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Sarcosine

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Sarcosine

Skeletal formula of sarcosine

IUPAC name

2-(Methylamino)acetic acid[1]

Identifiers

CAS number 107-97-1 Yes

PubChem 1088

ChemSpider 1057 Yes

UNII Z711V88R5F Yes

EC number 203-538-6

KEGG C00213 Yes

MeSH Sarcosine

ChEBI CHEBI:15611 Yes

ChEMBL CHEMBL304383 Yes

Beilstein Reference 1699442

Gmelin Reference 2018

3DMet B01190

Jmol-3D images Image 1

Image 2

SMILES

CNCc(:[o]):[oH]

CNCC(O)=O

InChI

InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) Yes

Key: FSYKKLYZXJSNPZ-UHFFFAOYSA-N Yes

Properties

Molecular formula C3H7NO2

Molar mass 89.09 g mol−1

Appearance White crystalline powder

Odor Odourless

Density 1.093 g/mL

Melting point 208 to 212 °C (406 to 414 °F; 481 to 485 K)

Boiling point 195.1 °C (383.2 °F; 468.2 K)

Solubility in water 89.09 g L−1 (at 20 °C)

log P 0.599

Acidity (pKa) 2.36

Basicity (pKb) 11.64

λmax 260 nm

Absorbance 0.05

Thermochemistry

Specific

heat capacity C 128.9 J K−1 mol−1

Std enthalpy of

formation ΔfHo298 −513.50–−512.98 kJ mol−1

Std enthalpy of

combustion ΔcHo298 −1667.84–−1667.54 kJ mol−1

Related compounds

Related alkanoic acids

Dimethylglycine

Glycocyamine

Creatine

N-Methyl-D-aspartic acid

beta-Methylamino-L-alanine

Guanidinopropionic acid

Related compounds Dimethylacetamide

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

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Infobox references

Sarcosine, also known as N-methylglycine, is an intermediate and byproduct in glycine synthesis and degradation. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. Sarcosine is a natural amino acid found in muscles and other body tissues. In the laboratory, it may be synthesized from chloroacetic acid and methylamine. Sarcosine is found naturally as an intermediate in the metabolism of choline to glycine. Sarcosine is sweet to the taste and dissolves in water. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications.

Sarcosine is ubiquitous in biological materials and is present in such foods as egg yolks, turkey, ham, vegetables, legumes, etc.

Sarcosine

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