Cardamonin
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MedKoo CAT#: 526268

CAS#: 19309-14-9

Description: Cardamonin is a modulator of STAT3 activation in prostate cancer, repressing proliferation, invasion, and causing apoptosis.


Chemical Structure

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Cardamonin
CAS# 19309-14-9

Theoretical Analysis

MedKoo Cat#: 526268
Name: Cardamonin
CAS#: 19309-14-9
Chemical Formula: C16H14O4
Exact Mass: 270.0892
Molecular Weight: 270.284
Elemental Analysis: C, 71.10; H, 5.22; O, 23.68

Price and Availability

Size Price Availability Quantity
10.0mg USD 250.0 2 Weeks
25.0mg USD 450.0 2 Weeks
50.0mg USD 850.0 2 Weeks
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Synonym: Cardamonin

IUPAC/Chemical Name: 2',4'-Dihydroxy-6'-methoxychalcone

InChi Key: NYSZJNUIVUBQMM-BQYQJAHWSA-N

InChi Code: InChI=1S/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3/b8-7+

SMILES Code: O=C(C1=C(OC)C=C(O)C=C1O)/C=C/C2=CC=CC=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

Preparing Stock Solutions

The following data is based on the product molecular weight 270.284 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: de Oliveira Cabral C, Campos A, da Silva LM, Boeing T, de Andrade SF, Filho VC, Nesello LÂN. Gastroprotective potential of methanolic extract and dimethyl cardamonin from Campomanesia reitziana fruits in mice. Naunyn Schmiedebergs Arch Pharmacol. 2017 Jun;390(6):661-666. doi: 10.1007/s00210-017-1369-0. Epub 2017 Apr 1. PubMed PMID: 28365824.

2: Peng S, Hou Y, Yao J, Fang J. Activation of Nrf2-driven antioxidant enzymes by cardamonin confers neuroprotection of PC12 cells against oxidative damage. Food Funct. 2017 Mar 22;8(3):997-1007. doi: 10.1039/c7fo00054e. PubMed PMID: 28271112.

3: Ali AA, Abd Al Haleem EN, Khaleel SA, Sallam AS. Protective effect of cardamonin against acetic acid-induced ulcerative colitis in rats. Pharmacol Rep. 2017 Apr;69(2):268-275. doi: 10.1016/j.pharep.2016.11.002. Epub 2016 Nov 9. PubMed PMID: 28129600.

4: Sambasevam Y, Omar Farouk AA, Tengku Mohamad TA, Sulaiman MR, Bharatham BH, Perimal EK. Cardamonin attenuates hyperalgesia and allodynia in a mouse model of chronic constriction injury-induced neuropathic pain: Possible involvement of the opioid system. Eur J Pharmacol. 2017 Feb 5;796:32-38. doi: 10.1016/j.ejphar.2016.12.020. Epub 2016 Dec 15. PubMed PMID: 27988285.

5: Mazzio EA, Bauer D, Mendonca P, Taka E, Soliman KF. Natural product HTP screening for attenuation of cytokine-induced neutrophil chemo attractants (CINCs) and NO2- in LPS/IFNγ activated glioma cells. J Neuroimmunol. 2017 Jan 15;302:10-19. doi: 10.1016/j.jneuroim.2016.11.012. Epub 2016 Dec 1. PubMed PMID: 27956075; PubMed Central PMCID: PMC5201440.

6: Zhang J, Sikka S, Siveen KS, Lee JH, Um JY, Kumar AP, Chinnathambi A, Alharbi SA, Basappa, Rangappa KS, Sethi G, Ahn KS. Cardamonin represses proliferation, invasion, and causes apoptosis through the modulation of signal transducer and activator of transcription 3 pathway in prostate cancer. Apoptosis. 2017 Jan;22(1):158-168. doi: 10.1007/s10495-016-1313-7. PubMed PMID: 27900636.

7: Mazzio EA, Li N, Bauer D, Mendonca P, Taka E, Darb M, Thomas L, Williams H, Soliman KF. Natural product HTP screening for antibacterial (E.coli 0157:H7) and anti-inflammatory agents in (LPS from E. coli O111:B4) activated macrophages and microglial cells; focus on sepsis. BMC Complement Altern Med. 2016 Nov 15;16(1):467. PubMed PMID: 27846826; PubMed Central PMCID: PMC5111180.

8: Voon FL, Sulaiman MR, Akhtar MN, Idris MF, Akira A, Perimal EK, Israf DA, Ming-Tatt L. Cardamonin (2',4'-dihydroxy-6'-methoxychalcone) isolated from Boesenbergia rotunda (L.) Mansf. inhibits CFA-induced rheumatoid arthritis in rats. Eur J Pharmacol. 2017 Jan 5;794:127-134. doi: 10.1016/j.ejphar.2016.11.009. Epub 2016 Nov 11. PubMed PMID: 27845065.

