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trans-3-Methyl-2-hexenoic acid

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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
ECHA InfoCard 100.225.656 Edit this at Wikidata
  • InChI=1S/C7H12O2/c1-3-4-6(2)5-7(8)9/h5H,3-4H2,1-2H3,(H,8,9)/b6-5+
    Key: NTWSIWWJPQHFTO-AATRIKPKSA-N
  • CCCC(=CC(=O)O)C
Properties
C7H12O2
Molar mass 128.171 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

trans-3-Methyl-2-hexenoic acid (TMHA) is an unsaturated short-chain fatty acid that occurs in sweat secreted by the axillary 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 axillary (underarm) odor, TMHA has the most prominent odor.[2]

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. 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. {{cite journal}}: Cite journal requires |journal= (help)


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