trans -3-methyl-2-hexenoic acid

Structural formula
General
Surname	trans -3-methyl-2-hexenoic acid
Molecular formula	C 7 H 12 O 2
External identifiers / databases
ECHA InfoCard	100.225.656
PubChem	6443739
Wikidata	Q3487540
properties
Molar mass	128.17 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	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 .

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[2] 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.

[3] Humans recognize diseases by their smell - they pay too little attention to it

[DOI10.1016/j.psychres.2006.03.005-4] 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-5] 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-6] 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).

[PMID4715330-7] 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 .