2,5-di-tert-butyl-4-hydroxyanisole, also known as butylated hydroxyanisole (BHA), is a synthetic antioxidant commonly used as a food additive to prevent rancidity. It is produced through a complex multi-step synthesis involving the alkylation of 4-methoxyphenol (hydroquinone monomethyl ether) with tert-butyl alcohol in the presence of a strong acid catalyst. BHA is widely studied for its antioxidant properties, which are attributed to its ability to donate a hydrogen atom to free radicals, thereby inhibiting lipid oxidation. Its effectiveness in preserving the freshness and extending the shelf life of foods makes it a valuable ingredient in a wide range of products, including fats, oils, cereals, and baked goods. However, concerns regarding its potential carcinogenicity have led to ongoing research and debates about its safety. Despite its controversial nature, BHA remains a widely used food additive, subject to strict regulatory control and monitoring.'
2,5-di-tert-butyl-4-hydroxyanisole: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 74812 |
| CHEMBL ID | 1600347 |
| CHEBI ID | 94135 |
| SCHEMBL ID | 39215 |
| MeSH ID | M0148034 |
| Synonym |
|---|
| 1991-52-2 |
| unii-593e9t2mwh |
| 593e9t2mwh , |
| inchi=1/c15h24o2/c1-14(2,3)10-9-13(17-7)11(8-12(10)16)15(4,5)6/h8-9,16h,1-7h |
| 2,5-di-tert-butyl-4-methoxyphenol, 97% |
| NCGC00095205-01 |
| SPECTRUM1505039 |
| 2,5-di-tert-butyl-4-methoxyphenol |
| einecs 217-873-0 |
| 2,5-di-tert-butyl-4-hydroxyanisole |
| ccris 5220 |
| 2,5-ditert-butyl-4-methoxyphenol |
| HMS1922N14 |
| AKOS005258340 |
| CHEMBL1600347 |
| GEO-01261 |
| phenol,2,5-bis(1,1-dimethylethyl)-4-methoxy- |
| phenol, 2,5-di-tert-butyl-4-methoxy- |
| phenol, 2,5-bis(1,1-dimethylethyl)-4-methoxy- |
| BRD-K88329126-001-01-0 |
| SCHEMBL39215 |
| 2,5-di-t-butyl-4-methoxyphenol |
| FLLRQABPKFCXSO-UHFFFAOYSA-N |
| 2,5-di-tert.-butyl-4-hydroxyanisole |
| 2,5-di-tert-butyl4-hydroxyanisole |
| J-660047 |
| W-200202 |
| 2,5-di-t-butyl-4-hydroxyanisole |
| DTXSID50173692 |
| mfcd00274238 |
| CHEBI:94135 |
| AS-66825 |
| BCP24015 |
| Q27165883 |
| 2,5-di-tert-butyl-4-methoxy-1-phenol |
| STARBLD0019187 |
| CS-0328386 |
| PD000638 |
| Class | Description |
|---|---|
| phenols | Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring. |
| methoxybenzenes | Any aromatic ether that consists of a benzene skeleton substituted with one or more methoxy groups. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 446.6840 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| 15-lipoxygenase, partial | Homo sapiens (human) | Potency | 25.1189 | 0.0126 | 10.6917 | 88.5700 | AID887 |
| USP1 protein, partial | Homo sapiens (human) | Potency | 28.1838 | 0.0316 | 37.5844 | 354.8130 | AID504865 |
| TDP1 protein | Homo sapiens (human) | Potency | 13.7782 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| 67.9K protein | Vaccinia virus | Potency | 18.2563 | 0.0001 | 8.4406 | 100.0000 | AID720579; AID720580 |
| heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa) | Homo sapiens (human) | Potency | 15.8489 | 0.0165 | 25.3078 | 41.3999 | AID602332 |
| cellular tumor antigen p53 isoform a | Homo sapiens (human) | Potency | 25.7877 | 0.3162 | 12.4435 | 31.6228 | AID902; AID924 |
| 15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1 | Homo sapiens (human) | Potency | 3.9811 | 0.0018 | 15.6638 | 39.8107 | AID894 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 35.4813 | 0.0079 | 8.2332 | 1,122.0200 | AID2546 |
| DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 5.0119 | 0.0316 | 22.3146 | 100.0000 | AID588579 |
| cytochrome P450 3A4 isoform 1 | Homo sapiens (human) | Potency | 12.5893 | 0.0316 | 10.2792 | 39.8107 | AID884; AID885 |
| histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 17.7828 | 0.2512 | 15.8432 | 39.8107 | AID504327 |
| lamin isoform A-delta10 | Homo sapiens (human) | Potency | 22.3872 | 0.8913 | 12.0676 | 28.1838 | AID1487 |
| Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Integrin beta-3 | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 11.4157 | 31.6228 | AID924 |
| Integrin alpha-IIb | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 11.4157 | 31.6228 | AID924 |
| Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| GABA theta subunit | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | Potency | 12.5893 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID602812 | Inhibition of Sarcoplasmic/endoplasmic reticulum calcium ATPase in rabbit hind leg tissue microsomes assessed as rate of NADH oxidation coupled to SERCA-catalyzed ATP hydrolysis by spectroscopic assay | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Discovery of novel SERCA inhibitors by virtual screening of a large compound library. |
| AID602814 | Inhibition of Sarcoplasmic/endoplasmic reticulum calcium ATPase in rabbit hind leg tissue microsomes assessed as inorganic phosphate release by malachite green dye based chromogenic assay | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Discovery of novel SERCA inhibitors by virtual screening of a large compound library. |
| AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
| AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (16.67) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 2 (33.33) | 29.6817 |
| 2010's | 3 (50.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (12.85) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 6 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||