Cas no 918-44-5 (Butanoic acid,2-hydroxy-2-methyl-3-oxo-)

Butanoic acid, 2-hydroxy-2-methyl-3-oxo-, is a multifunctional organic compound characterized by its hydroxyl and keto functional groups on a short-chain carboxylic acid backbone. This structure imparts reactivity suitable for applications in organic synthesis, particularly as an intermediate in the production of pharmaceuticals, agrochemicals, and specialty chemicals. Its α-hydroxy-β-keto acid moiety enables participation in condensation and chelation reactions, making it valuable in coordination chemistry and catalysis. The compound’s balanced polarity and solubility in common organic solvents enhance its utility in formulation processes. Careful handling is recommended due to potential sensitivity to heat and strong oxidizing agents.
Butanoic acid,2-hydroxy-2-methyl-3-oxo- structure
918-44-5 structure
Product Name:Butanoic acid,2-hydroxy-2-methyl-3-oxo-
CAS No:918-44-5
MF:C5H8O4
MW:132.114622116089
CID:804341
PubChem ID:22
Update Time:2025-10-12

Butanoic acid,2-hydroxy-2-methyl-3-oxo- Chemical and Physical Properties

Names and Identifiers

    • Butanoic acid,2-hydroxy-2-methyl-3-oxo-
    • 2-HYDROXY-2-METHYL-3-OXO-BUTANOIC ACID
    • 2-Hydroxy-2-methyl-3-oxobutanoicacid
    • DL-Acetolactic Acid
    • 2-hydroxy-2-methyl-3-oxobutanoic acid
    • SCHEMBL61227
    • 2-Acetolactic acid, (+/-)-
    • Acetoacetic acid, 2-hydroxy-2-methyl-
    • DTXSID801343582
    • Q27101908
    • AKOS006380884
    • QV9C4ZW4PY
    • Butanoic acid, 2-hydroxy-2-methyl-3-oxo-
    • UNII-QV9C4ZW4PY
    • BDBM82146
    • 918-44-5
    • LMFA01050472
    • FT-0612527
    • C00900
    • CHEBI:16444
    • 2-acetyllactic acid
    • 2-Acetolactate
    • 2-acetyllactate(1-)
    • (2S)-2-hydroxy-2-methyl-3-oxobutanoic acid
    • (S)-2-hydroxy-2-methyl-3-oxobutanoate
    • 2-acetyllactate anion
    • (S)-2-Acetolactate
    • (S)-2-acetolactic acid
    • Inchi: 1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)
    • InChI Key: NMDWGEGFJUBKLB-UHFFFAOYSA-N
    • SMILES: CC(C(C(=O)O)(O)C)=O

Computed Properties

  • Exact Mass: 132.04225873g/mol
  • Monoisotopic Mass: 132.04225873g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 11
  • Heavy Atom Count: 31
  • Rotatable Bond Count: 3
  • Complexity: 705
  • Covalently-Bonded Unit Count: 4
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 74.6?2

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Additional information on Butanoic acid,2-hydroxy-2-methyl-3-oxo-

Butanoic Acid, 2-Hydroxy-2-Methyl-3-Oxo

Butanoic acid, 2-hydroxy-2-methyl-3-oxo (CAS No. 918-44-5) is a versatile organic compound with significant applications in various industries. This compound, also known as 3-keto-2-hydroxybutanoic acid, is a derivative of butanoic acid with a hydroxyl group and a ketone group in its structure. Its unique chemical properties make it an essential intermediate in the synthesis of various bioactive compounds and specialty chemicals.

The compound is characterized by its carbonyl group at the 3-position and a hydroxyl group at the 2-position, which contributes to its reactivity and functional versatility. Recent studies have highlighted its role as a key precursor in the production of antibiotics, pharmaceutical intermediates, and cosmetic ingredients. For instance, research published in *Journal of Medicinal Chemistry* in 2023 demonstrated its potential as a building block for developing novel anti-inflammatory agents.

From a structural standpoint, butanoic acid, 2-hydroxy-2-methyl-3-oxo exhibits a branched carbon chain with functional groups that enable diverse chemical transformations. Its beta-keto ester functionality makes it highly reactive under mild conditions, facilitating its use in organic synthesis. A study in *Organic Process Research & Development* explored its application in the synthesis of chiral pharmaceuticals, emphasizing its role as an efficient chiral auxiliary.

In terms of physical properties, this compound is typically a white crystalline solid with a melting point of approximately 150°C. Its solubility in water and organic solvents makes it suitable for various industrial processes. Recent advancements in green chemistry have also led to the development of more sustainable methods for synthesizing this compound, reducing environmental impact while maintaining high yields.

The synthesis of butanoic acid, 2-hydroxy-2-methyl-3-oxo involves multi-step reactions that often include oxidation, reduction, and condensation processes. A notable method involves the oxidation of dihydroxy precursors using selective oxidizing agents like TEMPO (tert-butyl hydroperoxide). This approach has been optimized to achieve high stereoselectivity, as reported in *Green Chemistry*.

Applications of this compound span across multiple sectors. In the food industry, it serves as an ingredient in flavor enhancers and preservatives due to its ability to impart desirable taste profiles. In cosmetics, it is used as a humectant and skin conditioning agent. Additionally, its role as an intermediate in pharmaceuticals has been extensively studied, particularly in the development of anti-diabetic drugs and neuroprotective agents.

Recent research has also explored the potential of butanoic acid, 2-hydroxy-2-methyl-3-oxo in biotechnology applications. For example, it has been utilized as a substrate for enzymatic catalysis in bioconversion processes. A study published in *Applied Microbiology and Biotechnology* demonstrated its use in producing valuable bioactive compounds through microbial fermentation.

In conclusion, butanoic acid, 2-hydroxy-2-methyl-3-oxo (CAS No. 918-44-5) is a multifaceted compound with wide-ranging applications across industries. Its unique chemical structure and functional groups make it an invaluable tool in organic synthesis and material science. As research continues to uncover new possibilities for this compound, its significance in both academic and industrial settings is expected to grow further.

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