ZingeroneCAS# 122-48-5 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 122-48-5 | SDF | Download SDF |
| PubChem ID | 31211 | Appearance | Powder |
| Formula | C11H14O3 | M.Wt | 194.23 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Solubility | Soluble to 38 mg/mL warmed (195.64 mM) in DMSO | ||
| Chemical Name | 4-(4-hydroxy-3-methoxyphenyl)butan-2-one | ||
| SMILES | CC(=O)CCC1=CC(=C(C=C1)O)OC | ||
| Standard InChIKey | OJYLAHXKWMRDGS-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3 | ||
| 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 | Zingerone has anti-mutagenic, anti-carcinogenic, anti-obesity,anti-oxidative and anti-inflammatory activities. Zingerone can be recommended as a supplement to shrimp feed to increase growth, immunity, and disease resistance against the pathogen, V.alginolyticus , use of zingerone as appetizer and immunostimulant in shrimp is promising. It could as potential phytotherapeutic agent which in future can be employed to formulate preventive strategies against biofilm associated infections caused by P.aeruginosa. |
| Targets | TNF-α | IkB | COX | NOS | ROS | NF-kB | ERK | p38MAPK | p65 | IKK |
| In vitro | Structural alterations in Pseudomonas aeruginosa by zingerone contribute to enhanced susceptibility to antibiotics, serum and phagocytes.[Pubmed: 25277943]Life Sci. 2014 Nov 4;117(1):24-32.Excessive use of antibiotics has led to evolutionary adaptation resulting in emergence of multidrug resistance in P. aeruginosa. The aim of the present study was oriented towards exploiting Zingerone (active component of ginger) in making P. aeruginosa more susceptible to killing with antibiotics, humoral/cellular defences and studying its underlying mechanism.
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| In vivo | Modulation of age-related NF-kappaB activation by dietary zingerone via MAPK pathway.[Pubmed: 20211236 ]Exp Gerontol. 2010 Jun;45(6):419-26.Zingerone, a major component found in ginger root, has been known as anti-mutagenic and anti-carcinogenic activities that are often associated with its anti-oxidative and anti-inflammatory activities.
Dietary administration of zingerone to enhance growth, non-specific immune response, and resistance to Vibrio alginolyticus in Pacific white shrimp (Litopenaeus vannamei) juveniles.[Pubmed: 22173270 ]Fish Shellfish Immunol. 2012 Feb;32(2):284-90.Zingerone, one of the active components of ginger, is a phenolic alkanone with antioxidant and anti-inflammatory properties. The effects of Zingerone supplementation on the growth, immunity, and disease resistance of Pacific white shrimp (Litopenaeus vannamei) juveniles were studied. Four experimental diets, including a control diet (without Zingerone enrichment) and 1, 2.5, and 5 mg Zingerone (kg diet)(-1) were used. After 56 days of culture, shrimp fed diets supplemented with 1, 2.5, and 5 mg Zingerone (kg diet)(-1) had significantly greater weight gain and feed efficiency than the controls. Furthermore, after 56 days of culture, shrimp fed all doses of the Zingerone diet had higher survival rates compared to the controls after 24-72 h of challenge by the pathogen, Vibrio alginolyticus. Significantly increased phenoloxidase levels were found in shrimp fed the Zingerone diets at all doses, and respiratory bursts, lysozyme and phagocytic activities of shrimp fed 2.5 and 5 mg Zingerone (kg diet)(-1) also significantly increased. Neither the total hemocyte count nor superoxide dismutase activity of the experimental and control groups revealed significant differences at any dose. The results indicate that Zingerone can be recommended as a supplement to shrimp feed to increase growth, immunity, and disease resistance against the pathogen, V. alginolyticus. Use of Zingerone as appetizer and immunostimulant in shrimp is promising. |
| Cell Research | Lipolytic Effects of Zingerone in Adipocytes Isolated from Normal Diet-Fed Rats and High Fat Diet-Fed Ra[Reference: WebLink]Int.J.Pharmacol., 2011, 7(5):629-34.Zingerone is a non-volatile pungent compound mostly found in ginger which is a herbal medicine used for various purposes. The anti-obesity actions of ginger and Zingerone have also been documented.
