FComEx: Sarcosine (PC000004)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:13 UTC

Update date

2017-01-19 02:36:09 UTC

FoodComEx ID

PC000004

FoodDB Record

Not Available

Chemical Information

Name

Sarcosine

Description

Sarcosine is the N-methyl derivative of glycine. 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 naturally found 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 is formed from dietary intake of choline and from the metabolism of methionine, and is rapidly degraded to glycine. Sarcosine has no known toxicity, as evidenced by the lack of phenotypic manifestations of sarcosinemia, an inborn error of sarcosine metabolism. Sarcosinemia can result from severe folate deficiency because of the folate requirement for the conversion of sarcosine to glycine . Sarcosine has recently been identified as a biomarker for invasive prostate cancer. It was found to be greatly increased during prostate cancer progression to metastasis and could be detected in urine. Sarcosine levels were also increased in invasive prostate cancer cell lines relative to benign prostate epithelial cells.(PMID: 19212411) [HMDB]

CAS Number

107-97-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(methylamino)-Acetate	hmdb
(methylamino)-Acetic acid	hmdb
(Methylamino)acetate	hmdb
(Methylamino)acetic acid	hmdb
(Methylamino)ethanoate	hmdb
(Methylamino)ethanoic acid	hmdb
MeGly	ChEBI
Methylaminoacetate	Generator
Methylaminoacetic acid	ChEBI
Methylglycine	hmdb
N-methyl-Glycine	hmdb
N-Methylaminoacetate	hmdb
N-Methylaminoacetic acid	hmdb
N-Methylglycine	hmdb
Sar	ChEBI
Sarcosin	hmdb
Sarcosinate	hmdb
Sarcosine	hmdb
Sarcosinic acid	hmdb

Chemical Formula

Not Available

IUPAC name

Not Available

InChI Identifier

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

InChI Key

FSYKKLYZXJSNPZ-UHFFFAOYSA-N

Isomeric SMILES

CNCC(O)=O

Average Molecular Weight

89.0932

Monoisotopic Molecular Weight

89.047678473

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents