875685-44-2

Usage

Uses

Used in Pharmaceutical Industry:
9-Nitrooleate is used as an endogenous PPARγ agonist for the treatment of obesity and obesity-related conditions, offering an effective and safe therapeutic intervention.
Used in Cardiovascular Research:
9-Nitrooleate is used as a novel antagonist of Angiotensin II-induced hypertension, potentially providing a new approach to managing blood pressure and related cardiovascular conditions.
Used in Enzyme Inhibition:
9-Nitrooleate acts as an irreversible inhibitor of xanthine oxidoreductase, which may have implications in the treatment of gout and other conditions related to purine metabolism.

Upstream product

• 16700-68-8 (E)-methyl 9-nitrooctadec-9-enoate 
• 124-19-6 nonan-1-al 
• 41059-02-3 9-bromononanoic acid 
• 931-88-4 cis-Cyclooctene 
• 3884-92-2 methyl 8-oxooctanoate 
• 109849-93-6 9-bromononanoic acid allyl ester 
• 911029-14-6 10-acetoxy-9-nitro-octadecanoic acid allyl ester 
• 911029-07-7 9-nitrononanoic acid allyl ester 
• 911029-11-3 10-hydroxy-9-nitro-octadecanoic acid allyl ester 
• 911029-52-2 (E)-9-nitro-octadec-9-enoic acid allyl ester 
• 931-88-4 1,2-cyclooctene 
• 112-80-1 cis-Octadecenoic acid 
• 616-47-7 1-methyl-1H-imidazole 
• 4659-45-4 2,6-Dichlorobenzoyl chloride 

Relevant academic research and scientific papers

Streamlined One-Pot Synthesis of Nitro Fatty Acids

A novel method for the synthesis of nitro fatty acids (NFAs), an intriguing class of endogenously occurring lipid mediators, is reported. This one-pot procedure enables the controlled and stereoselective construction of nitro fatty acids from a simple set of common building blocks in a highly facile manner. Thereby, this methodology offers a streamlined, highly modular access to naturally occurring nitro fatty acids as well as non-natural NFA derivatives.

Synthesis of 1-Palmitoyl-2-((E)-9- and (E)-10-nitrooleoyl)- sn -glycero-3-phosphatidylcholines

Extensive investigation of nitrated phospholipids in connection with various biologically important processes requires reliable access to suitable material. A selective chemical synthesis introducing a defined nitrofatty acid at the sn -2 position of a 2-lyso sn -glycero-3-phosphatidylcholine was developed. Given that the nitroalkene moiety of both reactant nitrofatty acid derivative and the product esters is characterised by particular sensitivity to nucleophile addition and, depending on the intermediate, subsequent olefin isomerisation and retro-Henry-type reaction, a reliable two-step ester formation was introduced. The activation of the nitrofatty acid succeeded after reaction with trichlorobenzoyl chloride, and the mixed anhydride could be isolated via extractive work-up. Subsequent reaction with 1-palmitoyl-2-lyso- sn -glycero-3-phosphatidylcholine enabled the sn -2 esterification to be achieved with high yield by using a minimum of reagents, avoiding the formation of side products and facilitating final isolation and purification.

Nitrated Fatty Acids Modulate the Physical Properties of Model Membranes and the Structure of Transmembrane Proteins

Nitrated fatty acids (NO2-FAs) act as anti-inflammatory signal mediators, albeit the molecular mechanisms behind NO2-FAs’ influence on diverse metabolic and signaling pathways in inflamed tissues are essentially elusive. Here, we combine fluorescence measurements with surface-specific sum frequency generation vibrational spectroscopy and coarse-grained computer simulations to demonstrate that NO2-FAs alter lipid organization by accumulation at the membrane–water interface. As the function of membrane proteins strongly depends on both, protein structure as well as membrane properties, we consecutively follow the structural dynamics of an integral membrane protein in presence of NO2-FAs. Based on our results, we suggest a molecular mechanism of the NO2-FA in vivo activity: Driven by the NO2-FA-induced lipid layer reorganization, the structure and function of membrane-associated (signaling) proteins is indirectly affected.

Modular Regiospecific Synthesis of Nitrated Fatty Acids

Endogenous nitrated fatty acids are an important class of signaling molecules. Herein a modular route for the efficient and regiospecific preparation of nitrooleic acids as well as various analogues is described. The approach is based on a simple set of alkyl halides as common building blocks and a Henry reaction/Burgess dehydration sequence for the formation of the key nitroalkene moiety.

BIOPASSIVATING MEMBRANE STABILIZATION BY MEANS OF NITROCARBOXYLIC ACID-CONTAINING PHOSPHOLIPIDS IN PREPARATIONS AND COATINGS

The present invention relates to nitro-carboxylic acid (s)-containing phospholipids, to be used for coating of medical devices such as stents, catheter balloons, wound pads or surgical suture material and for bio-passivating compositions, such as rinses, waterproofing solutions, coating solutions, cryoprotection solutions, cold preservation media, lyoprotection solutions, contrast media solutions, preservation and reperfusion solutions containing these compounds as well as preparing solutions thereof and coating medical devices as well as their uses.

HETEROATOM CONTAINING SUBSTITUTED FATTY ACIDS

Activated fatty acids, pharmaceutical compositions including activated fatty acids, methods for using activated fatty acids to treat a variety of diseases, and methods for preparing activated fatty acids are provided herein.

VINYL SUBSTITUTED FATTY ACIDS

Activated fatty acids, pharmaceutical compositions including activated fatty acids, methods for using activated fatty acids to treat a variety of diseases, and methods for preparing activated fatty acids are provided herein.

Regio- and stereospecific syntheses and nitric oxide donor properties of (E)-9- and (E)-10-nitrooctadec-9-enoic acids

Nitrated fatty acids act as endogenous peroxisome proliferator-activated receptor γ (PPARγ) ligands and nitric oxide (NO) donors. We describe the first specific preparation of the two regioisomers of nitrooleic acid, (E)-9-nitrooctadec-9-enoic acid (1) an

Synthesis of nitrolipids. All four possible diastereomers of nitrooleic acids: (E)- and (Z)-, 9- and 10-nitro-octadec-9-enoic acids

Unsaturated fatty acids are nitrated endogenously to produce nitrated lipids. Recent studies have shown that these nitrated lipids have high chemical reactivity and profound biological implications. We report an efficient, scalable synthesis which is regiospecific and stereoselective for all possible isomers of nitrated oleic acid: (E)- and (Z)-, 9- and 10-octadec-9-enoic acids.

NITRATED LIPIDS AND METHODS OF MAKING AND USING THEREOF

Described herein are nitrated lipids and methods of making and using the nitrated lipids.