Biomaterial Database

A nitrosating agent from the reaction of atmospheric nitrogen dioxide (NO2) with methyl linoleate: comparison with a product from the skins of NO2-exposed mice. 1984

S S Mirvish, and J P Sams

We showed previously that exposure of mice to atmospheric nitrogen dioxide (NO2) leads to the formation of an ether-extractable nitrosating agent (NSA) in the skin, which produced N-nitrosomorpholine (NMOR) from morpholine in vitro but not in vivo (under our conditions). We now report that NO2 bubbled into hexane solutions of methyl linoleate (MLIN) produced a similar NSA that reacted with morpholine in dichloromethane solution to produce NMOR. The NSA yield increased sharply as MLIN concentration was raised, with a maximum 0.1% yield of NSA from MLIN. The NSA yield from MLIN was four times that from methyl oleate and seven times that from methyl stearate. The NSA derived from MLIN travelled on thin-layer chromatography more slowly than the main weight fraction; whereas TLC of NSA in the skin lipids of NO2-exposed mice and in untreated mouse skin lipids exposed in vitro to NO2 produced NSA that travelled more rapidly than the main weight fraction.

UI	MeSH Term	Description	Entries
D008041	Linoleic Acids	Eighteen-carbon essential fatty acids that contain two double bonds.	Acids, Linoleic
D008055	Lipids	A generic term for fats and lipoids, the alcohol-ether-soluble constituents of protoplasm, which are insoluble in water. They comprise the fats, fatty oils, essential oils, waxes, phospholipids, glycolipids, sulfolipids, aminolipids, chromolipids (lipochromes), and fatty acids. (Grant & Hackh's Chemical Dictionary, 5th ed)	Lipid
D009585	Nitrogen Dioxide	Nitrogen oxide (NO2). A highly poisonous gas. Exposure produces inflammation of lungs that may only cause slight pain or pass unnoticed, but resulting edema several days later may cause death. (From Merck, 11th ed) It is a major atmospheric pollutant that is able to absorb UV light that does not reach the earth's surface.	Nitrogen Peroxide,Dioxide, Nitrogen,Peroxide, Nitrogen
D009602	Nitrosamines	A class of compounds that contain a -NH2 and a -NO radical. Many members of this group have carcinogenic and mutagenic properties.	Nitrosamine
D002621	Chemistry	A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D002855	Chromatography, Thin Layer	Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Chromatography, Thin-Layer,Thin Layer Chromatography,Chromatographies, Thin Layer,Chromatographies, Thin-Layer,Thin Layer Chromatographies,Thin-Layer Chromatographies,Thin-Layer Chromatography
D000388	Air	The mixture of gases present in the earth's atmosphere consisting of oxygen, nitrogen, carbon dioxide, and small amounts of other gases.
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D012867	Skin	The outer covering of the body that protects it from the environment. It is composed of the DERMIS and the EPIDERMIS.
D051379	Mice	The common name for the genus Mus.	Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus