Cas no 17012-42-9 ((2S,3R)-3-Acetoxy-2-aminobutanoic acid)

(2S,3R)-3-Acetoxy-2-aminobutanoic acid is a chiral non-proteinogenic amino acid derivative characterized by its stereospecific (2S,3R) configuration. The compound features an acetoxy group at the 3-position and an amino group at the 2-position, making it a versatile intermediate in organic synthesis and pharmaceutical research. Its stereochemistry is critical for applications in asymmetric synthesis and peptide modification, where precise spatial orientation is required. The presence of both polar (acetoxy, amino, carboxyl) and nonpolar (methyl) functional groups enhances its utility in designing bioactive molecules. This compound is particularly valuable in medicinal chemistry for developing enzyme inhibitors or prodrugs due to its ability to mimic natural amino acids while offering tailored reactivity.
(2S,3R)-3-Acetoxy-2-aminobutanoic acid structure
17012-42-9 structure
Product Name:(2S,3R)-3-Acetoxy-2-aminobutanoic acid
CAS No:17012-42-9
MF:C6H11NO4
MW:161.155842065811
MDL:MFCD00190723
CID:122033
PubChem ID:16718064
Update Time:2025-06-13

(2S,3R)-3-Acetoxy-2-aminobutanoic acid Chemical and Physical Properties

Names and Identifiers

    • (2S,3R)-3-Acetoxy-2-aminobutanoic acid
    • (2S,3R)-3-acetyloxy-2-aminobutanoic acid
    • H-THR(AC)-OH
    • L-Threonine, O-acetyl-
    • Acetyl L-threonine
    • L-Threonine,O-acetyl
    • L-Threonium acetate
    • O-acetyl-Ls-threonine
    • O-Acetyl-L-threonin
    • O-acetyl-L-threonine
    • -3-Acetoxy-2-aminobutanoic acid
    • Q27466317
    • 17012-42-9
    • I5ABK2S28W
    • O-acetylthreonine
    • DS-16365
    • O-Acetyl-Threonine
    • GOVSRIMJZNIFHS-WUJLRWPWSA-N
    • CS-0162359
    • DTXSID40587325
    • SCHEMBL678145
    • C73273
    • MFCD00190723
    • Threonine, acetate (ester), L-
    • UNII-I5ABK2S28W
    • (2S,3R)-3-Acetoxy-2-aminobutanoic acid (H-L-Thr(Ac)-OH)
    • AKOS006275205
    • DB-160631
    • (2S,3R)-3-Acetoxy-2-aminobutanoic Acid;
    • MDL: MFCD00190723
    • Inchi: 1S/C6H11NO4/c1-3(11-4(2)8)5(7)6(9)10/h3,5H,7H2,1-2H3,(H,9,10)/t3-,5+/m1/s1
    • InChI Key: GOVSRIMJZNIFHS-WUJLRWPWSA-N
    • SMILES: O(C(C)=O)[C@H](C)[C@@H](C(=O)O)N

Computed Properties

  • Exact Mass: 161.06900
  • Monoisotopic Mass: 161.06880783g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 4
  • Complexity: 168
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -3
  • Topological Polar Surface Area: 89.6?2

Experimental Properties

  • PSA: 89.62000
  • LogP: 0.05020

(2S,3R)-3-Acetoxy-2-aminobutanoic acid Customs Data

  • HS CODE:2922509090
  • Customs Data:

    China Customs Code:

    2922509090

    Overview:

    2922509090. Other amino alcohol phenols\Amino acid phenols and other oxygenated amino compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:AB. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, The color of ethanolamine and its salt should be reported, The package of ethanolamine and its salt shall be declared

    Regulatory conditions:

    A.Customs clearance form for Inbound Goods
    B.Customs clearance form for outbound goods

    Inspection and quarantine category:

    R.Sanitary supervision and inspection of imported food
    S.Sanitary supervision and inspection of exported food

    Summary:

    2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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Additional information on (2S,3R)-3-Acetoxy-2-aminobutanoic acid

Introduction to (2S,3R)-3-Acetoxy-2-aminobutanoic Acid (CAS No. 17012-42-9)

(2S,3R)-3-Acetoxy-2-aminobutanoic acid, identified by its CAS number 17012-42-9, is a chiral amino acid derivative that has garnered significant attention in the field of pharmaceutical research and biotechnology. This compound, with its unique stereochemical configuration, exhibits a range of biological activities that make it a valuable candidate for drug development and therapeutic applications.

