5429-85-6

Usage

Uses

Used in Chemical Industry:
N-PHENYL-9Z-OCTADECENAMIDE is used as a chemical intermediate for the synthesis of various compounds, such as surfactants, lubricants, and additives. Its unique structure allows it to act as an emulsifier or stabilizer in the formulation of different products.
Used in Pharmaceutical Industry:
N-PHENYL-9Z-OCTADECENAMIDE is used as a pharmaceutical compound for its potential therapeutic applications. Its ability to interact with biological systems may make it a candidate for drug development, particularly in the areas of inflammation and pain management.
Used in Cosmetics Industry:
In the cosmetics industry, N-PHENYL-9Z-OCTADECENAMIDE is used as an ingredient in various formulations, such as creams, lotions, and ointments. Its emollient properties help to moisturize and protect the skin, while its compatibility with other ingredients allows for the creation of stable and effective cosmetic products.
Used in Research and Development:
N-PHENYL-9Z-OCTADECENAMIDE is also used in research and development for its potential applications in various fields. Its unique chemical structure makes it an interesting compound for studying its interactions with biological systems and exploring its potential uses in new technologies and products.

InChI:InChI=1/C24H39NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-24(26)25-23-20-17-16-18-21-23/h9-10,16-18,20-21H,2-8,11-15,19,22H2,1H3,(H,25,26)/b10-9-

Upstream product

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 62-53-3 aniline 
• 7647-01-0 hydrogenchloride 
• 112-79-8 Elaidic acid 
• 112-80-1 cis-Octadecenoic acid 

Downstream Products

• 637-54-7 N-phenylstearamide 

Relevant academic research and scientific papers

Development of pancellular toxicity in guinea pig lung by ingestion of oleylanilide.

Toxic oil syndrome (TOS), characterized by widespread thromboembolism, vasculotoxicity, and ARDS, develops in humans ingesting denatured edible oils. The mechanism(s) involved in targeted vasculocentric damage in this multi-system disorder is not known. Oleylanilide (OA) was synthesized and fed to male, young adult guinea pigs by gavage for 30 days at doses of 35, 50, and 100 mg/kg/day in groups of six animals each respective to weight. Controls were fed olive oil. Oleylanilide fed animals gained less weight than controls. At the end of experiment, right lungs were inflation fixed in appropriate fixative for histology and transmission electron microscopy (TEM) and left lungs were frozen at -70 degrees C for biochemical analyses. The activity of glycerophosphate acyltransferase (GAT) and cholinephosphotransferase (CPT), two key enzymes involved in phospholipid biosynthesis, were decreased in lung due to OA ingestion. All doses of OA induced marked perivascular and peribronchoiolar monocytic infiltrates that often formed prominent nodules; segmental vascular smooth muscle cell proliferation and derangement of myocytic polarity, subendothelial foamy infiltrates, and edema; nuclear pyknosis and dropout in vascular and bronchial targetoid myocytes; and denudation of bronchiolar epithelial cells. Alveoli contained large numbers of monocytes, macrophages, red cells, edema, and debris. Transmission electron microscopy showed type I cell cytoplasmic ballooning and disintegration of type I cell; contracted and blebbed endothelial cells, fibrin thrombi in capillaries, intracellular megalamellar bodies in type II cells, and surfactant lamellae; and liposomes and fine granular precipitates within alveoli, and contraction and lift off of bronchiolar epithelial cells. Monocytes, mast cells, and eosinophils infiltrated bronchial walls. Furthermore, there was deposition of electron dense particles on the surface of the alveolar wall.(ABSTRACT TRUNCATED AT 400 WORDS)

Toxic effects of fatty acid anilides on the oxygen defense systems of guinea pig lungs and erythrocytes.

Toxic oil syndrome (TOS) is caused by ingestion of denatured edible oils. Even though the etiology and pathogenesis of this disease are not fully known, it is quite clear that generation of free radicals caused by ingestion of fatty acid anilides is responsible for the pathogenetic mechanism in many TOS patients. Fatty acid anilides may also alter the free radical status of lungs and erythrocytes; this possibility may shed some light on understanding toxic oil syndrome. The present study describes the effects of oral administration of fatty acid anilides on the activities of major enzymes involved in the oxygen defense systems of lungs and erythrocytes. Feeding fatty acid anilides caused an increase in the superoxide dismutase (SOD) activity in erythrocytes, whereas it caused a decrease in the SOD activity in lungs. GSH-Px activity was not significantly changed in erythrocytes but was decreased in lungs. Although the activity of catalase was increased only by a higher dose in the erythrocytes, it was not affected in the lung at any dosage. Even though the ingestion of fatty acid anilides caused an increase in the SOD activity in the erythrocytes and a decrease in the SOD activity in the lungs, there was an increase in the lipid peroxidation in both cases. The increase in lipid peroxidation in erythrocytes is probably caused by the accumulation of H2O2, and that in the lungs is due to the accumulation of superoxide anion.

