trans -3-methyl-2-hexenoic acid
Structural formula | ||||||||||
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General | ||||||||||
Surname | trans -3-methyl-2-hexenoic acid | |||||||||
Molecular formula | C 7 H 12 O 2 | |||||||||
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properties | ||||||||||
Molar mass | 128.17 g mol −1 | |||||||||
safety instructions | ||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
trans -3-methyl-2-hexenoic acid is a short-chain fatty acid . It has a goat-like odor. At times it was assumed that the appearance of the odor could be used as a sign of schizophrenia . Subsequent re-examinations could not confirm this. However, there is evidence that the sick perceive such smells less than normal people.
Occurrence
trans -3-methyl-2-hexenoic acid occurs together with the isomeric cis-form cis -3-methyl-2-hexenoic acid in the vaginal secretion of rhesus monkeys . It is also a key component of armpit sweat .
Extraction and presentation
trans -3-methyl-2-hexenoic acid can be synthesized by the dehydrogenation and hydrolysis of ethyl 3-hydroxy-3-methylhexanoate, which in turn can be produced by the Reformatzki reaction of ethyl bromoacetate and 2-pentanone .
Individual evidence
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ^ Robert V. Smith, Ambrose Leong: Methods for the preparation of trans-3-methyl-2-hexenoic acid, the malodorous component of schizophrenics' sweat. In: Journal of Pharmaceutical Sciences , February 1972.
- ↑ Humans recognize diseases by their smell - they pay too little attention to it
- ↑ Warrick J. Brewer, Stephen J. Wood, Christos Pantelis, Gregor E. Berger, David L. Copolov, Patrick D. McGorry: Olfactory sensitivity through the course of psychosis: Relationships to olfactory identification, symptomatology and the schizophrenia odor. In: Psychiatry Research. 149, 2007, p. 97, doi : 10.1016 / j.psychres.2006.03.005 .
- ↑ Wolfgang Legrum: Fragrances, between stench and fragrance occurrence, properties and use of fragrances and their mixtures . Springer-Verlag, 2015, ISBN 978-3-658-07310-7 , pp. 23 ( limited preview in Google Book search).
- ↑ Markus Egert, Frank Thadeusz: A germ rarely comes alone How microbes determine our lives and we protect ourselves from them . Ullstein Buchverlage, 2018, ISBN 3-8437-1835-0 ( limited preview in Google book search).
- ↑ SG Gordon, K. Smith, JL Rabinowitz, PR Vagelos: Studies of trans-3-methyl-2-hexenoic acid in normal and schizophrenic humans. In: J. Lipid Res. 14, 1973, pp. 495-503, PMID 4715330 .