4359-97-1

Basic information

• Product Name: 4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one
• Synonyms: 2,6-Ditert-butyl-4-(3,5-ditert-butyl-4-hydroxybenzylidene)-2,5-cyclohexadien-1-one;2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2,5-cyclohexadiene-1-one;4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one;4-(4-Hydroxy-3,5-di-tert-butylbenzylidene)-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one;2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxybenzylidene)cyclohexa-2,5-dienone;2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
• CAS NO: 4359-97-1
• Molecular Formula: C₂₉H₄₂O₂
• Molecular Weight: 422.6426
• Mol File: 4359-97-1.mol

Chemical Properties

• Boiling Point: 512.6°Cat760mmHg
• Flash Point: 216.9°C
• Appearance: /
• Density: 1.012g/cm³
• CAS DataBase Reference: 4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one(4359-97-1)
• EPA Substance Registry System: 4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2,6-di-tert-butyl-2,5-cyclohexadiene-1-one(4359-97-1)

Safety Data

• Hazardous Substances Data: 4359-97-1(Hazardous Substances Data)

Usage

Uses

Used in Plastics Industry:
UvateneTM is used as a stabilizing agent in the plastics industry to enhance the longevity and performance of materials such as polyolefins and styrenic polymers. Its role in preventing oxidative degradation ensures that the plastics maintain their structural integrity and resist environmental stress cracking.
Used in Rubber Industry:
In the rubber industry, UvateneTM serves as an essential antioxidant, safeguarding rubber materials against the detrimental effects of oxidation. This helps in maintaining the elasticity and tensile strength of rubber, thereby extending its service life in various applications.
Used in Adhesives Industry:
UvateneTM is utilized as a stabilizing component in adhesives to improve their resistance to oxidative degradation. This ensures that the adhesives maintain their bonding strength and durability over time, even when exposed to harsh conditions.
Used in Polyesters Stabilization:
UvateneTM is employed as a stabilizer for polyesters, protecting them from oxidative damage that can lead to discoloration, embrittlement, and loss of mechanical properties. Its effectiveness in this application contributes to the preservation of the material's aesthetic and functional qualities.

Upstream product

• 79965-38-1 bromo-bis-(3,5-di-tert-butyl-4-hydroxy-phenyl)-methane 
• 22719-43-3 Coppinger's Radikal 
• 4610-03-1 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenylimino)-2,5-cyclohexadien-1-one 
• 927-62-8 N,N-dimethylbutylamine 
• 22534-19-6 tert-butyl ammonium ion 
• 22719-43-3 2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienylidenemethyl)-phenol anion 
• 17440-81-2 triethylammonium 
• 118-82-1 4,4'-Methylenebis(2,6-di-tert-butylphenol) 
• 2607-52-5 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one 
• 16999-97-6 N-butylammonium cation 
• 17033-39-5 propylammonium 
• 2498-25-1 2-dimethylamino-ethanol; protonated form 
• 29384-47-2 di-n-propyl ammonium ion 
• 21005-95-8 hexylammonium 

Downstream Products

• 103330-88-7 bis-(3,5-di-tert-butyl-4-hydroxy-phenyl)-methoxy-methane 
• 17033-39-5 propylammonium 
• 22719-43-3 2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienylidenemethyl)-phenol anion 
• 2498-25-1 2-dimethylamino-ethanol; protonated form 
• 21005-95-8 hexylammonium 
• 22719-43-3 Coppinger's Radikal 
• 29384-47-2 di-n-propyl ammonium ion 
• 22534-19-6 tert-butyl ammonium ion 
• 16999-97-6 N-butylammonium cation 
• 17440-81-2 triethylammonium 
• 22451-37-2 2-diethylamino-ethanol; protonated form 
• 2887-52-7 1,3-Di-tert-butyl-5--cyclohexadien-3,6-on-(2) 
• 33560-59-7 Tris-(4-hydroxy-3,5-di-tert.-butyl-phenyl)-methan 
• 147024-31-5 (C₆H₅)3GeCH(C₆H₂(C₄H₉)2(OH))2 

Relevant articles and documents

Substituent effect on the radical scavenging activity of 6-chromanol derivatives

Several 6-chromanol derivatives with various substituents (one or two amino, acetylamino, chloro or nitro substituents at the 5-, 7-, 8- or 5,7-positions on the phenyl ring of 2,2-dimethyl-6-chromanol) were synthesized, and their second order rate constan

