Thymohydroquinone
(Synonyms: 瑞香[草]氫醌) 目录号 : GC45578A quinone with diverse biological activities
Cas No.:2217-60-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Thymohydroquinone is a quinone that has been found in N. sativa seeds and has diverse biological activities.1,2 It scavenges 2,2-diphenyl-1-picrylhydrazyl free radicals in a cell-free assay (IC50 = 2.4 μg/ml) and has a Trolox equivalent value of 2.6 in an oxygen radical absorbance capacity (ORAC) assay when used at concentrations ranging from 1.6 to 6.4 μg/ml.1 Thymohydroquinone inhibits growth of A2780, OVCAR-8, and CIS-A2780 ovarian cancer cells (IC50s = 3.1, 8.9, and 9.8 μM, respectively), as well as immortalized human ovarian epithelial cells (IC50 = 14 μM).2 It is also active against P. falciparum in vitro (IC50 = 15.9 μM).
References
1. Tesarova, H., Svobodova, B., Kokoska, L., et al. Determination of oxygen radical absorbance capacity of black cumin (Nigella sativa) seed quinone compounds. Nat. Prod. Commun. 6(2), 213-216 (2011).
2. Johnson-Ajinwo, O.R., Ullah, I., Mbye, H., et al. The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents. Bioorg. Med. Chem. Lett. 28(7), 1219-1222 (2018).
| Cas No. | 2217-60-9 | SDF | |
| 别名 | 瑞香[草]氫醌 | ||
| Canonical SMILES | CC(C)C1=C(O)C=C(C)C(O)=C1 | ||
| 分子式 | C10H14O2 | 分子量 | 166.2 |
| 溶解度 | DMF: 1 mg/mL,DMSO: 1 mg/mL,Ethanol: 2 mg/mL,Ethanol:PBS (pH 7.2) (1:9): 0.1mg/mL | 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 | 6.0168 mL | 30.0842 mL | 60.1685 mL |
| 5 mM | 1.2034 mL | 6.0168 mL | 12.0337 mL |
| 10 mM | 0.6017 mL | 3.0084 mL | 6.0168 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。
In silico study of Thymohydroquinone interaction with blood-brain barrier disrupting proteins
Future Sci OA 2020 Sep 25;6(10):FSO632.PMID:33312701DOI:10.2144/fsoa-2020-0115.
Aim: To evaluate the inhibitory interaction of Thymohydroquinone against blood-brain barrier (BBB)-associated neuropsychiatric and neurodegenerative disorders. Materials & methods: An elaborated in silico study was designed to evaluate the interaction of Thymohydroquinone with BBB-disrupting proteins and to highlight its pharmacokinetic and safety attributes. Results: Thymohydroquinone demonstrated stable interaction with BBB-disrupting protein active site with Ki (inhibition constant) ranges of (2.71 mM-736.15 μM), binding energy (-4.3 to 5.6 Kcal/mol), ligand efficiency (-0.36 to 0.42 Kcal/mol) and root mean square deviation value of (0.80-2.59 Å). Conclusion: Further pharmacokinetic analysis revealed that Thymohydroquinone is BBB and central nervous system (CNS) permeant with high acute toxicity and could be a candidate drug for the treatment of these neurological conditions.
The co-adsorption of Thymohydroquinone dimethyl ether (THQ) and coumarin present in the aqueous extract of Ayapana triplinervis on mild steel and its protection in hydrochloric acid up to 323 K: computational and physicochemical studies
RSC Adv 2022 May 12;12(23):14328-14341.PMID:35702201DOI:10.1039/d2ra02109a.
This study evaluates the corrosion inhibition property of the aqueous and alcoholic leaf extracts of the medicinal plant Ayapana triplinervis. The major components in the extracts are Thymohydroquinone dimethyl ether (THQ) and coumarin. It is clear from the weight-loss studies that the water extract of the leaves (AYW) is superior to the alcoholic extract (AYA) in terms of offering corrosion inhibition. The 96% efficiency of 4% (v/v) AYW in 0.5 N HCl at room temperature changes to 84.62% at 323 K. The mixed-type inhibition behaviour of AYW shows slight dominance in the anodic direction. Studies suggest the multilayer adsorption of phytochemicals on the metal surface and that the adsorption follows the Temkin model. Theoretical studies using DFT and BIOVIA Materials Studio investigations establish THQ as a good inhibitor with high adsorption characteristics. Even though the concentration of coumarin in the extract is low, its presence in the extract facilitates the adsorption of THQ on the metal surface, which is evident from the MD simulation study. The changes in the surface topography and elemental composition of the metal specimen in the inhibited and uninhibited solution are monitored by SEM and EDX spectral studies. XPS data support the presence of both THQ and coumarin on the metal surface and the existence of co-ordinate bonding between the metal's d orbital and the O atoms of THQ. Theoretical and experimental studies support the mixed mode of adsorption of THQ as physisorption followed by chemisorption.
