156910-42-8

Basic information

• Product Name: methyl 4-<1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-methyl-1-propenyl>benzoate
• Synonyms: methyl 4-<1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-methyl-1-propenyl>benzoate
• CAS NO: 156910-42-8
• Molecular Weight: 376.539
• Mol File: 156910-42-8.mol

Chemical Properties

• CAS DataBase Reference: methyl 4-<1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-methyl-1-propenyl>benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-<1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-methyl-1-propenyl>benzoate(156910-42-8)
• EPA Substance Registry System: methyl 4-<1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-methyl-1-propenyl>benzoate(156910-42-8)

Safety Data

• Hazardous Substances Data: 156910-42-8(Hazardous Substances Data)

Upstream product

• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 6683-46-1 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene 
• 1571-08-0 methyl 4-formylbenzoate 
• 115665-61-7 methyl 4-(2-methylprop-1-en-1-yl)benzoate 
• 169126-64-1 (3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-boronic acid 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 117259-83-3 methyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]benzoate 

Relevant articles and documents

sp2-Bridged diaryl retinoids: Effects of bridge-region substitution on retinoid X receptor (RXR) selectivity

RXR class selectivity and RXR transcriptional activation activity compared to those for the retinoic acid receptor subtypes were enhanced on the 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenylethenyl)benzoic acid scaffold and its 3-methyl analogue by replacing their 1,1-ethenyl bridge by a 1,1-(2-methylpropenyl) or cyclopropylidenylmethylene group. (C) 2000 Elsevier Science Ltd. All rights reserved.

Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors

Bridged bicyclic aromatic compounds are provided having the structure STR1 wherein R1, R2, R3, R4, R5 and n are as defined herein. The novel compounds are useful for modulating gene expression of retinoic acid receptors, vitamin D receptors and thyroid receptors. Pharmaceutical compositions and methods for modulating gene expression are provided as well.

Conformational effects on retinoid receptor selectivity. 2. Effects of retinoid bridging group on retinoid X receptor activity and selectivity

The natural retinoid 9-cis-retinoic acid is an activating ligand for both the retinoic acid receptors (BARs) and the retinoid X receptors (RXRs), which are members of the retinoid/thyroid hormone/steroid hormone family of nuclear receptor proteins that activate gene transcription through specific response elements. The pharmacophoric groups necessary to confer RXR selectivity were established by evaluating the ability of 21 conformationally restricted retinoids to activate the TREpal retinoic acid receptor response element for gene transcription in the presence of one of the three PAR subtypes or RXRα. In contrast to those retinoids selective for the RARs, these RXR-selective retinoids have one less atom in the bridge linking the hydrophobic and carboxylic acid termini of the retinoid skeleton. Therefore, a one-carbon bridge replaces the 19-methyl group and 9E-double bond of 9-cis-retinoic acid and is further functionalized by inclusion in an isopropylidene group, a dioxolane ring, or a cyclopropane ring for optimal RXRα activity and selectivity. In addition, the β-geranylidene and 20-methyl-(11E,13E)- dienoic acid groups of 9-cis-retinoic acid are replaced by a 5,6,7,8- tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl ring and a 4-carboxylphenyl ring, respectively, for optimal activation and selectivity. RXRα selectivity is reduced on replacement of the 4-carboxylphenyl group by a 2-carboxyl-5- thienyl group or the 9-cis-retinoic acid methylpentadienoic acid terminus.