774603-04-2

Usage

Uses

Used in Pharmaceutical Industry:
(9E,12Z)-10-Nitrooctadecadienoic acid is used as a therapeutic agent for the treatment of various diseases, particularly those related to inflammation and metabolic disorders. As a PPARγ agonist, it modulates the activity of this nuclear receptor, which plays a crucial role in the regulation of cellular differentiation, inflammation, and lipid and glucose homeostasis. This makes it a promising candidate for the development of drugs targeting conditions such as type 2 diabetes, atherosclerosis, and obesity.
Used in Research Applications:
In the field of scientific research, (9E,12Z)-10-Nitrooctadecadienoic acid serves as an important tool for studying the role of PPARγ in cellular processes and disease mechanisms. It can be used to investigate the effects of PPARγ activation on gene expression, cellular signaling pathways, and the development of various pathologies. This knowledge can contribute to the understanding of disease etiology and the identification of novel therapeutic targets.
Used in Drug Development:
(9E,12Z)-10-Nitrooctadecadienoic acid is utilized in the development of new drugs targeting PPARγ, which may have applications in treating a range of diseases beyond metabolic disorders. Its use in drug development can lead to the creation of more effective and targeted therapies with fewer side effects, as it allows researchers to explore the potential of PPARγ agonism in various disease contexts.
Used in Chemical Synthesis:
In the chemical industry, (9E,12Z)-10-Nitrooctadecadienoic acid may be employed as a starting material or intermediate in the synthesis of other bioactive compounds or pharmaceuticals. Its unique structure and functional groups can be further modified or used to create novel molecules with specific biological activities, expanding the scope of its applications in various fields.

InChI:InChI=1/C18H31NO4/c1-2-3-4-5-8-11-14-17(19(22)23)15-12-9-6-7-10-13-16-18(20)21/h8,11,15H,2-7,9-10,12-14,16H2,1H3,(H,20,21)/b11-8-,17-15+

Upstream product

• 1051325-65-5 allyl (9E,12Z)-10-nitrooctadeca-9,12-dienoate 
• 60-33-3 linoleic acid 
• 774603-02-0 (9E,12Z)-methyl 10-nitrooctadeca-9,12-dienoate 

Relevant academic research and scientific papers

Stereocontrolled synthesis of the PPAR-γ agonist 10-nitrolinoleic acid

(Figure presented) The naturally occurring PPAR-γ ligand 10-nitrooctadeca-9(E),12(Z)-dienoic acid (10-nitrolinoleic acid) (2a) was prepared as a single regio- and geometrical isomer in a practical eight-step, convergent sequence. The synthetic route featured a nitro aldol reaction between 9-oxononanoic acid methyl ester (3) and 1-nitronon-3(Z)-ene (4) in the key carbon-carbon bond forming step. The ability of 2a (and its methyl ester 9) to bind to PPAR-γ in a ligand-binding assay is reported.

Chemistry of nitrated lipids: Remarkable instability of 9-nitrolinoleic acid in neutral aqueous medium and a novel nitronitrate ester product by concurrent autoxidation/nitric oxide-release pathways

(Chemical Equation Presented) Despite the mounting interest in nitrolinoleic acids and related nitrated polyunsaturated fatty acids as a novel class of bioactive signaling lipids, their chemistry and metabolic fate have remained poorly elucidated. Herein, we report an expedient nitroselenenylation/ oxidation route to 9-nitrolinoleic acid (1) and 10-nitrolinoleic acid (2), which enabled comparative product studies under physiologically relevant conditions. Under biomimetic conditions, 1 decayed at an unusually fast rate to give the hydroxy-, keto-, and nitronitrate ester derivatives 3, 4, and 5 as main products, identified by ESI-MS and 2D NMR spectroscopy, including 1H,15N HMBC experiments on the 15N-labeled derivatives. The 13-nitrato functionality in 5 suggested partitioning of 1 between concurrent peroxidation and nitric oxide (NO)-release pathways. Lipid 2 decayed at a much slower rate giving only the hydroxynitro derivative 6 as an isolable product. Diphenylpicrylhydrazide (DPPH) radical quenching experiments and DFT computations concurred to support a higher H-atom donating ability of 1 versus 2, due to more effective stabilization of the resulting pentadienyl radical by the terminal nitro group. The markedly different stability of isomeric nitrolinoleic acids disclosed in the present study may provide an explanation for the previous identification of 2, but not 1, in body fluids and offers a key for future insights into the biological activities of nitrated lipids.