17610-24-1

Basic information

• Product Name: 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)ethan-1-one
• Synonyms: 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)ethan-1-one;1,1,4,4,6-Pentamethyl-7-acetyl-1,2,3,4-tetrahydronaphthalene;1-[(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethylnaphthalen)-2-yl]ethanone;5',6',7',8'-Tetrahydro-3',5',5',8',8'-pentamethyl-2'-acetonaphthone;Einecs 241-585-4;Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-;6-ACETYL-1,1,4,4,7-PENTAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE;1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone
• CAS NO: 17610-24-1
• Molecular Formula: C₁₇H₂₄O
• Molecular Weight: 244.37186
• EINECS: 241-585-4
• Mol File: 17610-24-1.mol

Chemical Properties

• Melting Point: 62-63.5 °C(Solv: ethanol (64-17-5))
• Boiling Point: 347.6°Cat760mmHg
• Flash Point: 146.3°C
• Appearance: /
• Density: 0.936g/cm³
• Vapor Pressure: 5.34E-05mmHg at 25°C
• Refractive Index: 1.498
• CAS DataBase Reference: 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)ethan-1-one(17610-24-1)
• EPA Substance Registry System: 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)ethan-1-one(17610-24-1)

Safety Data

• Hazardous Substances Data: 17610-24-1(Hazardous Substances Data)

Usage

Uses

Used in Fragrance and Flavor Industry:
1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)ethan-1-one is used as a fragrance and flavor ingredient for its strong and long-lasting musky, woody, and citrusy aroma. It is commonly used in perfumes, colognes, and other scented products.
Used in Pharmaceutical Industry:
1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)ethan-1-one may be used in the pharmaceutical industry due to its specific chemical properties and fragrance characteristics.
Used in Cosmetic Industry:
1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)ethan-1-one may also have applications in the cosmetic industry due to its unique scent and chemical properties.

InChI:InChI=1/C17H24O/c1-11-9-14-15(10-13(11)12(2)18)17(5,6)8-7-16(14,3)4/h9-10H,7-8H2,1-6H3

Upstream product

• 6683-48-3 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene 
• 75-36-5 acetyl chloride 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 6223-78-5 2,5-dichloro-2,5-dimethyl hexane 
• 110-03-2 2,5-dimethyl-2,5-hexanediol 

Downstream Products

• 1347735-37-8 ethyl 6-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl)nicotinate 
• 153559-73-0 ethyl 6-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)nicotinate 
• 153559-76-3 6-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl)nicotinic acid 
• 1417652-27-7 (E)-4-methyl-N'-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethylidene)benzenesulfonohydrazide 
• 1261244-62-5 (E)-3-(3,4-dichlorophenyl)-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one 
• 1261244-53-4 (E)-3-(4-(dimethylamino)phenyl)-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one 
• 1261244-45-4 C₂₅H₂₇NO 
• 1261244-51-2 (E)-3-(4-bromophenyl)-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one 
• 1261244-54-5 (E)-3-(3-hydroxyphenyl)-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one 
• 1261244-59-0 (E)-3-(3,4-dimethoxyphenyl)-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one 
• 1261244-48-7 (E)-3-(4-methoxyphenyl)-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one 
• 1261244-64-7 (E)-3-(4-hydroxyphenyl)-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one 
• 1261244-46-5 C₂₄H₂₈O 
• 1261244-52-3 (E)-3-(4-nitrophenyl)-1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one 

Relevant articles and documents

Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical-Polar Crossover Cyclopropanation of Alkenes

A general protocol for visible-light-induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α-aryl or methyl-substituted Michael acceptors and styrene derivatives, the unactivated 1,1-dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3-bis(1-arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late-stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.

Retinoid compounds and their use

The invention relates to retinoid compounds of the formula (I): wherein V is a hydrophobic group;W is a non-polyenic linker; andX is a polar group comprising a hydrogen bond donor; or a salt thereof, and to the use of such compounds in the control of cell differentiation.

Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth

Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids was designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer cell line HT-29. Retinoid like moiety was introduced through Friedel-Crafts alkylation of toluene. Among the synthesized compounds, the cyano derivative (E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl) prop-1-enyl)benzonitrile 8 showed submicromolar inhibitory activity with an IC50 of 0.66 μM.

Disubstituted chalcone oximes as selective agonists of RAR retinoid receptors

Compounds of the formula where the variables are as defined in the specification, are useful for preventing or treating emphysema and related pulmonary conditions of mammals and other diseases and conditions which are responsive to RARγ agonist retinoids, such as skin related diseases, including but not limited to acne and psoriasis.

Ketone precursors for organoleptic compounds

The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.

Compounds, their preparation and use

Disclosed are novel compounds of formula I wherein R1, R2, R3, L, X and Y are as defined in the specification. These compounds are useful in the treatment of conditions mediated by nuclear receptors, in particular the Retinoid X Receptor (RXR) and the Peroxisome Proliferator-Activated Receptor (PPAR) families. Such conditions include diabetes and obesity.

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.

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.

Treatment of mammals afflicted with tumors with compounds having RXR retinoid receptor agonist activity

Retinoid-like compounds which act as agonists of the RXR retinoid receptor sites induce apoptosis of tumor cells in cell cultures, and are used as drugs to treat tumors in mammals including humans. Compounds which are specific agonists of RXR receptors and also compounds which are agonists of both RAR and RXR agonist (pan-agonists) induce apoptosis, although the RXR agonist compounds are preferred as drugs to avoid undesirable side effects associated with RAR agonist activity. The RXR agonists compounds are administered to mammals afflicted with tumors in pharmaceutical compositions adapted for systemic topical or for intralesional administration. The range of concentration of the active ingredient RXR agonist compound in the pharmaceutical compositions is approximately between 0.001 and 5 percent by weight, and such that the composition delivers approximately 0.1 mg to 100 mg of the active ingredient per kg body weight of the patient, per day of treatment.

Tetrahydronaphthyl and thiazole, oxazole or imidazole substituted ethene derivatives having retinoid-like activity, reduced skin toxicity and reduced teratogenecity

Compounds of the formula STR1 as herein defined, have retinoid-like activity and are substantially non-teratogenic and non-irritating to the skin.