Cas no 42137-04-2 (5-hydroxy-5-methylhexan-2-one)

5-Hydroxy-5-methylhexan-2-one is a versatile intermediate in organic synthesis, characterized by its hydroxyl and ketone functional groups. This compound is particularly valuable for its reactivity in condensation and reduction reactions, making it useful in the production of fragrances, pharmaceuticals, and specialty chemicals. Its structure allows for selective modifications, enabling the synthesis of complex molecules with high precision. The presence of both hydroxyl and carbonyl groups offers opportunities for further derivatization, enhancing its utility in multi-step synthetic routes. Additionally, its stability under standard conditions ensures consistent performance in industrial and laboratory applications. This compound is favored for its balanced reactivity and adaptability in fine chemical synthesis.
5-hydroxy-5-methylhexan-2-one structure
5-hydroxy-5-methylhexan-2-one structure
Product Name:5-hydroxy-5-methylhexan-2-one
CAS No:42137-04-2
MF:C7H14O2
MW:130.184862613678
MDL:MFCD21923299
CID:2636931
PubChem ID:11040732
Update Time:2025-11-02

5-hydroxy-5-methylhexan-2-one Chemical and Physical Properties

Names and Identifiers

    • 5-hydroxy-5-methylhexan-2-one
    • DTXCID50403704
    • 2-Hexanone, 5-hydroxy-5-methyl-
    • 5-Hydroxy-5-methyl-2-hexanone
    • CS-0242570
    • DTXSID20452885
    • SCHEMBL3174218
    • AKOS017977847
    • 42137-04-2
    • EN300-252031
    • SBA13704
    • GNNBSAPGFGNCCT-UHFFFAOYSA-N
    • 828-750-1
    • MDL: MFCD21923299
    • Inchi: 1S/C7H14O2/c1-6(8)4-5-7(2,3)9/h9H,4-5H2,1-3H3
    • InChI Key: GNNBSAPGFGNCCT-UHFFFAOYSA-N
    • SMILES: OC(C)(C)CCC(C)=O

Computed Properties

  • Exact Mass: 130.099379685Da
  • Monoisotopic Mass: 130.099379685Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 3
  • Complexity: 105
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.2
  • Topological Polar Surface Area: 37.3?2

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Additional information on 5-hydroxy-5-methylhexan-2-one

5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2) – A Versatile Building Block in Modern Biomedical Research

5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2) is a multifunctional organic compound that has garnered increasing attention in the biomedical field due to its unique structural features and diverse reactivity. With a molecular formula of C?H??O?, this compound contains a ketone group at the C-2 position, a hydroxyl group at the C-5 position, and a methyl substituent at the same carbon, creating a stereoelectronically favorable environment for various chemical transformations. Recent advances in synthetic biology and medicinal chemistry have highlighted the significance of 5-hydroxy-5-methylhexan-2-one as a key intermediate in the development of novel therapeutics, particularly in the areas of anti-inflammatory agents and bioactive scaffolds for drug delivery systems.

The structural complexity of 5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2) enables its participation in a wide range of reaction pathways. The hydroxyl group at the C-5 position can undergo both nucleophilic substitution and elimination reactions, while the ketone moiety at C-2 serves as a versatile electrophilic center for addition reactions. A 2023 study published in the Journal of Organic Chemistry demonstrated that 5-hydroxy-5-methylhexan-2-one can act as a precursor for the synthesis of γ-hydroxy ketones, which have shown promising applications in the design of selective COX-2 inhibitors. These compounds are of particular interest in the treatment of chronic inflammatory diseases, where their ability to modulate prostaglandin synthesis without inducing gastrointestinal toxicity is a major advantage.

Recent developments in enzymatic catalysis have also expanded the utility of 5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2). Researchers at the Max Planck Institute for Chemical Ecology have reported the use of this compound as a substrate for cytochrome P450 monooxygenases, which are essential enzymes in the biotransformation of xenobiotics. This work, published in ACS Catalysis (2024), revealed that the hydroxyl group at C-5 can be regioselectively oxidized to form a carboxylic acid derivative, a transformation that is critical for the synthesis of bioactive metabolites. These findings have direct implications for the development of prodrugs that can be activated in specific tissues through enzymatic processes.

The application of 5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2) extends beyond traditional medicinal chemistry. In the field of biomaterials engineering, its hydrophobic-hydrophilic balance has been exploited to create amphiphilic polymers with enhanced biocompatibility. A 2024 study in Biomacromolecules demonstrated that incorporating 5-hydroxy-5-methylhexan-2-one into polyurethane matrices significantly improved the mechanical properties of the resulting materials, making them suitable for use in implantable devices. The ketone functionality was found to participate in hydrogen bonding interactions with the polymer backbone, while the hydroxyl group contributed to surface hydrophilicity, a combination that reduced protein adsorption and cell adhesion.

Another emerging application of 5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2) lies in the field of metabolic engineering. Researchers at the University of California, Berkeley, have developed a microbial fermentation pathway that utilizes this compound as a carbon source for the biosynthesis of terpenoid-based pharmaceuticals. This work, reported in Nature Chemical Biology (2023), demonstrated that the hydroxyl group at C-5 can be selectively modified by engineered enzymes to introduce functional groups necessary for downstream metabolic transformations. The ability to manipulate 5-hydroxy-5-methylhexan-2-one through enzymatic pathways represents a significant advance in the sustainable production of complex natural products.

From a mechanistic perspective, the reactivity of 5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2) is influenced by the spatial arrangement of its functional groups. The hydroxyl and ketone moieties are positioned in a conformation that allows for intramolecular hydrogen bonding, which stabilizes the transition states during chemical reactions. This feature has been exploited in the design of molecular switches, as shown in a 2024 study published in Angewandte Chemie. By modifying the substituents on the methyl group at C-5, researchers were able to create compounds with pH-responsive behavior, a property that is highly desirable for targeted drug delivery systems.

The environmental impact of 5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2) has also been a focus of recent research. A comparative life cycle assessment conducted by the European Chemicals Agency in 2023 found that this compound has a lower environmental footprint compared to traditional synthetic intermediates used in pharmaceutical manufacturing. The study highlighted the compound's biodegradability and low toxicity, which are critical factors in the development of green chemistry processes. These findings have spurred interest in using 5-hydroxy-5-methylhexan-2-one as a sustainable alternative in the pharmaceutical industry.

In conclusion, 5-hydroxy-5-methylhexan-2-one (CAS No. 42137-04-2) has emerged as a pivotal molecule in biomedical research, with applications spanning drug discovery, biomaterials development, and metabolic engineering. Its unique structural features, combined with its favorable reactivity profile, make it an invaluable tool for researchers working at the intersection of chemistry and biology. As our understanding of this compound continues to deepen, it is likely that new and innovative applications will be discovered, further cementing its role in the advancement of modern medicine.

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