Version |
1.0 |
Creation Date |
2005-11-16 15:48:42 |
Update Date |
2009-05-28 10:24:19 |
Accession Number |
BMDB00043 |
Common Name |
Betaine |
Description |
Betaine or trimethylglycine is a methylated derivative of glycine. It functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. The donation of methyl groups is important to proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine has also been of interest for its role in osmoregulation. As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances. (From Martindale, The Extra Pharmacopoeia, 30th Ed, p1341) |
Synonyms |
- (Carboxymethyl)trimethylammonium hydroxide inner salt
- (Trimethylammonio)acetate
- 1-Carboxy-N,N,N-trimethylmethanaminium inner salt
- 1-carboxy-N,N,N-trimethyl-Methanaminium
- 1-carboxy-N,N,N-trimethyl-Methanaminium hydroxide
- Abromine
- Aminocoat
- Betafin
- Betafin BCR
- Betafin BP
- Betaine
- Cystadane
- Ektasolve EE
- FinnStim
- Glycine betaine
- Glycocoll betaine
- Glycylbetaine
- Greenstim
- Loramine AMB 13
- Loramine AMB-13
- Lycine
- N,N,N-Trimethylglycine
- Oxyneurine
- Rubrine C
- Trimethylaminoacetate
- Trimethylaminoacetic acid
- Trimethylglycine
- Trimethylglycocoll
- a-Earleine
- alpha-Earleine
- trimethylbetaine Glycine
|
Chemical IUPAC Name |
2-trimethylammonioacetate |
Chemical Formula |
C5H11NO2 |
Chemical Structure |
 |
Chemical Taxonomy |
Kingdom |
|
Super Class |
- Amino acids and Amino Acid conjugates
|
Class |
- Quaternary Amines; Amino Acids
|
Sub Class |
- Short chain quaternary ammonium salts
|
Family |
|
Species |
- cation; anion; quaternary ammonium salt; carboxylic acid salt
|
Biofunction |
- Osmolyte; Component of Glycine, serine and threonine metabolism; Component of Methionine metabolism
|
Application |
— |
Source |
|
|
Average Molecular Weight |
117.146 |
Monoisotopic Molecular Weight |
117.078979 |
Isomeric SMILES |
C[N+](C)(C)CC([O-])=O |
Canonical SMILES |
C[N+](C)(C)CC([O-])=O |
KEGG Compound ID |
C00719  |
BioCyc ID |
BETAINE  |
BiGG ID |
35786  |
Wikipedia Link |
Betaine  |
METLIN ID |
287  |
PubChem Compound |
247  |
PubChem Substance |
2165  |
ChEBI ID |
17750  |
CAS Registry Number |
107-43-7 |
InChI Identifier |
InChI=1/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 |
Synthesis Reference |
Mu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49. |
Melting Point (Experimental) |
293 oC ( Soicke, H., Fitoterapia 1988, V59(1), P73-5); 301 oC dec. |
Experimental Water Solubility |
611.0 mg/mL at 19 oC [YALKOWSKY,SH & DANENFELSER,RM (1992)]
Source: PhysProp
|
Predicted Water Solubility |
1.86 mg/mL [Predicted by ALOGPS]
Calculated using ALOGPS
|
Physiological Charge |
0 |
State |
Solid |
Experimental LogP/Hydrophobicity |
Not Available
Source: PhysProp
|
Predicted LogP/Hydrophobicity |
-2.70 [Predicted by ALOGPS]; -4.93 [MEYLAN,WM & HOWARD,PH (1995)]
Calculated using ALOGPS
|
Material Safety Data Sheet (MSDS) |
|
MOL File |
Show |
SDF File |
Show |
PDB File |
Show |
2D Structure |
|
3D Structure |
|
Experimental PDB ID |
Not Available |
Experimental 1H NMR Spectrum |
Download Spectrum Download FID (Varian) Show Experimental Conditions  |
Experimental 13C NMR Spectrum |
Download Spectrum Download FID (Bruker) Show Experimental Conditions  |
Experimental 13C HSQC Spectrum |
Download Spectrum Download FID (Bruker) Show Experimental Conditions  |
Predicted 1H NMR Spectrum |
Show Image Show Peaklist
|
Predicted 13C NMR Spectrum |
Show Image Show Peaklist
|
Mass Spectrum |
|
Simplified TOCSY Spectrum |
Not Available |
BMRB Spectrum |
Show Image Show Peaklist |
Cellular Location |
- Cytoplasm
- Extracellular
- mitochondria
|
Biofluid Location |
|
Tissue Location |
Tissue |
References |
Adipose Tissue |
— |
Adrenal Cortex |
— |
Adrenal Gland |
— |
Bladder |
— |
Epidermis |
— |
Fibroblasts |
— |
Gonads |
— |
Gut |
— |
Intestine |
— |
Kidney |
— |
Liver |
— |
Pancreas |
— |
Placenta |
— |
Platelet |
— |
Prostate |
— |
Skeletal Muscle |
— |
Skin |
— |
Spleen |
— |
Stratum Corneum |
— |
Testes |
— |
|
Concentrations (Normal) |
Biofluid |
Breast_Milk |
Value |
459 - 1410 uM |
Age |
N/A |
Sex |
N/A |
Condition |
Normal |
Comments |
Raw. skim. |
References |
|
Biofluid |
Breast_Milk |
Value |
597 +/- 44 uM |
Age |
N/A |
Sex |
N/A |
Condition |
Normal |
Comments |
Quantified by NMR in 2% milk |
References |
|
Biofluid |
Breast_Milk |
Value |
610 +/- 52 uM |
Age |
N/A |
Sex |
N/A |
Condition |
Normal |
Comments |
Quantified by NMR in skim milk |
References |
|
Biofluid |
Breast_Milk |
Value |
572 +/- 18 uM |
Age |
N/A |
Sex |
N/A |
Condition |
Normal |
Comments |
Quantified by NMR in 1% milk |
References |
|
Biofluid |
Breast_Milk |
Value |
631 +/- 57 uM |
Age |
N/A |
Sex |
N/A |
Condition |
Normal |
Comments |
Quantified by NMR in 3.25% milk |
References |
|
|
Concentrations (Abnormal) |
Not Available |
Pathway Names |
- Glycine, Serine and Threonine Metabolism
|
HMDB Pathways |
Name
|
Glycine, Serine and Threonine Metabolism
|
Image
|
Show  |
|
KEGG Pathways |
Name
|
Glycine, Serine and Threonine Metabolism
|
Image
|
Show  |
|
SimCell Pathways |
|
General References |
- Wikipedia

|