2-tert-Butyl-1,4-benzoquinone
Based on 1 Customer Validation
2-tert-Butyl-1,4-benzoquinone is a food additive oxidant, an electrophilic metabolite of Butylated hydroxyanisole (HY-B1066), and an antibacterial agent. 2-tert-Butyl-1,4-benzoquinone reduces virulence factors, activates Nrf2, and induces S-arylation of its negative regulator Keap1. 2-tert-Butyl-1,4-benzoquinone induces HO-1. 2-tert-Butyl-1,4-benzoquinone exhibits quorum sensing inhibitory activity against Chromobacterium violaceum.
For research use only. We do not sell to patients.
- Purity: 99.34%
- CAS No.: 3602-55-9
- Formula: C10H12O2
- Molecular Weight:164.20
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
Biological Activity
Description
IC50 & Target
[1]|
HO-1 |
Cellular Effect
|
Cell Line
|
Type | Value | Description | References |
|---|---|---|---|---|
| A2780 | IC50 |
5.7 μM
Compound: 12
|
Growth inhibition of human A2780 cells after 72 hrs by SRB assay
Growth inhibition of human A2780 cells after 72 hrs by SRB assay
|
[PMID: 29519737] |
| A2780cis | IC50 |
4.9 μM
Compound: 12
|
Growth inhibition of human A2780cis cells after 72 hrs by SRB assay
Growth inhibition of human A2780cis cells after 72 hrs by SRB assay
|
[PMID: 29519737] |
| A549 | IC50 |
47.02 μM
Compound: 2
|
Cytotoxicity against human A549 cells assessed as cell survival after 72 hrs by MTT assay
Cytotoxicity against human A549 cells assessed as cell survival after 72 hrs by MTT assay
|
[PMID: 26476666] |
| HaCaT | IC50 |
95 μM
Compound: 1; TBHQ
|
Cytotoxicity against human HaCaT cells after 72 hrs by MTT assay
Cytotoxicity against human HaCaT cells after 72 hrs by MTT assay
|
[PMID: 27128177] |
| HeLa | IC50 |
44.08 μM
Compound: 2
|
Cytotoxicity against human HeLa cells assessed as cell survival after 72 hrs by MTT assay
Cytotoxicity against human HeLa cells assessed as cell survival after 72 hrs by MTT assay
|
[PMID: 26476666] |
| K562 | IC50 |
15.54 μM
Compound: 2
|
Cytotoxicity against human K562 cells assessed as cell survival after 72 hrs by MTT assay
Cytotoxicity against human K562 cells assessed as cell survival after 72 hrs by MTT assay
|
[PMID: 26476666] |
| MDA-MB-453 | IC50 |
56.83 μM
Compound: 2
|
Cytotoxicity against human MDA-MB-453 cells assessed as cell survival after 72 hrs by MTT assay
Cytotoxicity against human MDA-MB-453 cells assessed as cell survival after 72 hrs by MTT assay
|
[PMID: 26476666] |
| MRC5 | IC50 |
>200 μM
Compound: 2
|
Cytotoxicity against human MRC5 cells assessed as cell survival after 72 hrs by MTT assay
Cytotoxicity against human MRC5 cells assessed as cell survival after 72 hrs by MTT assay
|
[PMID: 26476666] |
| NCI-H460 | IC50 |
>100 μM
Compound: 1; TBHQ
|
Cytotoxicity against human NCI-H460 cells after 72 hrs by MTT assay
Cytotoxicity against human NCI-H460 cells after 72 hrs by MTT assay
|
[PMID: 27128177] |
| NCI-H460 | IC50 |
72 μM
Compound: 1; TBHQ
|
Cytotoxicity against multidrug resistant human NCI-H460 cells after 72 hrs by MTT assay
Cytotoxicity against multidrug resistant human NCI-H460 cells after 72 hrs by MTT assay
|
[PMID: 27128177] |
| OVCAR-8 | IC50 |
10 μM
Compound: 12
|
Growth inhibition of human OVCAR8 cells after 72 hrs by SRB assay
Growth inhibition of human OVCAR8 cells after 72 hrs by SRB assay
|
[PMID: 29519737] |
In Vitro
2-tert-Butyl-1,4-benzoquinone (12.5-500 μg/mL; 17 h, MIC assay; 12.5-50 μg/mL; 24 h, growth curve assay) has a minimum inhibitory concentration of 125 μg/mL against Chromobacterium violaceum ATCC12472, and sub-MIC concentrations (12.5, 25, 50 μg/mL) do not significantly inhibit bacterial growth over 24 h[1].
