(-)-Stachydrine
Basic information
- CAS
471-87-4- Standard SMILES
C[N+]1(C)CCC[C@H]1C(=O)[O-]- InChIKey
CMUNUTVVOOHQPW-LURJTMIESA-N- Molecular formula
- C7H13NO2
- Average molar mass
- 143.18 g/mol
- Monoisotopic mass
- 143.09462866
Overview
L-proline betaine is an amino acid betaine that is L-proline zwitterion in which both of the hydrogens attached to the nitrogen are replaced by methyl groups. It has a role as a plant metabolite, a food component and a human blood serum metabolite. It is a N-methyl-L-alpha-amino acid, an alkaloid and an amino-acid betaine. It is functionally related to a L-prolinium. It is a conjugate base of a N,N-dimethyl-L-prolinium. It is an enantiomer of a D-proline betaine.
Names & identifiers
- Preferred name
- (-)-Stachydrine
- IUPAC
- (2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate
- English name
- N,N-Dimethyl-L-proline
- Molecular formula
- C7H14NO2
- Molecular weight
- 144.19
Names & synonyms
stachydrine471-87-4L-proline betaineN,N-dimethyl-L-prolinemethyl hygrate betaine(-)-Stachydrine(2S)-1,1-dimethylpyrrolidinium-2-carboxylateS1L688345CCHEBI:35280Pyrrolidinium, 2-carboxy-1,1-dimethyl-, inner salt, (2S)-DTXSID50274274RefChem:185292
Show more names
N-Dimethyl-L-proline1,1-dimethylpyrrolidinium-2-carboxylateCadabineL-stachydrineStachydrine, >98%methyl hygrate bine
DTXCID80225754(2R)-1,1-dimethylpyrrolidin-1-ium-2-carboxylic acid207-445-1dimethylprolineproline betaine(S)-1,1-Dimethylpyrrolidin-1-ium-2-carboxylate(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate(S)-2-Carboxylato-1,1-dimethylpyrrolidinium
Database identifiers
- CAS
471-87-4- PubChem CID
- 115244
- DTXSID
DTXSID20963744- ChEMBL
CHEMBL1456892
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 40.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 148
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 235 °C · 235°C
- Boiling point
- 261.28 °C · 261.28°C (rough estimate)
- Density
- 1.1095 · 1.1095 (rough estimate)
- refractive index
- 1.415 · 1.4150 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 100 mg/mL · Water: 100 mg/mL (698.42 mM); DMSO: 100 mg/mL (698.42 mM)
- form
- Solid
- color
- White to off-white
- FDA UNII
- 1 L688345C · S1L688345C
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- hs_code
- 29214980
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Applications
DescriptionThis alkaloid, which has been isolated from the leaves of Cadaba fruticosa, has been shown, by comparison of its hydrochloride and the NMR spectrum, to be stachydrine.
UsesStachydrine is used for various ethnobotany and ethnomedicinal uses. It can also be used to promote healthy neural development in an unborn baby, as well as to determine the differential effects of post-weaning diet and maternal obesity on mouse liver and brain metabolomes.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: L-proline betaine is an amino acid betaine that is L-proline zwitterion in which both of the hydrogens attached to the nitrogen are replaced by methyl groups. It has a role as a food component, a plant metabolite and a human blood serum metabolite. It is a N-methyl-L-alpha-amino acid, an alkaloid and an amino-acid betaine. It is functionally related to a L-prolinium. It is a conjugate base of a N,N-dimethyl-L-prolinium. It is an enantiomer of a D-proline betaine.
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