Dimethylsulfoniopropionate

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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).
☒N verify (what is checkY☒N ?)

Dimethylsulfoniopropionate (DMSP), is an

Polysiphonia fastigiata.[4]

Biosynthesis

In higher plants, DMSP is biosynthesized from S-methylmethionine. Two intermediates in this conversion are dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.[5] In algae, however, the biosynthesis starts with the replacement of the amino group in methionine by hydroxide.[6]

Degradation

DMSP is broken down by marine microbes to form two major volatile sulfur products, each with distinct effects on the environment. One of its breakdown products is

DMSP-lyase, although many non-marine species of bacteria convert methanethiol to DMS.[citation needed
]

DMS is also taken up by

abiotic and microbial uptake of methanethiol in seawater, and the comparatively low reactivity of DMS. However, a significant portion of DMS in seawater is oxidized to dimethyl sulfoxide
(DMSO).

Relevant to

solar radiation that reaches the Earth's surface. This occurs through degradation of DMS in the atmosphere into hygroscopic compounds that condense water vapor leading to the formation of clouds.[9]

DMSP has also been implicated in influencing the taste and odour characteristics of various products. For example, although DMSP is odourless and tasteless, it is accumulated at high levels in some marine

seafood products because of the action of bacterial DMSP-lyase, which cogenerates acrylate
.

Further reading

See also

References

  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. S2CID 27541024
    .
  4. .
  5. .
  6. .
  7. .
  8. .
  9. ^ "DMS: The Climate Gas You've Never Heard of".

External links