S-Methyl thioacetate

S-Methyl thioacetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.775
UNII
  • InChI=1S/C3H6OS/c1-3(4)5-2/h1-2H3
    Key: OATSQCXMYKYFQO-UHFFFAOYSA-N
  • CC(=O)SC
Properties
C3H6OS
Molar mass 90.14 g·mol−1
Density 1.013 g/cm3
Melting point 96–97 °C (205–207 °F; 369–370 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

S-Methyl thioacetate is the organosulfur compound with the formula CH3C(O)SCH3. This colorless, malodorous liquid is found in many plant species. In its pure form it has an unpleasant sulfurous smell, but when highly diluted and along with other simple alkyl thioacetates and related compounds, it is an important component of the odor and flavour profile of some foods, including Camembert cheese,[1][2] yogurt,[3] and baijiu.[4]

Alternate isomer

O-methyl ethanethioate, CAS# 21119-13-1[5]

The constitutional isomer in which the oxygen and sulfur atoms are interchanged, O-methyl thioacetate, is also known as methyl thioacetate. It is not found in nature. It has mainly been the subject of theoretical studies.[6]

See also

References

  1. ^ Sablé S, Cottenceau G (December 1999). "Current knowledge of soft cheeses flavor and related compounds". Journal of Agricultural and Food Chemistry. 47 (12): 4825–36. Bibcode:1999JAFC...47.4825S. doi:10.1021/jf990414f. PMID 10606538.
  2. ^ Martínez-Cuesta Mdel C, Peláez C, Requena T (2013). "Methionine metabolism: major pathways and enzymes involved and strategies for control and diversification of volatile sulfur compounds in cheese". Critical Reviews in Food Science and Nutrition. 53 (4): 366–85. doi:10.1080/10408398.2010.536918. PMID 23320908. S2CID 27793531.
  3. ^ Ott, Andreas; Fay, Laurent B.; Chaintreau, Alain (1997). "Determination and Origin of the Aroma Impact Compounds of Yogurt Flavor". Journal of Agricultural and Food Chemistry. 45 (3): 850–858. Bibcode:1997JAFC...45..850O. doi:10.1021/jf960508e.
  4. ^ Liu, Huilin; Sun, Baoguo (2018). "Effect of Fermentation Processing on the Flavor of Baijiu". Journal of Agricultural and Food Chemistry. 66 (22): 5425–5432. Bibcode:2018JAFC...66.5425L. doi:10.1021/acs.jafc.8b00692. PMID 29751730.
  5. ^ "Methyl thioacetate". PubChem. U.S. National Library of Medicine.
  6. ^ Abboud, J. L. M.; Mo, O.; De Paz, J. L. G.; Yanez, M.; Esseffar, M.; Bouab, W.; El-Mouhtadi, M.; Mokhlisse, R.; Ballesteros, E. (1993). "Thiocarbonyl versus carbonyl compounds: A comparison of intrinsic reactivities". Journal of the American Chemical Society. 115 (26): 12468–12476. Bibcode:1993JAChS.11512468A. doi:10.1021/ja00079a030.


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