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α-Zearalenol

Names

[ CAS No. ]:
36455-72-8

[ Name ]:
α-Zearalenol

[Synonym ]:
(3S,7R,11E)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one
1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S,7R,11E)-
trans-Zearalenol
α zearalenol
2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone
P-1496
cis-Zearalenol
Zearalenol
a-Zearalenol
α-zearalenol

Biological Activity

[Description]:

α-Zearalenol is a Mycotoxin with high affinity for the estrogen receptors (ER),α-Zearalenol is the derivative of zearalenone (ZEN), causes reproductive disorders in animals, due to its xenoestrogenic effects[1].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR
Research Areas >> Inflammation/Immunology

[In Vitro]

α-Zearalenol (α-zol) (0.001-10 μM; 24-72 hours) shows the highest RPE (90.5%) at 9.37 µM α-ZOL exposure in MFC-7 cells with an IC50 of 12.5 μM[1]. α-Zearalenol (α-zol) (0.001-10 μM; 24-72 hours) induces an increase of cell viability on MCF-7 cells mainly after 72 h of treatment whereas it is slightly cytotoxic on MDA-MB231 cells[2]. α-Zearalenol (α-zol) (0.001-10 μM; 24-72 hours) increases MCF7 cell population in the S phase and in the G2/M phase, no visible change in cell cycle phases is observed in MDA-MB231 cells[2]. α-Zearalenol (α-zol) (1-10 μM; 24 hours) reduces the expression of TNF-α, α-ZOL combines with β-ZOL shows an antagonistic effect on inflammation for IL-1β and act synergic for IL-8 at high toxin concentrations[2]. Cell Proliferation Assay[1] Cell Line: MFC-7 cells Concentration: 6.25 µM-25 µM Incubation Time: 24 hours Result: Observed the highest RPE (90.5%) at 9.37 µM α-ZOL exposure in MFC-7 cells. Cell Viability Assay[2] Cell Line: Breast cancer cell lines: MCF-7 and MDA-MB231 Concentration: 0.001 μM, 0.1 μM and 10 μM Incubation Time: 24 hours, 48 hours, 72 hours Result: Modified the cell growth in two breast cancer cell lines. Cell Cycle Analysis[2] Cell Line: MCF7 cells, MDA-MB231 cells Concentration: 0.001 μM, 0.1 μM and 10 μM Incubation Time: 72 hours Result: Observed an increase of cells in cell cycle in MCF7 cells. RT-PCR[2] Cell Line: HepG2 cells Concentration: 1 μM, 5 μM, 10 μM Incubation Time: 72 hours Result: Induced a decrease of the expression of TNF-α, IL-1β and IL-8, that was in most cases statistically significant for the higher doses.

[References]

[1]. .Tatay E, et al. Estrogenic activity of zearalenone, α-zearalenol and β-zearalenol assessed using the E-screen assay in MCF-7 cells. Toxicol Mech Methods. 2018 May;28(4):239-242.

[2]. Marin DE, et al. Cytotoxic and inflammatory effects of individual and combined exposure of HepG2 cells to zearalenone and its metabolites. Naunyn Schmiedebergs Arch Pharmacol. 2019 Aug;392(8):937-947.

[3]. Nittoli AC, et al. Effects of α-zearalenol on the metabolome of two breast cancer cell lines by 1H-NMR approach. Metabolomics. 2018 Feb 14;14(3):33.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
599.0±50.0 °C at 760 mmHg

[ Melting Point ]:
158-161°C

[ Molecular Formula ]:
C18H24O5

[ Molecular Weight ]:
320.380

[ Flash Point ]:
217.9±23.6 °C

[ Exact Mass ]:
320.162384

[ PSA ]:
86.99000

[ LogP ]:
4.17

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.549

[ Storage condition ]:
2-8°C

MSDS

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H319-H336-H340-H350-H361fd-H371-H373-H412

[ Precautionary Statements ]:
P201-P260-P280-P301 + P312 + P330-P305 + P351 + P338-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/21/22-40-52/53-68/20/21/22-36-11-62-48/20-63-46-45

[ Safety Phrases ]:
36/37-61-16-45-53

[ RIDADR ]:
UN 1648 3 / PGII

[ WGK Germany ]:
3

Synthetic Route

Precursor & DownStream


Related Compounds

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