| Identification | More | [Name]
D-DOPA | [CAS]
5796-17-8 | [Synonyms]
3-(3,4-DIHYDROXYPHENYL)-D-ALANINE
3,4-DIHYDROXY-D-PHENYLALANINE
3-HYDROXY-D-TYROSINE
D-3,4-DIHYDROXYPHENYLALANINE
D-3-HYDROXYTYROSINE
D-BETA-(3,4-DIHYDROXYPHENYL)ALANINE
D-DOPA
H-D-PHE(3,4-DI-HYDROXY)-OH
H-D-TYR(3-HYDROXY)-OH
D-3-(3,4-Dihydroxyphenyl)alanine
D-Tyrosine,3-hydroxy-
3,4-Dihydroxy-D-phenylanline
3-Hydroxy-D-tyrosine, D-3,4-Dihydroxyphenylalanine
Alanine, 3-(3,4-dihydroxyphenyl)-, D-(8CI)
b-(3,4-Dihydroxy)-D-phenylalanine
D-Tyrosine, 3-hydroxy-(9CI)
3,4-Dihydroxy-D-phenylaline
3-(3,4-Dihydroxyphenyl)-D-alanine, D-3-Hydroxytyrosine, D-DOPA
(R)-2-Amino-3-(3,4-dihydroxyphenyl)propionic acid
Dextrodopa | [EINECS(EC#)]
227-343-0 | [Molecular Formula]
C9H11NO4 | [MDL Number]
MFCD00063061 | [Molecular Weight]
197.19 | [MOL File]
5796-17-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Tan Solid | [Melting point ]
276-278 °C(lit.)
| [alpha ]
D11 +13.0° (c = 5.27 in 1N HCl) | [Boiling point ]
448.4±45.0 °C(Predicted) | [density ]
1.468±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
0.5 M HCl: soluble
| [form ]
powder
| [pka]
2.24±0.20(Predicted) | [color ]
white to tan
| [Usage]
A DOPA enantiomer that lacks biological activity.
| [Merck ]
13,3454 | [BRN ]
2417637 | [Stability:]
Hygroscopic | [CAS DataBase Reference]
5796-17-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Tan Solid | [Uses]
A DOPA enantiomer that lacks biological activity.
| [Definition]
ChEBI: The D-enantiomer of dopa. | [Biochem/physiol Actions]
DOPA enantiomer that lacks biological activity. | [storage]
Store at -20°C | [Purification Methods]
Likely impurities are vanillin, hippuric acid, 3-methoxytyrosine and 3-aminotyrosine. DOPA recrystallises from large volumes of H2O forming colourless white needles; its solubility in H2O is 0.165%, but it is insoluble in EtOH, *C6H6, CHCl3, and EtOAc. Also crystallise it by dissolving it in dilute HCl and adding dilute ammonia to give pH 5, under N2. Alternatively, crystallise it from dilute aqueous EtOH. It is rapidly oxidised in air when moist, and darkens, particularly in alkaline solution. Dry it in vacuo at 70o in the dark, and store it in a dark container preferably under N2. It has at 220.5nm (log 3.79) and 280nm (log 3.42) in 0.001N max HCl. [Yamada et al. Chem Pharm Bull Jpn 10 693 1962, Bretschneider et al. Helv Chim Acta 56 2857 1973, NMR: Jardetzky & Jardetzky J Biol Chem 233 383 1958, Beilstein 4 IV 2492, 2493.] |
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