14035-33-7

Usage

InChI:InChI=1/C16H24O2/c1-10(17)11-8-12(15(2,3)4)14(18)13(9-11)16(5,6)7/h8-9,18H,1-7H3

Upstream product

• 4130-42-1 2,6-di-tert-butyl-4-ethylphenol 
• 128-39-2 2,6-di-tert-butylphenol 
• 75-36-5 acetyl chloride 
• 108-22-5 Isopropenyl acetate 
• 108-24-7 acetic anhydride 
• 98-82-8 Isopropylbenzene 
• 80-15-9 Cumene hydroperoxide 
• 64-19-7 acetic acid 
• 19263-37-7 2,6-di-t-butyl-4-i-propenylphenol 
• 14681-20-0 2,6-Di-tert-butyl-4-(1-hydroxyethyl)phenol 
• 5427-02-1 2,6-di-tert-butyl-4-isopropylidene-cyclohexa-2,5-dienone 
• 5427-03-2 2,6-di-tert-butyl-4-isopropylphenol 

Downstream Products

• 116376-83-1 (E)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(3-thienyl)-2-propen-1-one 
• 154052-79-6 5-[1-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethylidene]-2-thioxo-4-thiazolidinone 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 81056-30-6 1-(7-tert-Butyl-2-methyl-5-benzoxazolyl)ethanon 
• 19263-37-7 2,6-di-t-butyl-4-i-propenylphenol 
• 135040-16-3 1,3-bis-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propenone 
• 728-39-2 4-hydroxy-3,5-di-tert-butyl-α-methylbenzylamine 
• 797035-86-0 (E/Z)-2-(4-chlorobenzenesulfonyl)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)but-2-enenitrile 
• 157397-08-5 2-[1-(3,5-Di-Tert-Butyl-4-Hydroxy-Phenyl)-Ethylidene]-Malononitrile 
• 1361383-65-4 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-N,2-dimethylpyrimidine-5-carboxamide 
• 1361383-64-3 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methoxy-N-methylpyrimidine-5-carboxamide 

Relevant academic research and scientific papers

Antioxidant building blocks I. The unexpected C-acetylation of 2,6-Di-tert-butylphenol with isopropenyl acetate

While the reaction of some 2-substituted and 2,6-disubstituted phenols with isopropenyl acetate resulted in the corresponding phenol acetates, in the reaction of 2,6-di-tert-butylphenol, a useful starting material of antioxidant building blocks, under the same conditions 4-acetyl-2,6-di-tert-butylphenol was the only product.

Synthesis, redox properties and antibacterial activity of hindered phenols linked to heterocycles

A series of benzotriazole, cyclic amides and pyrimidine derivatives, containing 2,6-di-tert-butyl-phenol fragments, were synthesized. The redox properties of obtained compounds were studied using the cyclic voltammetry on a platinum electrode in acetonitrile. The oxidation potentials of all substances were comparable to those of BHT. The obtained compounds were tested for their antibacterial activity, and N-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl)isatin (32 μg/mL) exerted good activity against Staphylococcus aureus.

Synthesis and evaluation of dithiolethiones as novel cyclooxygenase inhibitors

3H-1,2-Dithiole-3-thiones substituted with a 3,5-di-tert-butyl-4-hydroxyphenyl (DTBHP) or a 3,5-di-tert-butyl-4-methoxyphenyl group at the C5 position were prepared and their ability to inhibit the cyclooxygenase isoenzymes, COX-1 and COX-2 was evaluated. Both compounds were potent inhibitors of COX-2 (relative to rofecoxib), and while the phenol was a weak inhibitor of COX-1, the methyl ether gave no measurable inhibition. Docking studies of the two compounds into the COX-1 and -2 active sites showed that the methyl ether could only fit in the COX-2 active site whereas the phenol could be docked into both COX-1 and -2. This study reports a new mode for inhibitor binding to COX-1 and -2 and a novel structural scaffold for the development of COX-2 selective inhibitors.