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| Animal Research | Chemopreventive effect of zingerone against colon carcinogenesis induced by 1,2-dimethylhydrazine in rats.[Pubmed: 23903760]Zingerone attenuates lipopolysaccharide-induced acute lung injury in mice.[Pubmed: 24412620 ]Int Immunopharmacol. 2014 Mar;19(1):103-9.Zingerone, one of the active components of ginger, is a phenolic alkanone with antioxidant and anti-inflammatory properties. In the present study, we analyzed the role of Zingerone against RAW 264.7 cells and acute lung injury induced by lipopolysaccharide (LPS) in mice. RAW cells or BALB/c mice were pretreated with Zingerone one hour before stimulated with LPS. We found that Zingerone significantly inhibited the production of LPS-induced proinflammatory cytokines in vitro and in vivo. When pretreated with Zingerone, pulmonary histopathologic changes, as well as alveolar hemorrhage and neutrophil infiltration were substantially suppressed in lung tissues, with evidence of reduced myeloperoxidase (MPO) activity in murine acute lung injury model. The lung wet-to-dry weight (W/D) ratios, as the index of pulmonary edema, were markedly decreased by Zingerone pretreatment. Furthermore, we demonstrated that Zingerone attenuates the mitogen-activated protein kinases (MAPK) and nuclear factor-kappaB (NF-κB) signaling pathways through blocking the phosphorylation of ERK, p38/MAPK and IκBα, NF-κB/P65. These results suggest that Zingerone may provide protective effects against LPS-induced ALI. Eur J Cancer Prev. 2014 Sep;23(5):361-71.Animal Models: Male albino Wistar rats |
Zingerone Dilution Calculator
Zingerone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 5.1485 mL | 25.7427 mL | 51.4854 mL | 102.9707 mL | 128.7134 mL |
| 5 mM | 1.0297 mL | 5.1485 mL | 10.2971 mL | 20.5941 mL | 25.7427 mL |
| 10 mM | 0.5149 mL | 2.5743 mL | 5.1485 mL | 10.2971 mL | 12.8713 mL |
| 50 mM | 0.103 mL | 0.5149 mL | 1.0297 mL | 2.0594 mL | 2.5743 mL |
| 100 mM | 0.0515 mL | 0.2574 mL | 0.5149 mL | 1.0297 mL | 1.2871 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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Modulation of age-related NF-kappaB activation by dietary zingerone via MAPK pathway.[Pubmed:20211236]
Exp Gerontol. 2010 Jun;45(6):419-26.
Zingerone, a major component found in ginger root, has been known as anti-mutagenic and anti-carcinogenic activities that are often associated with its anti-oxidative and anti-inflammatory activities. In recent studies, we examined molecular mechanism of Zingerone treatment on pro-inflammatory NF-kappaB activation via the redox-related NIK/IKK and MAPK pathways. Action mechanism of Zingerone on NF-kappaB signaling was investigated in aged rat kidney and endothelial cells. The results showed that Zingerone had not only the antioxidant effect by constitutive suppression of ROS, but also anti-inflammatory effects by suppression of nuclear factor (NF)-kappaB activation in aged rat. In addition, Zingerone treatment suppressed gene activation of pro-inflammatory enzymes, COX-2 and iNOS, which were upregulated with aging through NF-kappaB activation and IKK/MAPK signaling pathway. These experiments strongly indicate that Zingerone treatment exerts a beneficial efficacy by suppressing both oxidative stress and age-related inflammation through the modulation of several key pro-inflammatory genes and transcription factors. Thus, the significance of our findings is that the Zingerone treatment may provide some preventive measure against chronic inflammatory conditions that underlie many age-related inflammatory diseases, such as metabolic syndrome, cardiovascular disease, dementia, arthritis, diabetes, osteoprosis, and cancers.
Chemopreventive effect of zingerone against colon carcinogenesis induced by 1,2-dimethylhydrazine in rats.[Pubmed:23903760]
Eur J Cancer Prev. 2014 Sep;23(5):361-71.
Zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butane], one of the active phenolic components isolated from Zingiber officinale, has antioxidant and anticarcinogenic properties. In our study, we have evaluated the effect of different doses of Zingerone on lipid peroxidation (thiobarbituric acid-reactive substances, lipid hydroxyl radical and conjugated dienes), tissue enzymatic antioxidants (superoxide dismutase, catalase, glutathione peroxidase and glutathione reductase), and nonenzymatic antioxidants (reduced glutathione, vitamin E, vitamin C), and also the formation of aberrant crypt foci (ACF) in male albino Wistar rats with colon cancer induced using 1,2-dimethylhydrazine (DMH). The rats were divided into six groups. Group 1 served as a control group and received a modified pellet diet; the rats in group 2 received a modified pellet diet along with Zingerone (40 mg/kg b.w., orally every day); groups 3-6 were administered DMH (20 mg/kg b.w., subcutaneously) once a week for the first 4 weeks; and groups 4-6 received Zingerone at three different doses of 10, 20 and 40 mg/kg b.w., respectively, every day for 16 weeks. Increased tumour incidence and ACF formation were accompanied by a decrease in the tissue lipid peroxidation, enzymatic and nonenzymatic antioxidant activities observed in the colon of DMH-treated rats. Supplementation with Zingerone in DMH-treated rats led to a significant decrease in the tumour incidence and ACF formation with simultaneous modulation in the level of tissue lipid peroxidation and antioxidant status. Thus, in conclusion, we can suggest that Zingerone effectively inhibits DMH-induced colon carcinogenesis in male Wistar rats.
