6110-53-8

Usage

Uses

Used in Pharmaceutical Industry:
1-BROMO-CIS-9-OCTADECENE is used as a starting material for the synthesis of oleylphosphonates, which are potential inhibitors of diacylglycerol lipase (DAGL) and monoacylglycerol lipase (MAGL). These enzymes play a crucial role in the regulation of endocannabinoid signaling pathways, which are involved in various physiological processes, including pain, inflammation, and mood regulation. By inhibiting these enzymes, oleylphosphonates may have potential therapeutic applications in the treatment of various diseases and conditions.
Used in Chemical Synthesis:
1-BROMO-CIS-9-OCTADECENE is also used as a versatile building block in the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure allows for a wide range of chemical reactions, including addition, substitution, and elimination reactions, making it a valuable intermediate in the development of new and innovative products.

InChI:InChI=1/C18H35Br/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10H,2-8,11-18H2,1H3/b10-9-

Upstream product

• 143-28-2 oleoyl alcohol 
• 35709-09-2 oleyl methanesulfonate 
• 112-62-9 Methyl oleate 
• 111-62-6 oleic acid ethyl ester 
• 558-13-4 carbon tetrabromide 
• 112-80-1 cis-Octadecenoic acid 
• 143-28-2 oleyl alcohol 
• 57205-42-2 (Z)-1-methoxyoctadec-9-ene 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 10035-10-6 hydrogen bromide 

Downstream Products

• 5561-99-9 11-eicosenoic acid 
• 62322-84-3 trans-11-eicosenoic acid 
• 31494-22-1 cis-octadec-9-enethiol 
• 14727-68-5 N,N-dimethyl-N-oleylamine 
• 1120-34-9 methyl cis-13-docosenoate 
• 108045-05-2 methyl (Z)-hexacos-17-enoate 
• 141735-39-9 C₃₉H₆₅NO₄S 
• 143262-32-2 9-(Z)-octadecenyl phenyl sulphide 
• 254963-99-0 (Z)-1-Benzyloxy-docos-13-en-4-ol 
• 254963-81-0 1-benzyloxy-heneicos-12-en-3-ol 
• 104162-47-2 DODMA 
• 926652-62-2 3,4-bis-octadec-9-enyloxy-benzoic acid ethyl ester 
• 926652-61-1 dioleyloxybenzaldehyde 
• 28728-55-4 1,3-propanediyl-bis(N,N-dimethyl-N-oleylammonium) dibromide 

Relevant academic research and scientific papers

A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids

Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the fatty acid field of a previously published protocol for manganese-based Wurtz type coupling of alkyl bromides. 22-Bromo-3(Z),6(Z),9(Z),12(Z),15(Z),18(Z)-docosahexaene, easily prepared from 4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)-docosahexaenoic acid, was coupled to homologous ω-bromoesters by stirring for 4 hours at 40°C in the presence of manganese powder, a nickel catalyst and terpyridine. This afforded in yields of 70–75% a series of ω3-hexaenoates of chain lengths of 32–40 carbons. The corresponding fatty acids of >98% purity were obtained following saponification and final purification. By using methyl [2,2,3,3,4,4-2H6]10-bromodecanoate as coupling partner it was possible to prepare a very long chain fatty acid in isotopically labeled form, i.e., [2,2,3,3,4,4-2H6]14(Z),17(Z),20(Z),23(Z),26(Z),29(Z)-dotriacontahexaenoic acid. Also prepared were the monounsaturated long chain fatty acids 15(Z)-octadecenoic acid and 15(Z)-tetracosenoic acid. Very long chain fatty acids have been isolated from retina and other tissues and are of biological relevance. The methodology described will assist in further analytical and biological studies in this field.

O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions were found to improve the formation of a main isomer during the O,O-silyl group migrations that could be integrated into the formal synthesis of vitamin D receptor modulator VS-105 and in the first total synthesis of a metabolite from the African ant Crematogaster nigriceps.

Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action

Here we report the synthesis and biological evaluation of a series of new 2-hydroxybenzylphosphonium salts (QPS) with antimicrobial and antitumor dual action. The most active compounds exhibit antimicrobial activity at a micromolar level against Gram-positive bacteria Sa (ATCC 209p and clinical isolates), Bc (1–2 μM) and fungi Tm and Ca, and induced no notable hemolysis at MIC. The change in nature of substituents of the same length led to a drastic change of biological activity. Self-assembly behavior of the octadecyl and oleyl derivatives was studied. QPS demonstrated self-assembly within the micromolar range with the formation of nanosized aggregates capable of the solubilizing hydrophobic probe. The synthesized phosphonium salts were tested for cytotoxicity. The most potent salt was active against on M?Hela cell line with IC50 on the level of doxorubicin and good selectivity. According to the cytofluorimetry analysis, the salts induced mitochondria-dependent apoptosis.

OLEIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION OR FOOD COMPOSITION COMPRISING SAID OLEIC ACID DERIVATIVES, AND THEIR USES

This invention relates to oleic acid derivative comprising a hydrophobic part C17H33 linked to a particular polar head part "A", especially for use as a medicament, for instance, for the treatment of a disorder caused by the GPR120 receptor and/or the CD36 receptor, comprising administering to a subject in need thereof a therapeutically effective amount of said oleic acid derivative or of said pharmaceutical composition. The invention also relates to the use of said oleic acid derivative as a food composition.

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.

At Long Last: Olefin Metathesis Macrocyclization at High Concentration

Macrocyclic lactones, ketones, and ethers can be obtained in the High-Concentration Ring-Closing Metathesis (HC-RCM) reaction in high yield and selectivity at concentrations 40 to 380 times higher than those typically used by organic chemists for similar macrocyclizations. The new method consists of using tailored ruthenium catalysts together with applying vacuum to distill off the macrocyclic product as it is formed by the metathetical backbiting of oligomers. Unlike classical RCM, no large quantities of organic solvents are used, but rather inexpensive nonvolatile diluents, such as natural or synthetic paraffin oils. Moreover, use of a protecting atmosphere or a glovebox is not needed, as the new catalysts are perfectly moisture and air stable. In addition, some other cyclic compounds previously reported as unobtainable by RCM in neat conditions, or in high dilutions even, can be formed with the help of the HC-RCM method.

Synthesis of Phosphonic Acid Ligands for Nanocrystal Surface Functionalization and Solution Processed Memristors

Here, we synthesized 2-ethylhexyl, 2-hexyldecyl, 2-[2-(2-methoxyethoxy)ethoxy]ethyl, oleyl, and n-octadecyl phosphonic acid and used them to functionalize CdSe and HfO2 nanocrystals. In contrast to branched carboxylic acids, postsynthetic surface functionalization of CdSe and HfO2 nanocrystals was readily achieved with branched phosphonic acids. Phosphonic acid capped HfO2 nanocrystals were subsequently evaluated as memristors using conductive atomic force microscopy. We found that 2-ethylhexyl phosphonic acid is a superior ligand, combining a high colloidal stability with a compact ligand shell that results in a record-low operating voltage that is promising for application in flexible electronics.

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.

COMPOSITIONS AND METHODS FOR DELIVERY OF THERAPEUTIC AGENTS

This disclosure provides improved lipid-based compositions, including lipid nanoparticle compositions, and methods of use thereof for delivering agents in vivo including nucleic acids and proteins. These compositions are not subject to accelerated blood clearance and they have an improved toxicity profile in vivo.

Lipid modified spermine derivatives and the use of the derivatives of the prepared liposome

The invention provides a liposome-modified spermine derivative and a liposome prepared by the derivative. The spermine derivative is directly applied or is mixed with one or more selected from cholesterol, neutral lipids and polyethylene glycol (PEG)-modified lipids, which can be adopted as a carrier for entrapping or absorbing bioactive molecular drugs to be loaded into cells. In this way, the effect of regulation, intervention or treatment is realized. In a general formula (1), X1 represents -(CH2)- or carbonyl group, wherein n represents 1, 2 or 3; X2 represents -(CH2)-, ester group, amide group, oxygen, or sulfur; R1 and R2 independently represent C6-C18 alkyl group or lipophilic cholesterol molecules, respectively.