S-Methyl thioacrylate
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| Other names
2-Propenethioic acid, S-methyl ester
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C4H6OS | |
| Molar mass | 102.15 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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S-Methyl thioacrylate is an organosulfur compound and a thioester with the chemical formula CH2=CHCOSCH3. It is the S-ester formed between acrylic acid and methanethiol.
Biological role
[edit]Asparagus metabolism
[edit]S-Methyl thioacrylate is one of the main metabolites responsible for the characteristic odor in the urine of some individuals after consuming asparagus.[1][2] When asparagus is digested, its characteristic asparagusic acid is broken down into several sulfur-containing volatile compounds, including methanethiol, S-methyl-3-(methylthio)thiopropionate, and S-methyl thioacrylate. These compounds are excreted in the urine, producing a smell often described as similar to cooked cabbage.[1] The ability to produce this odor, as well as the ability to perceive it, varies significantly among individuals due to genetic variations in both metabolic enzymes and olfactory receptors.
Food flavoring
[edit]In addition to its role as a metabolite, S-methyl thioacrylate is found as a natural product where it contributes to the aroma profile of certain foods. For example, it has been identified as a volatile constituent in the aroma of some fruits.[citation needed]
Preparation
[edit]A common laboratory synthesis for thioesters such as S-methyl thioacrylate involves the reaction of an acyl chloride with a thiolate. Specifically, acryloyl chloride can be reacted with sodium thiomethoxide (the sodium salt of methanethiol) to produce the target compound.[3]
See also
[edit]References
[edit]- ^ a b Coultate, T. P. (2002). Food: The Chemistry of its Components (4th ed.). Cambridge: Royal Society of Chemistry. p. 269. ISBN 978-0-85404-615-7.
- ^ White RH (September 1975). "Occurrence of S-methyl thioesters in urines of humans after they have eaten asparagus". Science. 189 (4205): 810–1. Bibcode:1975Sci...189..810W. doi:10.1126/science.1162354. PMID 1162354.
- ^ Aksakal S, Becer R (December 2016). "Poly(thioacrylate)s: Expanding the monomer toolbox of functional polymers". Polymer Chemistry. 7 (45): 7013–7022. doi:10.1039/C6PY01721E.