2-tert-Butyl-1,4-benzoquinone
目录号 : GC680432-tert-Butyl-1,4-benzoquinone 是 butylated hydroxyanisole 的亲电代谢产物，是 2-tert-butylhydroquinone 的氧化产物。
Cas No.:3602-55-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-tert-Butyl-1,4-benzoquinone is an electrophilic metabolite of butylated hydroxyanisole and an oxidation product of 2-tert-butylhydroquinone[1].
[1]. Abiko Y, Kumagai Y. Interaction of Keap1 modified by 2-tert-butyl-1,4-benzoquinone with GSH: evidence for S-transarylation. Chem Res Toxicol. 2013 Jul 15;26(7):1080-7.
| Cas No. | 3602-55-9 | SDF | Download SDF |
| 分子式 | C10H12O2 | 分子量 | 164.2 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.0901 mL | 30.4507 mL | 60.9013 mL |
| 5 mM | 1.218 mL | 6.0901 mL | 12.1803 mL |
| 10 mM | 0.609 mL | 3.0451 mL | 6.0901 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Colorimetric detection of 2-tert-Butyl-1,4-benzoquinone in edible oils based on a chromogenic reaction with commercial chemicals
Food Chem 2023 Jan 30;400:134037.PMID:36055146DOI:10.1016/j.foodchem.2022.134037.
2-tert-Butyl-1,4-benzoquinone (TBBQ) is the major oxidative product of tert-butylhydroquinone which is a widely used antioxidant in edible oils. The biotoxicity of TBBQ is a risk to human health, that the rapid and accurate monitoring of TBBQ is needed. Herein, a specific chromogenic reaction between TBBQ and polyethyleneimine (PEI) could generate adducts with maximum absorption at 478 nm. Amine groups of PEI are prone to link with TBBQ through Michael addition to form colored adducts. A colorimetric method for detecting TBBQ in edible oils was developed based on the aforesaid chromogenic reaction. The linear range for TBBQ was from 3.0 to 100.0 μg g-1, having a limit of detection of 1.8 μg g-1. Recoveries results ranged from 88.4 % to 93.1 %, which had a good agreement with that of high-performance liquid chromatography. Our study provides a rapid and simple strategy for the sensitive detection of TBBQ using commercial chemicals.
Distribution of 2-tert-Butyl-1,4-benzoquinone and its precursor, tert-butylhydroquinone, in typical edible oils and oleaginous foods marketed in Hangzhou City, China
Food Chem 2021 Nov 1;361:130039.PMID:34022482DOI:10.1016/j.foodchem.2021.130039.
This study aimed to obtain a reliable evaluation about addition of tert-butylhydroquinone (TBHQ), and distribution of TBHQ and 2-tert-Butyl-1,4-benzoquinone (TBBQ) contents in typical edible oils and oleaginous foods marketed in Hangzhou City. Briefly, the probability of labeled with addition of TBHQ in foods decreased from 36.45 ± 2.6% to 28.78 ± 3.7% in the period from 2018 to 2020. In the 135 analyzed samples, TBHQ contents were far less than the maximum legal additive amount, and TBBQ contents ranged from below its limit of quantification (LOQ) to 13.54 ± 1.15 mg/kg. The conversion rate from TBHQ to TBBQ in edible oils was 2.94 ± 1.17%, much lower than that in other food categories. Further research determined that the process method and food composition were the main factors for different conversion rates from TBHQ to TBBQ in various food categories. In addition, oil consumption was found to be the primary source of dietary intake of TBHQ and TBBQ.
Combination of 2- tert-Butyl-1,4-Benzoquinone (TBQ) and ZnO Nanoparticles, a New Strategy To Inhibit Biofilm Formation and Virulence Factors of Chromobacterium violaceum
mSphere 2023 Feb 21;8(1):e0059722.PMID:36645278DOI:10.1128/msphere.00597-22.
