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MedKoo Cat#: 540092 | Name: Coumestrol
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Description:

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

Coumestrol is an ERβ agonist inhibitor of aromatase and 3α-HSD found in plants such as soy and clover. It decreases immobility in animals undergoing for the forced swim test, suppresses pro-inflammatory cytokine release and limits T-cell differentiation and activation.

Chemical Structure

Coumestrol
Coumestrol
CAS#479-13-0

Theoretical Analysis

MedKoo Cat#: 540092

Name: Coumestrol

CAS#: 479-13-0

Chemical Formula: C15H8O5

Exact Mass: 268.0372

Molecular Weight: 268.22

Elemental Analysis: C, 67.17; H, 3.01; O, 29.82

Price and Availability

Size Price Availability Quantity
5mg USD 300.00 2 Weeks
10mg USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Coumestrol; Cumostrol; Cumoestrol; Coumesterol; NSC 22842; NSC22842; NSC-22842
IUPAC/Chemical Name
3,9-dihydroxy-6H-benzofuro[3,2-c]chromen-6-one
InChi Key
ZZIALNLLNHEQPJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
SMILES Code
O=C1C2=C(OC3=CC(O)=CC=C32)C4=C(O1)C=C(O)C=C4
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 268.22 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: Park G, Baek S, Kim JE, Lim TG, Lee CC, Yang H, Kang YG, Park JS, Augustin M, Mrosek M, Lee CY, Dong Z, Huber R, Lee KW. Flt3 is a target of coumestrol in protecting against UVB-induced skin photoaging. Biochem Pharmacol. 2015 Dec 1;98(3):473-83. doi: 10.1016/j.bcp.2015.08.104. Epub 2015 Sep 2. PubMed PMID: 26341390. 2: Chandsawangbhuwana C, Baker ME. 3D models of human ERα and ERβ complexed with coumestrol. Steroids. 2014 Feb;80:37-43. doi: 10.1016/j.steroids.2013.11.019. Epub 2013 Dec 5. PubMed PMID: 24315835. 3: Seo DB, Jeong HW, Lee SJ, Lee SJ. Coumestrol induces mitochondrial biogenesis by activating Sirt1 in cultured skeletal muscle cells. J Agric Food Chem. 2014 May 14;62(19):4298-305. doi: 10.1021/jf404882w. Epub 2014 Apr 30. PubMed PMID: 24712520. 4: Cho SY, Cho S, Park E, Kim B, Sohn EJ, Oh B, Lee EO, Lee HJ, Kim SH. Coumestrol suppresses hypoxia inducible factor 1α by inhibiting ROS mediated sphingosine kinase 1 in hypoxic PC-3 prostate cancer cells. Bioorg Med Chem Lett. 2014 Jun 1;24(11):2560-4. doi: 10.1016/j.bmcl.2014.03.084. Epub 2014 Apr 3. PubMed PMID: 24768446. 5: Liu S, Hsieh D, Yang YL, Xu Z, Peto C, Jablons DM, You L. Coumestrol from the national cancer Institute's natural product library is a novel inhibitor of protein kinase CK2. BMC Pharmacol Toxicol. 2013 Jul 11;14:36. doi: 10.1186/2050-6511-14-36. PubMed PMID: 23845105; PubMed Central PMCID: PMC3726451. 6: Castro CC, Pagnussat AS, Moura N, da Cunha MJ, Machado FR, Wyse AT, Netto CA. Coumestrol treatment prevents Na+, K+ -ATPase inhibition and affords histological neuroprotection to male rats receiving cerebral global ischemia. Neurol Res. 2014 Mar;36(3):198-206. doi: 10.1179/1743132813Y.0000000286. PubMed PMID: 24512013. 7: Lim W, Jeong W, Song G. Coumestrol suppresses proliferation of ES2 human epithelial ovarian cancer cells. J Endocrinol. 2016 Mar;228(3):149-60. doi: 10.1530/JOE-15-0418. Epub 2015 Dec 23. PubMed PMID: 26698565. 8: Ferreira-Dias G, Botelho M, Zagrajczuk A, Rebordão MR, Galvão AM, Bravo PP, Piotrowska-Tomala K, Szóstek AZ, Wiczkowski W, Piskula M, Fradinho MJ, Skarzynski DJ. Coumestrol and its metabolite in mares' plasma after ingestion of phytoestrogen-rich plants: potent endocrine disruptors inducing infertility. Theriogenology. 2013 Oct 1;80(6):684-92. doi: 10.1016/j.theriogenology.2013.06.002. Epub 2013 Jul 9. PubMed PMID: 23845774. 