A QUESTION CONCERNING THE pK RANGE WITHIN WHICH AN ORGANIC FREE RADICAL EXHIBITS NORMAL RADICAL BEHAVIOUR. THE CASE OF GALVINOXYL

Galvinoxyl (G.) reacts with a series of substituted acetic acids and forms hydrogalvinoxyl (GH) as the sole product.The kinetic data conform with a Bronsted type analysis.Hydrogalvinoxyl may dissociate to the relevant cation G+, in a

Antioxidant and antiproliferative activities of hydroxyl-substituted Schiff bases

Eight hydroxyl-substituted Schiff bases with the different number and position of hydroxyl group on the two asymmetric aromatic rings (A and B rings) were prepared by the reaction between the corresponding aromatic aldehyde and aniline. Their antioxidant effects against the stable galvinoxyl radical (GO{radical dot}) in ethyl acetate and methanol, and 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH)-induced DNA strand breakage, and their antiproliferative effects on human hepatoma HepG2 cells, were investigated. Structure-activity relationship analysis demonstrates that o-dihydroxyl groups on the aromatic A ring and 4-hydroxyl group attached to the aromatic B ring contribute critically to the antioxidant and antiproliferative activities.

Galvinoxyl radicals: Synthesis of new derivatives, determination of low oxygen contents, and stability studies

Two new derivatives of galvinoxyl (1), a perdeutered (2) and an adamantyl-analog (3) for potential applications as spin probes were synthesized. The synthesis with deuterated educts yielded 2 with 98% D. It exhibited an 18-line EPR spectrum in octanol wit

Involvement of electron transfer in the radical-scavenging reaction of resveratrol

Resveratrol (3,4′,5-trihydroxy-trans-stilbene) efficiently scavenges an oxygen radical via an electron transfer from resveratrol to the radical in deaerated acetonitrile, which is significantly accelerated by the presence of magnesium ion. Copyright

Effect of methyl substitution on the antioxidative property and genotoxicity of resveratrol

Resveratrol (trans-3,4′,5-trihydroxystilbene) is a natural phytoalexin with various biological activities including inhibition of lipid peroxidation and free radical scavenging properties. In addition to its beneficial effects, resveratrol also has significant genotoxicity that leads to a high frequency of chromosome aberration together with micronucleus and sister chromatid exchanges. To enhance the radical scavenging activities and to reduce the genotoxicity of resveratrol, we designed 4′-methyl resveratrol analogues where a methyl group was introduced at the ortho position relative to the 4′-hydroxy group, which is responsible for both antioxidative activities and genotoxicity of resveratrol. These synthesized methyl analogues of resveratrol showed increased antioxidative activities against galvinoxyl radical as an oxyl radical species. Furthermore, the methyl analogues also surprisingly showed reduced in vitro genotoxicities, suggesting that methyl substitution may improve resveratrol efficacy.

Electron-transfer mechanism in radical-scavenging reactions by a vitamin E model in a protic medium

The scavenging reaction of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH*) or galvinoxyl radical (GO*) by a vitamin E model, 2,2,5,7,8-pentamethylchroman-6-ol (1H), was significantly accelerated by the presence of Mg(ClO4)2 in de-aerated methanol (MeOH). Such an acceleration indicates that the radical-scavenging reaction of 1H in MeOH proceeds via an electron transfer from 1H to the radical, followed by a proton transfer, rather than the one-step hydrogen atom transfer which has been observed in acetonitrile (MeCN). A significant negative shift of the one-electron oxidation potential of 1H in MeOH (0.63 V vs. SCE), due to strong solvation as compared to that in MeCN (0.97 V vs. SCE), may result in change of the radical-scavenging mechanisms between protic and aprotic media.

Thermal decomposition of 2,6-di-tert-butyl-4-dimethylaminomethylphenol

Products of thermolysis of 2,6-di-tert-butyl-4-dimethylaminomethylphenol were determined qualitatively and quantitatively by GLC, UV, and 1H NMR methods. The kinetics of the reaction was studied. The thermolysis products were studied as the inhibitors in thermopolymerization of monomers.

7-substituted quinone methides as inhibitors for unsaturated monomers

Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.

SYNTHESIS OF 2,6-DI-tert-BUTYL-4-(3,5-DI-tert-BUTYL-4-HYDROXYBENZYLIDENE)-2,5-CYCLOHEXADIENONE

2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2,5-cyclohexadienone has been prepared in 63-92percent yield by oxidative dehydrogenation of 4,4'-methylenebis(2,6-di-tert-butylphenol) with various quinones.The products of quinone reduction have been isolated.