trans-3-Methyl-2-hexenoic acid

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trans-3-Methyl-2-hexenoic acid
Trans-3-methyl-2-hexenoic acid.svg
CAS number 027960-21-0 YesY
PubChem 6443739
ChemSpider 4947706 YesY
Jmol-3D images Image 1
Molecular formula 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)
Flash point 132 °C (270 °F; 405 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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]


  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. p. 308. doi:10.1007/0-387-25160-X_34.