1611-03-6

Basic information

• Product Name: 3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID
• Synonyms: (3,5-DI-T-BUTYL-4-HYDROXYPHENYL)ACETIC ACID;3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID;2-[3,5-DI(TERT-BUTYL)-4-HYDROXYPHENYL]ACETIC ACID;RARECHEM AL BO 0768
• CAS NO: 1611-03-6
• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.36
• Product Categories: Aromatic Phenylacetic Acids and Derivatives
• Mol File: 1611-03-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 157 °C
• Boiling Point: 348.9°Cat760mmHg
• Flash Point: 179°C
• Appearance: /
• Density: 1.063g/cm³
• Vapor Pressure: 1.83E-05mmHg at 25°C
• PKA: 4.51±0.10(Predicted)
• CAS DataBase Reference: 3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID(1611-03-6)
• EPA Substance Registry System: 3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID(1611-03-6)

Safety Data

• Hazardous Substances Data: 1611-03-6(Hazardous Substances Data)

Usage

General Description

3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID is a chemical compound with the molecular formula C20H30O3. It is a synthetic antioxidant commonly used in the food industry to prevent the oxidation of fats and oils, thus extending the shelf life of food products. 3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID is also used in the production of plastics, rubber, and other industrial materials to prevent degradation caused by oxidation. Additionally, 3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID is also used in the pharmaceutical industry for its potential anti-inflammatory and antioxidant properties. It is a white powder with a melting point of 140-142°C and is considered relatively safe for use in various applications.

InChI:InChI=1/C16H24O3/c1-15(2,3)11-7-10(9-13(17)18)8-12(14(11)19)16(4,5)6/h7-8,19H,9H2,1-6H3,(H,17,18)/p-1

Upstream product

• 124-38-9 carbon dioxide 
• 955-01-1 3,5-di-tert-butyl-4-hydroxy benzyl chloride 
• 156-38-7 4-hydroxyphenylacetate 
• 540-88-5 acetic acid tert-butyl ester 
• 2091-51-2 4-(bromomethyl)-2,6-di-tert-butylphenol 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 28441-16-9 (3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl acetate 
• 1611-07-0 3,5-Di-tert-butyl-4-hydroxyphenylacetonitrile 

Downstream Products

• 54117-97-4 3,5-di-tert-butyl-4-hydroxyphenylacetic acid tert-butyl ester 
• 183721-39-3 N,N-Diethyl-2-(3,5-di-tert-butyl-4-hydroxyphenyl)acetamide 
• 6386-40-9 ethyl 4-hydroxy-3,5-di-tert-butylphenylacetate 
• 161787-69-5 4-({[(4-chlorophenyl)sulfonyl]amino}carbonyl)benzoyl-N-ε-[(4-hydroxy-3,5-di-tert-butylphenyl)acetyl]-Lys-OH 
• 190833-96-6 ethyl 4-[({[4-chloro-3-({[(4-hydroxy-3,5-di-tert-butylphenyl)acetyl]amino}sulfonyl)phenyl]carbonyl}amino)sulfonyl]benzoate 
• 161787-52-6 4-[({[4-chloro-3-({[(4-hydroxy-3,5-di-tert-butylphenyl)acetyl]amino}sulfonyl)phenyl]carbonyl}amino)sulfonyl]benzoic acid 
• 190833-93-3 3-({[(4-hydroxy-3,5-di-tert-butylphenyl)acetyl]amino}sulfonyl)-4-chlorobenzoic acid 
• 161787-49-1 4-({[(4-hydroxy-3,5-di-tert-butylphenyl)acetyl]amino}sulfonyl)benzoic acid 
• 65559-25-3 methyl 2-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetate 
• 3673-68-5 2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol 
• 3673-72-1 1-bromo-2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethane 
• 666251-23-6 (cyclohexylmethyl-amino)-(3,5-di-tert-butyl-4-hydroxy-phenyl)-acetic acid tert-butyl ester 

Relevant articles and documents

Mechanism of photosolvolytic rearrangement of p-hydroxyphenacyl esters: Evidence for excited-state intramolecular proton transfer as the primary photochemical step

The photosolvolytic rearrangement of a variety of p-hydroxyphenacyl esters and related compounds 7-16 has been studied in solutions with up to 50% aqueous content, using product studies, triplet quenchers, and nanosecond laser flash photolysis. The p-hydroxyphenacyl moiety has recently been proposed as a new and efficient photoactivated protecting group in aqueous solution. Practical applications have been demonstrated, but much less is known about the mechanism of photoreaction. Our data support a novel mechanism in which the primary photochemical step from the singlet excited state is formal intramolecular proton transfer from the phenolic proton to the carbonyl oxygen of the distal ketone, mediated by solvent water, to generate the corresponding p-quinone methide phototautomer. This reactive intermediate (most likely in its excited state) subsequently expels the carboxylic acid with concerted rearrangement to a spiroketone intermediate, which subsequently leads to the final observed product, p- hydroxyphenylacetic acid. An alternative mechanism is deprotonation of the phenolic proton, loss of the carboxylate, and rearrangement to the spiroketone, all in one concerted primary photochemical step from S1.