2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00058 |
| Mol. Weight | 194.23 g/mol |
| LogP | 1.92 |
| Water solubility | 0.00295 mol/L at 20 °C |
| Hydrogen Bond Donor | 1 |
| Hydrogen Bond Acceptor | 3 |
| Rotatable Bonds | 4 |
| XLogP3 | 0.8 |
| Identifiers | |
|---|---|
| Formula | C11H14O3 |
| PubChem CID | 31211 |
| FEMA | 3124 |
| Flavor Profile | Strong, Pungent Odor Reminiscent Of Ginger, Sweet, Spicy Aroma, Sharp Taste Similar To Ginger, Sweet, Spicy Taste; Flavouring Agent: Flavouring_Agent |
| Smiles | COc1cc(CCC(C)=O)ccc1O |
| InChl Key | OJYLAHXKWMRDGS-UHFFFAOYSA-N |
| InChl | 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 |
| CAS Registry Number | 122-48-5 |
| IUPAC Systematic Name | 4-(4-hydroxy-3-methoxyphenyl)butan-2-one |
Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets
Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)
| English Name | Pinyin Name (Chinese Name) | Latin Name | Properties in TCM | merdians | View Graph |
|---|---|---|---|---|---|
| Common Ginger Dried Rhizome | Gan Jiang (干姜) | Zingiberis Rhizoma | Hot, Pungent | Lung, Spleen, Stomach, Heart, Kidney | View Graph |
| Lesser Galangal | Gao Liang Jiang (高良姜) | Alpiniae Officinarum Rhizoma | Hot,Pungent | Large Intestine, Stomach | View Graph |
| Fresh Common Ginger | Sheng Jiang (生姜) | Zingiber Rhizoma Recens | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Prepared Ginger | Pao Jiang(炮姜) | Rhizoma Zingiberis Praeparata | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
Zingerone, also called vanillylacetone, is thought by some to be a key component of the pungency of ginger, but imparts the "sweet" flavor of cooked ginger. Zingerone is a crystalline solid that is sparingly soluble in water and soluble in ether.
Zingerone was applied to the lumen of the colon to allow the drug to access from the mucosal side. Zingerone inhibited spontaneous contractile movements in the isolated colonic segments in a dose-dependent manner. Zingerone is a phenolic alkanone which is present in a significant amount of about 9% in ginger.
Zingerone, one of the active components, isolated from Z. officinale, is a phenolic alkanone that contains a vanilloid (4-hydroxy-3-methoxyphenyl) group in its structure. A significant amount of zingerone is present in dry ginger (approximately 9.25%), and this amount increases significantly on cooking or drying due to the conversion of gingerol into zingerone by a retroaldol reaction.
Zingerone, a natural polyphenol, possesses multiple biological activities, such as antioxidant and anti-inflammatory.
Zingerone, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, isolated from ginger is a phenolic alkanone.
Zingerone, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, isolated from ginger is a phenolic alkanone. In our earlier phases of our experiments, the preventive effects of zingerone on cardiac hypertrophy, hyperlipidaemia and tachycardia, left ventricular dysfunction, altered electrocardiogram, adenosine triphosphatases ysfunction and electrolytes imbalance , and plasma non-enzymatic antioxidants in isoproterenol induced myocardial infarcted rats were reported.
Ginger contains a considerable amount of zingerone, accounting for about 9.25 %, and the amount of zingerone increases when ginger is dried or roasted. Zingerone has potent anti-inflammatory, anti-diabetic, anti-lipophilic, antidiarrheic, and anti-spasmodic properties
Zingerone seems to be a promising tool to explore therapeutic alternatives in cardiovascular diseases in humans.
Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.
1. https://en.wikipedia.org/wiki/Zingerone
2. Prince P S M, Hemalatha K L. A molecular mechanism on the antiapoptotic effects of zingerone in isoproterenol induced myocardial infarcted rats[J]. European journal of pharmacology, 2018, 821: 105-111.
3. Hemalatha K L, Prince P S M. Anti-inflammatory and anti-thrombotic effects of zingerone in a rat model of myocardial infarction[J]. European journal of pharmacology, 2016, 791: 595-602.
4. Lee, W., Ku, S. K., Kim, M. A., Bae, J. S. Anti-factor Xa activities of zingerone with anti-platelet aggregation activity[J]. Food and Chemical Toxicology, 2017, 105: 186-193.
5. Hemalatha K L, Stanely Mainzen Prince P. Antihyperlipidaemic, antihypertrophic, and reducing effects of zingerone on experimentally induced myocardial infarcted rats[J]. Journal of biochemical and molecular toxicology, 2015, 29(4): 182-188.
6. Mani, V., Arivalagan, S., Siddique, A. I., Namasivayam, N. Antioxidant and anti-inflammatory role of zingerone in ethanol-induced hepatotoxicity[J]. Molecular and cellular biochemistry, 2016, 421(1-2): 169-181.
