Zearalanone
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04085 |
| CAS | 5975-78-0 |
| Molecular Weight | 320.38 |
| Molecular Formula | C18H24O5 |
| Purity | >99% by HPLC |
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Description
A minor component of the zearalenone complex produced by several species of fusarium. Zearalanone is an estrogen receptor agonist (EC50 = 0.11 µM).
Specification
| Synonyms | (S)-Zearalanone; P 1502; Zanone |
| Storage | Store at -20°C |
| IUPAC Name | (4S)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-triene-2,8-dione |
| Canonical SMILES | CC1CCCC(=O)CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1 |
| InChI | InChI=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 |
| InChI Key | APJDQUGPCJRQRJ-LBPRGKRZSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Boiling Point | 576.8°C at 760 mmHg |
| Melting Point | 184-186°C |
| Density | 1.148 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. 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
Yongjiang Wu, Zengxuan Cai, Hailong Zhou, Zheng Han, Yiping Ren, Lianjun Luan J Chromatogr B Analyt Technol Biomed Life Sci . 2011 Feb 15;879(5-6):411-20. doi: 10.1016/j.jchromb.2010.12.028.
A rapid and reliable ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method for simultaneous determination of zearalenone (ZEN), α-zearalenol (α-ZOL), β-zearalenol (β-ZOL), zearalanone (ZAN), α-zearalanol (α-ZAL) and β-zearalanol (β-ZAL) in traditional Chinese medicines (TCMs) was developed. The development of the method and investigations of the matrix influence were described in particular. After evaluation of the matrix effects of different TCMs, i.e., rhizomes and roots, seeds, flowers, grasses and leaves, by the post-extraction spiked method, a reliable sample clean-up method based on home-made clean-up cartridges, a suitable internal standard and the matrix calibration were combined using to minimize the matrix effects to ensure the accuracy of the method. The established method was further validated by determining the linearity (R(2)≥0.9990), sensitivity (limit of quantitation 0.11-0.99 ng mL(-1)), average recovery (86.6-113.5%) and precision (relative standard deviation ≤13.5%). It was shown to be a suitable method for simultaneous determination of ZEN, α-ZOL, β-ZOL, ZAN, α-ZAL and β-ZAL in different TCMs. Finally, the established method was successfully applied to the determination of the six mycotoxins in various TCMs and the results were presented to provide relevant insights to researchers in TCM analysis.
2. Validation of a UHPLC-MS/MS method for quantification of zearalenone, α-zearalenol, β-zearalenol, α-zearalanol, β-zearalanol and zearalanone in human urine
I Jiménez-Díaz, R Ghali, H Belhassen, J M Molina-Molina, N Olea, A Hedili, H Ghorbel J Chromatogr B Analyt Technol Biomed Life Sci . 2014 Jul 1;962:68-74. doi: 10.1016/j.jchromb.2014.05.019.
Humans can be exposed to mycotoxins through the diet. Evaluation of exposure levels to mycotoxins can be performed by direct determination in urine. The present work proposes a sensitive ultrahigh-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method for the determination of zearalenone (ZON) and its five metabolites (α-zearalenol [α-ZOL], β-zearalenol [β-ZOL], α-zearalanol [zeranol, α-ZAL], β-zearalanol [teranol, β-ZAL] and zearalanone [ZAN]) in human urine samples. The method involves the enzymatic hydrolysis of the samples, extraction of the analytes using liquid-liquid extraction (LLE) with ethyl acetate/formic acid (99:1 v/v) and a cleanup step using hexane, prior to their quantification by UHPLC-MS/MS, using an electrospray ionization (ESI) interface in the negative mode. Zearalenone-d6 (ZON-d6) was used as surrogate. The limits of detection and the limits of quantification ranged from 0.03 to 0.3ngmL(-1) and from 0.1 to 1.0ngmL(-1), respectively. The method was validated using matrix-matched calibration and a spike recovery assay. Recovery rates for spiked samples ranged from 96% to 104%, with relative standard deviations lower than 8.5%. This method was satisfactorily applied to 42 urine samples from Tunisian women for the determination of zearalenone and its five metabolites.
3. Determination of zeranol, taleranol, zearalanone, α-zearalenol, β-zearalenol and zearalenone in urine by LC-MS/MS
Barbara Wozniak, Jan Zmudzki, Iwona Matraszek-Zuchowska Food Addit Contam Part A Chem Anal Control Expo Risk Assess . 2013;30(6):987-94. doi: 10.1080/19440049.2013.787656.
An LC-MS/MS method was developed for the sensitive and selective determination of zeranol, taleranol, zearalanone, α-zearalenol, β-zearalenol and zearalenone in animal urine. Analysis was performed on the free compounds after enzymatic deconjugation. Sample preparation included liquid-liquid extraction followed by solid-phase extraction (SPE) with C18 and NH2 columns. For chromatographic separation of hormones an Inertsil(®) ODS-3 analytical column (150 mm × 2.1 mm, 3 µm) was used. The analytes were determined and identified by LC-MS/MS on a QTRAP5500 instrument with a TurboIon-Spray source operating in negative electrospray ionisation mode. For confirmatory purposes at least two transitions were obtained for each analyte. According to Commission Decision 2002 /657/EC the validation parameters - recovery, repeatability, reproducibility, linearity, specificity, decision limits and detection capabilities - were determined. All parameters were in agreement with 2002/657/EC performance criteria. The apparent recovery ranged from 76.2% to 116.3% for all examined compounds. The repeatability was below 20% and reproducibility did not exceed the limit of 25% for most analytes. Linearity was good for all analytes in the whole range of tested concentrations, as proved by the correlation coefficients greater than 0.99. The decision limits (CCα) ranged from 0.04 to 0.18 μg l(-1) for all analytes whereas the detection capabilities (CCβ) ranged from 0.07 to 0.31 μg l(-1), respectively. All CCα and CCβ values were below the recommended concentration of 2 μg l(-1). This analytical method will be used in an integrated system for Polish monitoring programmes for the confirmation of violative screened samples.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
