3,5-Di-tert-butyl-1,2-benzoquinone (DTBQ) is a bright orange organic compound that serves as a versatile reagent in organic chemistry. Its synthesis typically involves the oxidation of 3,5-di-tert-butylcatechol. DTBQ is known for its ability to act as a dienophile in Diels-Alder reactions, yielding substituted quinones. It also finds application in organic synthesis as an oxidizing agent, particularly for the oxidation of alcohols and phenols. The tert-butyl groups on the molecule contribute to its stability and solubility in organic solvents. Research on DTBQ focuses on its reactivity in various synthetic transformations, its role in organic reactions, and its potential for new applications in organic synthesis.'
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| ID Source | ID |
|---|---|
| PubMed CID | 76915 |
| CHEMBL ID | 365161 |
| SCHEMBL ID | 396841 |
| MeSH ID | M0153776 |
| Synonym |
|---|
| HMS2618F24 |
| 3,5-di-t-butyl-o-benzoquinone |
| einecs 222-189-0 |
| nsc 149061 |
| 3,5-di-tert-butyl-o-benzoquinone |
| o-benzoquinone, 3,5-di-tert-butyl- |
| bdbm22775 |
| 3,5-di-tert-butylcyclohexa-3,5-diene-1,2-dione |
| cid_76915 |
| 3,5-ditert-butylbenzo-1,2-quinone |
| AH-188/25003063 |
| 3,5-di-tert-butylbenzo-1,2-quinone |
| inchi=1/c14h20o2/c1-13(2,3)9-7-10(14(4,5)6)12(16)11(15)8-9/h7-8h,1-6h |
| 3,5-cyclohexadiene-1,2-dione, 3,5-bis(1,1-dimethylethyl)- |
| MLS000699499 |
| smr000226412 |
| 3,2-dione, 3,5-bis(1,1-dimethylethyl)- |
| nsc-149061 |
| 3383-21-9 |
| o-benzoquinone,5-di-tert-butyl- |
| nsc149061 |
| 3,5-di-tert-butyl-o-benzoquinone, 98% |
| 3,5-ditert-butyl-quinone |
| CHEMBL365161 |
| D2430 |
| 3,5-di-tert-butyl-1,2-benzoquinone |
| 3,5-ditert-butylcyclohexa-3,5-diene-1,2-dione |
| AKOS001667084 |
| NCGC00247199-01 |
| 3,5-ditert-butyl-[1,2]benzoquinone |
| FT-0614738 |
| 3,5-di(tert-butyl)benzo-1,2-quinone |
| 3,5-di-t-butyl-1,2-benzoquinone |
| 3,5-di-t-butyl-1,2-dioxobenzene |
| 3,5-di-tert-butyl-o-quinone |
| 3,5-di-tert-butyl-ortho-benzoquinone |
| 3,5-ditert-butylbenzo-1,2-quinone # |
| SCHEMBL396841 |
| mfcd00001647 |
| J-511242 |
| DTXSID70187478 |
| AS-60966 |
| D86498 |
| PD181128 |
| CS-0095759 |
| SY049535 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Putative fructose-1,6-bisphosphate aldolase | Giardia intestinalis | Potency | 7.0627 | 0.1409 | 11.1940 | 39.8107 | AID2451 |
| Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 17.7828 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 7.5686 | 0.0072 | 15.7588 | 89.3584 | AID588342 |
| Nrf2 | Homo sapiens (human) | Potency | 12.5893 | 0.0920 | 8.2222 | 23.1093 | AID624171 |
| glp-1 receptor, partial | Homo sapiens (human) | Potency | 12.5893 | 0.0184 | 6.8060 | 14.1254 | AID624417 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 1.1220 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| ATAD5 protein, partial | Homo sapiens (human) | Potency | 20.5962 | 0.0041 | 10.8903 | 31.5287 | AID504467 |
| GLS protein | Homo sapiens (human) | Potency | 5.6234 | 0.3548 | 7.9355 | 39.8107 | AID624170 |
| TDP1 protein | Homo sapiens (human) | Potency | 0.9754 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 35.4813 | 0.1800 | 13.5574 | 39.8107 | AID1460; AID1468 |
| thioredoxin glutathione reductase | Schistosoma mansoni | Potency | 19.9526 | 0.1000 | 22.9075 | 100.0000 | AID485364 |
| Smad3 | Homo sapiens (human) | Potency | 15.8489 | 0.0052 | 7.8098 | 29.0929 | AID588855 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 2.8184 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| hypothetical protein, conserved | Trypanosoma brucei | Potency | 8.9125 | 0.2239 | 11.2451 | 35.4813 | AID624173 |
| bromodomain adjacent to zinc finger domain 2B | Homo sapiens (human) | Potency | 28.1838 | 0.7079 | 36.9043 | 89.1251 | AID504333 |
| pyruvate kinase | Leishmania mexicana mexicana | Potency | 14.1254 | 0.3981 | 13.7447 | 31.6228 | AID1721; AID1722 |
| IDH1 | Homo sapiens (human) | Potency | 29.0929 | 0.0052 | 10.8652 | 35.4813 | AID686970 |
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 1.5849 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| serine-protein kinase ATM isoform a | Homo sapiens (human) | Potency | 6.3096 | 0.7079 | 25.1119 | 41.2351 | AID485349 |
| 15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1 | Homo sapiens (human) | Potency | 3.9811 | 0.0018 | 15.6638 | 39.8107 | AID894 |
| vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 39.8107 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