Zingerone attenuates lipopolysaccharide-induced acute lung injury in mice.[Pubmed:24412620]
Int Immunopharmacol. 2014 Mar;19(1):103-9.
Zingerone, one of the active components of ginger, is a phenolic alkanone with antioxidant and anti-inflammatory properties. In the present study, we analyzed the role of Zingerone against RAW 264.7 cells and acute lung injury induced by lipopolysaccharide (LPS) in mice. RAW cells or BALB/c mice were pretreated with Zingerone one hour before stimulated with LPS. We found that Zingerone significantly inhibited the production of LPS-induced proinflammatory cytokines in vitro and in vivo. When pretreated with Zingerone, pulmonary histopathologic changes, as well as alveolar hemorrhage and neutrophil infiltration were substantially suppressed in lung tissues, with evidence of reduced myeloperoxidase (MPO) activity in murine acute lung injury model. The lung wet-to-dry weight (W/D) ratios, as the index of pulmonary edema, were markedly decreased by Zingerone pretreatment. Furthermore, we demonstrated that Zingerone attenuates the mitogen-activated protein kinases (MAPK) and nuclear factor-kappaB (NF-kappaB) signaling pathways through blocking the phosphorylation of ERK, p38/MAPK and IkappaBalpha, NF-kappaB/P65. These results suggest that Zingerone may provide protective effects against LPS-induced ALI.
Dietary administration of zingerone to enhance growth, non-specific immune response, and resistance to Vibrio alginolyticus in Pacific white shrimp (Litopenaeus vannamei) juveniles.[Pubmed:22173270]
Fish Shellfish Immunol. 2012 Feb;32(2):284-90.
Zingerone, one of the active components of ginger, is a phenolic alkanone with antioxidant and anti-inflammatory properties. The effects of Zingerone supplementation on the growth, immunity, and disease resistance of Pacific white shrimp (Litopenaeus vannamei) juveniles were studied. Four experimental diets, including a control diet (without Zingerone enrichment) and 1, 2.5, and 5 mg Zingerone (kg diet)(-1) were used. After 56 days of culture, shrimp fed diets supplemented with 1, 2.5, and 5 mg Zingerone (kg diet)(-1) had significantly greater weight gain and feed efficiency than the controls. Furthermore, after 56 days of culture, shrimp fed all doses of the Zingerone diet had higher survival rates compared to the controls after 24-72 h of challenge by the pathogen, Vibrio alginolyticus. Significantly increased phenoloxidase levels were found in shrimp fed the Zingerone diets at all doses, and respiratory bursts, lysozyme and phagocytic activities of shrimp fed 2.5 and 5 mg Zingerone (kg diet)(-1) also significantly increased. Neither the total hemocyte count nor superoxide dismutase activity of the experimental and control groups revealed significant differences at any dose. The results indicate that Zingerone can be recommended as a supplement to shrimp feed to increase growth, immunity, and disease resistance against the pathogen, V. alginolyticus. Use of Zingerone as appetizer and immunostimulant in shrimp is promising.
Structural alterations in Pseudomonas aeruginosa by zingerone contribute to enhanced susceptibility to antibiotics, serum and phagocytes.[Pubmed:25277943]
Life Sci. 2014 Nov 4;117(1):24-32.
AIMS: Excessive use of antibiotics has led to evolutionary adaptation resulting in emergence of multidrug resistance in P. aeruginosa. The aim of the present study was oriented towards exploiting Zingerone (active component of ginger) in making P. aeruginosa more susceptible to killing with antibiotics, humoral/cellular defences and studying its underlying mechanism. MAIN METHOD: Effect of Zingerone treatment on antibiotic susceptibility, serum, and phagocytic killing of P. aeruginosa was studied. The underlying mechanism was evaluated in terms of cell surface hydrophobicity, alginate and LPS production. TNF-alpha and MIP-2 cytokine production by mouse macrophages was also checked. Structural analysis was carried out using scanning electron microscopy (SEM) and liquid chromatography-mass spectrometry (LC-MS) analysis. KEY FINDINGS: Zingerone treated cells showed increased susceptibility to variety of antibiotics, serum as well as macrophages (p<0.05). Zingerone treatment significantly reduced cell surface hydrophobicity, alginate and LPS production (p<0.05). Zingerone treated cells showed significant decrease in TNF-alpha and MIP-2 cytokine production as compared to non-treated cells. Coupled with this, reduction in the production of extracellular protective matrix and modulation of chemical structure of LPS was also observed by scanning electron microscopy and liquid chromatography-mass spectrometric (LC-MS) respectively. Zingerone significantly influence surface structure of P. aeruginosa which contributes towards enhanced susceptibility to antibiotics and innate immune system. SIGNIFICANCE: Use of phytochemicals may prove to be a novel therapeutic approach by enhancing susceptibility of pathogenic microorganisms to antibiotics and immune system. Zingerone has proved to be one such agent which can be employed as a potential anti-virulent drug candidate against P. aeruginosa infections.
