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MedKoo Cat#: 461252 | Name: Echinatin
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Description:

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

Echinatin is a compound isolated from the licorice and is a chalcone derivative called retrochalcone. Echinatin has exhibited diverse therapeutic effects, including anti-inflammatory and anti-oxidant effects. Echinatin exerts a protective effect against I/R-induced myocardial injury on hearts. This effect may be attributed to the antioxidant and anti-inflammatory activities of this compound.

Chemical Structure

Echinatin
Echinatin
CAS#34221-41-5

Theoretical Analysis

MedKoo Cat#: 461252

Name: Echinatin

CAS#: 34221-41-5

Chemical Formula: C16H14O4

Exact Mass: 270.0892

Molecular Weight: 270.28

Elemental Analysis: C, 71.10; H, 5.22; O, 23.68

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,350.00 2 Weeks
500mg USD 2,950.00 2 Weeks
1g USD 4,450.00 2 Weeks
2g USD 7,450.00 2 Weeks
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Synonym
Echinatin; Retrochalcone; Echinantin;
IUPAC/Chemical Name
(E)-3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
InChi Key
QJKMIJNRNRLQSS-WEVVVXLNSA-N
InChi Code
InChI=1S/C16H14O4/c1-20-16-10-14(18)8-4-12(16)5-9-15(19)11-2-6-13(17)7-3-11/h2-10,17-18H,1H3/b9-5+
SMILES Code
O=C(C1=CC=C(O)C=C1)/C=C/C2=CC=C(O)C=C2OC
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
>3 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Echinatin is a chalcone isolated from the Chinese herbal medicine Gancao with hepatoprotective and anti-inflammatory effects.
In vitro activity:
Ech (Echinatin) significantly inhibited growth of ESCC cells in a dose- and time- dependent manner compared to control (Figure 1b–f). The concentration for inhibiting 50% of cell growth (IC50) of Ech was 15 µM for KYSE 30, 15 µM for KYSE 70, 6 µM for KYSE 410, 13 µM for KYSE 450, and 10 µM for KYSE 510. In the three-dimensional culture of ESCC cells, colony numbers and sizes were decreased by treatment with Ech in KYSE 30 and KYSE 450 cells (Figure 1g). Reference: Molecules. 2019 Nov; 24(22): 4055. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891341/
In vivo activity:
This study pretreated mice with echinatin or MCC950, a best-studied selective inhibitor of NLRP3, and then conducted i.p. injection of LPS. Proinflammatory cytokines and neutrophils in peritoneal lavage fluids were measured. The data show that echinatin effectively attenuated LPS-induced IL-1β and TNF-α production, which was equivalent to the inhibitory effect of MCC950 (Figure 5, A and B). Moreover, consistent with the inhibitory effects of echinatin on proinflammatory cytokines, the proportion and the number of neutrophils in peritoneal lavage cells from mice pretreated with echinatin was also reduced (Figure 5, C and D). Reference: JCI Insight. 2021 Jan 25; 6(2): e134601. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7934863/
Solvent mg/mL mM
Solubility
Ethanol 27.0 99.90
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 270.28 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
Formulation protocol:
