Page last updated: 2024-12-07

2,6-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

This compound, also known as DTBP-hydroperoxide, is a key intermediate in the autoxidation of 2,6-di-tert-butyl-4-methylphenol (BHT), a widely used antioxidant. Its formation occurs via a free radical chain reaction involving the abstraction of a hydrogen atom from the phenolic hydroxyl group of BHT by reactive oxygen species. The resulting phenoxyl radical then reacts with oxygen to form the hydroperoxide. DTBP-hydroperoxide is a highly reactive species that can decompose to form radicals, contributing to the propagation of the autoxidation chain. Its presence in the autoxidation process is crucial for understanding the mechanism of BHT's antioxidant activity and its efficacy in various applications. The study of DTBP-hydroperoxide is important for understanding the chemical kinetics and mechanisms of autoxidation, as well as for developing new and improved antioxidants. It also provides valuable insights into the role of free radicals in various chemical reactions and biological processes.'

2,6-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone: a butylated hydroxytoluene hydroperoxide; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID114687
SCHEMBL ID8965707
MeSH IDM0134697

Synonyms (22)

Synonym
2,6-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadien-1-one
2,5-cyclohexadien-1-one, 2,6-di-tert-butyl-4-hydroperoxy-4-methyl-
2,6-di-t-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone
brn 2053915
2,6-di-tert-butyl-4-hydroperoxyl-2,5-cylohexadienone
2,6-di-tert-butyl-4-hydroperoxyl-4-methyl-2,5-cyclohexadienone
2,6-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone
bht-ooh
ccris 3709
2,6-di-tert-butyl-4-hydroperoxy-4-methylcyclohexa-2,5-dien-1-one
6485-57-0
hk05u8x26d ,
unii-hk05u8x26d
4-08-00-00143 (beilstein handbook reference)
4-methyl-4-hydroperoxy-2,6-di-tert-butyl-2,5-cyclohexadienone
4-hydroperoxy-4-methyl-2,6-di-tert-butyl-2,5-cyclohexadienone
2,5-cyclohexadien-1-one, 2,6-bis(1,1-dimethylethyl)-4-hydroperoxy-4-methyl-
hydroperoxide, 3,5-di-tert-butyl-1-methyl-4-oxo-2,5-cyclohexadien-1-yl
SCHEMBL8965707
FNLSGYWVCGOYGD-UHFFFAOYSA-N
DTXSID20215139
Q27279960

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The toxicity of BHTOOH was potentiated by glutathione depletion and inhibited by thiol compounds, indicating that BHTOOH is activated to a thiol-reactive, toxic intermediate."( Role of quinone methide in the in vitro toxicity of the skin tumor promoter butylated hydroxytoluene hydroperoxide.
Guyton, KZ; Kensler, TW; Thompson, JA,
)
0.13

Bioavailability

ExcerptReferenceRelevance
" To examine the bioavailability of membrane iron, we admixed membranes and t-butylhydroperoxide and found that sickle membranes show a tenfold greater peroxidation response than do normal membranes."( Nonheme iron in sickle erythrocyte membranes: association with phospholipids and potential role in lipid peroxidation.
Hebbel, RP; Kuross, SA, 1988
)
0.27

Dosage Studied

ExcerptRelevanceReference
" A similar dose-response relationship for papilloma and carcinoma formation was observed when BHTOOH was applied twice weekly for 50 weeks to mice previously initiated with 7,12-dimethylbenz[a]anthracene."( Tumor promotion by a hydroperoxide metabolite of butylated hydroxytoluene, 2,6-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone, in mouse skin.
Kensler, TW; Taffe, BG, 1988
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (45.45)18.7374
1990's4 (36.36)18.2507
2000's1 (9.09)29.6817
2010's1 (9.09)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.76

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.76 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]