Licochalcone CCAS# 144506-14-9 |
Quality Control & MSDS
3D structure
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Number of papers citing our products
| Cas No. | 144506-14-9 | SDF | Download SDF |
| PubChem ID | 9840805 | Appearance | Yellow powder |
| Formula | C21H22O4 | M.Wt | 338.40 |
| Type of Compound | Chalcones | Storage | Desiccate at -20°C |
| Synonyms | Licochalcone-C | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (E)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one | ||
| SMILES | CC(=CCC1=C(C=CC(=C1OC)C=CC(=O)C2=CC=C(C=C2)O)O)C | ||
| Standard InChIKey | WBDNTJSRHDSPSR-KPKJPENVSA-N | ||
| Standard InChI | InChI=1S/C21H22O4/c1-14(2)4-11-18-20(24)13-8-16(21(18)25-3)7-12-19(23)15-5-9-17(22)10-6-15/h4-10,12-13,22,24H,11H2,1-3H3/b12-7+ | ||
| 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 | 1. Licochalcone C shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. 2. Licochalcone C has cardioprotection effect, via antioxidant, anti-inflammatory, and anti-apoptotic activities. 3. Licochalcone C and licochalcone A exhibit inhibitory activity with cytotoxicity in a rat basophilic leukemia cell line, RBL-2H3. 4. Licochalcone C induces apoptosis via B-cell lymphoma 2 family proteins in T24 cells, it may be a potential adjuvant therapeutic agent for bladder cancer. |
| Targets | TNF-α | Caspase | Bcl-2/Bax |
Licochalcone C Dilution Calculator
Licochalcone C Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9551 mL | 14.7754 mL | 29.5508 mL | 59.1017 mL | 73.8771 mL |
| 5 mM | 0.591 mL | 2.9551 mL | 5.9102 mL | 11.8203 mL | 14.7754 mL |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 mL | 5.9102 mL | 7.3877 mL |
| 50 mM | 0.0591 mL | 0.2955 mL | 0.591 mL | 1.182 mL | 1.4775 mL |
| 100 mM | 0.0296 mL | 0.1478 mL | 0.2955 mL | 0.591 mL | 0.7388 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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Role of licochalcone C in cardioprotection against ischemia/reperfusion injury of isolated rat heart via antioxidant, anti-inflammatory, and anti-apoptotic activities.[Pubmed:25921769]
Life Sci. 2015 Jul 1;132:27-33.
AIMS: This study aimed to evaluate the protective effect of Licochalcone C against myocardial ischemia/reperfusion injury in rats. MAIN METHODS: Left ventricular developed pressure (LVDP) and its maximum up/down rate (+/-dp/dtmax) were recorded as myocardial function. Levels of creatine kinase (CK), lactate dehydrogenase (LDH), malondialdehyde (MDA), superoxide dismutase (SOD), glutathione/glutathione disulfide (GSH/GSSG) ratio, and tumor necrosis factor-alpha (TNF-alpha) were determined by using enzyme-linked immunosorbent assay. Cell morphology was observed and mitochondrial damage was assessed by HE coloration and transmission electron microscopy, respectively. Cardiomyocyte apoptosis was determined by using terminal deoxynucleotidyl transferased UTP nick-end labeling (TUNEL). KEY FINDINGS: Pretreatment with Licochalcone C significantly improved the recovery of LVDP and +/-dp/dtmax, and increased the levels of SOD and GSH/GSSG ratio. However, pretreatment with Licochalcone C not only decreased the TUNEL-positive cell ratio and morphological changes, but also weaken the mitochondrial injury and the levels of CK, LDH, MDA, and TNF-alpha. SIGNIFICANCE: These results suggested an important function of Licochalcone C extracted from traditional Chinese medicine in the cardioprotection via antioxidant, anti-inflammatory, and anti-apoptotic activities.
Licochalcone C induces apoptosis via B-cell lymphoma 2 family proteins in T24 cells.[Pubmed:26397392]
Mol Med Rep. 2015 Nov;12(5):7623-8.
The current study investigated the mechanisms by which Licochalcone C induces apoptosis of T24 human malignant bladder cancer cells. Cell viability was evaluated using an MTT assay. Apoptosis was investigated using a morphological assay, flow cytometry and a caspase3 activity assay. Alterations in the gene expression levels of Bcl2 family members were measured by semiquantitative reverse transcriptionpolymerase chain reaction assays. The protein levels of procaspase3 and cleaved poly(ADP ribose) polymerase were measured using western blotting. The results indicated that Licochalcone C induced T24 cell apoptosis in a concentrationdependent manner. Licochalcone C treatment reduced the levels of the antiapoptotic mRNAs (Bcl2, Bclw and BclXL) and increased expression of the proapoptotic mRNAs (Bax and Bim). The Bcl2 family inhibitor (ABT737) reduced apoptosis induced by Licochalcone C in T24 cells. The current study demonstrated that Licochalcone C may be a potential adjuvant therapeutic agent for bladder cancer.
Concise synthesis of licochalcone C and its regioisomer, licochalcone H.[Pubmed:23897165]
Arch Pharm Res. 2013 Dec;36(12):1432-6.
Licochalone C (7a) is a retrochalcone isolated from Glycyrrhiza inflata, which shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. Biological studies have suggested that Licochalcone C attenuates the lipopolysaccharide and interferon-gamma induced inflammatory response by decreasing the expression and activity of inducible nitric oxide synthase and modulating the antioxidant network activity of superoxide dismutase, catalase, and glutathione peroxidase activity. Licochalcone C also inhibits NADH-cytochrome C reductase in the membrane fraction of Micrococcus luteus. Since pharmacological activity studies of Licochalcone C are ongoing and the yield of the compound is poor from natural product, we report a concise four step synthesis of Licochalcone C (7a) and its regioisomer, tentatively called licochalcone H (7b), by employing acid-mediated Claisen-Schmidt condensation as a key step with 6 and 20 % overall yield, respectively.
Licochalcones suppress degranulation by decreasing the intracellular Ca2+ level and tyrosine phosphorylation of ERK in RBL-2H3 cells.[Pubmed:20399908]
Int Immunopharmacol. 2010 Jul;10(7):769-76.
Mast cells play a key role in allergic inflammation by releasing various mediators, such as histamine, serotonin, leukotrienes and cytokines. A signaling cascade of events activated by stimulation with antigens contributes to the regulation of mast cell degranulation. While various anti-inflammatory and anti-allergic drugs have been developed that inhibit degranulation of mast cells, the inhibitory mechanism has been poorly understood. Licochalcone A (Lico A) is a retrochalcone isolated from the root of Xinjiang liquorice and has been reported to exhibit various biological activities such as anti-inflammatory activity. We examined the effects of Lico A and related chalcones on degranulation in a rat basophilic leukemia cell line, RBL-2H3. Whereas Lico A and Licochalcone C (Lico C) exhibited inhibitory activity with cytotoxicity, licochalcone D (Lico D) significantly inhibited the degranulation in RBL-2H3 cells with low cytotoxicity. Moreover, Lico D significantly inhibited the Ca2+ influx and phosphorylation of extracellular signal regulated kinase (ERK) and MEK. These results suggest that Lico D inhibits mast cell degranulation via the inhibition of both extracellular Ca2+ influx and activation of the MEK-ERK pathway.
