Sarcosine

Sarcosine
Skeletal formula of sarcosine
Names
IUPAC name
N-Methylglycine
Systematic IUPAC name
(Methylamino)acetic acid
Identifiers
3D model (JSmol)
3DMet
1699442
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.217 Edit this at Wikidata
EC Number
  • 203-538-6
2018
KEGG
MeSH Sarcosine
UNII
  • InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) checkY
    Key: FSYKKLYZXJSNPZ-UHFFFAOYSA-N checkY
  • CNCC(O)=O
Properties
C3H7NO2
Molar mass 89.094 g·mol−1
Appearance White solid
Odor Odourless
Density 1.093 g/mL
Melting point 208 to 212 °C (406 to 414 °F; 481 to 485 K) experimental
89.09 g L−1 (at 20 °C)
log P 0.599
Acidity (pKa) 2.36
Basicity (pKb) 11.64
UV-vismax) 260 nm
Absorbance 0.05
Thermochemistry
128.9 J K−1 mol−1
−513.50–−512.98 kJ mol−1
−1667.84–−1667.54 kJ mol−1
Related compounds
Related alkanoic acids
Related compounds
Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sarcosine, also known as N-methylglycine, or monomethylglycine, is a amino acid with the formula CH3N(H)CH2CO2H. It exists at neutral pH as the zwitterion CH3N+(H)2CH2CO2, which can be obtained as a white, water-soluble powder. Like some amino acids, sarcosine converts to a cation at low pH and an anion at high pH, with the respective formulas CH3N+(H)2CH2CO2H and CH3N(H)CH2CO2. Sarcosine is a close relative of glycine, with a secondary amine in place of the primary amine.

Sarcosine is ubiquitous in biological materials. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications. It is also a reagent in organic synthesis.[1]

Sarcosine is sweet to the taste.[citation needed]

  1. ^ Ganesh M, Rao MP (2022). "N -Methylglycine". Encyclopedia of Reagents for Organic Synthesis. pp. 1–4. doi:10.1002/047084289X.rn02457. ISBN 9780471936237.