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N-methyltaurine

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EntityQ1959602· pop 5· linked from 2 articles

N-methyltaurine

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'''N-Methyltaurine (2-methylaminoethanesulfonic acid') is an aminosulfonic acid which is present as a zwitterion in the crystalline state and in polar solvents (just like amino acids). In contrast to the widespread taurine, N''-methyltaurine has been found in nature only in red algae, where it is formed by methylation of taurine. It is an important industrial chemical used in the production of taurates, which are used extensively as mild anionic surfactants.

Chemical data

Formula
C3H9NO3S
Molecular weight
139.18 g/mol
IUPAC name
2-(methylamino)ethanesulfonic acid
SMILES
CNCCS(=O)(=O)O
InChIKey
SUZRRICLUFMAQD-UHFFFAOYSA-N
XLogP
-3.6
Polar surface area
74.8 Ų
H-bond donors
2
H-bond acceptors
4
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
139.03
Show 3 more facts
canonical SMILES
CNCCS(=O)(=O)O
chemical formula
C₃H₉NO₃S
found in taxon
Aplysina
Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

4 sections
Contents
  • Preparation
  • Properties
  • Use
  • References

'''N-Methyltaurine (2-methylaminoethanesulfonic acid') is an aminosulfonic acid which is present as a zwitterion in the crystalline state and in polar solvents (just like amino acids). In contrast to the widespread taurine, N-methyltaurine has been found in nature only in red algae, where it is formed by methylation of taurine. It is an important industrial chemical used in the production of taurates, which are used extensively as mild anionic surfactants.

== Preparation == The synthesis of N-methyltaurine was reported as early as 1878, with methylamine being reacted with the silver salt of 2-chloroethanesulfonic acid. An obvious modification for this reaction is the replacement of the silver salt of 2-chloroethanesulfonic acid by the sodium salt of 2-chloroethanesulfonic acid. The addition of methylamine to sodium vinylsulfonate in aqueous solution gives N-methyltaurine in 85% yield after acidification with acetic acid. The purification of the crude product and preparation of the N-methyltaurine can also be accomplished by passage of the sodium salt solution through a cation exchange resin in its H form and then through an anion exchange resin in its OH form. The reaction of sodium isethionate with methylamine in water at high temperature and pressure yields the sodium salt of N-methyltaurine N-Methyltaurin Syntheseweg

Excerpted from Wikipedia’s “N-methyltaurine” article, available under the CC BY-SA 4.0 licence.

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