A catalyst-free, waste-less ethanol-based solvothermal synthesis of amides

A green, one-pot approach based on the solvothermal amidation of carboxylic acids with amines has been developed for the synthesis of diverse aliphatic and aromatic amides. It does not require the use of catalysts or coupling reagents and it occurs in the presence of ethanol that has been proved to have a key role in the process. The proposed strategy is also extendable to biologically active amides and could represent a low-cost and waste-less alternative to the common synthetic pathways.

Transdermal Penetration Enhancer and Their Uses

The present invention relates to a transdermal penetrating enhancer comprising an amino sugar-fatty acid conjugate. The conjugate included in the transdermal penetrating enhancer of the present invention can be industrially used in a cosmetic industry pursuing skin health and aesthetic enhancement of skin, and as well as used as a key material for a formulation of a transdermal drug delivery system. The transdermal penetrating enhancer of the present invention has effect of increasing permeability of a bioactive material or a drug into skin. Also, in some cases, the transdermal penetrating enhancer of the present invention can be applied as a single preparation for the therapeutic purpose by preparing a conjugate including a certain drug. Moreover, since the transdermal penetrating enhancer of the present invention uses a conjugate including a material in which skin safety is ensured, the transdermal penetrating enhancer can be applied to various fields besides a cosmetic or medicinal field.

A METHOD OF TREATING PERIPHERAL INFLAMMATORY DISEASE

An active for use in the treatment or inhibition of an inflammatory disease associated with over-activation of Toll-like Receptor 4 (TLR4), Toll-like Receptor 2 (TLR2) and Myeloid differentiating protein 88 (Myd88) adaptor-like protein (Mal) while maintaining a subject's ability to respond normally to a pathogen, in which the active is an oleamide or a derivative thereof.

Indium-mediated mild and facile method for the synthesis of amides

Indium-mediated coupling reactions of acyl chlorides and amines for the synthesis of amide bonds are described. The reaction afforded high yields of the desired amides under mild and neutral conditions, and it was applicable also to the preparation of peptides without epimerization.

A convenient acylation procedure of alcohols and amines

The reaction of carboxylic acids with primary and secondary alcohols in the presence of aromatic sulfochlorides (mesitylenesulfonyl chloride and 2,4,6-triisopropylbenzenesulfonyl chloride) or aromatic sulfotetrazoles (mesytilenesulfonyl tetrazolide and 2,4,6-triisopropylbenzenesulfonyltetrazole) and usual acylation catalysts was shown to be a convenient procedure for the synthesis of esters. Reaction of carboxylic acids with primary aliphatic or aromatic amines in the presence of the same tetrazolides and catalysts is a useful procedure for the synthesis of amides. Syntheses of twenty compounds are presented as examples.

The conversion of carboxylic acids into amides via NCS/triphenylphosphine

Amides can be generated in very high yields under mild conditions from the corresponding carboxylic acid and amine in the presence of equivalent amounts of triphenylphosphine and N-halosuccinimides, e.g., NCS or NBS.

Inhibitors of Acyl-CoA:cholesterol acyltransferase. I. Identification and structure-activity relationships of a novel series of fatty acid anilide hypocholesterolemic agents

A series of fatty acid anilides was prepared, and compounds were tested for their ability to inhibit the enzyme acyl-CoA:cholesterol acyltransferase (ACAT) in vitro and to lower plasma total cholesterol and elevate high- density lipoprotein cholesterol in cholesterol-fed rats in vivo. The compounds reported were found to fall into two subclasses with different anilide SAR. For nonbranched acyl analogues, inhibitory potency was found to be optimal with bulky 2,6-dialkyl substitution. For α-substituted acyl analogues, there was little dependence of in vitro potency on anilide substitution and 2,4,6-trimethoxy was uniquely preferred. Most of the potent inhibitors (IC50 50 nM) were found to produce significant reductions in plasma total cholesterol in cholesterol-fed rats. Additionally, in vivo activity could be improved significantly by the introduction of α,α- disubstitution into the fatty acid portion of the molecule. A narrow group of α,α-disubstituted trimethoxyanilides, exemplified by 2,2-dimethyl-N-(2,4,6- trimethoxyphenyl)dodecanamide (39), was found to not only lower plasma total cholesterol (-60%) in cholesterol-fed rats but also elevate levels of high- density lipoprotein cholesterol (+94%) in this model at the screening dose of 0.05% in the diet (ca. 50 mg/kg).