2-tert-Butyl-1,4-benzoquinone (12.5-50 μg/mL; 17 h) dose-dependently inhibits C10‒HSL production in Chromobacterium violaceum ATCC12472, reducing production by 65% at a concentration of 50 μg/mL after 17 h incubation[1].
2-tert-Butyl-1,4-benzoquinone (12.5-50 μg/mL; 17 h) dose-dependently inhibits the production of violacein, chitinase, and hemolysin in Chromobacterium violaceum ATCC12472, with maximum inhibitions of 70.6%, 72%, and 70.5%, respectively, at a concentration of 50 μg/mL after 17 h incubation[1].
2-tert-Butyl-1,4-benzoquinone (12.5-50 μg/mL; 48 h) dose-dependently inhibits the swimming motility of Chromobacterium violaceum ATCC12472, reducing motility by 88.45% at a concentration of 50 μg/mL after 48 h incubation[1].
2-tert-Butyl-1,4-benzoquinone (50 μg/mL; 24 h, combined with 0.2 μg/mL ciprofloxacin) synergistically inhibits biofilm formation by 73.27% and reduces cell survival in Chromobacterium violaceum ATCC12472 biofilms after 24 h incubation[1].
2-tert-Butyl-1,4-benzoquinone (50 μM; 0.5, 1, 3, 6, 9 h) activates Nrf2 (peaking at 3 h) and induces HO-1 in HepG2 cells, and these effects are enhanced by GSH depletion and diminished by thiol enhancement, consistent with GSH-dependent S-transarylation of TBQ-modified Keap1[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:HepG2 human hepatocellular carcinoma cells
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Concentration:50 μM (TBQ)
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Incubation Time:0.5, 1, 3, 6, 9 h (TBQ incubations)
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Result:Activates Nrf2, with peak activation at 3 h followed by a decline.
Induces HO-1 in a time-dependent manner.
Shows pretreatment with GSH-depleting BSO significantly maintains TBQ-mediated Nrf2 activation.
Shows pretreatment with NAC (which enhances thiol levels) markedly diminishes TBQ-mediated Nrf2 activation.
Shows analogous effects for HO-1 induction, with BSO sustaining and NAC reducing TBQ-mediated HO-1 expression.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:adult nematodes[1]
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Dosage:50 μg/mL
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Administration:continuous exposure; 120 h
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Result:Increased the 120-h survival rate of infected C. elegans to 44.4%.
Chemical Information
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CAS No. 3602-55-9
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Appearance Solid
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Molecular Weight 164.20
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Formula C10H12O2
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Color Light yellow to yellow
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SMILES
CC(C)(C1=CC(C=CC1=O)=O)C
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
In Vitro:
DMSO : 100 mg/mL (609.01 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (278 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Handling Instructions (2659 KB)
References
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 6.0901 mL | 30.4507 mL | 60.9013 mL | 152.2534 mL |
| 5 mM | 1.2180 mL | 6.0901 mL | 12.1803 mL | 30.4507 mL | |
| 10 mM | 0.6090 mL | 3.0451 mL | 6.0901 mL | 15.2253 mL | |
| 15 mM | 0.4060 mL | 2.0300 mL | 4.0601 mL | 10.1502 mL | |
| 20 mM | 0.3045 mL | 1.5225 mL | 3.0451 mL | 7.6127 mL | |
| 25 mM | 0.2436 mL | 1.2180 mL | 2.4361 mL | 6.0901 mL | |
| 30 mM | 0.2030 mL | 1.0150 mL | 2.0300 mL | 5.0751 mL | |
| 40 mM | 0.1523 mL | 0.7613 mL | 1.5225 mL | 3.8063 mL | |
| 50 mM | 0.1218 mL | 0.6090 mL | 1.2180 mL | 3.0451 mL | |
| 60 mM | 0.1015 mL | 0.5075 mL | 1.0150 mL | 2.5376 mL | |
| 80 mM | 0.0761 mL | 0.3806 mL | 0.7613 mL | 1.9032 mL | |
| 100 mM | 0.0609 mL | 0.3045 mL | 0.6090 mL | 1.5225 mL |