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MedKoo Cat#: 526583 | Name: Zeranol
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Description:

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

Zeranol is a non-steroidal estrogen agonist. It is a mycotoxin, derived from fungi in the Fusarium family, and may be found as a contaminant in fungus-infected crops. It is 3-4x more potent as an estrogen agonist than the related compound zearalenone. Zeranol increases cancer cell proliferation in already existing breast cancer. There are mixed results to whether zeranol has anticancer or carcinogenic properties in non cancer containing breast cells depending on dose. Overall evidence points to zeranol being a risk factor and promoter for cancer. However, dietary exposure from the use of zeranol-containing implants in cattle is insignificant.

Chemical Structure

Zeranol
Zeranol
CAS#26538-44-3

Theoretical Analysis

MedKoo Cat#: 526583

Name: Zeranol

CAS#: 26538-44-3

Chemical Formula: C18H26O5

Exact Mass: 322.1780

Molecular Weight: 322.40

Elemental Analysis: C, 67.06; H, 8.13; O, 24.81

Price and Availability

Size Price Availability Quantity
5mg USD 550.00
25mg USD 1,250.00
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Related CAS #
No Data
Synonym
MK188; MK-188; MK 188; Zeranol; Ralabol; Ralgro; Ralone
IUPAC/Chemical Name
(3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-benzo[c][1]oxacyclotetradecin-1-one
InChi Key
DWTTZBARDOXEAM-GXTWGEPZSA-N
InChi Code
InChI=1S/C18H26O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h10-12,14,19-21H,2-9H2,1H3/t12-,14+/m0/s1
SMILES Code
O=C1O[C@@H](C)CCC[C@H](O)CCCCCC2=CC(O)=CC(O)=C12
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, not in water
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 322.40 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: Zhu Y, Yao X, Leung LK. Zeranol induces COX-2 expression through TRPC-3 activation in the placental cells JEG-3. Toxicol In Vitro. 2016 May 17;35:17-23. doi: 10.1016/j.tiv.2016.05.007. [Epub ahead of print] PubMed PMID: 27224899. 2: Zhong S, Liu S, Chen S, Lin H, Wang W, Qin X. Zeranol stimulates proliferation and aromatase activation in human breast preadipocytes. Mol Med Rep. 2016 Jul;14(1):1014-1018. doi: 10.3892/mmr.2016.5293. Epub 2016 May 18. PubMed PMID: 27220457. 3: Bircher S, Card ML, Zhai G, Chin YP, Schnoor JL. Sorption, uptake, and biotransformation of 17β-estradiol, 17α-ethinylestradiol, zeranol, and trenbolone acetate by hybrid poplar. Environ Toxicol Chem. 2015 Dec;34(12):2906-13. doi: 10.1002/etc.3166. Epub 2015 Oct 30. PubMed PMID: 26184466. 4: Nakamura U, Rudolf FO, Pandey K, Kadokawa H. The non-steroidal mycoestrogen zeranol suppresses luteinizing hormone secretion from the anterior pituitary of cattle via the estradiol receptor GPR30 in a rapid, non-genomic manner. Anim Reprod Sci. 2015 May;156:118-27. doi: 10.1016/j.anireprosci.2015.03.009. Epub 2015 Mar 21. PubMed PMID: 25824341. 5: Yunin MA, Metalnikov PS, Komarov AA, Panin AN. Development of a rapid method for the analysis of trenbolone, nortestosterone, and zeranol in bovine liver using liquid chromatography tandem mass spectrometry. Anal Bioanal Chem. 2015 Jun;407(15):4363-71. doi: 10.1007/s00216-014-8346-y. Epub 2014 Dec 2. PubMed PMID: 25450054. 6: Echarte JM, Fernández DC, Chiacchio CA, Torres Leedham VM. Comparison of a Validated LC/MS/MS Method with a Validated GC/MS Method for the Analysis of Zeranol and its Related Mycotoxin Residues in Bovine Urine Samples Collected During Argentina's Residue Monitoring Control Program (2005-2012). J AOAC Int. 2014 Sep-Oct;97(5):1470-5. doi: 10.5740/jaoacint.13-283. PubMed PMID: 25903002. 7: Regiart M, Pereira SV, Spotorno VG, Bertolino FA, Raba J. Food safety control of zeranol through voltammetric immunosensing on Au-Pt bimetallic nanoparticle surfaces. Analyst. 2014 Sep 21;139(18):4702-9. doi: 10.1039/c4an00686k. PubMed PMID: 25057514. 