Cas no 58380-40-8 (Benzaldehyde, 4-hydroxy-2,3-dimethyl-)

Benzaldehyde, 4-hydroxy-2,3-dimethyl-, is a substituted aromatic aldehyde characterized by the presence of hydroxyl and methyl groups at the 4, 2, and 3 positions of the benzene ring. This structural modification enhances its reactivity and selectivity in organic synthesis, making it a valuable intermediate for pharmaceuticals, agrochemicals, and fine chemicals. The hydroxyl group provides a site for further functionalization, while the methyl groups influence steric and electronic properties, improving stability and compatibility in complex reactions. Its well-defined molecular structure ensures consistent performance in applications such as asymmetric synthesis and heterocyclic compound formation. The compound is typically handled under standard laboratory conditions, with attention to its sensitivity to oxidation.
Benzaldehyde, 4-hydroxy-2,3-dimethyl- structure
58380-40-8 structure
Product Name:Benzaldehyde, 4-hydroxy-2,3-dimethyl-
CAS No:58380-40-8
MF:C9H10O2
MW:150.174502849579
CID:342279
PubChem ID:14694998
Update Time:2025-05-28

Benzaldehyde, 4-hydroxy-2,3-dimethyl- Chemical and Physical Properties

Names and Identifiers

    • Benzaldehyde, 4-hydroxy-2,3-dimethyl-
    • 2,3-Dimethyl-4-hydroxybenzaldehyde
    • 4-hydroxy-2,3-dimethylbenzaldehyde
    • 58380-40-8
    • EN300-746800
    • SCHEMBL1002718
    • GEVILTWPAPSGDK-UHFFFAOYSA-N
    • MFCD22414657
    • 2,3-dimethyl-4-hydroxy-benzaldehyde
    • CS-0196250
    • DTXSID10563116
    • AKOS019823403
    • 4-hydroxy-2,3-dimethyl-benzaldehyde
    • E92215
    • DB-337865
    • Inchi: 1S/C9H10O2/c1-6-7(2)9(11)4-3-8(6)5-10/h3-5,11H,1-2H3
    • InChI Key: GEVILTWPAPSGDK-UHFFFAOYSA-N
    • SMILES: OC1=CC=C(C=O)C(C)=C1C

Computed Properties

  • Exact Mass: 150.0681
  • Monoisotopic Mass: 150.068079557g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 145
  • 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: 1.1
  • Topological Polar Surface Area: 37.3?2

Experimental Properties

  • PSA: 37.3

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Additional information on Benzaldehyde, 4-hydroxy-2,3-dimethyl-

Recent Advances in the Study of Benzaldehyde, 4-hydroxy-2,3-dimethyl- (CAS: 58380-40-8) and Its Applications in Chemical Biology and Medicine

Benzaldehyde, 4-hydroxy-2,3-dimethyl- (CAS: 58380-40-8) is a chemically modified benzaldehyde derivative that has garnered significant attention in recent years due to its potential applications in pharmaceutical and chemical biology research. This compound, characterized by the presence of hydroxyl and dimethyl substituents on the benzene ring, exhibits unique physicochemical properties that make it a promising candidate for drug development and biochemical studies. Recent studies have explored its synthesis, biological activity, and potential therapeutic uses, shedding light on its multifaceted roles in modern medicine.

One of the key areas of interest is the compound's role as an intermediate in the synthesis of more complex pharmaceutical agents. Researchers have developed optimized synthetic routes for Benzaldehyde, 4-hydroxy-2,3-dimethyl-, with a focus on improving yield and purity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated a novel catalytic method for its production, achieving a 92% yield under mild conditions. This advancement is particularly significant for scaling up production while minimizing environmental impact.

In terms of biological activity, recent investigations have revealed that Benzaldehyde, 4-hydroxy-2,3-dimethyl- exhibits moderate antimicrobial properties against certain Gram-positive bacteria, including Staphylococcus aureus. A team at the University of Cambridge reported in Bioorganic & Medicinal Chemistry Letters that the compound's mechanism of action may involve disruption of bacterial cell membrane integrity. While its standalone antimicrobial efficacy is limited, these findings suggest its potential as a scaffold for developing more potent derivatives.

Perhaps the most promising application lies in the compound's antioxidant properties. Studies conducted in 2024 have shown that Benzaldehyde, 4-hydroxy-2,3-dimethyl- can effectively scavenge reactive oxygen species (ROS) in cellular models. This activity, attributed to the phenolic hydroxyl group, has sparked interest in its potential use for treating oxidative stress-related disorders. Researchers at the National Institute of Health are currently evaluating its neuroprotective effects in preclinical models of Parkinson's disease.

From a chemical biology perspective, the compound has proven valuable as a building block for fluorescent probes. Its structure allows for easy modification to create sensors for detecting metal ions and small molecules in biological systems. A recent publication in Chemical Communications highlighted its use in developing a turn-on fluorescent probe for zinc ion detection, with applications in studying zinc homeostasis in live cells.

Despite these promising developments, challenges remain in fully characterizing the pharmacological profile of Benzaldehyde, 4-hydroxy-2,3-dimethyl-. Current research is focusing on improving its bioavailability and target specificity, as well as investigating potential synergistic effects with existing drugs. The compound's relatively low toxicity profile, as demonstrated in recent cytotoxicity assays, makes it an attractive candidate for further development.

Looking ahead, the versatility of Benzaldehyde, 4-hydroxy-2,3-dimethyl- suggests it will continue to be an important compound in chemical biology and medicinal chemistry research. Future directions may include exploring its use in combination therapies, developing more efficient synthetic methodologies, and investigating its potential in areas such as anti-inflammatory and anticancer applications. As research progresses, this compound may well emerge as a key player in the development of novel therapeutic agents.

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