1. Niu J, Li Y, Song X, Liu Y, Li Y, Li Y. Cardioprotective Effect of Echinatin Against Ischemia/Reperfusion Injury: Involvement of Hippo/Yes-Associated Protein Signaling. Front Pharmacol. 2021 Jan 11;11:593225. doi: 10.3389/fphar.2020.593225. PMID: 33584269; PMCID: PMC7874120. 2. Kwak AW, Choi JS, Lee MH, Oh HN, Cho SS, Yoon G, Liu K, Chae JI, Shim JH. Retrochalcone Echinatin Triggers Apoptosis of Esophageal Squamous Cell Carcinoma via ROS- and ER Stress-Mediated Signaling Pathways. Molecules. 2019 Nov 9;24(22):4055. doi: 10.3390/molecules24224055. PMID: 31717502; PMCID: PMC6891341. 3. Xu G, Fu S, Zhan X, Wang Z, Zhang P, Shi W, Qin N, Chen Y, Wang C, Niu M, Guo Y, Wang J, Bai Z, Xiao X. Echinatin effectively protects against NLRP3 inflammasome-driven diseases by targeting HSP90. JCI Insight. 2021 Jan 25;6(2):e134601. doi: 10.1172/jci.insight.134601. PMID: 33350984; PMCID: PMC7934863. 4. Hong P, Liu QW, Xie Y, Zhang QH, Liao L, He QY, Li B, Xu WW. Echinatin suppresses esophageal cancer tumor growth and invasion through inducing AKT/mTOR-dependent autophagy and apoptosis. Cell Death Dis. 2020 Jul 13;11(7):524. doi: 10.1038/s41419-020-2730-7. PMID: 32655130; PMCID: PMC7354992.
In vitro protocol:
1. Niu J, Li Y, Song X, Liu Y, Li Y, Li Y. Cardioprotective Effect of Echinatin Against Ischemia/Reperfusion Injury: Involvement of Hippo/Yes-Associated Protein Signaling. Front Pharmacol. 2021 Jan 11;11:593225. doi: 10.3389/fphar.2020.593225. PMID: 33584269; PMCID: PMC7874120. 2. Kwak AW, Choi JS, Lee MH, Oh HN, Cho SS, Yoon G, Liu K, Chae JI, Shim JH. Retrochalcone Echinatin Triggers Apoptosis of Esophageal Squamous Cell Carcinoma via ROS- and ER Stress-Mediated Signaling Pathways. Molecules. 2019 Nov 9;24(22):4055. doi: 10.3390/molecules24224055. PMID: 31717502; PMCID: PMC6891341.
In vivo protocol:
1. Xu G, Fu S, Zhan X, Wang Z, Zhang P, Shi W, Qin N, Chen Y, Wang C, Niu M, Guo Y, Wang J, Bai Z, Xiao X. Echinatin effectively protects against NLRP3 inflammasome-driven diseases by targeting HSP90. JCI Insight. 2021 Jan 25;6(2):e134601. doi: 10.1172/jci.insight.134601. PMID: 33350984; PMCID: PMC7934863. 2. Hong P, Liu QW, Xie Y, Zhang QH, Liao L, He QY, Li B, Xu WW. Echinatin suppresses esophageal cancer tumor growth and invasion through inducing AKT/mTOR-dependent autophagy and apoptosis. Cell Death Dis. 2020 Jul 13;11(7):524. doi: 10.1038/s41419-020-2730-7. PMID: 32655130; PMCID: PMC7354992.
1: Tian XH, Liu CL, Jiang HL, Zhang Y, Han JC, Liu J, Chen M. Cardioprotection provided by Echinatin against ischemia/reperfusion in isolated rat hearts. BMC Cardiovasc Disord. 2016 May 31;16:119. doi: 10.1186/s12872-016-0294-3. PubMed PMID: 27246834; PubMed Central PMCID: PMC4888219. 2: Inoue B, Inaba K, Mori T, Izushi F, Eto K, Sakai R, Ogata M, Utsumi K. The effects of echinatin and its related compounds on the mitochondrial energy transfer reaction. J Toxicol Sci. 1982 Nov;7(4):245-54. PubMed PMID: 6221118. 3: Aleixo de Carvalho LS, Geraldo RB, de Moraes J, Silva Pinto PL, de Faria Pinto P, Pereira Odos S Jr, Da Silva Filho AA. Schistosomicidal activity and docking of Schistosoma mansoni ATPDase 1 with licoflavone B isolated from Glycyrrhiza inflata (Fabaceae). Exp Parasitol. 2015 Dec;159:207-14. doi: 10.1016/j.exppara.2015.09.015. Epub 2015 Oct 8. PubMed PMID: 26454044. 4: Ji S, Li Z, Song W, Wang Y, Liang W, Li K, Tang S, Wang Q, Qiao X, Zhou D, Yu S, Ye M. Bioactive Constituents of Glycyrrhiza uralensis (Licorice): Discovery of the Effective Components of a Traditional Herbal Medicine. J Nat Prod. 2016 Feb 26;79(2):281-92. doi: 10.1021/acs.jnatprod.5b00877. Epub 2016 Feb 3. PubMed PMID: 26841168. 5: Ayabe S, Iida K, Furuya T. Induction of stress metabolites in immobilized Glycyrrhiza echinata cultured cells. Plant Cell Rep. 1986 Jun;5(3):186-9. doi: 10.1007/BF00269114. PubMed PMID: 24248128. 6: Funakoshi-Tago M, Tanabe S, Tago K, Itoh H, Mashino T, Sonoda Y, Kasahara T. Licochalcone A potently inhibits tumor necrosis factor alpha-induced nuclear factor-kappaB activation through the direct inhibition of IkappaB kinase complex activation. Mol Pharmacol. 2009 Oct;76(4):745-53. doi: 10.1124/mol.109.057448. Epub 2009 Jul 10. PubMed PMID: 19592502. 