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Identification
YMDB IDYMDB01516
NameBetaine
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionBetaine (glycine betaine or trimethylglycine) is a methylated derivative of glycine synthetized from choline. It is a very efficient osmolyte found in a wide range of bacteria and plants, where it is accumulated at high cytoplasmic concentrations in response to osmotic stress, to act as an osmoprotectant. Many organisms, including fungi, are also able to catabolize glycine betaine, using it as a sole source for both carbon and nitrogen. [Biocyc PWY-3721 and PWY-3661]
Structure
Thumb
Synonyms
  • (Trimethylammonio)acetate
  • (trimethylammoniumyl)acetate
  • 1-carboxy-N,N,N-trimethyl-Methanaminium
  • 1-carboxy-N,N,N-trimethyl-Methanaminium hydroxide
  • 1-Carboxy-N,N,N-trimethylmethanaminium inner salt
  • 2-(Trimethylammonio)ethanoic acid, hydroxide, inner salt
  • 2-N,N,N-trimethylammonio acetate
  • a-Earleine
  • Abromine
  • acidol
  • alpha-Earleine
  • Aminocoat
  • Bet
  • Betaine
  • Betaine hydrochloride
  • Cystadane
  • Glycine betaine
  • Glycine, trimethyl&beta
  • Glycine, trimethylbetaine
  • Glycocoll &beta
  • Glycocoll betaine
  • Glycylbetaine
  • Greenstim
  • ine
  • Lycine
  • Methanaminium, 1-carboxy-N,N,N-trimethyl-, hydroxide
  • Methanaminium, 1-carboxy-N,N,N-trimethyl-, inner salt
  • N,N,N-trimethylammonioacetate
  • N,N,N-Trimethylglycine
  • Oxyneurine
  • Rubrine C
  • trimethylaminoacetate
  • Trimethylaminoacetic acid
  • Trimethylammonioacetate
  • trimethylbetaine Glycine
  • Trimethylglycine
  • Trimethylglycocoll
  • (Trimethylammoniumyl)acetic acid
  • 2-N,N,N-Trimethylammonio acetic acid
  • N,N,N-Trimethylammonioacetic acid
  • Trimethylammonioacetic acid
  • (Carboxymethyl)trimethylammonium hydroxide inner salt
  • Betafin
  • Betafin BCR
  • Betafin BP
  • Ektasolve ee
  • FinnStim
  • Loramine amb 13
  • Loramine amb-13
  • Acidin pepsin
  • Beaufour brand OF betaine citrate
  • Byk brand OF betaine phosphate
  • Fournier brand OF betaine ascorbate and hydrate
  • Hydrochloride, betaine
  • Logeais brand OF betaine cyclobutyrate
  • Novobetaine
  • Betaine orphan brand
  • Boizot brand OF betaine aspartate
  • C.B.B.
  • Citrate de bétaïne upsa
  • Scorbo-bétaïne
  • Stea-16
  • Stea16
  • Acidin-pepsin
  • Citrate de bétaïne beaufour
  • Orphan brand OF betaine
  • Scorbo bétaïne
  • AcidinPepsin
  • Betaine, glycine
  • Hepastyl
  • Scorbobétaïne
  • UPSA brand OF betaine citrate
  • Stea 16
CAS number107-43-7
WeightAverage: 117.1463
Monoisotopic: 117.078978601
InChI KeyKWIUHFFTVRNATP-UHFFFAOYSA-N
InChIInChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
IUPAC Name2-(trimethylazaniumyl)acetate
Traditional IUPAC Name(trimethylammonio)acetate
Chemical FormulaC5H11NO2
SMILESC[N+](C)(C)CC([O-])=O
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
Physical Properties
StateSolid
Charge0
Melting point293 °C
Experimental Properties
PropertyValueReference
Water Solubility611 mg/mL at 19 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.86 g/LALOGPS
logP-2.7ALOGPS
logP-4.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.82 m³·mol⁻¹ChemAxon
Polarizability12.11 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BlandFDB009020
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
26 ± 0 µM grape juiceanaerobicBrewer's yeastAlcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9200000000-96ab6e2136fe7e03b63aJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-feacc600820771d2a77bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-e5bbda9fb66994576062JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-c382759eab7d0a87ac27JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-a7beb42e6944181ae5d9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-1900000000-77fbc4a2b76030d53644JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9100000000-2941e4997f202293bf71JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-9b9e3cecb77ed4b40b7cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-27bbb5f9642306216a0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-1900000000-82a41cbb0f697910b577JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0aor-9500000000-9a0f1853188052d798c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-066r-5900000000-a6291f86046f32ad3c81JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9200000000-709208d6782f1b588501JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-a7beb42e6944181ae5d9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-77fbc4a2b76030d53644JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9100000000-2941e4997f202293bf71JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-a2560fc2add75f79eadbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-27bbb5f9642306216a0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-b45353825d98488d752aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0aor-9500000000-3fdd9d17a169db5c58ddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-493791dfdd428fc3bd6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3900000000-b2afc99d27edd18d7f29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lk9-9500000000-5c3747866d41ab8df618JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-5cf478650fcc3a71b790JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-86832153dde465116f78JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-9600000000-2e90f09f2c87dfc45640JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-f32989f795eeceb8b692JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Synthesis Reference:Mu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49.
External Links:
ResourceLink
CHEBI ID17750
HMDB IDHMDB00043
Pubchem Compound ID247
Kegg IDC00719
ChemSpider ID242
FOODB IDFDB009020
Wikipedia IDTrimethylglycine
BioCyc IDBETAINE