Cas no 533-88-0 (2-Amino-5-hydroxypentanoic acid)

2-Amino-5-hydroxypentanoic acid is a non-proteinogenic amino acid derivative with a hydroxyl group at the fifth carbon position. This compound is of interest in organic synthesis and biochemical research due to its functional groups, which enable versatile reactivity, including peptide coupling and modification. The presence of both amino and hydroxyl groups allows for selective derivatization, making it useful in the development of specialized polymers, pharmaceutical intermediates, or bioactive molecules. Its structural features may also contribute to chelation or coordination chemistry applications. The compound is typically handled under controlled conditions due to its potential sensitivity to moisture or oxidation. Further characterization is recommended for specific applications.
2-Amino-5-hydroxypentanoic acid structure
533-88-0 structure
Product Name:2-Amino-5-hydroxypentanoic acid
CAS No:533-88-0
MF:C5H11NO3
MW:133.145741701126
MDL:MFCD12911768
CID:367592
PubChem ID:95562
Update Time:2025-05-20

2-Amino-5-hydroxypentanoic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-5-hydroxypentanoic acid
    • 5-Hydroxy-DL-norvaline
    • Norvaline, 5-hydroxy-
    • NSC 20896
    • Pentahomoserine
    • alpha-Amino-delta-hydroxy-n-valeric acid
    • alpha-Amino-delta-hydroxyvaleric acid
    • NSC206265
    • 2-Amino-5-hydroxyvaleric acid
    • .alpha.-Amino-.delta.-hydroxyvalerate
    • NSC-20896
    • L-.alpha.-Amino-.delta.-hydroxyvaleric acid
    • PENTAHOMOSERINE DL-FORM [MI]
    • NSC20896
    • EN300-84934
    • PENTAHOMOSERINE [MI]
    • 533-88-0
    • .ALPHA.-AMINO-.DELTA.-HYDROXYVALERIC ACID
    • NSC-206265
    • CHEBI:165867
    • 5-OH-2-NH2-Valerate
    • Hava-5 cpd
    • 5-Hydroxy-2-aminovalerate
    • 5-Hydroxynorvaline
    • CZWARROQQFCFJB-UHFFFAOYSA-N
    • FT-0689993
    • AKOS015892690
    • DTXSID901315938
    • .alpha.-Amino-.delta.-hydroxyvaleric cid
    • HYDROXYVALINE
    • SY269711
    • PENTAHOMOSERINE, (+/-)-
    • PKG8I0M67E
    • L-2-Amino-5-hydroxypentanoic acid
    • 2-Amino-5-hydroxypentanoicacid
    • .delta.-Hydroxynorvaline
    • SCHEMBL59755
    • Q27286597
    • MFCD00078391
    • delta-Hydroxynorvaline
    • Norvaline, 5-hydroxy-, L-
    • DL-.DELTA.-HYDROXY-.ALPHA.-AMINOVALERIC ACID
    • UNII-PKG8I0M67E
    • MDL: MFCD12911768
    • Inchi: 1S/C5H11NO3/c6-4(5(8)9)2-1-3-7/h4,7H,1-3,6H2,(H,8,9)
    • InChI Key: CZWARROQQFCFJB-UHFFFAOYSA-N
    • SMILES: OCCCC(C(=O)O)N

Computed Properties

  • Exact Mass: 133.074
  • Monoisotopic Mass: 133.074
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 4
  • Complexity: 94.2
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: _4.2
  • Topological Polar Surface Area: 83.6A^2

Experimental Properties

  • Density: 1.241±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 218-220 oC
  • Boiling Point: 306.1°Cat760mmHg
  • Flash Point: 138.9°C
  • Refractive Index: 1.504
  • Solubility: Extremely soluble (1000 g/l) (25 o C),
  • PSA: 83.55000
  • LogP: -0.12890

