(2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate
Basic information
- CAS
5796-17-8- Standard SMILES
[NH3+][C@H](Cc1ccc(O)c(O)c1)C(=O)[O-]- InChIKey
WTDRDQBEARUVNC-ZCFIWIBFSA-N- Molecular formula
- C9H11NO4
- Average molar mass
- 197.19 g/mol
- Monoisotopic mass
- 197.06880783
Overview
D-dopa zwitterion is an amino acid zwitterion obtained from the transfer of a proton from the carboxy group to the amino group of D-dopa. Major microspecies at pH 7.3. It is an enantiomer of a L-dopa zwitterion. It is a tautomer of a D-dopa.
Names & identifiers
- Preferred name
- (2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate
- IUPAC
- (2R)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate
- English name
- D-DOPA
- Molecular formula
- C9H11NO4
- Molecular weight
- 197.19
Names & synonyms
(2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoateD-dopa zwitterionCHEBI:149689Levodopa Impurity D3,4-DIHYDROXY-D-PHENYLALANINE(R)-2-AMino-3-(3,4-dihydroxyphenyl)propanoic acidD-DOPADextrodopaD-DOPA USP/EP/BP3-HydroxytyrosineD-3-HYDROXYTYROSINE3-HYDROXY-D-TYROSINE
Show more names
H-D-TYR(3-HYDROXY)-OH
Database identifiers
- CAS
5796-17-8- PubChem CID
- 6989908
- ChEBI
CHEBI:149689
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 108 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 203
Physicochemical properties
- Melting point
- 276 · 276-278 °C(lit.)
- alpha
- 11 · D11 +13.0° (c = 5.27 in 1N HCl)
- Boiling point
- 448.4 · 448.4±45.0 °C(Predicted)
- Density
- 1.468 · 1.468±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 0.5 M · 0.5 M HCl: soluble
- form
- powder
- pka
- 2.24 · 2.24±0.20(Predicted)
- color
- white to tan
- Merck
- 13 · 13,3454
- BRN
- 2417637 · 2417637
- Stability
- Hygroscopic
- InChI
- InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m1/s1
- InChIKey
- WTDRDQBEARUVNC-ZCFIWIBFSA-N
- SMILES
- C(O)(=O)[C@@H](CC1=CC=C(O)C(O)=C1)N
- CAS DataBase Reference
- 5796 · 5796-17-8(CAS DataBase Reference)
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
- F
- 10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2922500090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H335-H319
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Applications
UsesD-DOPA (Levodopa EP Impurity D) is a DOPA enantiomer that lacks biological activity.
UsesA DOPA enantiomer that lacks biological activity.
Additional notes
DefinitionChEBI: The D-enantiomer of dopa.
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Compound notes
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