7: Giri S, Lokesh CR, Sahu S, Gupta N. Luffa echinata: healer plant or potential killer. J Postgrad Med. 2014 Jan-Mar;60(1):72-4. doi: 10.4103/0022-3859.128819. PubMed PMID: 24625944. 8: Ayabe S, Udagawa A, Iida K, Yoshikawa T, Furuya T. Regulation of retrochalcone biosynthesis: Activity changes of O-methyltransferases in the yeast extract-induced Glycyrrhiza echinata cells. Plant Cell Rep. 1987 Feb;6(1):16-9. doi: 10.1007/BF00269729. PubMed PMID: 24248440. 9: Haraguchi H, Ishikawa H, Mizutani K, Tamura Y, Kinoshita T. Antioxidative and superoxide scavenging activities of retrochalcones in Glycyrrhiza inflata. Bioorg Med Chem. 1998 Mar;6(3):339-47. PubMed PMID: 9568287. 10: Haraguchi H, Tanimoto K, Tamura Y, Mizutani K, Kinoshita T. Mode of antibacterial action of retrochalcones from Glycyrrhiza inflata. Phytochemistry. 1998 May;48(1):125-9. PubMed PMID: 9621457. 11: Fu Y, Chen J, Li YJ, Zheng YF, Li P. Antioxidant and anti-inflammatory activities of six flavonoids separated from licorice. Food Chem. 2013 Nov 15;141(2):1063-71. doi: 10.1016/j.foodchem.2013.03.089. Epub 2013 Apr 13. PubMed PMID: 23790887. 12: Kuroda M, Mimaki Y, Honda S, Tanaka H, Yokota S, Mae T. Phenolics from Glycyrrhiza glabra roots and their PPAR-gamma ligand-binding activity. Bioorg Med Chem. 2010 Jan 15;18(2):962-70. doi: 10.1016/j.bmc.2009.11.027. Epub 2009 Nov 26. PubMed PMID: 20022509. 13: Nakamura K, Akashi T, Aoki T, Kawaguchi K, Ayabe S. Induction of isoflavonoid and retrochalcone branches of the flavonoid pathway in cultured Glycyrrhiza echinata cells treated with yeast extract. Biosci Biotechnol Biochem. 1999 Sep;63(9):1618-20. PubMed PMID: 10540749. 14: Furusawa J, Funakoshi-Tago M, Mashino T, Tago K, Inoue H, Sonoda Y, Kasahara T. Glycyrrhiza inflata-derived chalcones, Licochalcone A, Licochalcone B and Licochalcone D, inhibit phosphorylation of NF-kappaB p65 in LPS signaling pathway. Int Immunopharmacol. 2009 Apr;9(4):499-507. PubMed PMID: 19291859. 15: Otani K, Takahashi T, Furuya T, Ayabe S. Licodione Synthase, a Cytochrome P450 Monooxygenase Catalyzing 2-Hydroxylation of 5-Deoxyflavanone, in Cultured Glycyrrhiza echinata L. Cells. Plant Physiol. 1994 Aug;105(4):1427-1432. PubMed PMID: 12232298; PubMed Central PMCID: PMC159476. 16: Ayabe S, Udagawa A, Furuya T. Stimulation of chalcone synthase activity by yeast extract in cultured Glycyrrhiza echinata cells and 5-deoxyflavanone formation by isolated protoplasts. Plant Cell Rep. 1988 Jan;7(1):35-8. doi: 10.1007/BF00272973. PubMed PMID: 24241411. 17: Akashi T, Aoki T, Ayabe Si. Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice. Plant Physiol. 1999 Nov;121(3):821-8. PubMed PMID: 10557230; PubMed Central PMCID: PMC59444. 18: Ke Z, Su Z, Zhang X, Cao Z, Ding Y, Cao L, Ding G, Wang Z, Liu H, Xiao W. Discovery of a potent angiotensin converting enzyme inhibitor via virtual screening. Bioorg Med Chem Lett. 2017 Aug 15;27(16):3688-3692. doi: 10.1016/j.bmcl.2017.07.016. Epub 2017 Jul 5. PubMed PMID: 28712707. 19: Lin Y, Kuang Y, Li K, Wang S, Ji S, Chen K, Song W, Qiao X, Ye M. Nrf2 activators from Glycyrrhiza inflata and their hepatoprotective activities against CCl(4)-induced liver injury in mice. Bioorg Med Chem. 2017 Oct 15;25(20):5522-5530. doi: 10.1016/j.bmc.2017.08.018. Epub 2017 Aug 15. Erratum in: Bioorg Med Chem. 2018 Jul 30;26(13):3858. PubMed PMID: 28835349. 20: Wang XX, Liu GY, Yang YF, Wu XW, Xu W, Yang XW. Intestinal Absorption of Triterpenoids and Flavonoids from Glycyrrhizae radix et rhizoma in the Human Caco-2 Monolayer Cell Model. Molecules. 2017 Sep 29;22(10). pii: E1627. doi: 10.3390/molecules22101627. PubMed PMID: 28961192.