57717-80-3

Basic information

• Product Name: 3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXY-B,B-DIMETHYL-BENZENEPROPANOL
• Synonyms: CGP 7930;3-(3',5'-DI-TERT-BUTYL-4'-HYDROXY)PHENYL-2,2-DIMETHYLPROPANOL;3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXY-B,B-DIMETHYL-BENZENEPROPANOL;3,5-Bis(1,1-dimethylethyl)-4-hydroxy-beta,beta-dimethylbenzenepropanol;3,5-bis(1,1-Dimethylethyl)-4-hydroxy-β,β-dimethyl-benzenepropanol
• CAS NO: 57717-80-3
• Molecular Formula: C₁₉H₃₂O₂
• Molecular Weight: 292.46
• Product Categories: GABA/Glycine receptor
• Mol File: 57717-80-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 364.7°Cat760mmHg
• Flash Point: 152.6°C
• Appearance: white/solid
• Density: 0.971g/cm³
• Vapor Pressure: 5.87E-06mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: 22 mg/mL, soluble
• CAS DataBase Reference: 3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXY-B,B-DIMETHYL-BENZENEPROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXY-B,B-DIMETHYL-BENZENEPROPANOL(57717-80-3)
• EPA Substance Registry System: 3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXY-B,B-DIMETHYL-BENZENEPROPANOL(57717-80-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 57717-80-3(Hazardous Substances Data)

Usage

Description

CGP 7930 is a positive allosteric modulator of GABAB receptors. It enhances GABA binding with a maximal effect of 143% compared to a GABA-only control in CHO cells membranes expressing the GABAB(1b/2) receptor and enhances GABA binding to rat cortical membranes when used at a concentration of 30 μM. It is selective for GABA binding to heterodimeric GABAB(1b/2) over monomeric GABAB(1b) receptors. CGP 7930 potentiates the efficacy of the GABAB receptor agonist baclofen in decreasing the spontaneous firing rate of dopaminergic neurons in the rat ventral tegmental area (VTA) in vitro (EC50 = 0.27 μM). It also potentiates the sedative-reducing effects induced by the GABAB receptor agonists baclofen and γ-hydroxybutyric acid (GHB) in rats when administered at doses ranging from 10 to 170 mg/kg, effects that can be blocked by the GABAB receptor antagonist SCH 50911. CGP 7930 reduces self-administration of nicotine, alcohol, and cocaine in rodent models. It suppresses the acquisition of alcohol drinking behavior in alcohol-na?ve Sardinian alcohol-preferring rats over a five-day period when administered at doses ranging from 25 to 100 mg/kg and transiently reduces the maintenance of alcohol drinking behavior in alcohol-experienced rats at a dose of 100 mg/kg.

Biological Activity

Positive allosteric modulator of GABA B receptors. Increases the potency and efficacy of GABA at both native and recombinant GABA B receptors (EC 50 values are 5.37 and 4.60 μ M respectively) and enhances the inhibitory effect of the agonist L-baclofen in cultured cortical neurons. Reduces operant self-administration of ethanol in alcohol-preferring rats following i.p. administration.

InChI:InChI=1/C19H32O2/c1-17(2,3)14-9-13(11-19(7,8)12-20)10-15(16(14)21)18(4,5)6/h9-10,20-21H,11-12H2,1-8H3

Upstream product

• 56189-68-5 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,2-dimethyl-propionaldehyde 
• 128-39-2 2,6-di-tert-butylphenol 
• 87-97-8 2,6-di-tert-butyl-4-methoxymethylene-phenol 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 

Downstream Products

• 57717-16-5 2,6-Di-tert-butyl-4-(2,2-dimethyl-3-trimethylsilanyloxy-propyl)-phenol 
• 57717-02-9 Octadecanoic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl ester 
• 57717-90-5 (3,5-Di-tert-butyl-4-hydroxy-benzyl)-phosphonic acid bis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl] ester 
• 57717-36-9 Phosphoric acid tris-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl] ester 
• 57717-91-6 2-Dodecylsulfanyl-succinic acid bis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl] ester 
• 57717-66-5 2-Octylsulfanyl-succinic acid bis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl] ester 
• 57717-65-4 2-(2-Hydroxy-ethylsulfanyl)-succinic acid bis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl] ester 
• 57717-27-8 Diethyl-carbamic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl ester 
• 57717-63-2 Cyclohexanecarboxylic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl ester 
• 57717-35-8 {6-[3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propoxycarbonylamino]-hexyl}-carbamic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl ester 
• 57717-19-8 Malonic acid bis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl] ester 
• 57717-64-3 {3-[3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propoxycarbonylamino]-4-methyl-phenyl}-carbamic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl ester 
• 57717-34-7 Phenyl-thiocarbamic acid O-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl] ester 
• 57717-33-6 N-phenylcarbamic acid 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,2-dimethylpropyl ester 

Relevant articles and documents

Synthesis of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols and the properties of related sulfides

Reaction of 2,6-di-tert-butylphenol with aliphatic linear and branched diols in an alkaline medium at a temperature of 180-220°C leads to the formation of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols. The increase in the product yield and reducing the reaction temperature was reached at the catalysis of this reaction with zinc oxide. The structure of the diphenylalkane derivatives generated in side reaction was proved and the structural influence of the length of the aliphatic residue on the antioxidant effectiveness of the sulfides derived from the corresponding hydroxyalkylphenols was examined.

Preparation of 3-(hydroxyphenyl)propionaldehydes and their hydrogenation to 3-(hydroxyphenyl)propanols

A process for preparing 3-(hydroxyphenyl)propionaldehydes of the formula I STR1 and, where appropriate, for preparing 3-(hydroxyphenyl)propanols of the formula II STR2 where R1, R2, R3 and R4 are each hydrogen,

Antioxidant ester substituted phenols and process for their preparation

This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.