Identification of New Odoriferous Compounds in Human Axillary Sweat

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Abstract
3‐Hydroxy‐3‐methylhexanoic acid (1) and the 3‐sulfanylalkan‐1‐ols 2–5 were identified to contribute to the odor of human axillary sweat. Quantitative analyses of axillary sweat extracts from 50 healthy men showed an unambiguous correlation between the detected levels of 1 and the intensity of the axillary odor. Chiral‐GC analyses revealed 1 to be a 72 : 28 mixture of the (S)/(R)‐isomers. Optically pure (S)‐1 (>97% ee) emanated a strong spicy note, which recalled typical axillary odors. 3‐Methyl‐3‐sulfanylhexan‐1‐ol (2), the enantiomeric ratio of which equaled that of 1, was present in greater quantity than any of the other 3‐sulfanylalkanols. Optically pure (S)‐2 (>97% ee) had a strong meaty, fruity note, also reminiscent of axillary odor. The compounds identified, in particular (S)‐1 and (S)‐2, contribute significantly to the olfactory impression of human axillary odor.