7. Nageshwar Rao B, Satish Rao B S. Antagonistic effects of Zingerone, a phenolic alkanone against radiation-induced cytotoxicity, genotoxicity, apoptosis and oxidative stress in Chinese hamster lung fibroblast cells growing in vitro[J]. Mutagenesis, 2010, 25(6): 577-587.
8. Vinothkumar, R., Vinothkumar, R., Sudha, M., Nalini, N. Chemopreventive effect of zingerone against colon carcinogenesis induced by 1, 2-dimethylhydrazine in rats[J]. European journal of cancer prevention, 2014, 23(5): 361-371.
9. Rao, B. N., Rao, B. S., Aithal, B. K., Kumar, M. S. Radiomodifying and anticlastogenic effect of Zingerone on Swiss albino mice exposed to whole body gamma radiation[J]. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 2009, 677(1): 33-41.
10. Soliman A F, Anees L M, Ibrahim D M. Cardioprotective effect of zingerone against oxidative stress, inflammation, and apoptosis induced by cisplatin or gamma radiation in rats[J]. Naunyn-Schmiedeberg's archives of pharmacology, 2018: 1-14.
11. Kumar L, Chhibber S, Harjai K. Zingerone inhibit biofilm formation and improve antibiofilm efficacy of ciprofloxacin against Pseudomonas aeruginosa PAO1[J]. Fitoterapia, 2013, 90: 73-78.
12. Roshan, N., Riley, T. V., Knight, D. R., Hammer, K. A. Effect of natural products on the production and activity of Clostridium difficile toxins in vitro[J]. Scientific reports, 2018, 8(1): 15735.
13. Chen, J. C., Huang, L. J., Wu, S. L., Kuo, S. C., Ho, T. Y., Hsiang, C. Y. Ginger and its bioactive component inhibit enterotoxigenic Escherichia coli heat-labile enterotoxin-induced diarrhea in mice[J]. Journal of agricultural and food chemistry, 2007, 55(21): 8390-8397.
14. Hsiang, C. Y., Lo, H. Y., Huang, H. C., Li, C. C., Wu, S. L., Ho, T. Y. Ginger extract and zingerone ameliorated trinitrobenzene sulphonic acid-induced colitis in mice via modulation of nuclear factor-B activity and interleukin-1 signalling pathway[J]. Food chemistry, 2013, 136(1): 170-177.
15. Ahmad, B., Rehman, M. U., Amin, I., Arif, A., Rasool, S., Bhat, S. A., Bilal, S. A review on pharmacological properties of zingerone (4-(4-Hydroxy-3-methoxyphenyl)-2-butanone)[J]. The scientific world journal, 2015, 2015.
16. Cheong, K. O., Shin, D. S., Bak, J., Lee, C., Kim, K. W., Je, N. K., Moon, J. O. Hepatoprotective effects of zingerone on carbon tetrachloride-and dimethylnitrosamine-induced liver injuries in rats[J]. Archives of pharmacal research, 2016, 39(2): 279-291.
17. Iwami, M., Shiina, T., Hirayama, H., Shima, T., Takewaki, T., Shimizu, Y. Inhibitory effects of zingerone, a pungent component of Zingiber officinale Roscoe, on colonic motility in rats[J]. Journal of natural medicines, 2011, 65(1): 89-94.
18. Kim, H. S., Lee, S. H., Byun, Y., Park, H. D. 6-Gingerol reduces Pseudomonas aeruginosa biofilm formation and virulence via quorum sensing inhibition[J]. Scientific reports, 2015, 5: 8656.
19. Hemalatha K L, Prince P S M. Preventive Effects of Zingerone on Altered Lipid Peroxides and Nonenzymatic Antioxidants in the Circulation of Isoproterenol\Induced Myocardial Infarcted Rats[J]. Journal of biochemical and molecular toxicology, 2015, 29(2): 63-69.
20. Hemalatha K L, Prince P S M. A biochemical and 2, 3, 5-triphenyl tetrazolium chloride staining study on the preventive effects of zingerone (vanillyl acetone) in experimentally induced myocardial infarcted rats[J]. European journal of pharmacology, 2015, 746: 198-205.
21. Rajan, I., Narayanan, N., Rabindran, R., Jayasree, P. R., Kumar, P. M. Zingerone protects against stannous chloride-induced and hydrogen peroxide-induced oxidative DNA damage in vitro[J]. Biological trace element research, 2013, 155(3): 455-459.
22. Kim, M. K., Chung, S. W., Kim, D. H., Kim, J. M., Lee, E. K., Kim, J. Y., Park, K. Y. Modulation of age-related NF-B activation by dietary zingerone via MAPK pathway[J]. Experimental gerontology, 2010, 45(6): 419-426.
