3-Methyl-3-sulfanylhexan-1-ol
| Names | |
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| Preferred IUPAC name
3-Methyl-3-sulfanylhexan-1-ol | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C7H16OS | |
| Molar mass | 148.26 g·mol−1 |
Refractive index (nD)
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1.482 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Stench |
| GHS labelling:[1] | |
| Warning | |
| H315, H319, H335 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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3-Methyl-3-sulfanylhexan-1-ol (3M3SH) is a primary alcohol that is hexan-1-ol which is substituted by a methyl group and a thiol group at position 3. It is the odor component of human axilla sweat and the major species at pH 7.3.[2]
The molecule was identified in 2004.[3] The odor may be described as "rotten onions or meat"[4] while its (R)/(S) enantiomers are described as "sweat and onion-like" for (S) and "fruity and grapefruit-like" for (R).[3] Some variation between enantiomer ratios may exist due to gender differences in skin micribiota composition and in precursor molecule production.[5]
Synthesis
Apocrine sweat glands produce an S-glutathione conjugate secreted via ABCC11 transporters into vesicles. The conjugate is converted into a S-Cys-Gly-3M3SH thiol before excretion through the gland to the skin.[6]
Bacteria found to create 3M3SH from human sweat include primarily Staphylococcus haemolyticus,[7] other Staphylococcus clade members such as Staphylococcus hominis,[8] and Corynebacterium xerosis,[9] though at a lesser extent compared to S. haemolyticus. In S. hominis, the bacterial cell imports the thiol precursor via a proton-coupled oligopeptide transporter (proton pump).[4] After intake of the thiol precursor, the strains metabolize it to produce 3-methyl-3-sulfanylhexan-1-ol.[6]
See also
References
- ^ "SynQuest Labs, Inc". synquestlabs.com.
- ^ PubChem. "3-Methyl-3-sulfanylhexan-1-ol". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-04-16.
- ^ a b Troccaz, Myriam; Starkenmann, Christian; Niclass, Yvan; van de Waal, Matthijs; Clark, Anthony J. (July 2004). "3-Methyl-3-sulfanylhexan-1-ol as a major descriptor for the human axilla-sweat odour profile". Chemistry & Biodiversity. 1 (7): 1022–1035. doi:10.1002/cbdv.200490077. ISSN 1612-1880. PMID 17191896.
- ^ a b Khanna, Kanika (2021-12-30). "Microbial Origins of Body Odor". American Society for Microbiology. Retrieved 2025-11-09.
- ^ Troccaz, Myriam; Borchard, Gerrit; Vuilleumier, Christine; Raviot-Derrien, Sophie; Niclass, Yvan; Beccucci, Sabine; Starkenmann, Christian (March 2009). "Gender-specific differences between the concentrations of nonvolatile (R)/(S)-3-methyl-3-sulfanylhexan-1-Ol and (R)/(S)-3-hydroxy-3-methyl-hexanoic acid odor precursors in axillary secretions". Chemical Senses. 34 (3): 203–210. doi:10.1093/chemse/bjn076. ISSN 1464-3553. PMID 19147808.
- ^ a b Stevens, Bruce R.; Roesch, Luiz F. W. (2024-11-14). "Interplay of human ABCC11 transporter gene variants with axillary skin microbiome functional genomics". Scientific Reports. 14 (1): 28037. doi:10.1038/s41598-024-78711-w. ISSN 2045-2322. PMC 11564711.
- ^ Starkenmann, Christian; Niclass, Yvan; Troccaz, Myriam; Clark, Anthony J. (June 2005). "Identification of the precursor of (S)-3-methyl-3-sulfanylhexan-1-ol, the sulfury malodour of human axilla sweat". Chemistry & Biodiversity. 2 (6): 705–716. doi:10.1002/cbdv.200590048. ISSN 1612-1880. PMID 17192014.
- ^ Buguliskis, Jeffrey S. (2018-07-03). "Eww That Smell: Key Basis for BO Production Identified". GEN - Genetic Engineering and Biotechnology News. Retrieved 2025-11-09.
- ^ Starkenmann, Christian; Niclass, Yvan; Troccaz, Myriam; Clark, Anthony J. (2005). "Identification of the Precursor of (S)-3-Methyl-3-sulfanylhexan-1-ol, the Sulfury Malodour of Human Axilla Sweat". Chemistry & Biodiversity. 2 (6): 705–716. doi:10.1002/cbdv.200590048. ISSN 1612-1880.