8: Haiyang J, Wenjun W, Jinghui Z, Xiaoqi T, Jiancheng L, Xi X, Kai W, Fei X, Zhaopeng W, Min C, Xiangmei L, Xiaoping W, Shien W, Shuangyang D. Determination of zeranol and its metabolites in bovine muscle and liver by a chemiluminescence enzyme immunoassay: compared to an ultraperformance liquid chromatography tandem mass spectroscopy method. Luminescence. 2014 Jun;29(4):393-400. doi: 10.1002/bio.2559. Epub 2013 Aug 12. PubMed PMID: 23934682. 9: Wang Y, Li L, Wang CC, Leung LK. Effect of zeranol on expression of apoptotic and cell cycle proteins in murine placentae. Toxicology. 2013 Dec 6;314(1):148-54. doi: 10.1016/j.tox.2013.09.011. Epub 2013 Oct 8. PubMed PMID: 24120472. 10: Han H, Kim B, Lee SG, Kim J. An optimised method for the accurate determination of zeranol and diethylstilbestrol in animal tissues using isotope dilution-liquid chromatography/mass spectrometry. Food Chem. 2013 Sep 1;140(1-2):44-51. doi: 10.1016/j.foodchem.2013.02.070. Epub 2013 Feb 27. PubMed PMID: 23578613. 11: Wang Y, Tan W, Leung LK. Zeranol upregulates corticotropin releasing hormone expression in the placental cell line JEG-3. Toxicol Lett. 2013 Jun 7;219(3):218-22. doi: 10.1016/j.toxlet.2013.03.016. Epub 2013 Mar 26. PubMed PMID: 23538034. 12: Feng R, Zhang Y, Yu H, Wu D, Ma H, Zhu B, Xu C, Li H, Du B, Wei Q. Nanoporous PtCo-based ultrasensitive enzyme-free immunosensor for zeranol detection. Biosens Bioelectron. 2013 Apr 15;42:367-72. doi: 10.1016/j.bios.2012.10.031. Epub 2012 Oct 17. PubMed PMID: 23211452. 13: Eckerman SR, Lardy GP, Thompson MM, Van Emon ML, Neville BW, Berg PT, Schauer CS. Effects of increasing dosages of zeranol implants on lamb growth, carcass characteristics, blood hormones, and nitrogen metabolism. J Anim Sci. 2013 Feb;91(2):986-94. doi: 10.2527/jas.2011-4818. Epub 2012 Dec 10. PubMed PMID: 23230124. 14: Feng R, Zhang Y, Li H, Wu D, Xin X, Zhang S, Yu H, Wei Q, Du B. Ultrasensitive electrochemical immunosensor for zeranol detection based on signal amplification strategy of nanoporous gold films and nano-montmorillonite as labels. Anal Chim Acta. 2013 Jan 3;758:72-9. doi: 10.1016/j.aca.2012.11.009. Epub 2012 Nov 16. PubMed PMID: 23245898. 15: Matraszek-Zuchowska I, Wozniak B, Zmudzki J. Determination of zeranol, taleranol, zearalanone, α-zearalenol, β-zearalenol and zearalenone in urine by LC-MS/MS. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(6):987-94. doi: 10.1080/19440049.2013.787656. Epub 2013 May 24. PubMed PMID: 23705928. 16: Shidaifat F, Kulp SK, Lin YC. Zeranol induces deleterious effects on the testes and the prostate gland of mature rats. Endocr Res. 2013;38(4):232-41. doi: 10.3109/07435800.2013.774410. Epub 2013 Mar 15. PubMed PMID: 23496416. 17: Valenzuela-Grijalva NV, González-Rios H, Islava TY, Valenzuela M, Torrescano G, Camou JP, Núñez-González FA. Changes in intramuscular fat, fatty acid profile and cholesterol content induced by zeranol implantation strategy in hair lambs. J Sci Food Agric. 2012 May;92(7):1362-7. doi: 10.1002/jsfa.4707. Epub 2011 Dec 5. PubMed PMID: 22143996. 18: Fleck SC, Hildebrand AA, Pfeiffer E, Metzler M. Catechol metabolites of zeranol and 17β-estradiol: a comparative in vitro study on the induction of oxidative DNA damage and methylation by catechol-O-methyltransferase. Toxicol Lett. 2012 Apr 5;210(1):9-14. doi: 10.1016/j.toxlet.2012.01.010. Epub 2012 Jan 20. PubMed PMID: 22285433. 19: Hsieh HY, Shyu CL, Liao CW, Lee RJ, Lee MR, Vickroy TW, Chou CC. Liquid chromatography incorporating ultraviolet and electrochemical analyses for dual detection of zeranol and zearalenone metabolites in mouldy grains. J Sci Food Agric. 2012 Apr;92(6):1230-7. doi: 10.1002/jsfa.4687. Epub 2011 Oct 19. PubMed PMID: 22012692. 20: Thevis M, Fusshöller G, Schänzer W. Zeranol: doping offence or mycotoxin? A case-related study. Drug Test Anal. 2011 Nov-Dec;3(11-12):777-83. doi: 10.1002/dta.352. Epub 2011 Nov 17. PubMed PMID: 22095651.

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