23. Michlig, S., Merlini, J. M., Beaumont, M., Ledda, M., Tavenard, A., Mukherjee, R., Le Coutre, J. Effects of TRP channel agonist ingestion on metabolism and autonomic nervous system in a randomized clinical trial of healthy subjects[J]. Scientific reports, 2016, 6: 20795.
24. Xu, H., Delling, M., Jun, J. C., Clapham, D. E. Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels[J]. Nature neuroscience, 2006, 9(5): 628.
25. Ghareib, S. A., El-Bassossy, H. M., Elberry, A. A., Azhar, A., Watson, M. L., Banjar, Z. M., Alahdal, A. M. Protective effect of zingerone on increased vascular contractility in diabetic rat aorta[J]. European journal of pharmacology, 2016, 780: 174-179.
26. Min, G., Ku, S. K., Lee, T., & Bae, J. S.. Suppressive effects of zingerone on TGFBIp-mediated septic responses[J]. Archives of pharmacal research, 2018, 41(3): 276-287.
27. Mani, V., Arivalagan, S., Siddique, A. I., Namasivayam, N. Antihyperlipidemic and antiapoptotic potential of zingerone on alcohol induced hepatotoxicity in experimental rats[J]. Chemico-biological interactions, 2017, 272: 197-206.
28. Mani, V., Arivalagan, S., Siddique, A. I., Namasivayam, N. Antioxidant and anti-inflammatory role of zingerone in ethanol-induced hepatotoxicity[J]. Molecular and cellular biochemistry, 2016, 421(1-2): 169-181.
29. Singh, G., Kapoor, I. P. S., Singh, P., de Heluani, C. S., de Lampasona, M. P., Catalan, C. A. Chemistry, antioxidant and antimicrobial investigations on essential oil and oleoresins of Zingiber officinale[J]. Food and Chemical Toxicology, 2008, 46(10): 3295-3302.
30. Caglayan, C., Kandemir, F. M., Y?ld?r?m, S., Kucukler, S., K?l?nc, M. A., Saglam, Y. S. Zingerone ameliorates cisplatin\induced ovarian and uterine toxicity via suppression of sex hormone imbalances, oxidative stress, inflammation and apoptosis in female wistar rats[J]. Biomedicine & Pharmacotherapy, 2018, 102: 517-530.
31. Kandemir, F. M., Yildirim, S., Kucukler, S., Caglayan, C., Mahamadu, A., Dortbudak, M. B. Therapeutic efficacy of zingerone against vancomycin-induced oxidative stress, inflammation, apoptosis and aquaporin 1 permeability in rat kidney[J]. Biomedicine & Pharmacotherapy, 2018, 105: 981-991.
32. Mani, V., Siddique, A. I., Arivalagan, S., Thomas, N. S., Namasivayam, N. Zingerone ameliorates hepatic and renal damage in alcohol-induced toxicity in experimental rats[J]. International Journal of Nutrition, Pharmacology, Neurological Diseases, 2016, 6(3): 125.
33. Safhi M M. Nephroprotective effect of Zingerone against CCl4-induced renal toxicity in Swiss albino mice: molecular mechanism[J]. Oxidative medicine and cellular longevity, 2018, 2018.
34. Mani, V., Siddique, A. I., Arivalagan, S., Thomas, N. S., & Namasivayam, N. Zingerone ameliorates hepatic and renal damage in alcohol-induced toxicity in experimental rats[J]. International Journal of Nutrition, Pharmacology, Neurological Diseases, 2016, 6(3): 125.
35. Song, J., Fan, H. J., Li, H., Ding, H., Lv, Q., Hou, S. K. Zingerone ameliorates lipopolysaccharide-induced acute kidney injury by inhibiting Toll-like receptor 4 signaling pathway[J]. European journal of pharmacology, 2016, 772: 108-114.
36. Cui, Y., Shi, Y., Bao, Y., Wang, S., Hua, Q., Liu, Y. Zingerone attenuates diabetic nephropathy through inhibition of nicotinamide adenine dinucleotide phosphate oxidase 4[J]. Biomedicine & Pharmacotherapy, 2018, 99: 422-430.
37. Rehman, M. U., Ahmad, B., Arif, A., Rasool, S., Farooq, A., Razzaq, R., Masoodi, M. Zingerone protects against cisplatin-induced oxidative damage in the jejunum of Wistar rats[J]. Oriental pharmacy and experimental medicine, 2015, 15(3): 199-206.
38. Iwami, M., Shiina, T., Hirayama, H., Shima, T., Takewaki, T., Shimizu, Y. Inhibitory effects of zingerone, a pungent component of Zingiber officinale Roscoe, on colonic motility in rats[J]. Journal of natural medicines, 2011, 65(1): 89-94.
39. Monge P, Scheline R, Solheim E. The metabolism of zingerone, a pungent principle of ginger[J]. Xenobiotica, 1976, 6(7): 411-423.