Structural identification of a heterocyclic compound implicated in the Spanish toxic oil syndrome

G S Nomura; D L Ashley; A H Pendergrast; J T Bernert Jr; D G Patterson Jr; J Grainger; D Vanderveer

doi:10.1016/0278-6915(89)90065-3

Structural identification of a heterocyclic compound implicated in the Spanish toxic oil syndrome

Food Chem Toxicol. 1989 Mar;27(3):165-71. doi: 10.1016/0278-6915(89)90065-3.

Authors

G S Nomura¹, D L Ashley, A H Pendergrast, J T Bernert Jr, D G Patterson Jr, J Grainger, D Vanderveer

Affiliation

¹ Centers for Disease Control, Center for Environmental Health and Injury Control, Atlanta, GA 30333.

PMID: 2731813
DOI: 10.1016/0278-6915(89)90065-3

Abstract

The compound 1-phenyl-5-vinylimidazolidine-2-thione was previously reported to be the causative agent in the outbreak referred to as Spanish toxic oil syndrome. X-ray crystallography, together with nuclear magnetic resonance and infra-red spectroscopy, now show the correct structure of this compound to be N-(5-vinyl-1,3-thiazolidin-2-ylidene)phenylamine (5-VTPA). Data for the structural characterization of 5-VTPA and the closely related isomer N-(4-vinyl-1,3-thiazolidin-2-ylidene)phenylamine are reported.

MeSH terms

Brassica*
Crystallography
Fatty Acids, Monounsaturated
Magnetic Resonance Spectroscopy
Molecular Structure
Plant Oils / poisoning*
Rapeseed Oil
Spectrum Analysis
Syndrome
Thiazoles / isolation & purification*
Thiazolidines

Substances

Fatty Acids, Monounsaturated
Plant Oils
Rapeseed Oil
Thiazoles
Thiazolidines
N-(4-vinyl-1,3-thiazolidin-2-ylidene)phenylamine