Zingerone

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584413

CAS#: 122-48-5

Description: Zingerone is absent in fresh ginger but cooking or heating transforms gingerol to zingerone. The compound has potent anti-inflammatory, antidiabetic, antilipolytic, antidiarrheal, and antispasmodic properties. It behaves as appetite stimulant, anxiolytic, antithrombotic, radiation protective, and antimicrobial. Also, it inhibits the reactive nitrogen species important in causing Alzheimer's disease and many other disorders.


Chemical Structure

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Zingerone
CAS# 122-48-5

Theoretical Analysis

MedKoo Cat#: 584413
Name: Zingerone
CAS#: 122-48-5
Chemical Formula: C11H14O3
Exact Mass: 194.0943
Molecular Weight: 194.23
Elemental Analysis: C, 68.02; H, 7.27; O, 24.71

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Zingerone; AI3-31837; Gingerone

IUPAC/Chemical Name: 4-(4-Hydroxy-3-methoxyphenyl)butan-2-one

InChi Key: OJYLAHXKWMRDGS-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CC(CCC1=CC=C(O)C(OC)=C1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 194.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ahmad B, Rehman MU, Amin I, Arif A, Rasool S, Bhat SA, Afzal I, Hussain I, Bilal S, Mir Mu. A Review on Pharmacological Properties of Zingerone (4-(4-Hydroxy-3-methoxyphenyl)-2-butanone). ScientificWorldJournal. 2015;2015:816364. doi: 10.1155/2015/816364. Epub 2015 May 27. Review. PubMed PMID: 26106644; PubMed Central PMCID: PMC4461790.

2: Kumar L, Chhibber S, Kumar R, Kumar M, Harjai K. Zingerone silences quorum sensing and attenuates virulence of Pseudomonas aeruginosa. Fitoterapia. 2015 Apr;102:84-95. doi: 10.1016/j.fitote.2015.02.002. Epub 2015 Feb 20. PubMed PMID: 25704369.

3: Hsiang CY, Cheng HM, Lo HY, Li CC, Chou PC, Lee YC, Ho TY. Ginger and Zingerone Ameliorate Lipopolysaccharide-Induced Acute Systemic Inflammation in Mice, Assessed by Nuclear Factor-κB Bioluminescent Imaging. J Agric Food Chem. 2015 Jul 8;63(26):6051-8. doi: 10.1021/acs.jafc.5b01801. Epub 2015 Jun 24. PubMed PMID: 26073629.

4: Xie X, Sun S, Zhong W, Soromou LW, Zhou X, Wei M, Ren Y, Ding Y. Zingerone attenuates lipopolysaccharide-induced acute lung injury in mice. Int Immunopharmacol. 2014 Mar;19(1):103-9. doi: 10.1016/j.intimp.2013.12.028. Epub 2014 Jan 9. PubMed PMID: 24412620.

5: Choi JS, Bae WY, Park C, Jeong JW. Zingerone activates VMAT2 during MPP(+) -induced Cell Death. Phytother Res. 2015 Nov;29(11):1783-90. doi: 10.1002/ptr.5435. Epub 2015 Aug 17. PubMed PMID: 26282055.

6: Vinothkumar R, Vinothkumar R, Sudha M, Nalini N. Chemopreventive effect of zingerone against colon carcinogenesis induced by 1,2-dimethylhydrazine in rats. Eur J Cancer Prev. 2014 Sep;23(5):361-71. doi: 10.1097/CEJ.0b013e32836473ac. PubMed PMID: 23903760.

7: Cheong KO, Shin DS, Bak J, Lee C, Kim KW, Je NK, Chung HY, Yoon S, Moon JO. Hepatoprotective effects of zingerone on carbon tetrachloride- and dimethylnitrosamine-induced liver injuries in rats. Arch Pharm Res. 2016 Feb;39(2):279-91. doi: 10.1007/s12272-015-0696-2. Epub 2015 Dec 14. PubMed PMID: 26667466.

8: Kumar L, Chhibber S, Harjai K. Zingerone suppresses liver inflammation induced by antibiotic mediated endotoxemia through down regulating hepatic mRNA expression of inflammatory markers in Pseudomonas aeruginosa peritonitis mouse model. PLoS One. 2014 Sep 3;9(9):e106536. doi: 10.1371/journal.pone.0106536. eCollection 2014. PubMed PMID: 25184525; PubMed Central PMCID: PMC4159778.

