40232-93-7

Usage

Uses

Used in Pharmaceutical Industry:
Bis(4-hydroxyphenyl)acetic acid is used as a reagent for the synthesis of N-[6-chloro-4-(2,6-dimethoxyphenyl)quinazolin-2-yl]carbonyl-L-leucine, a novel nonpeptide chemotype selective for neurotensin receptor 2, due to its bis-phenolic structure and ability to undergo O-demethylation and dechlorination.
Used in Chemical Synthesis:
Bis(4-hydroxyphenyl)acetic acid is used as a reagent in the synthesis of elemonic acid derivatives as Pin 1 inhibitors, contributing to the development of potential therapeutic agents for various diseases.
Used in Insecticide Production:
Bis(4-hydroxyphenyl)acetic acid is used as a byproduct in the O-demethylation and dechlorination process of methoxychlor, an insecticide, highlighting its role in the agricultural industry.

InChI:InChI=1/C14H12O4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8,13,15-16H,(H,17,18)

Upstream product

• 4541-73-5 2,2-bis-(4-methoxyphenyl)acetic acid 
• 298-12-4 Glyoxilic acid 
• 108-95-2 phenol 
• 101097-05-6 2-(4-hydroxyphenyl)-2-(4-methoxyphenyl)acetonitrile 
• 2132-70-9 1,1-dichloro-2,2-bis(p-methoxyphenyl)ethylene 
• 33646-40-1 4-methoxymandelonitrile 

Downstream Products

• 5129-00-0 methyl 2,2-bis(4-hydroxyphenyl)acetate 
• 5359-41-1 methyl ester of 2,2-bis(4,4'-dimethoxyphenyl)ethanoic acid 
• 94159-41-8 bis(4-hydroxy-3,5-dibromo-phenyl)ethanoic acid 
• 109596-97-6 4-[bis-(4-hydroxy-phenyl)-acetyl]-morpholine 
• 102756-92-3 4-[bis-(4-acetoxy-phenyl)-acetyl]-morpholine 
• 103758-81-2 Bis-glycerylether des Bis-(4-hydroxyphenyl)-acetomorpholid 
• 101293-63-4 2,2-bis(4-hydroxyphenyl)-N,N-dimethylacetamide 
• 101734-67-2 Bis-(4-acetoxyphenyl)-acetamid 
• 102012-86-2 Bis-(4-acetoxyphenyl)-N-dimethylacetamid 
• 100870-54-0 Bis-<4-hydroxy-phenyl>-essigsaeure-hydrazid 
• 102079-03-8 Bis-(4-hydroxyphenyl)-acetanilid 
• 102664-61-9 Bis-(4-acetoxyphenyl)-acetanilid 
• 116601-31-1 4-Hydroxy-anilid der Bis-(4-acetoxy-phenyl)-essigsaeure 
• 114162-33-3 Bis-glycerylaether des Bis-(4-hydroxyphenyl)-acetanilids 

Relevant academic research and scientific papers

methyl-2,2-bis(4-hydroxyphenyl)methyl acetate synthesis method

The present invention relates to the field of production of chemical industry products, particularly to a methyl-2,2-bis(4-hydroxyphenyl)methyl acetate synthesis method. According to the synthesis method, phenol and glyoxylic acid are adopted as main raw materials, and a condensation and esterification two-step process route is performed; in the condensation reaction step, phenol, water and glyoxylic acid are firstly added at a low temperature condition and then concentrated sulfuric acid is added in a dropwise manner, or glyoxylic acid and water are firstly added and then phenol and concentrated sulfuric acid are simultaneously added in a dropwise manner, or phenol and water are firstly added and then glyoxylic acid and concentrated sulfuric acid are simultaneously added in a dropwise manner; and the filter cake obtained through the condensation reaction is added with methanol and concentrated sulfuric acid, a heating reflux esterification reaction is performed, concentration and filtration are performed to obtain a crude product, the crude product is dried, and the dried crude product is subjected to recrystallization purification to obtain the methyl-2,2-bis(4-hydroxyphenyl)methyl acetate. According to the present invention, the extraction with a large amount of the organic solvent is avoided, the operation is simple, the pollution is low, the yield is high, and the synthesis method is suitable for large-scale industrial production.

