Diphenolic acid

Base Information

• Chemical Name: Diphenolic acid
• CAS No.: 126-00-1
• Molecular Formula: C17H18O4
• Molecular Weight: 286.328
• Hs Code.: 29182900
• European Community (EC) Number: 204-763-2
• NSC Number: 55069,34824,3371
• UNII: 2SIZ2CO5L3
• DSSTox Substance ID: DTXSID0022436
• Nikkaji Number: J151.237D
• Wikipedia: Diphenolic_acid
• Wikidata: Q3604519
• ChEMBL ID: CHEMBL1325931
• Mol file: 126-00-1.mol

Synonyms:diphenolic acid

Chemical Property of Diphenolic acid

Chemical Property:

• Appearance/Colour: Light brown particles
• Vapor Pressure: 3.48E-11mmHg at 25°C
• Melting Point: 167-170 °C(lit.)
• Refractive Index: 1.675
• Boiling Point: 507 °C at 760 mmHg
• PKA: 4.66±0.10(Predicted)
• Flash Point: 274.5 °C
• PSA: 77.76000
• Density: 1.26 g/cm³
• LogP: 3.26860
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 286.12050905
• Heavy Atom Count: 21
• Complexity: 317

Purity/Quality:

99% ^*data from raw suppliers

4- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
• Uses: Diphenolic acid (DPA) has been identified as a potential replacement for bisphenol A, which is one of the monomers for epoxy resins and polycarbonates. DPA also can Intermediate for surface coatings, lubricating oil additives, cosmetics, surfactants, plasticizers, textile chemicals. Diphenolic Acid is a flux compound. Adhesives for semiconductor devices. Since diphenolic acid is a close structural analog of bisphenol A, diphenolic acid has the potential to displace bisphenol A. A possible endocrine disruptor, bisphenol A is used in polymer applications such as for use in baby bottles, dental resins, and lacquers to coat food cans.

Technology Process of Diphenolic acid

There total 9 articles about Diphenolic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.2%

levulinic acid (123-76-2) + phenol (108-95-2,27073-41-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1)

Guidance literature:

With 3-(sulfobutyl)-5-methyl-2-mercapto-1,3,4-thiadiazole-3-mercaptopropane sulfonate; at 60 ℃; for 12h;

Reference yield:

4-oxopentanoic acid ethyl ester (539-88-8) + phenol (108-95-2,27073-41-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1)

Guidance literature:

With sulfuric acid; In water; at 0 - 20 ℃; for 18h;

DOI:10.1021/jm000180n

Reference yield:

levulinic acid (123-76-2) + phenol (108-95-2,27073-41-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + o,p′ -DPA (1033556-25-0)

Guidance literature:

With ethanethiol; at 99.84 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c2cc30239j

upstream raw materials:

levulinic acid

phenol

4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester

methyl iodide

Downstream raw materials:

4,4-Bis-(4-diphenoxymethoxy-phenyl)-pentanoic acid diphenoxymethyl ester

4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester

benzyl 4,4-bis[4-(benzyloxy)phenyl]pentanoate

4,4-Bis-(4-hydroxyphenyl)pentanoic acid dibenzylamide

Refernces

Symmetrical bis(heteroarylmethoxyphenyl)alkylcarboxylic acids as inhibitors of leukotriene biosynthesis

10.1021/jm000180n

The research focuses on the investigation of symmetrical bis(heteroarylmethoxyphenyl)alkylcarboxylic acids as potent inhibitors of leukotriene biosynthesis, with the aim of developing new drug candidates for the treatment of asthma and related inflammatory disorders. The study centers on the compound 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentanoic acid sodium salt (47?Na), which demonstrated high selectivity for inhibiting leukotriene C4 (LTC4) over prostaglandin E2 (PGE2) and showed promising pharmacokinetic properties in rat and cynomolgus monkey models. The experiments involved the synthesis of various bis-QMP analogues, their evaluation in vitro using human neutrophils and in vivo using animal models, and the analysis of their inhibitory activity on leukotriene biosynthesis. The research utilized a range of analytical techniques, including NMR spectroscopy, mass spectrometry, and elemental analysis, to characterize the synthesized compounds and assess their potency, selectivity, and pharmacokinetic properties. The main reactants used in the synthesis included commercially available diphenolic acid, quinolylmethoxyphenyl derivatives, and various reagents for the synthesis and modification of the target compounds. The study concluded that 47?Na (ABT-080) met the design parameters for a drug candidate and has proceeded to phase I human studies for safety and pharmacokinetic evaluation.