Linked Life Data

1855862

Source:http://linkedlifedata.com/resource/pubmed/id/1855862

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
105
pubmed:dateCreated
1991-8-29
pubmed:abstractText
Possible routes to the formation of the sunscreen contaminant, 2-ethylhexyl 4-N-methyl-N-nitrosoaminobenzoate, have been investigated in a study of the nitrosation chemistry of 2-ethylhexyl 4-N,N-dimethylaminobenzoate (Padimate-O) and related tertiary and secondary amines. Padimate-O and the corresponding ethyl ester nitrosate rapidly at 25 degrees C in either N2O3:ether or HNO2:HOAc to produce a mixture of alkyl 4-N-methyl-N-nitrosoaminobenzoate and alkyl 4-N,N-dimethylamino-3-nitrobenzoate, the former of which is the major product. The nitrosative dealkylation of these amines at this low temperature is unusual. Asymmetrical amines exhibit a preference for nitrosative demethylation (methyl versus ethyl or benzyl), but the cleavage ratios in N2O3:ether are time-dependent, suggesting competing mechanisms with different reactant kinetic orders. A radical cation route would explain the unusual reactivity, which may compete with the established nitrosative dealkylation mechanism. 2-Ethylhexyl 4-N-methyl-N-nitrosoaminobenzoate was mutagenic in two strains of Salmonella typhimurium in the Ames assay.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:issn
0300-5038
pubmed:author
pubmed:issnType
Print
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
244-52
pubmed:dateRevised
2000-12-18
pubmed:meshHeading
pubmed:year
1991
pubmed:articleTitle
Nitrosation of tertiary aromatic amines related to sunscreen ingredients.
pubmed:affiliation
Department of Chemistry, University of Missouri, Columbia.
pubmed:publicationType
Journal Article