Cas no 606-14-4 ((S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid)

(S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid is a chiral amino acid derivative featuring both amino and hydroxyl functional groups on its aromatic ring, along with a ketone moiety. This compound is of interest in medicinal chemistry and biochemical research due to its structural similarity to intermediates in neurotransmitter synthesis and potential applications in peptide modification. Its stereospecificity and multifunctional groups make it a valuable building block for designing enzyme inhibitors or receptor ligands. The presence of the hydroxyl group enhances solubility in polar solvents, while the aromatic ring provides stability. This compound is typically used under controlled conditions due to its reactive functional groups.
(S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid structure
606-14-4 structure
Product Name:(S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
CAS No:606-14-4
MF:C10H12N2O4
MW:224.213282585144
CID:516500
PubChem ID:11811
Update Time:2025-08-05

(S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid Chemical and Physical Properties

Names and Identifiers

    • (S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
    • 2-amino-4-(2-amino-3-hydroxy-phenyl)-4-oxo-butanoic acid
    • Benzenebutanoic acid, a,2-diamino-3-hydroxy-g-oxo-, (aS)-
    • (+-)-2-amino-4-(2-amino-3-hydroxy-phenyl)-4-oxo-butyric acid
    • 3-(3-Hydroxyanthraniloyl)alanine
    • 3-Hydroxykynurenine
    • 3-OH-DL-kynurenine
    • DL-3-hydroxykynurenine
    • Paralysin II
    • rac 3-Hydroxy Kynurenine
    • REF DUPL: 2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
    • REF DUPL: DL-3-Hydroxykynurenine
    • 3-(2-amino-3-hydroxybenzoyl)-L-alanine
    • DTXSID501314352
    • Q27102345
    • 3-hydroxy-kynurenine
    • L-3-Hydroxykynurenine
    • Benzenebutanoic acid, alpha,2-diamino-3-hydroxy-gamma-oxo-, (S)-
    • SCHEMBL134058
    • BDBM50501801
    • (S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoicacid
    • CHEMBL4071755
    • BENZENEBUTANOIC ACID, .ALPHA.,2-DIAMINO-3-HYDROXY-.GAMMA.-OXO-, (.ALPHA.S)-
    • 3-hydroxy-L-kynurenine
    • CHEBI:17380
    • 3-(3-Hydroxyanthraniloyl)-L-alanine
    • (.ALPHA.S)-.ALPHA.,2-DIAMINO-3-HYDROXY-.GAMMA.-OXOBENZENEBUTANOIC ACID
    • (2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
    • L-3-HK
    • VCKPUUFAIGNJHC-LURJTMIESA-N
    • UNII-F459WK6M6B
    • 3-Hydroxykynurenine, (S)-
    • 3DJ
    • F459WK6M6B
    • C03227
    • 606-14-4
    • Alanine, 3-(3-hydroxyanthraniloyl)-, L-
    • Hydroxykynurenine
    • 484-78-6
    • MDL: MFCD00210302
    • Inchi: 1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)/t6-/m0/s1
    • InChI Key: VCKPUUFAIGNJHC-LURJTMIESA-N
    • SMILES: O=C(C1C=CC=C(C=1N)O)C[C@@H](C(=O)O)N

Computed Properties

  • Exact Mass: 224.07976
  • Monoisotopic Mass: 224.08
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 282
  • 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
  • Topological Polar Surface Area: 127A^2
  • XLogP3: -2.5

Experimental Properties

  • Density: 1.2995 (rough estimate)
  • Melting Point: 187.5°C (rough estimate)
  • Boiling Point: 365.61°C (rough estimate)
  • Flash Point: 267.9°C
  • Refractive Index: 1.6620 (estimate)
  • PSA: 126.64
  • LogP: 1.24060

(S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid Pricemore >>

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Additional information on (S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid

Introduction to (S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic Acid (CAS No. 606-14-4)

(S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid, identified by its CAS number 606-14-4, is a compound of significant interest in the field of chemical and biomedical research. This molecule, featuring a chiral center, has garnered attention due to its structural complexity and potential biological activities. The presence of both amino and hydroxyl functional groups, along with its oxobutanoic acid moiety, makes it a versatile scaffold for the development of various pharmacological agents.

The compound’s stereochemistry, specifically the (S) configuration at the chiral center, plays a crucial role in determining its biological efficacy. Chiral drugs often exhibit different pharmacological profiles depending on their stereochemical orientation, making the precise synthesis and characterization of such compounds essential for therapeutic applications. Recent advancements in asymmetric synthesis have enabled the production of enantiomerically pure forms of this compound, which is critical for ensuring the safety and efficacy of derivative drugs.

In the realm of drug discovery, (S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid has been explored as a precursor for novel therapeutic agents. Its structural features suggest potential applications in the treatment of inflammatory diseases, metabolic disorders, and even certain types of cancer. The hydroxyl group, in particular, can serve as a site for further functionalization, allowing chemists to design molecules with tailored biological activities.

Recent studies have highlighted the compound’s role in modulating enzyme activity. For instance, derivatives of this molecule have been shown to inhibit specific kinases involved in cellular signaling pathways. These pathways are often dysregulated in diseases such as cancer and autoimmune disorders, making such inhibitors promising candidates for therapeutic intervention. The oxobutanoic acid moiety also contributes to the compound’s reactivity, enabling it to participate in various biochemical transformations that could be exploited for drug development.

The synthesis of (S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid presents both challenges and opportunities. Traditional synthetic routes often require multiple steps and harsh conditions, which can lead to low yields and the formation of byproducts. However, recent innovations in green chemistry have led to more sustainable methods for producing this compound. These methods leverage catalytic systems that minimize waste and energy consumption while maintaining high selectivity and yield.

Another area of interest is the use of computational modeling to predict the biological activity of this compound. Advanced computational techniques can simulate how the molecule interacts with biological targets such as enzymes and receptors. This approach not only accelerates the drug discovery process but also helps in understanding the molecular basis of its pharmacological effects. Such insights are invaluable for designing next-generation drugs with improved efficacy and reduced side effects.

The pharmaceutical industry has shown significant interest in developing derivatives of (S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid for clinical use. Preclinical studies have demonstrated its potential as an anti-inflammatory agent, with promising results in animal models of arthritis and other inflammatory conditions. Additionally, its ability to modulate metabolic pathways makes it a candidate for treating metabolic syndrome and related disorders.

In conclusion, (S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid (CAS No. 606-14-4) is a multifaceted compound with significant potential in biomedical research and drug development. Its unique structural features and stereochemistry make it an attractive scaffold for designing novel therapeutic agents. With ongoing advancements in synthetic chemistry and computational biology, the future looks promising for harnessing this compound’s full potential in addressing various human diseases.

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