Sarcosine
Chemical compound / From Wikipedia, the free encyclopedia
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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.
Names | |
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IUPAC name
N-Methylglycine | |
Systematic IUPAC name
(Methylamino)acetic acid | |
Identifiers | |
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3D model (JSmol) |
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3DMet | |
1699442 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.003.217 |
EC Number |
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2018 | |
KEGG |
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MeSH | Sarcosine |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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-vis (λmax) | 260 nm |
Absorbance | 0.05 |
Thermochemistry | |
Heat capacity (C) |
128.9 J K−1 mol−1 |
Std enthalpy of formation (ΔfH⦵298) |
−513.50–−512.98 kJ mol−1 |
Std enthalpy of combustion (ΔcH⦵298) |
−1667.84–−1667.54 kJ mol−1 |
Related compounds | |
Related alkanoic acids |
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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 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]