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2-Amino-5-hydroxypentanoic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrogen ,  Phosphoric acid Catalysts: Rhodium ,  Molybdenum oxide Solvents: Water ;  6 h, pH 1.8, 70 bar, 100 °C
Reference
Rh-Catalyzed Hydrogenation of Amino Acids to Biobased Amino Alcohols: Tackling Challenging Substrates and Application to Protein Hydrolysates
Vandekerkhove, Annelies ; Claes, Laurens ; De Schouwer, Free; Van Goethem, Cedric ; Vankelecom, Ivo F. J.; et al, ACS Sustainable Chemistry & Engineering, 2018, 6(7), 9218-9228

2-Amino-5-hydroxypentanoic acid Raw materials

2-Amino-5-hydroxypentanoic acid Preparation Products

Additional information on 2-Amino-5-hydroxypentanoic acid

Introduction to 2-Amino-5-hydroxypentanoic acid (CAS No. 533-88-0)

2-Amino-5-hydroxypentanoic acid, identified by the Chemical Abstracts Service Number (CAS No.) 533-88-0, is a significant compound in the field of biochemistry and pharmaceutical research. This amino acid derivative has garnered attention due to its unique structural properties and potential applications in drug development, enzyme inhibition, and metabolic studies. The compound features both an amino group and a hydroxyl group on a five-carbon chain, making it a versatile building block for synthesizing more complex molecules.

The molecular structure of 2-Amino-5-hydroxypentanoic acid contributes to its reactivity and functionality. The presence of both functional groups allows it to participate in various chemical reactions, including peptide bond formation, chelation, and redox processes. These characteristics make it a valuable intermediate in organic synthesis and a candidate for developing novel therapeutic agents.

In recent years, research on 2-Amino-5-hydroxypentanoic acid has been expanding, particularly in the context of its role in biological systems. Studies have explored its potential as a precursor for neurotransmitter analogs and as a component in enzyme inhibitors. For instance, modifications of this compound have been investigated for their ability to modulate the activity of certain enzymes involved in metabolic pathways. This has opened up new avenues for treating metabolic disorders and inflammatory conditions.

One of the most intriguing aspects of 2-Amino-5-hydroxypentanoic acid is its potential application in peptide mimetics. Peptide mimetics are designed to mimic the biological activity of natural peptides but with improved stability and pharmacokinetic properties. The structural features of 2-Amino-5-hydroxypentanoic acid make it an ideal candidate for such applications, as it can be incorporated into peptide chains to enhance their binding affinity and specificity. This has implications for the development of targeted therapies in oncology and immunology.

The pharmaceutical industry has also shown interest in 2-Amino-5-hydroxypentanoic acid due to its potential as a scaffold for drug discovery. By modifying its structure, researchers can generate libraries of compounds with varying biological activities. High-throughput screening techniques combined with computational modeling have accelerated the process of identifying lead compounds for further development. This approach has led to several promising candidates that are currently undergoing preclinical studies.

Another area where 2-Amino-5-hydroxypentanoic acid has found utility is in the field of materials science. Its ability to form stable complexes with metal ions makes it useful in developing metal-organic frameworks (MOFs) and coordination polymers. These materials have applications in catalysis, gas storage, and separation technologies. The versatility of 2-Amino-5-hydroxypentanoic acid as a ligand has opened up new possibilities for designing functional materials with tailored properties.

The synthesis of 2-Amino-5-hydroxypentanoic acid has also been optimized to meet the demands of industrial-scale production. Various synthetic routes have been developed, including enzymatic synthesis and solid-phase peptide synthesis (SPPS). These methods ensure high yield and purity, which are critical for pharmaceutical applications. Advances in synthetic chemistry have made it possible to produce large quantities of this compound efficiently.

In conclusion, 2-Amino-5-hydroxypentanoic acid (CAS No. 533-88-0) is a multifaceted compound with significant potential in biochemistry, pharmaceuticals, and materials science. Its unique structural features and reactivity make it a valuable tool for researchers working on drug development, enzyme inhibition, and metabolic studies. As research continues to uncover new applications for this compound, its importance is likely to grow further.

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