FComEx: Betaine (PC000001)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:11 UTC

Update date

2017-01-19 02:36:09 UTC

FoodComEx ID

PC000001

FoodDB Record

FDB009020

Chemical Information

Name

Betaine

Description

Betaine, also known as Bet or trimethylglycine, 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). Betaine is a moderately acidic compound (based on its pKa). Betaine exists in all eukaryotes, ranging from yeast to humans. In humans, betaine is involved in betaine metabolism. Betaine is a bland tasting compound. Outside of the human body, Betaine is found, on average, in the highest concentration within a few different foods, such as swamp cabbages, quinoa, and lambsquarters and in a lower concentration in common buckwheats, burdocks, and yellow zucchinis. Betaine has also been detected, but not quantified in, several different foods, such as lemon verbena, wasabis, endives, chickpea, and pomegranates. This could make betaine a potential biomarker for the consumption of these foods. Intracellular accumulation of betaines permits water retention in cells, thus protecting from the effects of dehydration (Wikipedia). Betaine comes from either the diet or by the oxidation of choline. Betaine, with regard to humans, has been found to be associated with several diseases such as chronic renal failure, colorectal cancer, and alzheimer's disease; betaine has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and propionic acidemia. In an acute toxicology study in rats, death frequently occurred at doses equal to or greater than 10,000 mg/kg. Betaine has been shown to have an inhibitory effect on NO release in activated microglial cells and may be an effective therapeutic component to control neurological disorders (PMID: 22801281). Betaine insufficiency is associated with metabolic syndrome, lipid disorders, and diabetes, and may have a role in vascular and other diseases (PMID: 20346934). Many reports have shown that betaine's therapeutic effectiveness is limited, and does not lower tHcy levels or prevent clinical symptoms .

CAS Number

107-43-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(carboxymethyl)trimethylammonium hydroxide inner salt	biospider
(carboxymethyl)trimethylammonium hydroxide, inner salt	biospider
(carboxymethyl)trimethylammonium inner salt	biospider
(trimethyl-α-earleine	biospider
(trimethylammonio)acetate	biospider
(trimethylammoniumyl)acetate	biospider
(Trimethylammoniumyl)acetic acid	Generator
α-earleine	biospider
βine	biospider
βine (van)	biospider
1-carboxy-N,N,N-trimethyl-Methanaminium	biospider
1-carboxy-N,N,N-trimethyl-Methanaminium hydroxide	biospider
1-Carboxy-N,N,N-trimethylmethanaminium inner salt	biospider
2-(Trimethylammonio)ethanoic acid, hydroxide, inner salt	biospider
2-N,N,N-Trimethylammonio acetate	ChEBI
2-N,N,N-Trimethylammonio acetic acid	Generator
A-earleine	biospider
Abromine	biospider
Acidin-pepsin	biospider
Acidol	ChEBI
Alpha-earleine	biospider
Aminocoat	biospider
Aquadew AN 100	biospider
Bet	ChEBI
Betafin	biospider
Betafin BCR	biospider
Betafin BP	biospider
Betaine	biospider
Betaine (8CI)	biospider
Betaine hydrochloride	biospider
Betaine, anhydrous	biospider
Betainum muriaticum	biospider
Cystadane	biospider
Cystadane (TN)	biospider
Ektasolve ee	HMDB
Finnstim	biospider
Glycine βine	biospider
Glycine betaine	biospider
Glycine, trimethylβine	biospider
Glycine, trimethylbetaine	biospider
Glycocoll βine	biospider
Glycocoll betaine	biospider
GLYCYLβine	biospider
Glycylbetaine	biospider
Glykokollbetain	biospider
Greenstim	biospider
Jortaine	biospider
Loramine amb 13	HMDB
Loramine AMB-13	biospider
Lycine	biospider
Methanaminium, 1-carboxy-N,N,N-trimethyl-, hydroxide	biospider
Methanaminium, 1-carboxy-N,N,N-trimethyl-, inner salt	biospider
Methanaminium, 1-carboxy-N,N,N-trimethyl-, inner salt (9CI)	biospider
Methanaminium, carboxy-n,n,n-trimethyl-, inner salt	biospider
N,n,n-trimethylammonioacetate	biospider
N,N,N-Trimethylammonioacetic acid	Generator
N,n,n-trimethylglycine	biospider
Oxyneurine	biospider
Rubrine c	biospider
Trimethylaminoacetate	biospider
Trimethylaminoacetic acid	biospider
Trimethylammonioacetate	biospider
Trimethylammonioacetic acid	Generator
Trimethylbetaine glycine	biospider
Trimethylglycine	biospider
Trimethylglycocoll	biospider
Trimethylglycocoll anhydride	biospider

Chemical Formula

C5H11NO2

IUPAC name

2-(trimethylazaniumyl)acetate

InChI Identifier

InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3

InChI Key

KWIUHFFTVRNATP-UHFFFAOYSA-N

Isomeric SMILES

C[N+](C)(C)CC([O-])=O

Average Molecular Weight

117.1463

Monoisotopic Molecular Weight

117.078978601

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

Substituents

Alpha-amino acid
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid
Organopnictogen compound
Hydrocarbon derivative
Organic salt
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic nitrogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glycine derivative (CHEBI:17750 )
amino-acid betaine (CHEBI:17750 )
a methylated methyl acceptor (BETAINE )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	Not Available
Experimental Water Solubility	611 mg/mL at 19 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	293 oC ( Soicke, H., Fitoterapia 1988, V59(1), P73-5)

Foods of Origin