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MedKoo Cat#: 527652 | Name: Dimethoxycurcumin

Description:

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

Dimethoxycurcumin is a more metabolically stable analog of curcumin, inducing epigenetic changes in leukemia cells and the expression of promoter methylated genes.

Chemical Structure

Dimethoxycurcumin
CAS#160096-59-3

Theoretical Analysis

MedKoo Cat#: 527652

Name: Dimethoxycurcumin

CAS#: 160096-59-3

Chemical Formula: C23H24O6

Exact Mass: 396.1573

Molecular Weight: 396.44

Elemental Analysis: C, 69.68; H, 6.10; O, 24.21

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Dimethoxycurcumin
IUPAC/Chemical Name
1,7-Bis-(3,4-dimethoxy-phenyl)-hepta-1,6-diene-3,5-dione
InChi Key
HMJSBVCDPKODEX-NXZHAISVSA-N
InChi Code
InChI=1S/C23H24O6/c1-26-20-11-7-16(13-22(20)28-3)5-9-18(24)15-19(25)10-6-17-8-12-21(27-2)23(14-17)29-4/h5-14H,15H2,1-4H3/b9-5+,10-6+
SMILES Code
O=C(CC(/C=C/C1=CC=C(OC)C(OC)=C1)=O)/C=C/C2=CC=C(OC)C(OC)=C2
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 396.44 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
1: Zhao H, Liu Q, Wang S, Dai F, Cheng X, Cheng X, Chen W, Zhang M, Chen D. In vitro additive antitumor effects of dimethoxycurcumin and 5-fluorouracil in colon cancer cells. Cancer Med. 2017 Jul;6(7):1698-1706. doi: 10.1002/cam4.1114. Epub 2017 Jun 2. PubMed PMID: 28573788; PubMed Central PMCID: PMC5504307. 2: Teymouri M, Barati N, Pirro M, Sahebkar A. Biological and pharmacological evaluation of dimethoxycurcumin: A metabolically stable curcumin analogue with a promising therapeutic potential. J Cell Physiol. 2018 Jan;233(1):124-140. doi: 10.1002/jcp.25749. Epub 2017 Mar 31. Review. PubMed PMID: 27996095. 3: Chen D, Dai F, Chen Z, Wang S, Cheng X, Sheng Q, Lin J, Chen W. Dimethoxy Curcumin Induces Apoptosis by Suppressing Survivin and Inhibits Invasion by Enhancing E-Cadherin in Colon Cancer Cells. Med Sci Monit. 2016 Sep 11;22:3215-22. PubMed PMID: 27614381; PubMed Central PMCID: PMC5021015. 4: Hassan HE, Keita JA, Narayan L, Brady SM, Frederick R, Carlson S, Glass KC, Natesan S, Buttolph T, Fandy TE. The combination of dimethoxycurcumin with DNA methylation inhibitor enhances gene re-expression of promoter-methylated genes and antagonizes their cytotoxic effect. Epigenetics. 2016 Sep 2:1-10. [Epub ahead of print] PubMed PMID: 27588609; PubMed Central PMCID: PMC5094623. 5: Adeyeni TA, Khatwani N, San K, Ezekiel UR. BMI1 is downregulated by the natural compound curcumin, but not by bisdemethoxycurcumin and dimethoxycurcumin. Physiol Rep. 2016 Aug;4(16). pii: e12906. doi: 10.14814/phy2.12906. PubMed PMID: 27550987; PubMed Central PMCID: PMC5002914. 6: Veldman ER, Jia Z, Halldin C, Svedberg MM. Amyloid binding properties of curcumin analogues in Alzheimer's disease postmortem brain tissue. Neurosci Lett. 2016 Sep 6;630:183-8. doi: 10.1016/j.neulet.2016.07.045. Epub 2016 Jul 25. PubMed PMID: 27461789. 7: Jayakumar S, Patwardhan RS, Pal D, Sharma D, Sandur SK. Dimethoxycurcumin, a metabolically stable analogue of curcumin enhances the radiosensitivity of cancer cells: Possible involvement of ROS and thioredoxin reductase. Biochem Biophys Res Commun. 2016 Sep 9;478(1):446-454. doi: 10.1016/j.bbrc.2016.06.144. Epub 2016 Jul 2. PubMed PMID: 27381867. 8: Benediktsdottir BE, Baldursson O, Gudjonsson T, Tønnesen HH, Masson M. Curcumin, bisdemethoxycurcumin and dimethoxycurcumin complexed with cyclodextrins have structure specific effect on the paracellular integrity of lung epithelia in vitro. Biochem Biophys Rep. 2015 Nov 10;4:405-410. doi: 10.1016/j.bbrep.2015.11.004. eCollection 2015 Dec. PubMed PMID: 29124231; PubMed Central PMCID: PMC5669517. 9: Liu H, Xu H, Jiang Y, Hao S, Gong F, Mu H, Liu K. Preparation, characterization, in vivo pharmacokinetics, and biodistribution of polymeric micellar dimethoxycurcumin for tumor targeting. Int J Nanomedicine. 2015 Oct 8;10:6395-410. doi: 10.2147/IJN.S91961. eCollection 2015. PubMed PMID: 26504386; PubMed Central PMCID: PMC4605235. 10: Lee Y, Lim Y, Kwon O. Selected Phytochemicals and Culinary Plant Extracts Inhibit Fructose Uptake in Caco-2 Cells. Molecules. 2015 Sep 18;20(9):17393-404. doi: 10.3390/molecules200917393. PubMed PMID: 26393568. 11: Soh SF, Yin X, Sun J, Li J, Yong EL, Wei Q, Gong Y. Simultaneous determination of multiple androgens in mice organs with liquid chromatography tandem mass spectrometry. J Pharm Biomed Anal. 2015 Nov 10;115:457-66. doi: 10.1016/j.jpba.2015.07.039. Epub 2015 Jul 29. PubMed PMID: 26291790. 12: Wada K, Lee JY, Hung HY, Shi Q, Lin L, Zhao Y, Goto M, Yang PC, Kuo SC, Chen HW, Lee KH. Novel curcumin analogs to overcome EGFR-TKI lung adenocarcinoma drug resistance and reduce EGFR-TKI-induced GI adverse effects. Bioorg Med Chem. 2015 Apr 1;23(7):1507-1514. doi: 10.1016/j.bmc.2015.02.003. Epub 2015 Feb 13. PubMed PMID: 25753330; PubMed Central PMCID: PMC4782611. 13: Hassan HE, Carlson S, Abdallah I, Buttolph T, Glass KC, Fandy TE. Curcumin and dimethoxycurcumin induced epigenetic changes in leukemia cells. Pharm Res. 2015 Mar;32(3):863-75. doi: 10.1007/s11095-014-1502-4. Epub 2014 Sep 4. PubMed PMID: 25186441. 14: Yoon MJ, Kang YJ, Lee JA, Kim IY, Kim MA, Lee YS, Park JH, Lee BY, Kim IA, Kim HS, Kim SA, Yoon AR, Yun CO, Kim EY, Lee K, Choi KS. Stronger proteasomal inhibition and higher CHOP induction are responsible for more effective induction of paraptosis by dimethoxycurcumin than curcumin. Cell Death Dis. 2014 Mar 13;5:e1112. doi: 10.1038/cddis.2014.85. PubMed PMID: 24625971; PubMed Central PMCID: PMC3973237. 15: Duan W, Guo Y, Xiao J, Chen X, Li Z, Han H, Li C. Neuroprotection by monocarbonyl dimethoxycurcumin C: ameliorating the toxicity of mutant TDP-43 via HO-1. Mol Neurobiol. 2014 Feb;49(1):368-79. doi: 10.1007/s12035-013-8525-4. Epub 2013 Aug 10. PubMed PMID: 23934646. 16: Barik A, Indira Priyadarsini K. Solvent dependent photophysical properties of dimethoxy curcumin. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Mar 15;105:267-72. doi: 10.1016/j.saa.2012.12.036. Epub 2012 Dec 20. PubMed PMID: 23314392. 17: Hadjidemetriou M, Pippa N, Pispas S, Demetzos C. Incorporation of dimethoxycurcumin into charged liposomes and the formation kinetics of fractal aggregates of uncharged vectors. J Liposome Res. 2013 Jun;23(2):94-100. doi: 10.3109/08982104.2012.747534. Epub 2013 Jan 7. PubMed PMID: 23294394. 18: Lu J, Duan W, Guo Y, Jiang H, Li Z, Huang J, Hong K, Li C. Mitochondrial dysfunction in human TDP-43 transfected NSC34 cell lines and the protective effect of dimethoxy curcumin. Brain Res Bull. 2012 Dec 1;89(5-6):185-90. doi: 10.1016/j.brainresbull.2012.09.005. Epub 2012 Sep 15. PubMed PMID: 22986236. 19: Hu TY, Liu CL, Chyau CC, Hu ML. Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells. J Agric Food Chem. 2012 Aug 22;60(33):8190-6. doi: 10.1021/jf302188a. Epub 2012 Aug 14. PubMed PMID: 22849714. 20: Kunwar A, Jayakumar S, Srivastava AK, Priyadarsini KI. Dimethoxycurcumin-induced cell death in human breast carcinoma MCF7 cells: evidence for pro-oxidant activity, mitochondrial dysfunction, and apoptosis. Arch Toxicol. 2012 Apr;86(4):603-14. doi: 10.1007/s00204-011-0786-y. Epub 2011 Nov 27. PubMed PMID: 22119759.