Some unusual oxidation products of 2,6-di-tert-butyl-4-methylphenol

Benjamin, Ben M.; Raaen, Vernon F.; Hagaman, Edward W.; Brown, Lloyd L.

doi:10.1021/jo00409a011

Cited by 25 publications

(15 citation statements)

References 2 publications

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“…Although structures of the alteration products remain unidentified, it appears that the products are less polar than their corresponding parent antioxidants, as indicated by their elution sequence from the silica column. As shown by various model studies (12)(13)(14), autoxidation of phenolic compounds or their oxidation by other reagents produced compounds of quinone or epoxide nature. Monte and Maga (15) have demonstrated the formation of BHA dimers in water under stresses of sterilization.…”

Section: Discussionmentioning

confidence: 99%

Alteration of phenolic antioxidants in heated vegetable oil

Lin

Warner

Fazio

1981

J Americ Oil Chem Soc

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Studies were conducted to follow the fate of antioxidant~ in heated vegetable oll at temperatures approximating those of frying cond/-don~ Samples of vegetable oils spiked with 0.02% [ t'Cl BHA or 0.02% [t4CI TBHQ were heated at ca. 180-190 C for 4.5 hr. It was found thXt 24 and 48% of the radioactivity added as BHA and TBHO. respectively, remained in the oils. Normal-phase HPLC analyses revealed that 55% of the radiolabe[ in the heated BHA-oil and 95% in the heated TBHQ-oil were not eluted as parent substances. The as-yet unidentified alteration products in the heated oil appear to be less polar than the added antioxidants. ABBREVIATIONSBHA, 2-or 3-t-butylhydroxyanisole; BHT, 2,6-di-t-butylhydroxytoluene; TBHQ, t-butylhydroquinone; HPLC, high pressure liquid chromatography.

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Section: Discussionmentioning

confidence: 99%

Alteration of phenolic antioxidants in heated vegetable oil

Lin

Warner

Fazio

1981

J Americ Oil Chem Soc

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“…The oxidation of BHT by potassium permanganate has also been investigated, and has been found to lead to the formation of BHT-Q and several other unusual products, such as BHT-dimer. 57 The oxidation of BHT by bromine can generate BHT-CHO, 2,6-di-tert-butyl-4-methyl-4-methoxy-2,5cyclohexadienone, and 3,5-di-tert-butyl-4-hydroxybenzyl acetate, with 2,6-di-tert-butyl-4-bromo-4-methyl-2,5-cyclohexadienone as an intermediate. 58 The ozone microbubble technique was demonstrated to oxidize BHT more efficiently than the conventional ozone technique due to improved ozone gas transfer.…”

Section: Environmental Behavior Of Spasmentioning

confidence: 99%

Synthetic Phenolic Antioxidants: A Review of Environmental Occurrence, Fate, Human Exposure, and Toxicity

Liu

Mabury

2020

Environ. Sci. Technol.

203

148

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Synthetic phenolic antioxidants (SPAs) are widely used in various industrial and commercial products to retard oxidative reactions and lengthen product shelf life. In recent years, numerous studies have been conducted on the environmental occurrence, human exposure, and toxicity of SPAs. Here, we summarize the current understanding of these issues and provide recommendations for future research directions. SPAs have been detected in various environmental matrices including indoor dust, outdoor air particulates, sea sediment, and river water. Recent studies have also observed the occurrence of SPAs, such as 2,6-ditert-butyl-4-methylphenol (BHT) and 2,4-di-tert-butyl-phenol (DBP), in humans (fat tissues, serum, urine, breast milk, and fingernails). In addition to these parent compounds, some transformation products have also been detected both in the environment and in humans. Human exposure pathways include food intake, dust ingestion, and use of personal care products. For breastfeeding infants, breast milk may be an important exposure pathway. Toxicity studies suggest some SPAs may cause hepatic toxicity, have endocrine disrupting effects, or even be carcinogenic. The toxicity effects of some transformation products are likely worse than those of the parent compound. For example, 2,6-di-tertbutyl-p-benzoquinone (BHT-Q) can cause DNA damage at low concentrations. Future studies should investigate the contamination and environmental behaviors of novel high molecular weight SPAs, toxicity effects of coexposure to several SPAs, and toxicity effects on infants. Future studies should also develop novel SPAs with low toxicity and low migration ability, decreasing the potential for environmental pollution.

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“…In addition, a crystalline product was obtained in 16% yield, which proved to be 4-(4-hydroxybenzyl)cyclohexadienone 5. In spite of a number of studies on the oxidation of 3, 5 has seldom been obtained (13,14), and the formation of this phenolic product in low yields has received only limited attention. The decay of 2 by use of la was similarly undertaken in other solvents inert to 4 ( Table 1).…”

Section: Resultsmentioning

confidence: 99%