beta-Zearalanol
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| Category | Others |
| Catalog number | BBF-04351 |
| CAS | 42422-68-4 |
| Molecular Weight | 322.40 |
| Molecular Formula | C18H26O5 |
| Purity | >99% by HPLC |
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Description
It is a minor analogue of the zearalenone family of resorcinyl macrocyclic lactones produced by several species of fusarium. It exhibits estrogenic activity in animals and is a growth promotant for animals.
Specification
| Synonyms | Taleranol; β-Zearanol; β-Zeranol; 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7R*))-; P 1560 |
| Storage | Store at -20°C |
| IUPAC Name | (4S,8S)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-2-one |
| Canonical SMILES | CC1CCCC(CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O |
| InChI | 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 |
| InChI Key | DWTTZBARDOXEAM-JSGCOSHPSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Boiling Point | 576°C at 760 mmHg |
| Melting Point | 134-137°C |
| Density | 1.153 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Testing the extraction of 12 mycotoxins from aqueous solutions by insoluble beta-cyclodextrin bead polymer
Violetta Mohos, Zelma Faisal, Miklós Poór, Eszter Fliszár-Nyúl, Lajos Szente Environ Sci Pollut Res Int . 2022 Jan;29(1):210-221. doi: 10.1007/s11356-021-15628-1.
Mycotoxins are toxic metabolites of filamentous fungi; they are common contaminants in numerous foods and beverages. Cyclodextrins are ring-shaped oligosaccharides, which can form host-guest type complexes with certain mycotoxins. Insoluble beta-cyclodextrin bead polymer (BBP) extracted successfully some mycotoxins (e.g., alternariol and zearalenone) from aqueous solutions, including beverages. Therefore, in this study, we aimed to examine the ability of BBP to remove other 12 mycotoxins (including aflatoxin B1, aflatoxin M1, citrinin, dihydrocitrinone, cyclopiazonic acid, deoxynivalenol, ochratoxin A, patulin, sterigmatocystin, zearalanone, α-zearalanol, and β-zearalanol) from different buffers (pH 3.0, 5.0, and 7.0). Our results showed that BBP can effectively extract citrinin, dihydrocitrinone, sterigmatocystin, zearalanone, α-zearalanol, and β-zearalanol at each pH tested. However, for the removal of ochratoxin A, BBP was far the most effective at pH 3.0. Based on these observations, BBP may be a suitable mycotoxin binder to extract certain mycotoxins from aqueous solutions for decontamination and/or for analytical purposes.
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. Development and validation of a screening method for DES, zeranol, and beta-zearalanol in bovine urine by HRGC-MS and evaluation of robustness for routine survey of the Brazilian herd
L A Lima, F R Neto, J N Cardoso, M A Marques, C H Bizarri J Anal Toxicol . 1998 Sep;22(5):367-73. doi: 10.1093/jat/22.5.367.
A method and evaluated for screening and confirmation of diethylstilbestrol (DES), alpha- and beta-zearalanol in bovine urine was developed. The residues were extracted from urine by C18 cartridges and purified on alumina columns. For screening and confirmation purposes, the anabolic derivatives were analyzed by gas chromatography-mass spectrometry after derivatization with BSTFA + 1% TMCS or a solution of PFPA/acetone (1:2, v/v), respectively. The recovery of most analytes for the whole procedure was higher than 96%, with a detection limit of 0.5 ppb. This procedure is being routinely applied to the Brazilian National Program for the Control of Residues in Meat (PNCRBC).
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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 ╳