The biosynthesis of thymol, carvacrol, and Thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase
Proc Natl Acad Sci U S A 2021 Dec 28;118(52):e2110092118.PMID:34930840DOI:10.1073/pnas.2110092118.
Thymol and carvacrol are phenolic monoterpenes found in thyme, oregano, and several other species of the Lamiaceae. Long valued for their smell and taste, these substances also have antibacterial and anti-spasmolytic properties. They are also suggested to be precursors of Thymohydroquinone and thymoquinone, monoterpenes with anti-inflammatory, antioxidant, and antitumor activities. Thymol and carvacrol biosynthesis has been proposed to proceed by the cyclization of geranyl diphosphate to γ-terpinene, followed by a series of oxidations via p-cymene. Here, we show that γ-terpinene is oxidized by cytochrome P450 monooxygenases (P450s) of the CYP71D subfamily to produce unstable cyclohexadienol intermediates, which are then dehydrogenated by a short-chain dehydrogenase/reductase (SDR) to the corresponding ketones. The subsequent formation of the aromatic compounds occurs via keto-enol tautomerisms. Combining these enzymes with γ-terpinene in in vitro assays or in vivo in Nicotiana benthamiana yielded thymol and carvacrol as products. In the absence of the SDRs, only p-cymene was formed by rearrangement of the cyclohexadienol intermediates. The nature of these unstable intermediates was inferred from reactions with the γ-terpinene isomer limonene and by analogy to reactions catalyzed by related enzymes. We also identified and characterized two P450s of the CYP76S and CYP736A subfamilies that catalyze the hydroxylation of thymol and carvacrol to Thymohydroquinone when heterologously expressed in yeast and N. benthamiana Our findings alter previous views of thymol and carvacrol formation, identify the enzymes involved in the biosynthesis of these phenolic monoterpenes and Thymohydroquinone in the Lamiaceae, and provide targets for metabolic engineering of high-value terpenes in plants.
In vitro potential antiviral SARS-CoV-19- activity of natural product Thymohydroquinone and dithymoquinone from Nigella sativa
Bioorg Chem 2022 Mar;120:105587.PMID:35026560DOI:10.1016/j.bioorg.2021.105587.
Inflammation, oxidation, and compromised immunity all increase the dangers of COVID-19, whereas many pharmaceutical protocols may lead to increased immunity such as ingesting from sources containing vitamin E and zinc. A global search for natural remedies to fight COVID-19 has emerged, to assist in the treatment of this infamous coronavirus. Nigella satvia is a world-renowned plant, an esteemed herbal remedy, which can be used as a liquid medicine to increase immunity while decreasing the dangers of acute respiratory distress syndrome. Thymoqinone (TQ), dithymoqinone (DTQ) and Thymohydroquinone (THQ), are major compounds of the essential oil contained in N.sativa. A current study aims to discover the antiviral activity of two compounds, Thymohydroquinone and Dithymoquinone, which are synthesized through simple chemical procedures, deriving from thymoquinone, which happens to be a major compound of Nigella sativa. A half-maximal cytotoxic concentration, "CC50", was calculated by MTT assay for each individual drug, The sample showed anti-SARS-CoV-2 activity at non-cytotoxic nanomolar concentrations in vitro with a low selectivity index (CC50/IC50 = 31.74/23.15 = 1.4), whereby Dimthymoquinone shows high cytotoxicity.
Antioxidant and Prooxidant Effects of Thymoquinone and Its Hydroquinone Metabolite
Biol Pharm Bull 2022;45(9):1389-1393.PMID:36047210DOI:10.1248/bpb.b22-00199.
Thymoquinone is a popular health-promoting antioxidant supplement, but it may induce toxicity to cells and organs because of its propensity to promote oxidation of biomolecules under some conditions. Furthermore, as hydroquinones have been found to exhibit more potent antioxidant and prooxidant activities than their parent quinones, the reduced metabolite Thymohydroquinone may have stronger effects than thymoquinone. In this study, the antioxidant and prooxidant activities of thymoquinone and Thymohydroquinone were assessed to determine whether they both act as antioxidants and induce oxidative damage to biomolecules as do other quinones. Using ESR spectroscopy, we demonstrated that Thymohydroquinone exhibits more potent antioxidant activity than does thymoquinone. In addition, Thymohydroquinone was found to act as a prooxidant to induce oxidative damage of isolated plasmid DNA in the presence of free Cu2+ or Fe2+-ethylenediaminetetraacetic acid (EDTA). Interestingly, the prooxidant effect of Thymohydroquinone in the presence of Fe2+ was not observed in the absence of EDTA. Thymohydroquinone thus was demonstrated to have two biologically relevant activities: as an antioxidant and a prooxidant.