166978-49-0

Basic information

• Product Name: 4-[2-(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl]benzoic Acid Ethyl Ester
• Synonyms: 4-[2-(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl]benzoic Acid Ethyl Ester;Ethyl 4-[2-(5,6,7,8-Tetrahydro-5,5-diMethyl-8-oxo-2-naphthalenyl)ethynyl]benzoate;ethyl 4-[(5,6,7,8-tetrahydro-5,5-diMethyl-8-oxo-2-naphthalenyl)ethynyl]benzoate;ethyl 4-[(5,5-diMethyl-8-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)ethynyl]benzoate
• CAS NO: 166978-49-0
• Molecular Formula: C₂₃H₂₂O₃
• Molecular Weight: 346.41898
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 166978-49-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 506.8°Cat760mmHg
• Flash Point: 221.2°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 2.15E-10mmHg at 25°C
• Refractive Index: 1.599
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-[2-(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl]benzoic Acid Ethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl]benzoic Acid Ethyl Ester(166978-49-0)
• EPA Substance Registry System: 4-[2-(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl]benzoic Acid Ethyl Ester(166978-49-0)

Safety Data

• Hazardous Substances Data: 166978-49-0(Hazardous Substances Data)

Usage

Chemical Properties

Off White Solid

Uses

Intermediate in the production of high affinity retinoic acid receptor (RAR) antagonists.

InChI:InChI=1/C23H22O3/c1-4-26-22(25)18-10-7-16(8-11-18)5-6-17-9-12-20-19(15-17)21(24)13-14-23(20,2)3/h7-12,15H,4,13-14H2,1-3H3

Upstream product

• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 166978-48-9 7-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1-(2H)-one 
• 166978-47-8 7-(trimethylsilyl)ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1-(2H)-one 
• 166978-46-7 7-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one 
• 2979-69-3 3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone 

Downstream Products

• 226250-05-1 4-((R)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid ethyl ester 
• 226250-06-2 4-((S)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid ethyl ester 
• 226250-19-7 4-((R)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid 
• 226250-19-7 4-((S)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid 
• 166977-92-0 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethynyl]benzoate 
• 188887-70-9 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(3-methylphenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-72-1 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(2-methylphenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-79-8 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(4-chlorophenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-81-2 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(4-methoxyphenyl)-2-naphthalenyl)ethynyl]benzoate 
• 188887-92-5 4-[8-(4-hydroxy-phenyl)-5,5-dimethyl-5,6-dihydro-naphthalen-2-ylethynyl]-benzoic acid ethyl ester 
• 188887-90-3 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(3-hydroxyphenyl)-2-naphthalenyl)ethynyl]benzoate 

Relevant articles and documents

Method for inhibiting gene expression promoted by AP1 protein with RAR beta selective retinoids and method for treatment of diseases and conditions with such retinoids

Retinoid compounds which repress expression of the gene promoted by AP1 protein but which do not significantly activate expression of the genes having RA-responsive elements in their promoter region through RAR alpha and RAR GAMMA receptor subtypes, are u

Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities

Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity. These assays are based on the ability of negative hormones to down-regulate the activity of chimeric retinoid receptors engineered to possess a constitutive transcription activator domain.

Synthesis and characterization of a highly potent and effective antagonist of retinoic acid receptors

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