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
CAS Number	27960-21-0
3D model (Jmol)	Interactive image
ChemSpider	4947706
PubChem	6443739
InChI 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 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
SMILES CCCC(=CC(=O)O)C
Properties
Chemical formula	C7H12O2
Molar mass	128.17 g·mol^−1
Density	0.97 g/cm^3
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 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): 557–63. 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.