Drug-resistant bacteria have been raising serious social problems. Bacterial biofilms and different virulence factors are the main reasons for persistent infections. As a conditioned pathogen, Chromobacterium violaceum has evolved a vast network of regulatory mechanisms to modify and fine-tune biofilm development, contributing to multidrug resistance. However, there are few therapies to combat drug-resistant bacteria. Quorum sensing (QS) inhibitors (QSIs) are a promising strategy to solve antibiotic resistance. Our previous work suggested that 2-tert-Butyl-1,4-benzoquinone (TBQ) is a potent QSI. In this study, the combination of zinc oxide nanoparticles (ZnO-NPs) and TBQ (ZnO-TBQ) was investigated for the treatment of Chromobacterium violaceum ATCC 12472 infection. ZnO-NPs attach to cell walls or biofilms, and the local dissolution of ZnO-NPs can lead to increased Zn2+ concentrations, which could destroy metal homeostasis, corresponding to disturbances in amino acid metabolism and nucleic acid metabolism. ZnO-NPs significantly improved the efficiency of TBQ in inhibiting the QS-related virulence factors and biofilm formation of C. violaceum ATCC 12472. ZnO-TBQ effectively reduces the expression of genes related to QS, which is conducive to limiting the infectivity of C. violaceum ATCC 12472. Caenorhabditis elegans nematodes treated with ZnO-TBQ presented a significant improvement in the survival rate by 46.7%. Overall, the combination of ZnO-NPs and TBQ offers a new strategy to attenuate virulence factors and biofilm formation synergistically in some drug-resistant bacteria. IMPORTANCE The combination of ZnO-NPs and TBQ (ZnO-TBQ) can compete with the inducer N-decanoyl-homoserine lactone (C10-HSL) by binding to CviR and downregulate genes related to the CviI/CviR system to interrupt the QS system of C. violaceum ATCC 12472. The downstream genes responding to cviR were also downregulated so that virulence factors and biofilm formation were inhibited. Furthermore, ZnO-TBQ presents multiple metabolic disturbances in C. violaceum ATCC 12472, which results in the reduced multidrug resistance and pathogenicity of C. violaceum ATCC 12472. In an in vivo assay, C. elegans nematodes treated with ZnO-TBQ presented a significant improvement in the survival rate by 46.7% by limiting the infectivity of C. violaceum ATCC 12472. In addition, ZnO-TBQ inhibited the generation of virulence factors and biofilm formation 2-fold compared to either ZnO-NPs or TBQ alone. The combination of ZnO-NPs with TBQ offers a potent synergistic strategy to reduce multidrug resistance and pathogenicity.
Interaction of Keap1 modified by 2-tert-Butyl-1,4-benzoquinone with GSH: evidence for S-transarylation
Chem Res Toxicol 2013 Jul 15;26(7):1080-7.PMID:23718696DOI:10.1021/tx400085h.
2-tert-Butyl-1,4-benzoquinone (TBQ), an electrophilic metabolite of butylated hydroxyanisole (BHA), causes activation of Nrf2 together with S-arylation of its negative regulator Keap1 in RAW264.7 cells. In a previous study, we found that glyceraldehyde-3-phosphate dehydrogenase (GAPDH) covalently modified with 1,2-naphthoquinone (1,2-NQ) undergoes S-transarylation by GSH, resulting in a decline of the GAPDH-1,2-NQ adduct and formation of a 1,2-NQ-SG adduct ( Miura , T. et al. ( 2011 ) Chem. Res. Toxicol. 24 , 1836 -1844 ). In the present study, we explored the possibility of GSH-dependent S-transarylation of the Keap1-TBQ adduct. Pretreatment with l-buthionine-(S,R)-sulfoximine and N-acetylcysteine prior to TBQ exposure of HepG2 cells suggested that the Keap1-TBQ adduct appears to undergo GSH-mediated S-transarylation because the resulting alterations in the intracellular GSH concentration affected Nrf2 activation caused by TBQ. In support of this hypothesis, a cell-free study demonstrated that incubation of the Keap1-TBQ adduct with GSH results in the removal of TBQ from Keap1 with the production of mono- and di-GSH adducts of TB(H)Q. These results suggest that GSH plays a role in reversible covalent modification of TBQ derived from BHA to Keap1 through the formation of a C-S bond.
Simultaneous Analysis of Tertiary Butylhydroquinone and 2-tert-Butyl-1,4-benzoquinone in Edible Oils by Normal-Phase High-Performance Liquid Chromatography
J Agric Food Chem 2015 Sep 30;63(38):8584-91.PMID:26365419DOI:10.1021/acs.jafc.5b03002.
During the process of antioxidation of tertiary butylhydroquinone (TBHQ) in oil and fat systems, 2-tert-Butyl-1,4-benzoquinone (TQ) can be formed. The toxicity of TQ was much more than that of TBHQ. In the work, a normal-phase high-performance liquid chromatography (NP-HPLC) method for the accurate and simultaneous detection of TBHQ and TQ in edible oils was investigated. A C18 column was used to separate TBHQ and TQ, and the gradient elution solutions consisted of n-hexane containing 5% ethyl acetate and n-hexane containing 5% isopropanol. The ultraviolet (UV) detector was set at dual wavelength mode (280 nm for TBHQ and 310 nm for TQ). The column temperature was 30 °C. Before the NP-HPLC analysis, TBHQ and TQ were first extracted by methanol, subjected to vortex treatment, and then filtered through a 0.45 μm membrane filter. Results showed that linear ranges of TBHQ and TQ were both within 0.10-500.00 μg/mL (R(2) > 0.9999). The limit of detection (LOD) and limit of quantification (LOQ) of TBHQ and TQ were below 0.30 and 0.91 μg/mL and below 0.10 and 0.30 μg/mL, respectively. The recoveries of TBHQ and TQ were 98.92-102.34 and 96.28-100.58% for soybean oil and 96.11-99.42 and 98.83-99.24% for lard, respectively. These results showed that NP-HPLC can be successfully used to analyze simultaneously TBHQ and TQ in the oils and fats.