Cas no 52275-04-4 (4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde)

4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde is a phenolic aldehyde compound featuring two prenyl (3-methylbut-2-en-1-yl) substituents at the 3- and 5-positions of the aromatic ring. This structural configuration imparts notable reactivity and potential biological activity, making it a valuable intermediate in organic synthesis and pharmaceutical research. The presence of the hydroxyl and aldehyde functional groups enhances its utility in further derivatization, such as condensation or oxidation reactions. Its prenyl groups contribute to increased lipophilicity, which may improve membrane permeability in bioactive applications. The compound is typically characterized by high purity and stability under standard storage conditions, ensuring reliable performance in experimental or industrial processes.
4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde structure
52275-04-4 structure
Product Name:4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde
CAS No:52275-04-4
MF:C17H22O2
MW:258.355385303497
CID:836900
PubChem ID:71519781
Update Time:2025-05-28

4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde Chemical and Physical Properties

Names and Identifiers

    • 4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde
    • 3,5-Diprenyl-4-hydroxybenzaldehy
    • 3,5-Diprenyl-4-hydroxybenzaldehyde
    • 4-hydroxy-3,5-bis[(E)-3-methylbut-1-enyl]benzaldehyde
    • FS-9298
    • CS-0017644
    • HY-N1791
    • CCA27504
    • AKOS022184716
    • 52275-04-4
    • 4-Hydroxy-3,5-bis(3-methylbut-2-enyl)benzaldehyde
    • [ "" ]
    • DB-339042
    • Inchi: 1S/C17H22O2/c1-12(2)5-7-15-9-14(11-18)10-16(17(15)19)8-6-13(3)4/h5-6,9-11,19H,7-8H2,1-4H3
    • InChI Key: OHVUELCNFASQGY-UHFFFAOYSA-N
    • SMILES: OC1C(=CC(C=O)=CC=1C/C=C(\C)/C)C/C=C(\C)/C

Computed Properties

  • Exact Mass: 258.16206
  • Monoisotopic Mass: 258.161979940g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 5
  • Complexity: 316
  • 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: 4.9
  • Topological Polar Surface Area: 37.3?2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.0±0.1 g/cm3
  • Boiling Point: 383.5±42.0 °C at 760 mmHg
  • Flash Point: 163.7±20.5 °C
  • PSA: 37.3
  • Vapor Pressure: 0.0±0.9 mmHg at 25°C

4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde Security Information

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4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde Related Literature

Additional information on 4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde

Recent Advances in the Study of 4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde (CAS: 52275-04-4)

4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde (CAS: 52275-04-4) is a naturally occurring phenolic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its potential therapeutic properties. Recent studies have explored its structural characteristics, biosynthesis pathways, and pharmacological activities, particularly its antioxidant, anti-inflammatory, and anticancer effects. This research brief aims to provide an overview of the latest findings related to this compound, highlighting its molecular mechanisms and potential applications in drug development.

The compound, often referred to as a prenylated benzaldehyde derivative, is structurally characterized by the presence of two 3-methylbut-2-en-1-yl (prenyl) groups attached to a benzaldehyde core. This unique structure is believed to contribute to its bioactivity, particularly in modulating cellular signaling pathways. Recent research has focused on elucidating the biosynthesis of this compound in natural sources, such as certain plant species, and its potential for synthetic production. Advances in synthetic biology and metabolic engineering have enabled the heterologous production of 4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde in microbial hosts, offering a scalable and sustainable alternative to traditional extraction methods.

Pharmacological studies have demonstrated that 4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde exhibits potent antioxidant activity, scavenging reactive oxygen species (ROS) and protecting cells from oxidative stress. This property is particularly relevant in the context of neurodegenerative diseases and aging-related disorders. Additionally, the compound has shown promising anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines and modulating the NF-κB signaling pathway. These findings suggest its potential as a lead compound for developing novel anti-inflammatory drugs.

In the realm of cancer research, 4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde has been investigated for its ability to induce apoptosis and inhibit proliferation in various cancer cell lines. Mechanistic studies have revealed that the compound targets key oncogenic pathways, including the PI3K/AKT and MAPK/ERK cascades, which are frequently dysregulated in cancers. Furthermore, its selectivity towards cancer cells, while sparing normal cells, enhances its appeal as a potential chemotherapeutic agent. Recent in vivo studies using animal models have corroborated these findings, showing significant tumor growth inhibition with minimal toxicity.

Despite these promising results, challenges remain in the clinical translation of 4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde. Issues such as bioavailability, metabolic stability, and formulation optimization need to be addressed to fully harness its therapeutic potential. Current research is exploring various drug delivery systems, including nanoparticles and liposomes, to improve its pharmacokinetic profile. Additionally, structure-activity relationship (SAR) studies are being conducted to identify derivatives with enhanced efficacy and reduced side effects.

In conclusion, 4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde (CAS: 52275-04-4) represents a promising candidate for further drug development, with its multifaceted pharmacological activities and relatively low toxicity. Continued research into its molecular mechanisms, synthetic production, and formulation strategies will be crucial in advancing this compound from the laboratory to the clinic. The integration of interdisciplinary approaches, including chemical biology, pharmacology, and nanotechnology, will likely play a pivotal role in overcoming current limitations and unlocking its full therapeutic potential.

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