Cas no 59748-15-1 (4-(pentyloxy)-4'-biphenylcarboxylic acid)

4-(Pentyloxy)-4'-biphenylcarboxylic acid is a biphenyl derivative featuring a pentyloxy substituent and a carboxylic acid functional group. This compound is of interest in liquid crystal research and organic synthesis due to its rigid biphenyl core and flexible alkoxy chain, which contribute to mesomorphic properties. The carboxylic acid moiety enhances its utility as an intermediate for further functionalization, such as esterification or amidation. Its well-defined structure and purity make it suitable for applications in advanced materials, particularly in the development of liquid crystalline phases and supramolecular assemblies. The compound is typically characterized by high thermal stability and consistent performance in synthetic protocols.
4-(pentyloxy)-4'-biphenylcarboxylic acid structure
59748-15-1 structure
Product Name:4-(pentyloxy)-4'-biphenylcarboxylic acid
CAS No:59748-15-1
MF:C18H20O3
MW:284.349605560303
CID:950605
PubChem ID:13862784
Update Time:2025-09-27

4-(pentyloxy)-4'-biphenylcarboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 4-(pentyloxy)-4'-biphenylcarboxylic acid
    • 4-(4-pentoxyphenyl)benzoic acid
    • 4-(HEXYLOXY)-4'-BIPHENYLCARBOXYLIC ACID
    • 4-(4-pentyloxyphenyl)benzoic acid
    • 4'-n-pentyloxybiphenyl-4-carboxylic acid
    • 4'-pentyloxy-4-biphenylcarboxylic acid
    • 4'-Pentyloxy-biphenyl-4-carbonsaeure
    • 4'-pentyloxybiphenyl-4-carboxylic acid
    • DTXSID60551422
    • CS-0152125
    • 4-(pentyloxy)biphenyl-4'-carboxylic acid
    • A832450
    • MFCD00799361
    • 4'-(pentyloxy)biphenyl-4-carboxylic acid
    • AKOS004116829
    • 59748-15-1
    • 4'-(PENTYLOXY)-[1,1'-BIPHENYL]-4-CARBOXYLIC ACID
    • 4-n-Pentyloxybiphenyl-4'-carboxylic acid
    • BS-52258
    • 4'-(PENTYLOXY)-[1,1'-BIPHENYL]-4-CARBOXYLICACID
    • SCHEMBL2490183
    • 4'-(Pentyloxy)[1,1'-biphenyl]-4-carboxylic acid
    • MDL: MFCD00799361
    • Inchi: 1S/C18H20O3/c1-2-3-4-13-21-17-11-9-15(10-12-17)14-5-7-16(8-6-14)18(19)20/h5-12H,2-4,13H2,1H3,(H,19,20)
    • InChI Key: RBJMVQVMVYPYED-UHFFFAOYSA-N
    • SMILES: O(C1C=CC(=CC=1)C1C=CC(C(=O)O)=CC=1)CCCCC

Computed Properties

  • Exact Mass: 284.14100
  • Monoisotopic Mass: 284.14124450g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 7
  • Complexity: 300
  • 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
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 46.5?2

Experimental Properties

  • Color/Form: Not determined
  • PSA: 46.53000
  • LogP: 4.62080

4-(pentyloxy)-4'-biphenylcarboxylic acid Customs Data

  • HS CODE:2918990090
  • Customs Data:

    China Customs Code:

    2918990090

    Overview:

    2918990090. Other additional oxy carboxylic acids(Including anhydrides\Acyl halide\Peroxides, peroxyacids and derivatives of this tax number). VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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Additional information on 4-(pentyloxy)-4'-biphenylcarboxylic acid

Recent Advances in the Study of 4-(Pentyloxy)-4'-Biphenylcarboxylic Acid (CAS: 59748-15-1)

4-(Pentyloxy)-4'-biphenylcarboxylic acid (CAS: 59748-15-1) is a biphenyl derivative that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. Recent studies have explored its role in liquid crystal materials, drug delivery systems, and as a precursor for bioactive compounds. This research brief synthesizes the latest findings on this compound, highlighting its chemical behavior, biological interactions, and emerging applications in biomedicine.

A 2023 study published in the Journal of Medicinal Chemistry investigated the molecular interactions of 4-(pentyloxy)-4'-biphenylcarboxylic acid with lipid bilayers, revealing its potential as a membrane-targeting agent. The compound's amphiphilic nature, conferred by its pentyloxy tail and carboxylic acid headgroup, enables selective insertion into lipid membranes, making it a candidate for drug delivery vehicles targeting cellular membranes. Molecular dynamics simulations demonstrated stable binding to phosphatidylcholine-rich domains, suggesting applications in targeted therapy.

In materials science, researchers at the University of Cambridge (2024) reported the compound's exceptional self-assembly properties when combined with metal-organic frameworks (MOFs). The biphenyl core facilitates π-π stacking interactions, while the pentyloxy chain enhances solubility in organic solvents. This dual functionality has led to the development of novel hybrid materials with tunable porosity, potentially useful for controlled drug release systems. The study (DOI: 10.1039/D3SC04562J) characterized these assemblies using X-ray diffraction and atomic force microscopy.

Pharmacological studies have identified 59748-15-1 as a promising scaffold for anti-inflammatory agents. A Nature Communications paper (2024) demonstrated that derivatives of this compound exhibit selective COX-2 inhibition with IC50 values comparable to celecoxib. The carboxylic acid moiety appears critical for binding to the COX-2 active site, while the pentyloxy chain modulates lipophilicity and tissue distribution. These findings were validated through in vitro enzyme assays and in vivo models of inflammation.

Recent synthetic chemistry advancements have improved the production yield of 4-(pentyloxy)-4'-biphenylcarboxylic acid. A Green Chemistry publication (2024) described a solvent-free mechanochemical synthesis route that achieves 92% yield while reducing hazardous waste by 78% compared to traditional methods. This sustainable approach utilizes ball milling to facilitate the Suzuki-Miyaura coupling reaction between 4-pentyloxyphenylboronic acid and 4-bromobenzoic acid, followed by in situ crystallization.

Analytical characterization techniques for this compound have also advanced. A 2024 Analytical Chemistry study established a robust HPLC-MS method for quantifying 59748-15-1 in biological matrices with a detection limit of 0.1 ng/mL. The method was successfully applied to pharmacokinetic studies in rodent models, revealing favorable absorption profiles and tissue distribution patterns that support further drug development efforts.

In conclusion, 4-(pentyloxy)-4'-biphenylcarboxylic acid represents a versatile compound with applications spanning materials science to pharmaceutical development. Current research directions include optimizing its derivatives for enhanced bioactivity, exploring its potential in photodynamic therapy, and developing large-scale green synthesis methods. The compound's unique structural features continue to inspire innovative applications at the chemistry-biology interface.

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