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D-DOPA

D-DOPA ??? ???
?? ??:
5796-17-8
???:
D-DOPA
???(??):
Levodopa Impurity D;3,4-DIHYDROXY-D-PHENYLALANINE;(R)-2-AMino-3-(3,4-dihydroxyphenyl)propanoic acid;D-DOPA;Dextrodopa;D-DOPA USP/EP/BP;3-Hydroxytyrosine;D-3-HYDROXYTYROSINE;3-HYDROXY-D-TYROSINE;H-D-TYR(3-HYDROXY)-OH
CBNumber:
CB0470294
???:
C9H11NO4
??? ??:
197.19
MOL ??:
5796-17-8.mol
MSDS ??:
SDS

D-DOPA ??

???
276-278 °C(lit.)
??
D11 +13.0° (c = 5.27 in 1N HCl)
?? ?
448.4±45.0 °C(Predicted)
??
1.468±0.06 g/cm3(Predicted)
?? ??
-20°C
???
0.5M HCl: ???
?? ?? (pKa)
2.24±0.20(Predicted)
??? ??
??
??
???? ?????
Merck
13,3454
BRN
2417637
???
???
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 ??????
5796-17-8(CAS DataBase Reference)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
WGK ?? 3
F ?????? 10-23
HS ?? 2922500090
???? ??? 11 - Combustible Solids
????(GHS): Exclamation Mark (GHS07)
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? P264, P280, P305+P351+P338,P337+P313P
H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ??
??????:
P264 ?? ??? ?? ??? ????.
P264 ?? ??? ?? ??? ????.
P280 ????/???/???/?????? ?????.
P302+P352 ??? ??? ??? ?? ????.
P305+P351+P338 ?? ??? ? ?? ?? ???? ????. ???? ?????? ?????. ?? ????.
P321 (…) ??? ???.
P332+P313 ?? ??? ??? ???? ??· ??? ????.
P362 ??? ??? ?? ?? ?? ?????
NFPA 704
0
2 0

D-DOPA C??? ??, ??, ??

??? ??

Tan Solid

??

D-DOPA (Levodopa EP Impurity D) is a DOPA enantiomer that lacks biological activity.

??

ChEBI: The D-enantiomer of dopa.

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.]

D-DOPA ?? ?? ? ???

???

?? ??


D-DOPA ?? ??

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D-DOPA ?? ??:

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