Cas no 27244-64-0 ((2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid)

(2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid is a chiral amino acid derivative characterized by a phenolic side chain with hydroxyl groups at the 2, 4, and 5 positions. This structure imparts unique reactivity, making it valuable in synthetic and medicinal chemistry applications. The compound’s stereochemistry at the α-carbon enhances its utility in peptide synthesis and enzyme studies, while the polyhydroxylated aromatic moiety contributes to metal chelation and antioxidant properties. Its high purity and well-defined configuration ensure reproducibility in research settings. The compound is particularly relevant in studies involving oxidative stress, neurodegenerative diseases, and as a precursor for bioactive molecules. Suitable for analytical and preparative applications, it offers versatility in biochemical and pharmaceutical research.
(2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid structure
27244-64-0 structure
Product Name:(2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid
CAS No:27244-64-0
MF:C9H11NO5
MW:213.187342882156
MDL:MFCD22577205
CID:255039
PubChem ID:33755
Update Time:2025-11-02

(2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid Chemical and Physical Properties

Names and Identifiers

    • Levodopa Related Compound A
    • L-3-(2,4,5-trihydroxyphenyl)-Alanine
    • 6-Hydroxy-L-DOPA
    • (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid
    • 2,4,5-Trihydroxy-L-phenylalanine
    • 2,4,5-Trihydroxyphenylalanine
    • 2,5-Dihydroxy-L-tyrosine
    • 3-(3,4,6-Trihydroxyphenyl)-L-alanine
    • Alanine,3-(2,4,5-trihydroxyphenyl)-, L- (8CI)
    • Hydroxy-L-dopa
    • L-6-Hydroxydopa
    • TOPA
    • 3-(2,4,5-Trihydroxyphenyl)-L-alanine
    • 27244-64-0
    • Lopac-H-2380
    • 2,5-Dihydroxytyrosinato(3-)
    • HY-121939
    • CHEMBL1256516
    • MFCD22577205
    • LEVODOPA IMPURITY A [EP IMPURITY]
    • DTXSID90949974
    • L-2,4,5-Trihydroxyphenylalanine
    • 2,4,5-trihydroxyphenyl-L-alanine
    • CHEBI:72753
    • ALANINE, 3-(2,4,5-TRIHYDROXYPHENYL)-, L-
    • L-Hydroxydopa
    • L-Tyrosine, 2,5-dihydroxy-
    • 580PK2O48O
    • P19978
    • PS-15518
    • (S)-2-Amino-3-(2,4,5-trihydroxyphenyl)propanoic acid
    • AKOS027322904
    • Q27140120
    • 6-OH-DOPA
    • UNII-580PK2O48O
    • 2,4,5-Trihydroxyphenylalanine, L-
    • CS-0083719
    • 6-Hydroxydopa, L-
    • A816687
    • NCGC00015503-01
    • SCHEMBL594845
    • 3-(3,4,6-Trihydroxyphenyl)-alanine
    • Levodopa EP Impurity A
    • Tyrosine, 2,5-dihydroxy-
    • LEVODOPA IMPURITY A (EP IMPURITY)
    • L-Tyrosine, 2,5-dihydroxy-(9CI)
    • MDL: MFCD22577205
    • 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: YLKRUSPZOTYMAT-YFKPBYRVSA-N
    • SMILES: OC1C=C(C(=CC=1C[C@@H](C(=O)O)N)O)O

Computed Properties

  • Exact Mass: 213.06373
  • Monoisotopic Mass: 213.06372245g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 235
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.5
  • Topological Polar Surface Area: 124?2

Experimental Properties

  • PSA: 124.01

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

  • Hazardous Material transportation number:NONH for all modes of transport

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

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(2S)-2-Amino-3-(2,4,5-trihydroxyphenyl)propanoic acid; .
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Additional information on (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid

Exploring the Unique Properties and Applications of (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid (CAS No. 27244-64-0)

In the realm of specialized amino acid derivatives, (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid (CAS No. 27244-64-0) stands out as a compound of significant scientific interest. This naturally occurring aromatic amino acid, characterized by its unique trihydroxyphenyl side chain, has garnered attention from researchers across multiple disciplines, including biochemistry, pharmacology, and nutraceutical development.

The molecular structure of this compound features an L-configuration amino acid backbone attached to a 2,4,5-trihydroxyphenyl group, giving it distinctive chemical properties. Its three hydroxyl groups at positions 2, 4, and 5 on the phenyl ring contribute to its polarity and potential for hydrogen bonding, making it particularly interesting for studies of molecular interactions. The compound's systematic name, (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid, precisely describes its stereochemistry and functional group arrangement.

Recent scientific literature has highlighted the potential role of 27244-64-0 in various biological processes. Its structural similarity to tyrosine and other phenolic amino acids suggests possible involvement in metabolic pathways. Researchers are particularly interested in its antioxidant properties, which stem from its polyphenolic nature. The compound's ability to scavenge free radicals has prompted investigations into its potential health benefits, aligning with current consumer interest in natural antioxidants and functional food ingredients.

From a biochemical perspective, the trihydroxyphenyl moiety of this amino acid derivative may participate in electron transfer reactions, making it relevant to studies of redox biochemistry. Its structural features have drawn comparisons to other biologically active phenolic compounds, such as those found in green tea and berries, which are currently popular in nutraceutical research. This connection to trending topics in nutritional science and preventive health enhances the compound's relevance in contemporary scientific discourse.

The synthesis and characterization of (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid present interesting challenges for organic chemists. The multiple hydroxyl groups require careful protection and deprotection strategies during chemical synthesis, making it a valuable subject for methodology development. Analytical techniques such as HPLC, mass spectrometry, and NMR spectroscopy are typically employed to verify its purity and structure, addressing common questions from researchers about compound characterization.

In pharmaceutical research, the compound's unique structure has prompted investigations into its potential as a molecular scaffold for drug development. Its combination of amino acid functionality and phenolic groups offers multiple sites for chemical modification, making it attractive for medicinal chemistry applications. Current studies explore its possible role in designing compounds that target oxidative stress-related conditions, a hot topic in age-related disease research.

The commercial availability of CAS 27244-64-0 has increased in recent years to meet growing research demand. Suppliers typically provide the compound with detailed certificates of analysis, addressing researchers' need for quality assurance. Proper storage conditions (typically at low temperatures and protected from light) are crucial due to the compound's photosensitivity and potential for oxidation, important considerations frequently searched by laboratory professionals.

From a regulatory perspective, (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid is generally regarded as safe for research purposes when handled according to standard laboratory protocols. Its natural occurrence in certain biological systems contributes to its favorable safety profile, though proper material safety data should always be consulted before use. This information is particularly valuable for researchers concerned with laboratory safety standards and compliance requirements.

Future research directions for this compound may include exploring its potential in cosmeceutical applications, given the current market interest in anti-aging ingredients with antioxidant properties. Additionally, its possible role in plant biochemistry could make it relevant to agricultural science studies, particularly in understanding stress responses in crops. These potential applications align with trending topics in green chemistry and sustainable technology development.

In summary, (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid represents a fascinating subject for scientific investigation across multiple disciplines. Its unique structural features, combined with potential biological activities, make it a compound of continuing interest in both academic and industrial research settings. As scientific understanding of phenolic compounds expands, this particular amino acid derivative will likely remain an important focus for studies in bioactive molecules and their applications in health and technology.

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