9: Młynarczuk J, Wróbel MH, Kotwica J. Adverse influence of coumestrol on secretory function of bovine luteal cells in the first trimester of pregnancy. Environ Toxicol. 2013 Jul;28(7):411-8. doi: 10.1002/tox.20735. Epub 2011 Jun 7. PubMed PMID: 21656645. 10: Wang M, Sugimoto M, Ikeda S, Kume S. Effects of coumestrol administration to maternal mice during pregnancy and lactation on immunoblogulin A-secreting cells in mammary glands. Anim Sci J. 2013 Apr;84(4):322-7. doi: 10.1111/asj.12007. Epub 2012 Dec 3. PubMed PMID: 23590506. 11: Bianchi SE, Teixeira HF, Kaiser S, Ortega GG, Schneider PH, Bassani VL. A bioanalytical HPLC method for coumestrol quantification in skin permeation tests followed by UPLC-QTOF/HDMS stability-indicating method for identification of degradation products. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 1;1020:43-52. doi: 10.1016/j.jchromb.2016.03.012. Epub 2016 Mar 15. PubMed PMID: 27010353. 12: Lim W, Song G. Stimulatory Effects of Coumestrol on Embryonic and Fetal Development Through AKT and ERK1/2 MAPK Signal Transduction. J Cell Physiol. 2016 Dec;231(12):2733-40. doi: 10.1002/jcp.25381. Epub 2016 Mar 30. PubMed PMID: 26991852. 13: Lee YH, Yuk HJ, Park KH, Bae YS. Coumestrol induces senescence through protein kinase CKII inhibition-mediated reactive oxygen species production in human breast cancer and colon cancer cells. Food Chem. 2013 Nov 1;141(1):381-8. doi: 10.1016/j.foodchem.2013.03.053. Epub 2013 Mar 23. PubMed PMID: 23768371. 14: Jang YJ, Son HJ, Ahn J, Jung CH, Ha T. Coumestrol modulates Akt and Wnt/β-catenin signaling during the attenuation of adipogenesis. Food Funct. 2016 Dec 7;7(12):4984-4991. PubMed PMID: 27868125. 15: Canal Castro C, Pagnussat AS, Orlandi L, Worm P, Moura N, Etgen AM, Alexandre Netto C. Coumestrol has neuroprotective effects before and after global cerebral ischemia in female rats. Brain Res. 2012 Sep 20;1474:82-90. doi: 10.1016/j.brainres.2012.07.025. Epub 2012 Jul 21. PubMed PMID: 22824334. 16: Leuner O, Havlik J, Hummelova J, Prokudina E, Novy P, Kokoska L. Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes. J Sci Food Agric. 2013 Feb;93(3):575-9. doi: 10.1002/jsfa.5835. Epub 2012 Aug 28. PubMed PMID: 22926873. 17: Lee HI, Lee JH, Park KH, Sangurdekar D, Chang WS. Effect of soybean coumestrol on Bradyrhizobium japonicum nodulation ability, biofilm formation, and transcriptional profile. Appl Environ Microbiol. 2012 Apr;78(8):2896-903. doi: 10.1128/AEM.07336-11. Epub 2012 Feb 3. PubMed PMID: 22307307; PubMed Central PMCID: PMC3318843. 18: Liu H, Wang L, Ma H, Guo R, Kang R, Han J, Dong Z. Coumestrol inhibits carotid sinus baroreceptor activity by cAMP/PKA dependent nitric oxide release in anesthetized male rats. Biochem Pharmacol. 2015 Jan 1;93(1):42-8. doi: 10.1016/j.bcp.2014.11.001. Epub 2014 Nov 13. PubMed PMID: 25449602. 19: Zafar A, Singh S, Naseem I. Cu(II)-coumestrol interaction leads to ROS-mediated DNA damage and cell death: a putative mechanism for anticancer activity. J Nutr Biochem. 2016 Jul;33:15-27. doi: 10.1016/j.jnutbio.2016.03.003. Epub 2016 Mar 29. PubMed PMID: 27260464. 20: Hu YC, Wu CT, Lai JN, Tsai YT. Detection of a negative correlation between prescription of Chinese herbal products containing coumestrol, genistein or daidzein and risk of subsequent endometrial cancer among tamoxifen-treated female breast cancer survivors in Taiwan between 1998 and 2008: A population-based study. J Ethnopharmacol. 2015 Jul 1;169:356-62. doi: 10.1016/j.jep.2015.04.028. Epub 2015 Apr 28. PubMed PMID: 25934515.

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