7459-35-0

Usage

InChI:InChI=1/C18H33ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3/b10-9+

Upstream product

• 79-37-8 oxalyl dichloride 
• 112-79-8 Elaidic acid 

Downstream Products

• 537-39-3 trielaidin 
• 10564-36-0 cis-5-elaidoyloxy-2-phenyl-[1,3]dioxane 
• 112-90-3 trans-oleylamine 
• 150988-85-5 8-((2S,3S)-3-Octyl-oxiranyl)-octanoic acid 4-hydroxy-3-methoxy-benzylamide 
• 210980-89-5 elaidic acid chloramphenicol ester 
• 1345866-03-6 hydroxytyrosol elaidate 
• 72809-08-6 2-(oleamido)propane-1,3-diol 
• 4303-70-2 (E)-9-octadecenoic acid amide 
• 112-79-8 Elaidic acid 
• 93452-41-6 1-Stearo-2,3-dielaidin 
• 68069-77-2 1-Palmito-2,3-dielaidin 
• 77262-56-7 (E)-Octadec-9-enoic acid 1-{4-[4-(3-chloro-tetrahydro-furan-2-yloxy)-butoxy]-phenyl}-propyl ester 
• 95548-23-5 N-vanillyl-9E-octadecenamide 
• 74420-96-5 N-isobutyl-elaidamide 

Relevant academic research and scientific papers

Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids

A decarboxylative borylation of aliphatic acids for the synthesis of a variety of alkylboronates has been developed by mixing m-chloroperoxybenzoic acid (mCPBA)-activated fatty acids with bis(catecholato)diboron in N,N-dimethylformamide (DMF) at room temperature. A radical chain process is involved in the reaction which initiates from the B-B bond homolysis followed by the radical transfer from the boron atom to the carbon atom with subsequent decarboxylation and borylation.

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.

Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration

N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.

Synthesis and evaluation of fatty acid amides on the N-oleoylethanolamide-like activation of peroxisome proliferator activated receptor α

A series of fatty acid amides were synthesized and their peroxisome proliferator-activated receptor α (PPAR-α) agonistic activities were evaluated in a normal rat liver cell line, clone 9. The mRNAs of the PPAR-α downstream genes, carnitine-palmitoyltransferase-1 and mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase, were determined by real-time reverse transcription-polymerase chain reaction (RT-PCR) as PPAR-α agonistic activities. We prepared nine oleic acid amides. Their PPAR-α agonistic activities were, in decreasing order, N-oleoylhistamine (OLHA), N-oleoylglycine, Oleamide, N-oleoyltyramine, N-oleoylsertonin, and Olvanil. The highest activity was found with OLHA. We prepared and evaluated nine N-acylhistamines (N-acyl-HAs). Of these, OLHA, C16:0-HA, and C18:1Δ9-trans-HA showed similar activity. Activity due to the different chain length of the saturated fatty acid peaked at C16:0-HA. The PPAR-α antagonist, GW6471, inhibited the induction of the PPAR-α downstream genes by OLHA and N-oleoylethanolamide (OEA). These data suggest that N-acyl-HAs could be considered new PPAR-α agonists.

Electrospray ionization and collision induced dissociation mass spectrometry of primary fatty acid amides

Primary fatty acid amides are a group of bioactive lipids that have been linked with a variety of biological processes such as sleep regulation and modulation of monoaminergic systems. As novel forms of these molecules continue to be discovered, more emphasis will be placed on selective, trace detection. Currently, there is no published experimental determination of collision induced dissociation of PFAMs. A select group of PFAM standards, 12 to 22 length carbon chains, were directly infused into an electrospray ionization source Quadrupole Time of Flight Mass Spectrometer. All standards were monitored in positive mode using the [M + H]+ peak. Mass Hunter Qualitative Analysis software was used to calculate empirical formulas of the product ions. All PFAMs showed losses of 14 m/z indicative of an acyl chain, while the monounsaturated group displayed neutral losses corresponding to H2O and NH3. The resulting spectra were used to propose fragmentation mechanisms. Isotopically labeled PFAMs were used to validate the proposed mechanisms. Patterns of saturated versus unsaturated standards were distinctive, allowing for simple differentiation. This determination will allow for fast, qualitative identification of PFAMs. Additionally, it will provide a method development tool for selection of unique product ions when analyzed in multiple reaction monitoring mode.

FATTY ACID ESTERS OF GLUCOCORTICOIDS AS ANTI-INFLAMMATORY AND ANTI-CANCER AGENTS

The present invention relates to certain unsaturated fatty acid derivatives of therapeutically active glucocorticoides-fatty acid esters of glucocorticoids as anti-inflammatory and anti-cancer agents and pharmaceutical formulations containing them.

Synthesis of carnitine benzyl esters as prodrugs

The introduction of C-2 acyl groups and a benzyl ester onto L-carnitine generated a series of carnitine benzyl esters as prodrug with improved liposolubility, stability and bioavailability.

Synthesis of 1-oxo-1-(3-pyridazinyl) derivatives - Potent inhibitors of Fatty Acid Amide Hydrolase (FAAH): An improved and optimized procedure

A greatly improved procedure for the preparation of long-chain α-ketopyridazines, a class of potent inhibitors of fatty acid amide hydrolase (FAAH), is described. This optimization study shows a great dependence of the yields of desired products on the pyrididazinyl lithium/Weinreb amide ratio and offers a general approach to this kind of compound. Georg Thieme Verlag Stuttgart.

Process for the preparation of saturated or unsaturated primary fatty amines

Process for the preparation of unsaturated and saturated primary fatty amines comprising the steps of chlorination, treatment by ammonia, reduction and purification

Chemical compounds

This invention relates to certain unsaturated fatty acid derivatives of therapeutically active 1,3-dioxolane nucleoside analogues and to pharmaceutical formulations containing them. The said derivatives are referred to as “Compounds of formula I” herein. Compounds of formula I can be used in the treatment of a cancerous disease. Treatment of both solid tumours and haematological cancers such as leukaemias, lymphomas and multiple myelomas are included.