(3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one

• ChemBase ID: 156494
• Molecular Formular: C18H24O5
• Molecular Mass: 320.38016
• Monoisotopic Mass: 320.16237387
• SMILES: C[C@H]1CCC[C@@H](CCC/C=C/c2cc(cc(c2C(=O)O1)O)O)O
• Canonical SMILES: O[C@@H]1CCC/C=C/c2cc(O)cc(c2C(=O)O[C@H](CCC1)C)O
• 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/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/t12-,14+/m0/s1
• InChIKey: FPQFYIAXQDXNOR-GXTWGEPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one
• IUPAC Traditional name: zeranol
• Synonyms: 2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone solution; α-Zearalenol solution; 2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone; α-Zearalenol; (3S,7R,11E)-3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one; (-)-α-Zearalenol; Zearalenol; trans-Zearalenol; α-Zearalenol

Database IDs

• CAS Number: 36455-72-8
• MDL Number: MFCD16657008
• PubChem SID: 162250632
• PubChem CID: 5284645

CALCULATED PROPERTIES

• Acid pKa: 8.537725
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.16627
• LogD (pH = 7.4): 4.136334
• Log P: 4.1666646
• Molar Refractivity: 89.3676 cm^3
• Polarizability: 34.10992 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 158-161°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• 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
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Concentration: 10 μg/mL in acetonitrile
• Grade: analytical standard
• Impurities: dichloromethane
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C18H24O5

DETAILS

Toronto Research Chemicals - Z270470

The major metabolites of Zearalenone (Z270500) are α and β-Zearalenol. β-Zearalenol being the more active of the two metabolites.

REFERENCES

• Olsen, M., et al.: Acta Pharmacol. Toxicol., 48, 15 (1981)
• Chang, W., et al.: Food Chem. Toxicol., 22, 887 (1981)
• El Golli, E., et al.: Toxicol Lett., 166, 122 (1981)
• Hassen, W., et al.: Toxicology, 232, 294 (1981)
• Benzoni, E., et al.: Reprod. Toxicol