Allyl methyl sulfide
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| Names | |
|---|---|
| Preferred IUPAC name
3-(Methylsulfanyl)prop-1-ene | |
| Other names
Methyl propenyl sulfide
3-Methylthio-1-propene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.030.371 |
| EC Number |
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| MeSH | allyl+methyl+sulfide |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 1993 |
CompTox Dashboard (EPA)
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| Properties | |
| C4H8S | |
| Molar mass | 88.17 g·mol−1 |
| Odor | Garlic |
| Density | 0.803 g cm−3 |
| Boiling point | 92 °C; 197 °F; 365 K |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H225 | |
| P210 | |
| Flash point | 18.0 °C (64.4 °F; 291.1 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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Allyl methyl sulfide is an organosulfur compound with the chemical formula CH2=CHCH2SCH3. The molecule features two functional groups, an allyl (CH2=CHCH2) and a sulfide. It is a colourless liquid with a strong odor characteristic of alkyl sulfides. It is a metabolite of garlic, and "garlic breath" and/or "garlic body odor" is attributed to its presence.[1][2] Consumption of polyphenol-containing foods has been shown to suppress the release of allyl methyl sulfide from the body.[3]
It is prepared by the reaction of allyl chloride with sodium hydroxide and methanethiol.
- CH2=CHCH2Cl + NaOH (aq) + CH3SH → CH2=CHCH2SCH3 + NaCl + H2O
References
- ^ Eric Block (2010-01-04). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. ISBN 978-0-85404-190-9.
- ^ Sato, S.; Sekine, Y.; Kakumu, Y. (2020). "Measurement of diallyl disulfide and allyl methyl sulfide emanating from human skin surface and influence of ingestion of grilled garlic". Scientific Reports. 10: 465. doi:10.1038/s41598-019-57258-1.
- ^ Hiramoto, T.; Kakumu, Y.; Sato, S.; Sekine, Y. (2024). "Deodorising Garlic Body Odour by Ingesting Natural Food Additives Containing Phenolic Compounds and Polyphenol Oxidase". Applied Sciences. 14 (21): 9631. doi:10.3390/app14219631.