(3S)-14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecine-1,7-dione

• ChemBase ID: 133648
• Molecular Formular: C18H24O5
• Molecular Mass: 320.38016
• Monoisotopic Mass: 320.16237387
• SMILES: C[C@H]1CCCC(=O)CCCCCc2cc(cc(c2C(=O)O1)O)O
• Canonical SMILES: C[C@H]1CCCC(=O)CCCCCc2c(C(=O)O1)c(O)cc(c2)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/h10-12,20-21H,2-9H2,1H3/t12-/m0/s1
• InChIKey: APJDQUGPCJRQRJ-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecine-1,7-dione
• IUPAC Traditional name: zanone
• Synonyms: (3S)-3,4,5,6,9,10,11,12-Octahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione; 6-(10-hydroxy-6-oxoundecyl)-β-resorcylic Acid μ-Lactone; P 1502; Zanone; Zearalanone; ZAN; (S)-Zearalanone; 2,4-Dihydroxy-6-(10-hydroxy-6-oxoundecyl)benzoic acid μ-lactone; Zearalanone

Database IDs

• CAS Number: 5975-78-0
• MDL Number: MFCD00135821
• PubChem SID: 162227925; 24902160
• PubChem CID: 108003

CALCULATED PROPERTIES

• Acid pKa: 8.677321
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.6531005
• LogD (pH = 7.4): 4.6311846
• Log P: 4.653387
• Molar Refractivity: 87.2229 cm^3
• Polarizability: 33.664333 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 184-186°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-40
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335-H351
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• 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

Pharmacology Properties

• Gene Information: rat ... Ar(24208)

DETAILS

Toronto Research Chemicals - Z270450

A secondary metabolite of Zearalenone (ZON). The macrocyclic lactone Zearalanone used in the synthesis of d,l-Zearalanol.

REFERENCES

• Hurd, R.N., et al.: J. Med. Chem., 16(5)
• 543 (5)
• Baughman, R., et al.: Science, 297, 787 (5)
• Zinedine, A., et al.: Food Chem. Toxicol., 45, 1 (5)
• Chailapakul, O., et al.: Food Chem., 109, 876 (5)