide-ligand conjugates using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) or click reaction. Three click reaction approaches were evaluated for their feasibility and suitability for high-throughput synthesis: the CuAAC reaction at the monomer level prior to oligonucleotide synthesis, the solution-phase postsynthetic "click conjugation", and the "click conjugation" on an immobilized and completely protected alkyne-oligonucleotide scaffold. Nucleosides bearing 5′-alkyne moieties were used for conjugation to the 5′-end of the oligonucleotide. Previously described 2′-and 3′-O-propargylated nucleosides were prepared to introduce the alkyne moiety to the 3′ and 5′ termini and to the internal positions of the scaffold. Azido-functionalized ligands bearing lipophilic long chain alkyls, cholesterol, oligoamine, and carbohydrate were utilized to study the effect of physicochemical characteristics of the incoming azide on click conjugation to the alkyne-oligonucleotide scaffold in solution and on immobilized solid support. We found that microwave-assisted click conjugation of azido-functionalized ligands to a fully protected solid-support bound alkyne-oligonucleotide prior to deprotection was the most efficient "click conjugation" strategy for site-specific, high-throughput oligonucleotide conjugate synthesis tested. The siRNA conjugates synthesized using this approach effectively silenced expression of a luciferase gene in a stably transformed HeLa cell line.(Figure Presented)

Hypocholesterolemic activity of hesperetin derivatives

Hesperetin ester and ether derivatives possessing a long alkyl chain were synthesized for examining their hypocholesterolemic activities in high cholesterol-fed mice. Hesperetin 7-O-lauryl ether (4b) and hesperetin 7-O-oleyl ether (4e) exhibited strong cholesterol-lowering effects.