14035-34-8

Basic information

• Product Name: 1-Propanone, 1-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-
• CAS NO: 14035-34-8
• Molecular Formula: C17H26O2
• Molecular Weight: 262.392
• Mol File: 14035-34-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1-Propanone, 1-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 1-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-(14035-34-8)
• EPA Substance Registry System: 1-Propanone, 1-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-(14035-34-8)

Safety Data

• Hazardous Substances Data: 14035-34-8(Hazardous Substances Data)

Usage

+ Antioxidant

Prevents rancidity and preserves the shelf life of products.

+ Used in food industry

To prevent oxidative damage in food products.

+ Used in personal care products

As an antioxidant and preservative.

+ Used as a stabilizer

In plastics and rubber to prevent oxidative degradation.

+ Inhibits free radicals

Protects cells and tissues from oxidative damage.

+ Safe for use in small amounts

In food and cosmetics, but its safety at higher doses is debated.

+ 1-Propanone

A ketone functional group that provides the molecule with its solvent and flavor properties.

+ 1-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]

A substituted phenol group that provides the molecule with its antioxidant properties. The hydroxyl group (-OH) is responsible for its antioxidant activity, while the two tert-butyl groups (-C(CH3)3) provide stability and lipophilicity.

Upstream product

• 4973-24-4 2,6-di-tert-butyl-4-propyllphenol 
• 67-56-1 methanol 
• 17540-78-2 4-(1-methoxypropyl)-2,6-di-t-butylphenol 
• 75697-72-2 4-bromo-4-(1-hydroxypropyl)-2,6-di-t-butylcyclohexa-2,5-dienone 
• 20017-35-0 1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-propanol 
• 108-24-7 acetic anhydride 
• 77469-01-3 5,7-di-t-butyl-2-ethyl-1-oxaspiro<2.5>octa-4,7-dien-6-one 
• 108-95-2 phenol 
• 128-39-2 2,6-di-tert-butylphenol 
• 123-62-6 propionic acid anhydride 
• 79-03-8 propionyl chloride 
• 645-56-7 4-n-Propylphenol 

Downstream Products

• 17055-13-9 4-(2-bromopropionyl)-2,6-di-tert-butylphenol 
• 40662-90-6 1-(3,5-Di-tert-butyl-4-methoxy-phenyl)-propan-1-ol 
• 842-42-2 1-(3,5-di-tert-butyl-4-hydroxyphenyl)propylamine 
• 96672-45-6 3,4-bis<3,5-di(tert-butyl)-4-hydroxyphenyl>hexane 
• 141075-84-5 3,4-bis<3,5-di(tert-butyl)-4-hydroxyphenyl>hexane-2,4-diene 
• 40662-88-2 1-(3,5-Di-tert-butyl-4-methoxy-phenyl)-propan-1-one 
• 88408-50-8 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methylisoxazole 
• 77469-05-7 4-acetoxy-3,5-di-t-butylpropiophenone 
• 141075-83-4 3,4-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-3,4-hexanediol 
• 20017-35-0 1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-propanol 

Relevant articles and documents

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.

Formation of Diphenyl Ethers from Cyclohexa-2,5-dienones via 4-phenoxy-4-(1-alkoxy)cyclohexa-2,5-dienones as Probable Intermediates

Acid-catalysed reactions of the cyclohexa-2,5-dienones (3) and (14) with phenol afford diphenyl ethers.Quinol ethers are considered to be intermediates in these reactions, with aromatisation of the cyclohexa-2,5-dienone ring by loss of the 4-(1-alkoxy) side-chain as an aldehyde constituting the driving force.

The Cleavage of the 4-(1-Hydroxyalkyl) Side-Chain from a Cyclohexa-2,5-dienone. A Model Reaction for the Biodegradation of Lignin

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