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

Symmetrical bis(quinolylmethoxyphenyl)alkylcarboxylic acids were investigated as inhibitors of leukotriene biosynthesis and 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentanoic acid sodium salt (47·Na) met our design parameters for a drug candidate (ABT-080). This compound was readily synthesized in three steps from commercially available diphenolic acid. Against intact human neutrophils, 47·Na inhibited ionophore-stimulated LTB4 formation with an IC50 = 20 nM. In zymosan-stimulated mouse peritoneal macrophages producing both LTC4 and PGE2, 47·Na showed 9000-fold selectivity for inhibition of LTC4 (IC50 = 0.16 nM) over PGE2 (IC50 = 1500 nM). Preliminary pharmacokinetic evaluation in rat and cynomolgus monkey demonstrated good oral bioavailability and elimination half-lives of 9 and 5 h, respectively. Pharmacological evaluation of leukotriene inhibition with oral dosing was demonstrated in a rat pleural inflammation model (ED50 = 3 mg/kg) and a rat peritoneal passive anaphylaxis model (LTB4, ED50 = 2.5 mg/kg; LTE4, ED50 = 1.0 mg/kg). In a model of airway constriction induced by antigen challenge in actively sensitized guinea pigs, 47·Na dosed orally blocked bronchoconstriction with an ED50 = 0.4 mg/kg, the most potent activity we have observed for any leukotriene inhibitor in this model. The mode of inhibitory action of 47·Na occurs at the stage of 5-lipoxygenase biosynthesis as it blocks both leukotriene pathways leading to LTB4 and LTC4 but not PGH2 biosynthesis. However, 47·Na does not inhibit 5-lipoxygenase catalysis in a broken cell enzyme assay; therefore it is likely that 47·Na acts as a FLAP inhibitor.

THE CHEMISTRY OF SOME METHOXYCHLOR DERIVATIVES

The preparation of 1-chloro-2,2-bis(p-methoxyphenyl)ethylene (3a) and of 1-chloro-2,2-bis(p-hydroxyphenyl)ethylene (3b), required for a study of the microbial degradation of methoxychlor (1a) was reinvestigated.The methoxy compound (3a) was readily obtained by alkaline dehydrohalogenation of 1,1-dichloro-2,2-bis(p-methoxyphenyl)ethane (2a), but similar treatment of 1,1-dichloro-2,2-bis(p-hydroxyphenyl)ethane (2b) gave a chlorine-free compound, characterized as the diethyl acetal of 2,2-bis(p-hydroxyphenylacetaldehyde (5a) on the basis of spectroscopic evidence and comparison with a model compound.Also, 2,2-bis(p-methoxyphenyl)acetic acid (4a) and 2,2-bis(p-hydroxyphenyl)acetic acid (4b) were prepared and the solubility and p-values (ethyl acetate / water) of these acids were determined.

Lowering lipid and sugar levels in the blood with a bis(4-hydroxyphenyl)alkanoic acid or ester thereof

Pharmaceutical compositions acting on the metabolism which contain as active substance bis(4-hydroxy-phenyl)alkanoic acids corresponding to the formulae I and II STR1 wherein R1 and R2 wich may be identical or different, each stands for a hydrogen or halogen atom or an alkyl group having 1 to 4 carbon atoms, R3 stands for a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R4 stands for hydroxy, alkoxy having 1 to 18 carbon atoms, phenyl-alkoxy having 1 to 4 alkyl carbon atoms, cycloalkoxy having 5 to 8 carbon atoms or a group of the formula STR2 in which Z and Z', which may be identical or different, each stands for hydrogen, alkyl of 1 to 18 carbon atoms, phenyl or cycloalkyl of 5 to 8 carbon atoms, or both together with the nitrogen atom may form a heterocyclic ring, R6 stands for an alkylene radical having 2 to 12 atoms and n stands for zero or an integer of 1 to 6, and process for preparing them.