9: Jaiswal S, Shukla M, Sharma A, Rangaraj N, Vaghasiya K, Malik MY, Lal J. Preclinical pharmacokinetics and ADME characterization of a novel anticancer chalcone, cardamonin. Drug Test Anal. 2016 Oct 28. doi: 10.1002/dta.2128. [Epub ahead of print] PubMed PMID: 27794181.

10: Wang S, Zhai C, Zhang Y, Yu Y, Zhang Y, Ma L, Li S, Qiao Y. Cardamonin, a Novel Antagonist of hTRPA1 Cation Channel, Reveals Therapeutic Mechanism of Pathological Pain. Molecules. 2016 Aug 29;21(9). pii: E1145. doi: 10.3390/molecules21091145. PubMed PMID: 27589700.

11: Shrivastava S, Jeengar MK, Thummuri D, Koval A, Katanaev VL, Marepally S, Naidu VGM. Cardamonin, a chalcone, inhibits human triple negative breast cancer cell invasiveness by downregulation of Wnt/β-catenin signaling cascades and reversal of epithelial-mesenchymal transition. Biofactors. 2017 Mar;43(2):152-169. doi: 10.1002/biof.1315. Epub 2016 Sep 1. PubMed PMID: 27580587.

12: Li W, Wu X, Li M, Wang Z, Li B, Qu X, Chen S. Cardamonin Alleviates Pressure Overload-induced Cardiac Remodeling and Dysfunction Through Inhibition of Oxidative Stress. J Cardiovasc Pharmacol. 2016 Dec;68(6):441-451. PubMed PMID: 27560458.

13: Kim SM, Neuendorff N, Chapkin RS, Earnest DJ. Role of Inflammatory Signaling in the Differential Effects of Saturated and Poly-unsaturated Fatty Acids on Peripheral Circadian Clocks. EBioMedicine. 2016 May;7:100-11. doi: 10.1016/j.ebiom.2016.03.037. Epub 2016 Mar 31. PubMed PMID: 27322464; PubMed Central PMCID: PMC4913702.

14: Ng TL, Karim R, Tan YS, Teh HF, Danial AD, Ho LS, Khalid N, Appleton DR, Harikrishna JA. Amino Acid and Secondary Metabolite Production in Embryogenic and Non-Embryogenic Callus of Fingerroot Ginger (Boesenbergia rotunda). PLoS One. 2016 Jun 3;11(6):e0156714. doi: 10.1371/journal.pone.0156714. eCollection 2016. PubMed PMID: 27258536; PubMed Central PMCID: PMC4892522.

15: Nesello LA, Campos A, Wagner T, Feliciano AS, de Campos Buzzi F, Filho VC. Chemical Composition and Antinociceptive Potential of Campomanesia reitziana Fruits. J Med Food. 2016 May;19(5):518-20. doi: 10.1089/jmf.2015.0092. Epub 2016 Apr 22. PubMed PMID: 27104741.

16: Mi XG, Song ZB, Sun LG, Bao YL, Yu CL, Wu Y, Li YX. Cardamonin inhibited cell viability and tumorigenesis partially through blockade of testes-specific protease 50-mediated nuclear factor-kappaB signaling pathway activation. Int J Biochem Cell Biol. 2016 Apr;73:63-71. doi: 10.1016/j.biocel.2016.02.001. Epub 2016 Feb 19. PubMed PMID: 26855338.

17: Je HD, Jeong JH. Cardamonin inhibits agonist-induced vascular contractility via Rho-kinase and MEK inhibition. Korean J Physiol Pharmacol. 2016 Jan;20(1):69-74. doi: 10.4196/kjpp.2016.20.1.69. Epub 2015 Dec 31. PubMed PMID: 26807025; PubMed Central PMCID: PMC4722193.

18: De Spirt S, Eckers A, Wehrend C, Micoogullari M, Sies H, Stahl W, Steinbrenner H. Interplay between the chalcone cardamonin and selenium in the biosynthesis of Nrf2-regulated antioxidant enzymes in intestinal Caco-2 cells. Free Radic Biol Med. 2016 Feb;91:164-71. doi: 10.1016/j.freeradbiomed.2015.12.011. Epub 2015 Dec 15. PubMed PMID: 26698667.

19: Yu WG, He H, Yao JY, Zhu YX, Lu YH. Dimethyl Cardamonin Exhibits Anti-inflammatory Effects via Interfering with the PI3K-PDK1-PKCα Signaling Pathway. Biomol Ther (Seoul). 2015 Nov;23(6):549-56. doi: 10.4062/biomolther.2015.048. Epub 2015 Nov 1. PubMed PMID: 26535080; PubMed Central PMCID: PMC4624071.

20: Jia D, Tan Y, Liu H, Ooi S, Li L, Wright K, Bennett S, Addison CL, Wang L. Cardamonin reduces chemotherapy-enriched breast cancer stem-like cells in vitro and in vivo. Oncotarget. 2016 Jan 5;7(1):771-85. doi: 10.18632/oncotarget.5819. PubMed PMID: 26506421; PubMed Central PMCID: PMC4808032.