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

• ChemBase ID: 119062
• Molecular Formular: C18H22O5
• Molecular Mass: 318.36428
• Monoisotopic Mass: 318.1467238
• SMILES: C1(=O)c2c(cc(cc2O)O)/C=C/CCCC(=O)CCC[C@@H](O1)C
• 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-QBODLPLBSA-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: (S,E)-14,16-dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-benzo[c][1]oxacyclotetradecine-1,7(8H)-dione; F-2 toxin; Zearalenone; ZON; Zearalenone solution; (3S,11E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione; (-)-Zearalenone; Mycotoxin F 2; Toxin F2; Zenone; trans-Zearalenone; FES; Mycotoxin F2; Zearalenone; 玉米烯酮; 玉米烯酮 溶液

Database IDs

• CAS Number: 17924-92-4
• EC Number: 200-835-2
• MDL Number: MFCD00133085
• Beilstein Number: 1350216
• PubChem SID: 162102968; 24860918
• PubChem CID: 5281576
• CHEBI ID: 10106
• CHEMBL: 454173
• Chemspider ID: 4444897
• KEGG ID: C09981
• Wikipedia Title: Zearalenone

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

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 164-165°C
• Flash Point: 2 °C; 35.6 °F

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: DM2550000
• European Hazard Symbols: Corrosive (C); Flammable (F); Harmful (Xn)
• UN Number: 1648; 3261
• German water hazard class: 2; 3
• Hazard Class: 3; 8
• Packing Group: 2
• Risk Statements: 11-20/21/22-36; 63-34-62
• Safety Statements: 16-36/37; 26-36/37/39-45
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H319-H332; H314-H361
• GHS Precautionary statements: P210-P280-P305 + P351 + P338; P280-P305 + P351 + P338-P310
• 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; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1648 3/PG 2; UN 3261 8/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

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

Product Information

• Purity: ≥98.0% (TLC)
• Concentration: 100 μg/mL in acetonitrile
• Grade: analytical standard, for environmental analysis
• Empirical Formula (Hill Notation): C18H22O5
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 34126

General description
Certan Vial

Sigma Aldrich - 96093

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

Toronto Research Chemicals - Z270500

Estrogenic mycotoxin produced by Fusarium fungi commonly found in grains. One of a group of compounds known as resorcylic acid lactones.

REFERENCES

• Tanaka, T., et al.: J. Agric. Food Chem., 36, 979 (1988)
• Hamilton, S., et al.: Anticancer Res., 16, 3597 (1988)
• Hecht, S., et al.: Cancer Lett., 150, 49 (1988)
• Hussein, H., et al.: Toxicology, 167, 101 (1988)
• Lim, H., et al.: J. Immunol., 175, 4180 (2