6-Hydroxy-L-DOPA

CAS: 27244-64-0

Ref. TR-H941725

Product Information

• Name: 6-Hydroxy-L-DOPA
• Synonyms: 3-(3,4,6-Trihydroxyphenyl)-alanine, (2S)-2-Amino-3-(2,4,5-trihydroxyphenyl)propanoic acid, 2,4,5-Trihydroxy-<span class="text-smallcaps">L</span>-phenylalanine, 2,4,5-Trihydroxy-L-phenylalanine, 2,4,5-Trihydroxyphenylalanine, 2,5-Dihydroxy-<span class="text-smallcaps">L</span>-tyrosine, 2,5-Dihydroxy-L-tyrosine, 3-(3,4,6-Trihydroxyphenyl)-<span class="text-smallcaps">L</span>-alanine, 3-(3,4,6-Trihydroxyphenyl)-L-alanine, 6-Hydroxy-<span class="text-smallcaps">L</span>-DOPA, <span class="text-smallcaps">L</span>-6-Hydroxydopa, <span class="text-smallcaps">L</span>-Tyrosine, 2,5-dihydroxy-, Alanine, 3-(2,4,5-trihydroxyphenyl)-, <span class="text-smallcaps">L</span>-, Alanine,3-(2,4,5-trihydroxyphenyl)-, L- (8CI), Hydroxy-<span class="text-smallcaps">L</span>-dopa, Hydroxy-L-dopa, L-6-Hydroxydopa, Topa, L-Tyrosine, 2,5-dihydroxy-, Alanine, 3-(2,4,5-trihydroxyphenyl)-, L-

Description

Impurity Levodopa EP Impurity A; Levodopa USP Related Compound A
Stability Hygroscopic
Applications 6-Hydroxy-L-DOPA (Levodopa EP Impurity A; Levodopa USP Related Compound A) is the 6-hydroxy derivative of the amino acid L-DOPA (D533751) with neurotoxic properties. Studies show that exogenously administered 6-Hydroxy-L-DOPA is biotransformed by amino acid decarboxylase to the highly potent and catecholamine-selective neurotoxin, 6-Hydroxydopamine. The treatment of 6-Hydroxy-L-DOPA in rats resulted in the stimulation of acetylcholinesterase.
References Jaim-Etcheverry, G. et al.: Brain Res., 100, 699 (1975); Kostrzewa, R.M. et al.: Amino Acids, 14, 175 (1998); Berthet, A. et al.: J. Neurosci., 29, 4829 (2009);

• Brand: TRC

Chemical properties

• Molecular weight: 213.19
• Formula: C₉H₁₁NO₅
• Color/Form: Brown To Black
• InChI: InChI=1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)/t5-/m0/s1
• InChI key: InChIKey=YLKRUSPZOTYMAT-YFKPBYRVSA-N
• SMILES: N[C@@H](Cc1cc(O)c(O)cc1O)C(=O)O