CAS 27244-64-0

6-Hydroxy-L-DOPA

Description:

6-Hydroxy-L-DOPA, with the CAS number 27244-64-0, is a chemical compound that is a derivative of L-DOPA, an amino acid precursor to dopamine. This compound features a hydroxyl group at the 6-position of the aromatic ring, which distinguishes it from its parent compound. It is typically characterized by its role in biochemical pathways, particularly in the synthesis of neurotransmitters. 6-Hydroxy-L-DOPA is of interest in neuropharmacology and research related to Parkinson's disease, as it may influence dopaminergic activity. The compound is generally soluble in water and exhibits properties typical of phenolic compounds, such as potential antioxidant activity. Its stability and reactivity can be influenced by environmental factors such as pH and temperature. As with many biochemical substances, it is important to handle 6-Hydroxy-L-DOPA with care in laboratory settings, adhering to safety protocols to mitigate any potential risks associated with its use.

Formula: C₉H₁₁NO₅

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: C([C@@H](C(O)=O)N)C1=C(O)C=C(O)C(O)=C1

Synonyms:

• (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
• 6-Hydroxy-L-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-

Levodopa EP Impurity A

CAS: 27244-64-0

Formula: C₉H₁₁NO₅

Molecular weight: 213.19

Ref: ST-EA-CP-L16001

Levodopa Related Compound A (3-(2,4,5-Trihydroxyphenyl)-L-alanine)

CAS: 27244-64-0

Aromatic amino-alcohol-phenols, aromatic amino-acid-phenols and other aromatic amino compounds with oxygen function

Formula: C₉H₁₁NO₅

Color and Shape: Brown Grey Powder

Molecular weight: 213.06372

Ref: 45-1361010

2,5-Dihydroxy-L-tyrosine

CAS: 27244-64-0

Formula: C₉H₁₁NO₅

Purity: 97%

Color and Shape: Solid

Molecular weight: 213.1873

Ref: IN-DA00C28S

(S)-2-Amino-3-(2,4,5-trihydroxyphenyl)propanoic acid

CAS: 27244-64-0

(S)-2-Amino-3-(2,4,5-trihydroxyphenyl)propanoic acid

Purity: 97%

Molecular weight: 213.19g/mol

Ref: 54-OR1074264

Levodopa EP Impurity A (Levodopa USP Related Compound A, 6-Hydroxy L-DOPA)

CAS: 27244-64-0

Formula: C₉H₁₁NO₅

Molecular weight: 213.19

Ref: 4Z-D-3229

6-Hydroxy-L-DOPA

Controlled Product

CAS: 27244-64-0

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);

Formula: C₉H₁₁NO₅

Color and Shape: Brown To Black

Molecular weight: 213.19

Ref: TR-H941725

6-Hydroxy-L-DOPA

CAS: 27244-64-0

6-Hydroxy-L-DOPA is a quinone, which is the cofactor of tetracycline resistance. It is also a component of tricyclic antidepressant drugs, and has been shown to have neuroprotective effects. 6-Hydroxy-L-DOPA binds to the polymerase chain reaction (PCR) by way of a signal peptide sequence and can be used as a pharmacological agent in patients with oxidative injury. 6-Hydoxy-L-DOPA is bound in the form of an oxidized quinone ring, which coordinates with copper ions via two oxygen atoms and two nitrogen atoms. The structure has been determined using x-ray crystal structures. This compound has an oxidase activity that generates hydrogen peroxide from hydrogen peroxide and water, which results in oxidative injury.

Formula: C₉H₁₁NO₅

Purity: Min. 95%

Molecular weight: 213.19 g/mol

Ref: 3D-FH24378

6-Hydroxy-L-DOPA

CAS: 27244-64-0

Levadopa Related Compound A is the 6-hydroxy derivative of the amino acid L-DOPA with neurotoxic properties. Exogenously administered 6-Hydroxy-L-DOPA is biotransformed by an amino acid decarboxylase to the highly potent and catecholamine-selective neurot

Formula: C₉H₁₁NO₅

Purity: 98%

Color and Shape: Solid

Molecular weight: 213.19

Ref: TM-T20396