3-HydroxybakuchiolCAS# 178765-54-3 |
Quality Control & MSDS
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| Cas No. | 178765-54-3 | SDF | Download SDF |
| PubChem ID | 56833075 | Appearance | Oil |
| Formula | C18H24O2 | M.Wt | 272.4 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]benzene-1,2-diol | ||
| SMILES | CC(=CCCC(C)(C=C)C=CC1=CC(=C(C=C1)O)O)C | ||
| Standard InChIKey | ZHKCOGVKHHAUBK-NCUBBLFSSA-N | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 3-Hydroxybakuchiol exerts cytotoxic and anti-proliferative effects on the TA3/Ha mouse mammary adenocarcinoma cell line and induces a decrease in the mitochondrial transmembrane potential, the activation of caspase-3, the opening of the mitochondrial permeability transport pore (MPTP) and nuclear DNA fragmentation.3-Hydroxybakuchiol has antitumor activity resulting from interactions with the ETC, a system that is already deficient in cancer cells. |
| Targets | Caspase | ATP |
| In vitro | Tumor cell death induced by the inhibition of mitochondrial electron transport: the effect of 3-hydroxybakuchiol.[Pubmed: 23777606]Toxicol Appl Pharmacol. 2013 Oct 15;272(2):356-64.Changes in mitochondrial ATP synthesis can affect the function of tumor cells due to the dependence of the first step of glycolysis on mitochondrial ATP. The oxidative phosphorylation (OXPHOS) system is responsible for the synthesis of approximately 90% of the ATP in normal cells and up to 50% in most glycolytic cancers; therefore, inhibition of the electron transport chain (ETC) emerges as an attractive therapeutic target. |
3-Hydroxybakuchiol Dilution Calculator
3-Hydroxybakuchiol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.6711 mL | 18.3554 mL | 36.7107 mL | 73.4214 mL | 91.7768 mL |
| 5 mM | 0.7342 mL | 3.6711 mL | 7.3421 mL | 14.6843 mL | 18.3554 mL |
| 10 mM | 0.3671 mL | 1.8355 mL | 3.6711 mL | 7.3421 mL | 9.1777 mL |
| 50 mM | 0.0734 mL | 0.3671 mL | 0.7342 mL | 1.4684 mL | 1.8355 mL |
| 100 mM | 0.0367 mL | 0.1836 mL | 0.3671 mL | 0.7342 mL | 0.9178 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Tumor cell death induced by the inhibition of mitochondrial electron transport: the effect of 3-hydroxybakuchiol.[Pubmed:23777606]
Toxicol Appl Pharmacol. 2013 Oct 15;272(2):356-64.
Changes in mitochondrial ATP synthesis can affect the function of tumor cells due to the dependence of the first step of glycolysis on mitochondrial ATP. The oxidative phosphorylation (OXPHOS) system is responsible for the synthesis of approximately 90% of the ATP in normal cells and up to 50% in most glycolytic cancers; therefore, inhibition of the electron transport chain (ETC) emerges as an attractive therapeutic target. We studied the effect of a lipophilic isoprenylated catechol, 3-Hydroxybakuchiol (3-OHbk), a putative ETC inhibitor isolated from Psoralea glandulosa. 3-OHbk exerted cytotoxic and anti-proliferative effects on the TA3/Ha mouse mammary adenocarcinoma cell line and induced a decrease in the mitochondrial transmembrane potential, the activation of caspase-3, the opening of the mitochondrial permeability transport pore (MPTP) and nuclear DNA fragmentation. Additionally, 3-OHbk inhibited oxygen consumption, an effect that was completely reversed by succinate (an electron donor for Complex II) and duroquinol (electron donor for Complex III), suggesting that 3-OHbk disrupted the electron flow at the level of Complex I. The inhibition of OXPHOS did not increase the level of reactive oxygen species (ROS) but caused a large decrease in the intracellular ATP level. ETC inhibitors have been shown to induce cell death through necrosis and apoptosis by increasing ROS generation. Nevertheless, we demonstrated that 3-OHbk inhibited the ETC and induced apoptosis through an interaction with Complex I. By delivering electrons directly to Complex III with duroquinol, cell death was almost completely abrogated. These results suggest that 3-OHbk has antitumor activity resulting from interactions with the ETC, a system that is already deficient in cancer cells.
