64833-92-7

Usage

Uses

Used in Diagnostic Applications:
Oleoylimidazolide is used as an intermediate in the synthesis of Oleoyl-L-carnitine-d3 (O526702), which is a labelled version of Oleoyl-L-carnitine (O526700, HCl salt). Oleoyl-L-carnitine is a long-chain fatty ester of carnitine that is accumulated and released into the circulation in cases of fatty-acid oxidation defects. The pattern of Oleoyl-L-carnitine can be diagnostic for a number of β-oxidation defects, making oleoylimidazolide an essential component in the development of diagnostic tools for these conditions.
Used in Pharmaceutical Industry:
Oleoylimidazolide is used as a key intermediate in the synthesis of Oleoyl-L-carnitine, which has potential therapeutic applications in the treatment of fatty-acid oxidation defects. By facilitating the production of Oleoyl-L-carnitine, oleoylimidazolide plays a crucial role in the development of pharmaceuticals that can help address these metabolic disorders.

InChI:InChI=1/C21H36N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)23-19-18-22-20-23/h9-10,18-20H,2-8,11-17H2,1H3/b10-9-

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 10335-69-0 Oleylhydroxamic acid 
• 103634-10-2 1-trityl-2-(octadec-cis-9-enoyl)-sn-glycero-3-phosphocholine 

Relevant academic research and scientific papers

Unveiling the Structure and Reactivity of Fatty-Acid Based (Nano)materials Thanks to Efficient and Scalable 17O and 18O-Isotopic Labeling Schemes

Fatty acids are ubiquitous in biological systems and widely used in materials science, including for the formulation of drugs and the surface-functionalization of nanoparticles. However, important questions regarding the structure and reactivity of these molecules are still to be elucidated, including their mode of binding to certain metal cations or materials surfaces. In this context, we have developed novel, efficient, user-friendly, and cost-effective synthetic protocols based on ball-milling, for the 17O and 18O isotopic labeling of two key fatty acids which are widely used in (nano)materials science, namely stearic and oleic acid. Labeled molecules were analyzed by 1H and 13C solution NMR, IR spectroscopy, and mass spectrometry (ESI-TOF and LC-MS), as well as 17O solid state NMR (for the 17O labeled species). In both cases, the labeling procedures were scaled-up to produce up to gram quantities of 17O- or 18O-enriched molecules in just half-a-day, with very good synthetic yields (all ≥84%) and enrichment levels (up to an average of 46% per carboxylic oxygen). The 17O-labeled oleic acid was then used for the synthesis of a metal soap (Zn-oleate) and the surface-functionalization of ZnO nanoparticles (NPs), which were characterized for the first time by high-resolution 17O NMR (at 14.1 and 35.2 T). This allowed very detailed insight into (i) the coordination mode of the oleate ligand in Zn-oleate to be achieved (including information on Zn···O distances) and (ii) the mode of attachment of oleic-acid at the surface of ZnO (including novel information on its photoreactivity upon UV-irradiation). Overall, this work demonstrates the high interest of these fatty acid-enrichment protocols for understanding the structure and reactivity of a variety of functional (nano)materials systems using high resolution analyses like 17O NMR.

An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives

An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high-energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies. (Figure presented.).

Synthesis of Benzophenone-Containing Analogues of Phosphatidylcholine

As part of a collaborative study of cellular efflux of cholesterol and phospholipids, photoactivable analogues 4-8 of phosphatidylcholine (PC) having benzophenone groups in the choline moiety and at the end of the C2 and C1 alkyl chains have been synthesized. The efficient preparation via Suzuki coupling of the appropriate long-chain benzophenone-containing carboxylic acid and alcohol and their incorporation by adaptation of known approaches into the acyl- and ether-linked PC analogues 6-8 are described. Development of a method for radiolabeling these PC analogues, via hydrogenation of a double bond in modified side chains, is also described.

Synthesis of phosphatidylcholines containing ricinoleic acid

1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields. The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final products. Several protecting groups were assayed but only β-methoxyethoxymethyl chloride (MEMCl) and 2,2,2-trichloroethyl chloroformate (TRECCl) gave reasonable yields and good optical purities of the final products. The overall yields for 1,2-diricinoleoyl-sn-glycero-3-phosphocholine and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were 32.1% (with respect to ricinoleic acid methyl ester using TREC as protecting group) and 10.3% (with respect to 1-trityl-glycero-3-phosphocholine), respectively.