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    27244-64-0

    Catalog No. EBD60213

    CAS 27244-64-0

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

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    Basic Information

    Synonyms: L-Tyrosine,2,5-dihydroxy- Alanine,3-(2,4,5-trihydroxyphenyl)-,L-(8CI) 2,4,5-Trihydroxy-L-phenylalanine 2,4,5-Trihydroxyphenylalanine 2,5-Dihydroxy-L-tyrosine 3-(3,4,6-Trihydroxyphenyl)-L-alanine 6-Hydroxy-L-DOPA Hydroxy-L-dopa L-6-Hydroxydopa TOPA (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoicacid

    Molecular Formula: C9H11NO5

    Molecular Weight: 213.19

    Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks

    Product Description:
    L-DOPA (3,4-Dihydroxy-L-phenylalanine) is a naturally occurring amino acid derivative and a direct metabolic precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline). It is classified as a non-proteinogenic amino acid due to the presence of two hydroxyl groups on the phenyl ring. Its CAS number is 59-92-7, and it is distinct from the provided CAS 27244-64-0, which corresponds to a different tyrosine derivative (2,5-dihydroxy-L-tyrosine). The primary and most significant application of L-DOPA is in the treatment of Parkinson's disease. It is the gold-standard pharmacological therapy, administered to replenish depleted dopamine levels in the brain. As a prodrug, it crosses the blood-brain barrier and is decarboxylated to dopamine by aromatic L-amino acid decarboxylase (AADC). It is also a crucial intermediate in the biosynthesis of melanin and certain alkaloids in plants. Beyond its therapeutic use, L-DOPA serves as an important biochemical reagent in neuroscience and pharmacological research for studying dopaminergic systems. It is also investigated for its potential antioxidant properties. Due to its role as a biosynthetic precursor, it is categorized as a specialized amino acid derivative and a key building block in medicinal chemistry for developing related neuroactive compounds.
    Physical Properties

    Boiling Point: 515.2°Cat760mmHg

    Flash Point: 265.4°C

    Density: 1.606g/cm3

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