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Dimethylsulfoniopropionate information


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
CAS Number
  • 7314-30-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 22195 ☒N
ECHA InfoCard 100.228.826 Edit this at Wikidata
PubChem CID
  • 23736
UNII
  • C884XA7QGG checkY
CompTox Dashboard (EPA)
  • DTXSID0041014 Edit this at Wikidata
InChI
  • 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
SMILES
  • C[S+](C)CCC(=O)[O-]
Properties
Chemical formula
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).
☒N verify (what is checkY☒N ?)
Infobox references

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.

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Dimethylsulfoniopropionate

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Dimethylsulfoniopropionate (DMSP), is an organosulfur compound with the formula (CH3)2S+CH2CH2COO−. This zwitterionic metabolite can be found in marine...

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Dimethyl sulfide

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in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate (DMSP), and is also produced by the bacterial metabolism of methanethiol...

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Sulfonium

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species are S-methylmethionine (methioninium) and the related dimethylsulfoniopropionate (DMSP). Sulfonium salts are precursor to sulfur ylides, which...

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Alpha hydroxycarboxylic acid

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2-Hydroxy-4-(methylthio)butyric acid is an intermediate in the biosynthesis of 3-dimethylsulfoniopropionate, precursor to natural dimethyl sulfide. Alpha hydroxy acids are...

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Plankton

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Artificial seawater Autotrophs Biological pump Diel vertical migration Dimethylsulfoniopropionate f-ratio Fish diseases and parasites Heterotroph HNLC Macroalgae...

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Methanethiol

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methanethiol is the primary breakdown product of the algal metabolite dimethylsulfoniopropionate (DMSP). Marine bacteria appear to obtain most of the sulfur in...

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Ruegeria pomeroyi

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Diatom

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Roseovarius nubinhibens

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nubinhibens is a species of Gram-negative, rod-shaped, aerobic dimethylsulfoniopropionate-demethylating bacteria. Its type strain is ISMT (=ATCC BAA-591T...

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Seafood

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freshwater fish and invertebrates. Also, a chemical substance called dimethylsulfoniopropionate (DMSP) that is found in red and green algae is transferred into...

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Sulfur

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ions have three groups attached to a cationic sulfur center. Dimethylsulfoniopropionate (DMSP) is one such compound, important in the marine organic sulfur...

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Glossary of chemical formulae

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Zooplankton

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Artificial seawater Autotrophs Biological pump Diel vertical migration Dimethylsulfoniopropionate f-ratio Fish diseases and parasites Heterotroph HNLC Macroalgae...

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Phytoplankton

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Crevalle jack

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spawning aggregations over coral reefs based on the release of dimethylsulfoniopropionate (DMSP) from the reef. DMSP is a naturally occurring chemical produced...

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DMSP

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Gephyrocapsa huxleyi

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Osmolyte

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act as osmoprotectants include trimethylamine N-oxide (TMAO), dimethylsulfoniopropionate, sarcosine, betaine, glycerophosphorylcholine, myo-inositol, taurine...

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Microfluidics

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Simó R, Ahmed T, Stocker R (July 2010). "Chemoattraction to dimethylsulfoniopropionate throughout the marine microbial food web". Science. 329 (5989):...

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Ichthyoplankton

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Prymnesium parvum

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coordinate these aggregations over coral reefs based on the release of dimethylsulfoniopropionate (DMSP) from the reef. DMSP is a naturally occurring chemical produced...

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Coccolithophore

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Methylophaga thiooxydans

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the algae Emiliania huxleyi, where it grows by breaking down dimethylsulfoniopropionate from E. hexleyi into dimethylsulfide and acrylate. M. thiooxydans...

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Desulfovibrio acrylicus

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Stam, Wytze T.; Hansen, T. A. (27 August 1996). "Cleavage of dimethylsulfoniopropionate and reduction of acrylate by Desulfovibrio acrylicus sp. nov"...

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