DITHIOLE COMPOUNDS AS COX INHIBITORS

A compound of formula (I) wherein: R1 and R2 are the same or different and are independently selected from H and a shielding group; X and Y are each independently selected from N and CH; R3 is hydroxy, alkoxy, acyloxy or a

Synthesis and biological evaluation of acyclic triaryl (Z)-olefins possessing a 3,5-di-tert-butyl-4-hydroxyphenyl pharmacophore: Dual inhibitors of cyclooxygenases and lipoxygenases

A new class of regioisomeric acyclic triaryl (Z)-olefins possessing a 3,5-di-tert-butyl-4-hydroxyphenyl (DTBHP) 5-lipoxygenase (5-LOX) pharmacophore that is vicinal to a para-methanesulfonylphenyl cyclooxygenase-2 (COX-2) pharmacophore were designed for evaluation as selective COX-2 and/or 5-LOX inhibitors. The target compounds were synthesized via a highly stereoselective McMurry olefination cross-coupling reaction. This key synthetic step afforded a (Z):(E) olefinic mixture with a predominance for the (Z)-olefin stereoisomer. Structure-activity studies for the (Z)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(4-methanesulfonylphenyl)-1-phenylalk-1-ene regioisomers showed that COX-1 inhibition decreased, COX-2 inhibition increased, and the COX-2 selectivity index (SI) increased as the chain length of the alkyl substituent attached to the olefinic double bond was increased (Et → n-butyl → n-heptyl). In this group of compounds, inhibition of both 5-LOX and 15-LOX was dependent upon the length of the alkyl substituent with the hex-1-ene compound 9c having a n-butyl substituent exhibiting potent inhibition of both 5-LOX (IC50 = 0.3 μM) and 15-LOX (IC50 = 0.8 μM) relative to the inactive (IC50 > 10 μM) Et and n-heptyl analogs. Compound 9c is of particular interest since it also exhibits a dual inhibitory activity against the COX (COX-1 IC50 = 3.0 μM, and COX-2 IC50 = 0.36 μM, COX-2 SI = 8.3) isozymes. A comparison of the relative inhibitory activities of the two groups of regioisomers investigated shows that the regioisomers in which the alkyl substituent is attached to the same olefinic carbon atom (C-2) as the para-methanesulfonylphenyl moiety generally exhibit a greater potency with respect to COX-2 inhibition. The 4-hydroxy substituent in the 3,5-di-tert-butyl-4-hydroxyphenyl moiety is essential for COX and LOX inhibition since 3,5-di-tert-butyl-4-acetoxyphenyl derivatives were inactive inhibitors. These structure-activity data indicate acyclic triaryl (Z)-olefins constitute a suitable template for the design of dual COX-2/LOX inhibitors.

Retinoic acid receptor antagonist compounds and methods

Trienoic compounds having activity as antagonists for retinoic acid receptors are provided. Also provided are pharmaceutical compositions incorporating such compounds and methods for their therapeutic use.

Synthesis and Electrochemical Characteristics of 1-(3,5-Di-tert-butyl-4-hydroxyphenyl)alkyl(aryl)ketones and Radicals Obtained Therefrom

1-(3,5-Di-tert-butyl-4-hydroxyphenyl)alkyl(aryl) ketones were prepared by treating 2,6-di-tert-butylphenol with aliphatic acids anhydrides and aroyl chlorides. The products were characterized with IR and 1H NMR spectra. Electrochemical reductio

Pharmaceutically active bicyclic-heterocyclic amines

The pharmaceutically active bicyclic heterocyclic amines (XXX) STR1 where W1 is --N= or --CH=; W3 is --N= or --CH=; W5 is --N= or --CR5 -- with the proviso that W5 is --CR5 -- when both W1 and W3 are --N= which are useful as pharmaceuticals in treating mild and/or moderate to severe head injury, subarachnoid hemorrhage and subsequent ischemic stroke, asthma and reduction of mucous formation/secretion in the lung and other diseases and injuries.

Functionalized tris(hydroxyphenyl) compounds

Compounds useful as polymer stabilizers which are polymerizable into condensation polymer systems are disclosed and claimed. A particularly preferred embodiment is 1-(3'-(benzotriazol-2"-yl)-4'-hydroxyphenyl)-1,1-bis(4-hydroxyphenyl)ethane.

Aryl-substituted rhodanine derivatives

Provided are certain aryl-substituted rhodanine derivatives, treatment methods and pharmaceutical formulations thereof.