Identification of New Odoriferous Compounds in Human Axillary Sweat

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.

Olfaction in vector-host interactions

“…the females express a preference for biting humans to get their blood meal (Gillies 1964, Harrington 2001, White 1974. Several hundred volatile compounds emitted by humans have been identified, especially in the last twenty years , Curran et al 2005, Deng et al 2004, Ellin et al 1974, Gallagher et al 2008, Hasegawa et al 2004, Haze et al 2001, Healy and Copland 2000, Krotoszynski et al 1997, Meijerink et al 2000, Natsch et al 2006, Penn et al 2007, Perry et al 1970, Philips 1997, Zeng et al 1991. It is assumed that the host-seeking behaviour of mosquitoes is mediated by a blend of specific compounds, and not by the complete assemblage of compounds present in host odour .…”

Body odour of monozygotic human twins: a common pattern of odorant carboxylic acids released by a bacterial aminoacylase from axilla secretions contributing to an inherited body odour type

“…In total, the list of these analytes comprised 35 compounds. Many of them had been found before (Zeng et al 1991;Natsch et al 2006) and their odour had been characterized (Zeng et al 1991;Natsch et al 2003Natsch et al , 2006Hasegawa et al 2004). They primarily comprised methyl esters of series of methylbranched, unsaturated or hydroxylated acids.…”

High throughput volatile fatty acid skin metabolite profiling by thermal desorption secondary electrospray ionisation mass spectrometry

“…Individual skin profiles have been developed as 'barcodes' of scent for forensic [21] and diagnostic application [22], and gender and age specific signatures have been proposed as contributing factors to an individual's profile [23][24][25][26]. Olfactory analysis, either in-vivo or by organoleptic analysis of chromatographic eluents [27], combined with analytical measurement have established levels of odour to correlate with VSCs and VFAs, with 3-methyl-2-hexenoic acid cited as a critical molecular factor [26][27][28]. Finally, the quantity of anecdotal evidence of canine olfaction of disease, increasingly supported by scientific studies [29][30][31][32], reinforces the proposition of non-invasive skin VOC profiling for diagnosis and condition monitoring.…”