Zearalanone | CAS#5975-78-0 | mycotoxin

MedKoo Cat#: 146206 | Name: Zearalanone

Description:

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

Zearalanone is a non-steroidal estrogenic mycotoxin derived from zearalenone, produced by certain Fusarium species that contaminate grains and cereals. It mimics the structure and activity of natural estrogens, binding to estrogen receptors and disrupting endocrine functions in animals and humans. This compound is primarily studied for its effects on reproductive systems and has been used experimentally to promote growth in livestock, though its use is restricted due to health concerns. Zearalanone's mechanism centers on its high affinity for estrogen receptors, leading to altered gene expression and hormonal imbalances.

Chemical Structure

Zearalanone

CAS#5975-78-0

Theoretical Analysis

MedKoo Cat#: 146206

Name: Zearalanone

CAS#: 5975-78-0

Chemical Formula: C18H24O5

Exact Mass: 320.1624

Molecular Weight: 320.39

Elemental Analysis: C, 67.48; H, 7.55; O, 24.97

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Zearalanone; Zanone;

IUPAC/Chemical Name

(S)-14,16-dihydroxy-3-methyl-3,4,5,6,9,10,11,12-octahydro-1H-benzo[c][1]oxacyclotetradecine-1,7(8H)-dione

InChi Key

APJDQUGPCJRQRJ-LBPRGKRZSA-N

InChi Code

1S/C18H24O5/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/h10-12,20-21H,2-9H2,1H3/t12-/m0/s1

SMILES Code

C[C@H]1CCCC(=O)CCCCCC2=CC(O)=CC(O)=C2C(=O)O1

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 320.39 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.

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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PMID: 39255344. 4: Balasubramanian S, Gunasekaran K, Sasidharan S, Jeyamanickavel Mathan V, Perumal E. MicroRNAs and Xenobiotic Toxicity: An Overview. Toxicol Rep. 2020 May 4;7:583-595. doi: 10.1016/j.toxrep.2020.04.010. PMID: 32426239; PMCID: PMC7225592. 5: Drzymala S, Kraus W, Emmerling F, Koch M. (3S)-14,16-Dihy- droxy-3-methyl-3,4,5,6,9,10,11,12-octa-hydro-1H-2-benzoxacyclo-tetra- decine-1,7(8H)-dione (zearalanone) monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2012 May 1;68(Pt 5):o1577. doi: 10.1107/S1600536812018168. Epub 2012 Apr 28. PMID: 22590434; PMCID: PMC3344672. 6: Aoyama K, Ishikuro E, Noriduki H, Ichinoe M. Formation Ratios of Zearalanone, Zearalenols, and Zearalanols versus Zearalenone during Incubation of Fusarium semitectum on Sorghum and Ratios in Naturally Contaminated Sorghum. Shokuhin Eiseigaku Zasshi. 2015;56(6):247-51. doi: 10.3358/shokueishi.56.247. PMID: 26699272. 7: Hurd RN, Shah DH. Total synthesis of the macrolide, (R,S)-zearalanone. J Med Chem. 1973 May;16(5):543-5. doi: 10.1021/jm00263a030. PMID: 4718472. 8: Martin PM, Keen P. The occurrence of zearalanone in raw and fermented products from Swaziland and Lesotho. Sabouraudia. 1978 Mar;16(1):15-22. doi: 10.1080/00362177885380031. PMID: 635723. 9: Belhassen H, Jiménez-Díaz I, Ghali R, Ghorbel H, Molina-Molina JM, Olea N, Hedili A. Validation of a UHPLC-MS/MS method for quantification of zearalenone, α-zearalenol, β-zearalenol, α-zearalanol, β-zearalanol and zearalanone in human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jul 1;962:68-74. doi: 10.1016/j.jchromb.2014.05.019. Epub 2014 May 19. PMID: 24907545. 10: 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. PMID: 23705928. 11: Feng M, Liu S, Gao Y, Zhou S, Guo Z, Li X, Zhang Q. [Qualitative identification of impurities and principal component quantitative analysis of zearalanone on purity certified reference material]. Se Pu. 2019 Aug 8;37(8):911-917. Chinese. doi: 10.3724/SP.J.1123.2019.04028. PMID: 31642263. 12: Han Z, Ren Y, Zhou H, Luan L, Cai Z, Wu Y. A rapid method for simultaneous determination of zearalenone, α-zearalenol, β-zearalenol, zearalanone, α-zearalanol and β-zearalanol in traditional Chinese medicines by ultra-high- performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Feb 15;879(5-6):411-20. doi: 10.1016/j.jchromb.2010.12.028. Epub 2010 Dec 31. PMID: 21242113. 13: Liu J, Applegate T. Zearalenone (ZEN) in Livestock and Poultry: Dose, Toxicokinetics, Toxicity and Estrogenicity. Toxins (Basel). 2020 Jun 7;12(6):377. doi: 10.3390/toxins12060377. PMID: 32517357; PMCID: PMC7354539. 14: Peters CA, Hurd RN. A stereoselective synthetic route to (R)-zearalanone. J Med Chem. 1975 Feb;18(2):215-7. doi: 10.1021/jm00236a026. PMID: 1120992. 15: Shipchandler MT. Allyl derivatives of zearalenone. J Pharm Sci. 1980 Sep;69(9):1017-8. doi: 10.1002/jps.2600690909. PMID: 6447777. 16: Erbs M, Hartmann N, Bucheli TD. Determination of the cross-reactivities for alpha-zearalenol, beta-zearalenol, zearalanone, alpha-zearalanol, and beta- zearalanol on three commercial immunoaffinity columns targeting zearalenone. J AOAC Int. 2007 Jul-Aug;90(4):1197-202. PMID: 17760358. 17: Mohos V, Faisal Z, Fliszár-Nyúl E, Szente L, Poór M. Testing the extraction of 12 mycotoxins from aqueous solutions by insoluble beta-cyclodextrin bead polymer. Environ Sci Pollut Res Int. 2022 Jan;29(1):210-221. doi: 10.1007/s11356-021-15628-1. Epub 2021 Jul 28. PMID: 34322792; PMCID: PMC8724181. 18: Bories GF, Perdu-Durand EF, Sutra JF, Tulliez JE. Evidence for glucuronidation and sulfation of zeranol and metabolites (taleranol and zearalanone) by rat and pig hepatic subfractions. Drug Metab Dispos. 1991 Jan- Feb;19(1):140-3. PMID: 1673387. 19: Llorens Castelló P, Sacco MA, Aquila I, Moltó Cortés JC, Juan García C. Evaluation of Zearalenones and Their Metabolites in Chicken, Pig and Lamb Liver Samples. Toxins (Basel). 2022 Nov 11;14(11):782. doi: 10.3390/toxins14110782. PMID: 36422956; PMCID: PMC9692590. 20: Falkauskas R, Bakutis B, Jovaišienė J, Vaičiulienė G, Gerulis G, Kerzienė S, Jacevičienė I, Jacevičius E, Baliukonienė V. Zearalenone and Its Metabolites in Blood Serum, Urine, and Milk of Dairy Cows. Animals (Basel). 2022 Jun 27;12(13):1651. doi: 10.3390/ani12131651. PMID: 35804550; PMCID: PMC9264949.