9: Bae WY, Choi JS, Kim JE, Park C, Jeong JW. Zingerone suppresses angiogenesis via inhibition of matrix metalloproteinases during tumor development. Oncotarget. 2016 Jul 26;7(30):47232-47241. doi: 10.18632/oncotarget.10030. PubMed PMID: 27323807; PubMed Central PMCID: PMC5216937.

10: Kumar L, Chhibber S, Harjai K. Structural alterations in Pseudomonas aeruginosa by zingerone contribute to enhanced susceptibility to antibiotics, serum and phagocytes. Life Sci. 2014 Nov 4;117(1):24-32. doi: 10.1016/j.lfs.2014.09.017. Epub 2014 Sep 30. PubMed PMID: 25277943.

11: Hemalatha KL, Prince PS. Preventive effects of zingerone on altered lipid peroxides and nonenzymatic antioxidants in the circulation of isoproterenol-induced myocardial infarcted rats. J Biochem Mol Toxicol. 2015 Feb;29(2):63-9. doi: 10.1002/jbt.21668. Epub 2014 Sep 30. PubMed PMID: 25271244.

12: Song J, Fan HJ, Li H, Ding H, Lv Q, Hou SK. Zingerone ameliorates lipopolysaccharide-induced acute kidney injury by inhibiting Toll-like receptor 4 signaling pathway. Eur J Pharmacol. 2016 Feb 5;772:108-14. doi: 10.1016/j.ejphar.2015.12.027. Epub 2015 Dec 14. PubMed PMID: 26698392.

13: Rajan I, Narayanan N, Rabindran R, Jayasree PR, Manish Kumar PR. Zingerone protects against stannous chloride-induced and hydrogen peroxide-induced oxidative DNA damage in vitro. Biol Trace Elem Res. 2013 Dec;155(3):455-9. doi: 10.1007/s12011-013-9801-x. Epub 2013 Sep 5. PubMed PMID: 24006104.

14: Hemalatha KL, Stanely Mainzen Prince P. Antihyperlipidaemic, antihypertrophic, and reducing effects of zingerone on experimentally induced myocardial infarcted rats. J Biochem Mol Toxicol. 2015 Apr;29(4):182-8. doi: 10.1002/jbt.21683. Epub 2015 Jan 5. PubMed PMID: 25558849.

15: Yue HY, Jiang CY, Fujita T, Kumamoto E. Zingerone enhances glutamatergic spontaneous excitatory transmission by activating TRPA1 but not TRPV1 channels in the adult rat substantia gelatinosa. J Neurophysiol. 2013 Aug;110(3):658-71. doi: 10.1152/jn.00754.2012. Epub 2013 May 8. PubMed PMID: 23657286.

16: Kumaran N, Hayes RA, Clarke AR. Cuelure but not zingerone make the sex pheromone of male Bactrocera tryoni (Tephritidae: Diptera) more attractive to females. J Insect Physiol. 2014 Sep;68:36-43. doi: 10.1016/j.jinsphys.2014.06.015. Epub 2014 Jul 7. PubMed PMID: 25010549.

17: Hemalatha KL, Stanely Mainzen Prince P. 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. Eur J Pharmacol. 2015 Jan 5;746:198-205. doi: 10.1016/j.ejphar.2014.10.057. Epub 2014 Nov 12. PubMed PMID: 25445034.

18: Hsiang CY, Lo HY, Huang HC, Li CC, Wu SL, Ho TY. Ginger extract and zingerone ameliorated trinitrobenzene sulphonic acid-induced colitis in mice via modulation of nuclear factor-κB activity and interleukin-1β signalling pathway. Food Chem. 2013 Jan 1;136(1):170-7. doi: 10.1016/j.foodchem.2012.07.124. Epub 2012 Aug 10. PubMed PMID: 23017409.

19: Banji D, Banji OJ, Pavani B, Kranthi Kumar Ch, Annamalai AR. Zingerone regulates intestinal transit, attenuates behavioral and oxidative perturbations in irritable bowel disorder in rats. Phytomedicine. 2014 Mar 15;21(4):423-9. doi: 10.1016/j.phymed.2013.10.007. Epub 2013 Nov 18. PubMed PMID: 24262066.

20: Muniandy Narayanan J, Jesudoss VA. Hepatoprotective potential of zingerone against nonalcoholic fatty liver disease in rats fed with fructose-enriched diet. Gen Physiol Biophys. 2016 Apr;35(2):185-94. doi: 10.4149/gpb_2015041. Epub 2016 Feb 26. PubMed PMID: 26915720.