14417-88-0

Basic information

• Product Name: Melinamide
• Synonyms: Melinamide;9,12-Octadecadienamide, N-(1-phenylethyl)-, (9Z,12Z)- (9CI);9,12-Octadecadienamide, N-(1-phenylethyl)-, (Z,Z)-;AC 223;DL-a-Methylbenzyl linoleamide;DL-N-(a-Methylbenzyl)linoleamide;Linoleamide, N-(a-methylbenzyl)- (8CI);N-(a-Methylbenzyl)linoleamide
• CAS NO: 14417-88-0
• Molecular Formula: C₂₆H₄₁NO
• Molecular Weight: 383.68
• Mol File: 14417-88-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: <4°
• Boiling Point: bp0.03 200-215°; bp0.07 200-204°
• Flash Point: 333.3°C
• Appearance: /
• Density: 0.928g/cm³
• Vapor Pressure: 1.27E-11mmHg at 25°C
• Refractive Index: nD23 1.5050; nD30 1.4863
• PKA: 15.56±0.46(Predicted)
• CAS DataBase Reference: Melinamide(CAS DataBase Reference)
• NIST Chemistry Reference: Melinamide(14417-88-0)
• EPA Substance Registry System: Melinamide(14417-88-0)

Safety Data

• Hazardous Substances Data: 14417-88-0(Hazardous Substances Data)

Usage

Description

Melinamide is an amide of linoleic acid useful in the treatment of hypercholesterolemia. The mechanism of action of melinamide appears to involve the inhibition of cholesterol absorption from the gastrointestinal tract.

Originator

Sumitomo (Japan)

Uses

Melinamide is used in the synthesis and biological screening of library of macamides as TNF alpha inhibitors with greater anti-inflammatory activity in human monocytic cell.

Brand name

ARTES OIL

Hazard

Low toxicity by ingestion.

InChI:InChI=1/C26H41NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-23-26(28)27-24(2)25-21-18-17-19-22-25/h7-8,10-11,17-19,21-22,24H,3-6,9,12-16,20,23H2,1-2H3,(H,27,28)/b8-7+,11-10+

Upstream product

• 7459-33-8 linoleyl chloride 
• 618-36-0 rac-methylbenzylamine 

Relevant articles and documents

Synthesis and biological screening of a library of macamides as TNF-α inhibitors

Thirty-five macamide analogues were synthesised by modifying the initial molecular structure. The resulting structures were confirmed using NMR and MS. Cytotoxicity and the anti-inflammatory activity of these synthetic macamides were evaluated in the THP-1 cell line. Preliminary biological evaluation indicated that most of these synthetic macamides did not present cytotoxicity (MTT assay) in the tested cell line with respect to the control (actinomycin D). Regarding the anti-inflammatory activity, several analogues had a greater potential for inhibition of TNF-α than natural macamides. Synthetic macamide 4a was the most active (IC50 = 0.009 ± 0.001 μM) compared to the C87 (control). Through looking at the link between the chemical structure and the activity, our study proves that changes made to natural macamides at the level of the alkyl chain, the benzyl position, the amide bond, and the addition of two methyl groups to the aromatic ring (meta position) lead us to obtaining new macamides with greater anti-inflammatory activity. This journal is