| chromobox protein homolog 1 | Homo sapiens (human) | Potency | 19.9526 | 0.0060 | 26.1688 | 89.1251 | AID540317 |
| nuclear factor erythroid 2-related factor 2 isoform 2 | Homo sapiens (human) | Potency | 23.1093 | 0.0041 | 9.9848 | 25.9290 | AID504444 |
| parathyroid hormone/parathyroid hormone-related peptide receptor precursor | Homo sapiens (human) | Potency | 10.0000 | 3.5481 | 19.5427 | 44.6684 | AID743266 |
| pyruvate kinase PKM isoform a | Homo sapiens (human) | Potency | 1.4125 | 0.0401 | 7.4590 | 31.6228 | AID1631; AID1634 |
| flap endonuclease 1 | Homo sapiens (human) | Potency | 70.7946 | 0.1337 | 25.4129 | 89.1251 | AID588795 |
| serine/threonine-protein kinase PLK1 | Homo sapiens (human) | Potency | 3.7686 | 0.1683 | 16.4040 | 67.0158 | AID720504 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 11.2947 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
| geminin | Homo sapiens (human) | Potency | 20.7329 | 0.0046 | 11.3741 | 33.4983 | AID624296; AID624297 |
| histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 25.1189 | 0.2512 | 15.8432 | 39.8107 | AID504327 |
| neuropeptide S receptor isoform A | Homo sapiens (human) | Potency | 12.5893 | 0.0158 | 12.3113 | 615.5000 | AID1461 |
| Glycoprotein hormones alpha chain | Homo sapiens (human) | Potency | 1.2589 | 4.4668 | 8.3448 | 10.0000 | AID624291 |
| Endothelin receptor type B | Rattus norvegicus (Norway rat) | Potency | 14.1254 | 0.5623 | 15.1609 | 31.6228 | AID1721 |
| Endothelin-1 receptor | Rattus norvegicus (Norway rat) | Potency | 14.1254 | 0.5623 | 15.1609 | 31.6228 | AID1721 |
| ATP-dependent phosphofructokinase | Trypanosoma brucei brucei TREU927 | Potency | 3.7933 | 0.0601 | 10.7453 | 37.9330 | AID485367 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| MPI protein | Homo sapiens (human) | IC50 (µMol) | 9.8436 | 0.1900 | 13.8256 | 50.1000 | AID1220 |
| selectin E | Homo sapiens (human) | IC50 (µMol) | 10.0000 | 2.0900 | 3.6767 | 6.1900 | AID1288 |
| Cocaine esterase | Homo sapiens (human) | Ki | 1.3500 | 0.0063 | 0.9835 | 8.0000 | AID239272 |
| Coagulation factor XII | Homo sapiens (human) | Ki | 40.4349 | 0.0025 | 1.8669 | 7.2500 | AID1798224 |
| Cholinesterase | Homo sapiens (human) | Ki | 50.3624 | 0.0000 | 1.5173 | 9.7300 | AID1798224; AID239166 |
| Liver carboxylesterase 1 | Oryctolagus cuniculus (rabbit) | Ki | 33.8184 | 0.0136 | 1.7025 | 7.2500 | AID1798224; AID239167 |
| Acetylcholinesterase | Homo sapiens (human) | Ki | 50.3624 | 0.0000 | 1.2786 | 9.7300 | AID1798224; AID239122 |
| Liver carboxylesterase 1 | Homo sapiens (human) | Ki | 33.7105 | 0.0025 | 2.0136 | 8.4800 | AID1798224; AID239197 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID239166 | Inhibition constant against human Butyrylcholinesterase (hBuChE) using butyrylthiocholine (BuTCh) as substrate | 2005 | Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8 | Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. |
| AID239167 | Inhibition constant against rabbit liver carboxylesterase (rCE) using nitrophenyl acetate (o-NPA) as substrate | 2005 | Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8 | Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. |
| AID239197 | Inhibition constant against human liver carboxylesterase 1 (hCE1) using nitrophenyl acetate (o-NPA) as substrate | 2005 | Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8 | Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. |
| AID239272 | Inhibition constant against human intestinal carboxylesterase 2 (hiCE) using nitrophenyl acetate (o-NPA) as substrate | 2005 | Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8 | Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. |
| AID239122 | Inhibition constant against human Acetylcholinesterase (hAcChE) using acetylthiocholine (AcTCh) as substrate | 2005 | Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8 | Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. |
| AID1798224 | Enzyme Inhibition Assay from Article 10.1021/jm049011j: \\Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases.\\ | 2005 | Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8 | Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. |
| [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 (7.69) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 6 (46.15) | 29.6817 |
| 2010's | 5 (38.46) | 24.3611 |
| 2020's | 1 (7.69) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (18.97) 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 | 14 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||