Dimethylsulfoniopropionate

Dimethylsulfoniopropionate
Skeletal formula of dimethylsulfoniopropionate
Ball-and-stick model of the dimethylsulfoniopropionate zwitterion
Names
IUPAC name
3-dimethylsulfoniopropanoate
Other names
dimethyl-β-propiothetin
S,S-dimethyl-β-propiothetin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.228.826 Edit this at Wikidata
UNII
  • InChI=1S/C5H10O2S/c1-8(2)4-3-5(6)7/h3-4H2,1-2H3 ☒N
    Key: DFPOZTRSOAQFIK-UHFFFAOYSA-N ☒N
  • InChI=1/C5H10O2S/c1-8(2)4-3-5(6)7/h3-4H2,1-2H3
    Key: DFPOZTRSOAQFIK-UHFFFAOYAW
  • C[S+](C)CCC(=O)[O-]
Properties
C5H10O2S
Molar mass 134.1967
Appearance white crystalline hygroscopic powder with a characteristic odor.[1]
Melting point 120 to 125 °C (248 to 257 °F; 393 to 398 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethylsulfoniopropionate (DMSP), is an organosulfur compound with the formula (CH3)2S+CH2CH2COO−. This zwitterionic metabolite can be found in marine phytoplankton, seaweeds, and some species of terrestrial and aquatic vascular plants. It functions as an osmolyte as well as several other physiological and environmental roles have also been identified.[3] DMSP was first identified in the marine red alga Polysiphonia fastigiata.[4]

  1. ^ "Http 404". Archived from the original on 2013-03-06. Retrieved 2013-02-05.
  2. ^ "Http 404". Archived from the original on 2013-03-06. Retrieved 2013-02-05.
  3. ^ DeBose, Jennifer L.; Sean C. Lema; Gabrielle A. Nevitt (2008-03-07). "Dimethylsulfoniopropionate as a foraging cue for reef fishes". Science. 319 (5868): 1356. Bibcode:2008Sci...319.1356D. doi:10.1126/science.1151109. PMID 18323445. S2CID 20782786.Vila-Costa, Maria; Rafel Simo; Hyakubun Harada; Josep M. Gasol; Doris Slezak; Ronald P. Kiene (2006-10-27). "Dimethylsulfoniopropionate uptake by marine phytoplankton". Science. 314 (5799): 652–654. Bibcode:2006Sci...314..652V. doi:10.1126/science.1131043. PMID 17068265. S2CID 27541024.
  4. ^ Challenger, Frederick; Margaret Isabel Simpson (1948). "Studies on biological methylation. Part XII. A precursor of the dimethyl sulphide evolved by Polysiphonia fastigiata. Dimethyl-2-carboxyethylsulphonium hydroxide and its salts". Journal of the Chemical Society. 3: 1591–1597. doi:10.1039/JR9480001591. PMID 18101461.