(3S)-14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione

• ChemBase ID: 134209
• Molecular Formular: C18H22O5
• Molecular Mass: 318.36428
• Monoisotopic Mass: 318.1467238
• SMILES: C[C@H]1CCCC(=O)CCC/C=C\c2cc(cc(c2C(=O)O1)O)O
• Canonical SMILES: C[C@H]1CCCC(=O)CCC/C=C\c2c(C(=O)O1)c(O)cc(c2)O
• InChI: InChI=1S/C18H22O5/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/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3-/t12-/m0/s1
• InChIKey: MBMQEIFVQACCCH-MIBUCLJRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione
• IUPAC Traditional name: (-)-zearalenone
• Synonyms: F-2 toxin; Zearalenone; 玉米烯酮

Database IDs

• CAS Number: 17924-92-4
• MDL Number: MFCD00133085
• Beilstein Number: 1350216
• PubChem SID: 162228486; 24902175
• PubChem CID: 12445020

CALCULATED PROPERTIES

• Acid pKa: 8.5377245
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.3737707
• LogD (pH = 7.4): 4.3438344
• Log P: 4.3741655
• Molar Refractivity: 88.3395 cm^3
• Polarizability: 33.566185 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 1759
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 63-34-62
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H361
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• RID/ADR: UN 1759 8/PG 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: mouse ... Esr1(13982)

Product Information

• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - Z2125

Biochem/physiol Actions
Zearalenone, a fungal mycotoxin produced by Fusarium, binds the estrogen receptor (ER) and is uterotropic in the newborn rat. It is a common contaminant in cereal grain used for animal and human food, and exerts an estrogenic activity that modulates/disrupts endocrine function in animals and possibly humans.1