The molecular structure of (2S,3R)-3-Acetoxy-2-aminobutanoic acid consists of a four-carbon backbone with an amine group at the second carbon and an acetoxyl group at the third carbon. The specific stereochemistry at the second and third positions, denoted as (2S,3R), is crucial for its biological function and interaction with target enzymes and receptors. This stereochemical arrangement influences the compound's solubility, metabolic stability, and binding affinity, making it a critical factor in its potential therapeutic applications.

In recent years, there has been growing interest in the development of chiral amino acid derivatives for their ability to mimic natural biomolecules and interact selectively with biological targets. (2S,3R)-3-Acetoxy-2-aminobutanoic acid is no exception and has been studied for its potential role in various pharmacological pathways. Its structural features make it a promising candidate for inhibiting key enzymes involved in metabolic disorders, inflammation, and cancer.

One of the most compelling aspects of (2S,3R)-3-Acetoxy-2-aminobutanoic acid is its ability to serve as a building block for more complex molecules. In drug design, chiral amino acids are often used to enhance the efficacy and selectivity of therapeutic agents. The presence of both an amine and an acetoxyl group provides multiple sites for functionalization, allowing chemists to tailor the compound's properties for specific applications.

The synthesis of (2S,3R)-3-Acetoxy-2-aminobutanoic acid is a challenging but well-studied process. Researchers have developed various synthetic routes to achieve high enantiomeric purity, which is essential for pharmaceutical applications. One common approach involves asymmetric synthesis using chiral auxiliaries or catalysts. These methods ensure that the final product retains the desired stereochemical configuration, which is critical for its biological activity.

The pharmacological profile of (2S,3R)-3-Acetoxy-2-aminobutanoic acid has been extensively evaluated in preclinical studies. These studies have revealed its potential as an inhibitor of various enzymes, including those involved in the metabolism of lipids and carbohydrates. Additionally, the compound has shown promise in reducing inflammation and preventing the progression of certain types of cancer.

In particular, research has highlighted the compound's ability to modulate the activity of acetyl-CoA carboxylase (ACC), an enzyme critical for fatty acid synthesis. By inhibiting ACC, (2S,3R)-3-Acetoxy-2-aminobutanoic acid can help regulate lipid metabolism and potentially reduce the risk of obesity-related diseases such as type 2 diabetes and cardiovascular disorders.

The anti-inflammatory properties of (2S,3R)-3-Acetoxy-2-aminobutanoic acid

In cancer research, (2S,3R-Acetoxy-butanoyl amine hydrochloride salt ) has shown potential as an anti-proliferative agent. It has been found to induce apoptosis in certain cancer cell lines by disrupting key signaling pathways involved in cell growth and survival. This makes it a promising candidate for developing novel anti-cancer therapies.

The future prospects for (CAS No 17012- 42- 9 ) are bright, with ongoing research aimed at optimizing its pharmacological properties and exploring new therapeutic applications. Advances in synthetic chemistry and biotechnology are expected to further enhance the production efficiency and purity of this compound, making it more accessible for clinical trials and commercialization.

In conclusion, ((2S, 3R) - 3 - Acetoxy - 2 - Aminobutanoic Acid ) is a versatile chiral amino acid derivative with significant potential in pharmaceutical research. Its unique structural features and biological activities make it a valuable tool for developing new drugs targeting metabolic disorders, inflammation, and cancer. As research continues, the therapeutic applications of this compound are expected to expand, offering new hope for patients suffering from various diseases.

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