''trans''-3-Methyl-2-hexenoic acid

trans-3-Methyl-2-hexenoic acid
Names
IUPAC name
(E)-3-Methylhex-2-enoic acid
Other names
E3M2H
3M2H
TMHA
MHA
C7:2 (Lipid numbers)
Identifiers
3D model (JSmol)
ChemSpider
Properties
C7H12O2
Molar mass 128.17 g·mol−1
Density 0.97 g/cm3
Melting point −3.4 °C (25.9 °F; 269.8 K)
Boiling point 225.2 °C (437.4 °F; 498.3 K)
Hazards
Flash point 132 °C (270 °F; 405 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

trans-3-Methyl-2-hexenoic acid (TMHA) is an unsaturated short-chain fatty acid that occurs in sweat secreted by the axillary (underarm) apocrine glands of Caucasians and some Asians.[1]

Hexanoic acids such as TMHA have an hircine odor. Of the fatty acids contributing to Caucasian men's underarm odor, TMHA has the most prominent odor.[2]

Schizophrenia odour

It has long been claimed that schizophrenia patients exhibit a particular peculiar body odour, and it has been postulated the odour may be caused by underlying metabolic abnormalities associated with the condition, among other factors.[3][4] Initial studies identified the causal component as TMHA,[5] however, subsequent studies failed to reproduce such results,[3][6] with subsequent researchers suggesting the initial research may have had misidentified impurities in samples as TMHA due to poor methodology.[3] However, a 2007 study found schizophrenia patients to have reduced olfactory sensitivity to TMHA, possibly indicating sensory habituation; the decreased ability to smell the substance due to the presence of the substance as a constant component of subjects' own sweat/body odour. Furthermore, the researchers noted a positive association between reduced ability to smell TMHA and greater severity of disorganised and negative symptoms.[4]

An allusion to TMHA and its purported link to the smell of the mentally ill is made in the 1996 David Foster Wallace novel, Infinite Jest.[7]

References

  1. ↑ Akutsu, T.; Sekiguchi, K; Ohmori, T; Sakurada, K (2006). "Individual Comparisons of the Levels of (E)-3-Methyl-2-Hexenoic Acid, an Axillary Odor–Related Compound, in Japanese". Chemical Senses. 31 (6): 557–63. doi:10.1093/chemse/bjj060. PMID 16690870.
  2. ↑ Sun, Lixing; Williams, Wendy A.; Avalos, Corinna (2005). "Human sweaty smell does not affect women's menstrual cycle": 308. doi:10.1007/0-387-25160-X_34.
  3. 1 2 3 Perry, Thomas L.; Melançon, Serge B.; Lesk, Donna; Hansen, Shirley (1970-12). "Failure to detect trans-3-methyl-2-hexenoic acid in the sweat of schizophrenic patients". Clinica Chimica Acta. 30 (3): 721–725. doi:10.1016/0009-8981(70)90266-4. ISSN 0009-8981. Check date values in: |date= (help)
  4. 1 2 Brewer, Warrick J.; Wood, Stephen J.; Pantelis, Christos; Berger, Gregor E.; Copolov, David L.; McGorry, Patrick D. (2007-01). "Olfactory sensitivity through the course of psychosis: Relationships to olfactory identification, symptomatology and the schizophrenia odour". Psychiatry Research. 149 (1–3): 97–104. doi:10.1016/j.psychres.2006.03.005. ISSN 0165-1781. Check date values in: |date= (help)
  5. ↑ Smith, K.; Thompson, G. F.; Koster, H. D. (1969-10-17). "Sweat in schizophrenic patients: identification of the odorous substance". Science. 166 (3903): 398–399. ISSN 0036-8075. PMID 5818039.
  6. ↑ Gordon, S. G.; Smith, K.; Rabinowitz, J. L.; Vagelos, P. R. (1973-7). "Studies of trans-3-methyl-2-hexenoic acid in normal and schizophrenic humans". Journal of Lipid Research. 14 (4): 495–503. ISSN 0022-2275. PMID 4715330. Check date values in: |date= (help)
  7. ↑ Foster., Wallace, David (1996). Infinite jest : a novel (1st ed.). Boston: Little, Brown and Co. pp. 748–749. ISBN 9780316073851. OCLC 669069481.


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