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Identifiers | |
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3D model (
JSmol)
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.192 |
EC Number |
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PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C3H9NO3S | |
Molar mass | 139.17 g·mol−1 |
Hazards | |
GHS labelling: | |
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Danger | |
H314, H315, H319 | |
P260, P264, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P332+P313, P337+P313, P362, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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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). [1] In contrast to the widespread taurine, N-methyltaurine has been found in nature only in red algae, [2] where it is formed by methylation of taurine. It is suitable for esterification (actually amide formation) with long-chain carboxylic acids to taurides (acylaminoethansulfonaten) because of its high polarity and the relatively good solubility of its alkaline earth metal salts, which are also used as mild anionic surfactants. [3]
The synthesis of N-methyltaurine was reported as early as 1878, [4] 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. [5] The addition of methylamine to sodium vinylsulfonate in aqueous solution gives N-methyltaurine in 85% yield after acidification with acetic acid. [6] 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. [7] The reaction of sodium isethionate with methylamine in water at high temperature and pressure yields the sodium salt of N-methyltaurine [8]
which yields pure N-methyltaurine upon saturation with CO2 and removal of the precipitated sodium bicarbonate. [9]
N-Methyltaurine is a white powdery solid which is readily soluble in water.
N-Methyltaurine (or its sodium salt) is used as a polar head group in surfactants from the class of taurides (acylaminoethanesulfonates), sometimes also called methyltaurates. The Taurides are characterized by excellent foaming - even in the presence of oil and skin fats - and foam stability, with good skin compatibility and broad pH stability. [10] The market breakthrough for N-methyltaurine as a hair restorer is still pending.[ citation needed]