Record Information
Version1.0
Creation date2015-10-09 22:27:11 UTC
Update date2017-01-19 02:36:09 UTC
FoodComEx IDPC000001
FoodDB RecordFDB009020
Chemical Information
NameBetaine
DescriptionBetaine, 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 Number107-43-7
Structure
Thumb
Synonyms
SynonymSource
(carboxymethyl)trimethylammonium hydroxide inner saltbiospider
(carboxymethyl)trimethylammonium hydroxide, inner saltbiospider
(carboxymethyl)trimethylammonium inner saltbiospider
(trimethyl-α-earleinebiospider
(trimethylammonio)acetatebiospider
(trimethylammoniumyl)acetatebiospider
(Trimethylammoniumyl)acetic acidGenerator
α-earleinebiospider
βinebiospider
βine (van)biospider
1-carboxy-N,N,N-trimethyl-Methanaminiumbiospider
1-carboxy-N,N,N-trimethyl-Methanaminium hydroxidebiospider
1-Carboxy-N,N,N-trimethylmethanaminium inner saltbiospider
2-(Trimethylammonio)ethanoic acid, hydroxide, inner saltbiospider
2-N,N,N-Trimethylammonio acetateChEBI
2-N,N,N-Trimethylammonio acetic acidGenerator
A-earleinebiospider
Abrominebiospider
Acidin-pepsinbiospider
AcidolChEBI
Alpha-earleinebiospider
Aminocoatbiospider
Aquadew AN 100biospider
BetChEBI
Betafinbiospider
Betafin BCRbiospider
Betafin BPbiospider
Betainebiospider
Betaine (8CI)biospider
Betaine hydrochloridebiospider
Betaine, anhydrousbiospider
Betainum muriaticumbiospider
Cystadanebiospider
Cystadane (TN)biospider
Ektasolve eeHMDB
Finnstimbiospider
Glycine βinebiospider
Glycine betainebiospider
Glycine, trimethylβinebiospider
Glycine, trimethylbetainebiospider
Glycocoll βinebiospider
Glycocoll betainebiospider
GLYCYLβinebiospider
Glycylbetainebiospider
Glykokollbetainbiospider
Greenstimbiospider
Jortainebiospider
Loramine amb 13HMDB
Loramine AMB-13biospider
Lycinebiospider
Methanaminium, 1-carboxy-N,N,N-trimethyl-, hydroxidebiospider
Methanaminium, 1-carboxy-N,N,N-trimethyl-, inner saltbiospider
Methanaminium, 1-carboxy-N,N,N-trimethyl-, inner salt (9CI)biospider
Methanaminium, carboxy-n,n,n-trimethyl-, inner saltbiospider
N,n,n-trimethylammonioacetatebiospider
N,N,N-Trimethylammonioacetic acidGenerator
N,n,n-trimethylglycinebiospider
Oxyneurinebiospider
Rubrine cbiospider
Trimethylaminoacetatebiospider
Trimethylaminoacetic acidbiospider
Trimethylammonioacetatebiospider
Trimethylammonioacetic acidGenerator
Trimethylbetaine glycinebiospider
Trimethylglycinebiospider
Trimethylglycocollbiospider
Trimethylglycocoll anhydridebiospider
Chemical FormulaC5H11NO2
IUPAC name2-(trimethylazaniumyl)acetate
InChI IdentifierInChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
InChI KeyKWIUHFFTVRNATP-UHFFFAOYSA-N
Isomeric SMILESC[N+](C)(C)CC([O-])=O
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water Solubility611 mg/mL at 19 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point293 oC ( Soicke, H., Fitoterapia 1988, V59(1), P73-5)
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 5 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci G671
Glentham GE1604
MetaSci HMDB0000043
Sigma-Aldrich HMDB0000043
Toronto Research Chemicals B325005