EurekaMag
+ Translate
+ Most Popular
The pigeon tick (Argas reflexus): its biology, ecology, and epidemiological aspects
Prevalence of hemoglobin abnormalities in Kebili (Tunisian South)
Lipogranuloma: a preventable complication of dacryocystorhinostomy
Value of basal plasma cortisol assays in the assessment of pituitary-adrenal insufficiency
Bees from the Belgian Congo. The acraensis group of Anthophora
Placing gingival retraction cord
Total serum IgE, allergy skin testing, and the radioallergosorbent test for the diagnosis of allergy in asthmatic children
Acariens plumicoles Analgesoidea parasites des oiseaux du Maroc
Injuries of terminal phalanges of the fingers in children
Biology of flowering and nectar production in pear (Pyrus communis)
Das Reliktvorkommen der Aspisviper (Vipera aspis L.) im Schwarzwald
Hydrological modelling of drained blanket peatland
Pathologic morphology and clinical significance of the anomalous origin of the left circumflex coronary artery from the right coronary artery. General review and autopsy analysis of 30 cases
Cyto genetic analyses of lymphocyte cultures after exposure to calcium cyclamate
Axelrodia riesei, a new characoid fish from Upper Rio Meta in Colombia With remarks concerning the genus Axelrodia and description of a similar, sympatric, Hyphessobrycon-species
Favorable evolution of a case of tuberculosis of pancreas under antibiotic action
RIFM fragrance ingredient safety assessment, Valencene, CAS Registry Number 4630-07-3
Parenteral microemulsions: an overview
Temperate pasture: management for grazing and conservation
Evaluation of a new coprocessed compound based on lactose and maize starch for tablet formulation
Thermal expansion and cracking of three confined water-saturated igneous rocks to 800C
Revision of the genera of the tribe Stigmoderini (Coleoptera: Buprestidae) a discussion of phylogenetic relationships
Anal tuberculosis. Report of a case
Gastric tuberculosis in the past and present
Adaptive responses of the cardiovascular system to prolonged spaceflight conditions: assessment with Holter monitoring

Pyrethroid chemistry reactive alpha beta unsaturated keto aldehydes from peracid oxidation oxidative photodecomposition and metabolism of 5 benzyl 3 furylmethyl derivatives


Pyrethroid chemistry reactive alpha beta unsaturated keto aldehydes from peracid oxidation oxidative photodecomposition and metabolism of 5 benzyl 3 furylmethyl derivatives



Journal of Agricultural and Food Chemistry 33(4): 622-625



ISSN/ISBN: 0021-8561

DOI: 10.1021/jf00064a014

Oxidation of 5-benzyl-3-furylmethyl 2,2,3,3-tetramethylcyclopropanecarboxylate or the analogous methyl ether with 1.5 equiv of m-chloroperoxybenzoic acid proceeds by 4,5-addition, furan ring opening, and rearrangement to form the (Z)-2-[(acyloxy)methyl]-or (Z)-2(methoxymethyl)-4-keto-5-phenyl-2-pentenal, respectively, together with small amounts of the corresponding carboxylic acids. The 2-methoxymethyl keto aldehyde also forms in small yield on oxidative photodecomposition and microsomal metabolism. In biomimetic systems, both this methoxymethyl .alpha.,.beta.-unsaturated keto aldehyde and peracid-oxidized 5-benzyl-3-furylmethyl cis-chrysanthemate (resmethrin) form covalent derivatives with bovine serum albumin and the methoxymethyl keto aldehyde also forms a thioether derivative with 3,4-dichlorobenzenethiol. Oxidative furan ring opening of 5-benzyl-3-furylmethyl derivatives, including pyrethroids, may therefore contribute to their photochemical and metabolic lability and to tissue binding and persisting fragments in mammals. The 7a,.beta.-unsaturated keto aldehyde products are not detected as mutagens in several types of Salmonella typhimurium assays.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 006235609

Download citation: RISBibTeXText

Related references

Pyrethroid chemistry: reactive a,b-unsaturated keto aldehydes from peracid oxidation, oxidative photodecomposition, and metabolism of 5-benzyl-3-furylmethyl derivatives. Journal of Agricultural and Food Chemistry 33: 2-5, 1985

The chemistry of coumarin derivatives part 2. reaction of 4 hydroxycoumarin with alpha beta unsaturated aldehydes. Helvetica Chimica Acta 73(7): 1865-1878, 1990

Peracid oxidation of 4 isoxazolines as a method for the preparation of alpha beta unsaturated carbonyl compounds. Journal of Organic Chemistry 53(10): 2238-2245, 1988

Direct oxidation of beta-aryl substituted aldehydes to alpha,beta-unsaturated aldehydes promoted by an o-anisidine-Pd(OAc)2 co-catalyst. Chemistry An Asian Journal 4(11): 1712-1716, 2009

Catalytic asymmetric synthesis of alpha,beta-epoxy esters, aldehydes, amides, and gamma,delta-epoxy beta-keto esters: unique reactivity of alpha,beta-unsaturated carboxylic acid imidazolides. Journal of the American Chemical Society 123(38): 9474-9475, 2001

A convenient method for converting saturated aldehydes to alpha beta unsaturated aldehydes elongated by one carbon atom the palladium ii promoted oxidation of methyl enol ethers. Journal of Organic Chemistry 57(7): 2173-2176, 1992

Alpha,beta-unsaturated aldehydes accelerate oxymyoglobin oxidation. Journal of Agricultural and Food Chemistry 47(8): 3140-3144, 1999

Cytochromes P450 catalyze oxidation of alpha,beta-unsaturated aldehydes. Archives of Biochemistry and Biophysics 464(2): 187-196, 2007

Asymmetric 1,3-dipolar cycloadditions of N-benzyl and N-diphenylmethyl nitrones and alpha,beta-unsaturated aldehydes catalyzed by bis-titanium chiral Lewis acids. Chemistry An Asian Journal 3(2): 407-412, 2008

Organocatalytic Michael addition of aldehydes to gamma-keto-alpha,beta-unsaturated esters. an efficient entry to versatile chiral building blocks. Organic Letters 10(23): 5425-5428, 2008

Reactive oxygen species and alpha,beta-unsaturated aldehydes as second messengers in signal transduction. Annals of the new York Academy of Sciences 1203: 35-44, 2010

Methods for preparation of hetero bi functional nitroxides alpha beta unsaturated ketones beta keto esters cyano nitro derivatives. Canadian Journal of Chemistry 60(12): 1432-1438, 1982

Derivatization of keto fatty acids part ix. reaction of ethanedithiol with alpha bromo alpha beta unsaturated and beta gamma unsaturated ketones. Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 28(1): 32-36, 1989

Chemistry and biology of DNA containing 1,N(2)-deoxyguanosine adducts of the alpha,beta-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal. Chemical Research in Toxicology 22(5): 759-778, 2009

Use of gamma-carboxy-alpha,beta-unsaturated aldehydes as synthetic equivalents of beta,gamma-unsaturated aldehydes in a novel stereoselective approach to diketides. Organic Letters 2(2): 107-110, 2000