CAS 42422-68-4|b-Zearalanol
| Common Name | b-Zearalanol | ||
|---|---|---|---|
| CAS Number | 42422-68-4 | Molecular Weight | 322.396 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 576.0±50.0 °C at 760 mmHg |
| Molecular Formula | C18H26O5 | Melting Point | 134-137ºC |
| MSDS | ChineseUSA | Flash Point | 207.9±23.6 °C |
| Symbol | GHS07, GHS08 | Signal Word | Danger |
Names
| Name | (7S,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one |
|---|---|
| Synonym | More Synonyms |
b-Zearalanol BiologicalActivity
| Description | Beta-zearalenol is an mycotoxin produced by Fusarium spp, which causes apoptosis and oxidative stress in mammalian reproductive cells[1]. Beta-zearalenol is the derivative of zearalenone (ZEA) which can conjugate with glucuronic acid[2]. |
|---|---|
| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>Metabolic Disease |
| In Vitro | βeta-zearalenol (0-200 μM; 24 hours) inhibits BGC proliferation in a dose-dependent manner, with an IC50 of 25 μM[1]. βeta-Zearalenol (0-100 μM; 72 hours) shows high toxic with an IC50 of 15.2 μM in the HepG2 cells, synergistic effect of β-ZOL+ZEN or β-ZOL+α-ZOL with IC50 values of 19.8 uM, 16.8 uM, respectively[2]. βeta-Zearalenol (0-10 μM; 72 hours) has the highest inhibition effect on the all three investigated cytokines: IL-8, IL-1β and TNF-α by comparation with ZEA or α-Zearalenol[2]. Cell Viability Assay[2] Cell Line: HepG2 cells Concentration: 0–100 μM Incubation Time: 72 hours Result: Shown a dose-dependent reduction of viability of cells treated with β-ZOL. Cell Proliferation Assay[1] Cell Line: BGC cells Concentration: 0 μM, 5 μM, 10 μM, 15 μM, 25 μM, 50 μM, 100 μM, and 200 μM Incubation Time: 24 hours Result: Inhibited cell proliferation in a dose-dependent manner. RT-PCR[2] Cell Line: HepG2 cells Concentration: 1 μM, 5 μM, 10 μM Incubation Time: 72 hours Result: Had the higher cytotoxic effect in comparation with α-Zearalenol. |
| References | [1]. Yang F, et al. Melatonin alleviates β-zearalenol and HT-2 toxin-induced apoptosis and oxidative stress in bovine ovarian granulosa cells. Environ Toxicol Pharmacol. 2019 May;68:52-60. [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. |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 576.0±50.0 °C at 760 mmHg |
| Melting Point | 134-137ºC |
| Molecular Formula | C18H26O5 |
| Molecular Weight | 322.396 |
| Flash Point | 207.9±23.6 °C |
| Exact Mass | 322.178009 |
| PSA | 86.99000 |
| LogP | 3.86 |
| Vapour Pressure | 0.0±1.7 mmHg at 25°C |
| Index of Refraction | 1.536 |
| InChIKey | DWTTZBARDOXEAM-JSGCOSHPSA-N |
| SMILES | CC1CCCC(O)CCCCCc2cc(O)cc(O)c2C(=O)O1 |
| Storage condition | −20°C |
Safety Information
| Symbol | GHS07, GHS08 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H315-H319-H335-H360 |
| Precautionary Statements | P201-P261-P305 + P351 + P338-P308 + P313 |
| Personal Protective Equipment | Eyeshields;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 | T,Xn,F |
| Risk Phrases | 60-36/37/38 |
| Safety Phrases | 53-36/37/39-45 |
| RIDADR | UN 1648 3 / PGII |
| WGK Germany | 3 |
Articles18
More Articles| Determination of resorcylic acid lactones in biological samples by GC-MS. Discrimination between illegal use and contamination with fusarium toxins. Anal. Bioanal. Chem 384(5) , 1221-7, (2006) An EU project, FAIR5-CT-1997-3443, has been undertaken to distinguish illegal use of zeranol from consumption of food contaminated with Fusarium spp. toxin. One of the tasks was development of screeni... | |
| Cytosol protein regulation in H295R steroidogenesis model induced by the zearalenone metabolites, α- and β-zearalenol. Toxicon 59(1) , 17-24, (2012) α- and β-zearalenol (α-ZOL and β-ZOL, respectively) are metabolites of the mycotoxin zearalenone (ZEN). All three individual mycotoxins have shown to be biological active i.e. being estrogenic and abl... | |
| 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. 90(4) , 1197-202, (2007) Immunoaffinity extraction has become increasingly important as a sample preparation and cleanup method in mycotoxin analysis. In this study, the antibody specificities of 3 commercial immunoaffinity c... |
Synonyms
| |A-Zearanol |
| Taleranol |
| (6S,10S)-6-(6,10-Dihydroxyundecyl)-b-resorcyclic acid m-lactone |
| 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-, (3S,7S)- |
| |A-Zearalanol |
| Taleranolum |
| |A-Zeranol |
| (6S,10S)-6-(6,10-Dihydroxyundecyl)-β-resorcyclic acid μ-lactone |
| β-Zearalanol |
| β zearalanol |
| b-Zearalanol |
| (3S,7S)-3,4,5,6,7,8,9 |
| (3S,7S)-3,4,5,6,7,8,9,10,11,12-Decahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one |
| (3S,7S)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one |
| [3S-(3R*,7R*)]-3,4,5,6,7,8,9,10,11,12-Decahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one |
