4-{[4-(acetyloxy)phenyl](cyclohexylidene)methyl}phenyl acetate

• ChemBase ID: 153190
• Molecular Formular: C23H24O4
• Molecular Mass: 364.43426
• Monoisotopic Mass: 364.16745925
• SMILES: CC(=O)Oc1ccc(cc1)C(=C1CCCCC1)c1ccc(cc1)OC(=O)C
• Canonical SMILES: CC(=O)Oc1ccc(cc1)C(=C1CCCCC1)c1ccc(cc1)OC(=O)C
• InChI: InChI=1S/C23H24O4/c1-16(24)26-21-12-8-19(9-13-21)23(18-6-4-3-5-7-18)20-10-14-22(15-11-20)27-17(2)25/h8-15H,3-7H2,1-2H3
• InChIKey: GVOUFPWUYJWQSK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[4-(acetyloxy)phenyl](cyclohexylidene)methyl}phenyl acetate
• IUPAC Traditional name: cyclofenil
• Synonyms: 4,4'-(Cyclohexylidenemethylene)bisphenol 1,1'-Diacetate; 4,4'-(Cyclohexylidenemethylene)diphenol Diacetate Ester; Bis(p-acetoxyphenyl)cyclohexylidenemethane; Cyclofenyl; Cyclopenil; Cyclophenyl; F 6066; Fertodur; H 3452; ICI 48213; NSC 86464; Neoclym; Oginex; Ondogyne; Ondonid; Rehibin; Sanocrisin; Sexadieno; Sexovar; Sexovid; α-(p-Hydroxyphenyl)-α-cyclohexylidene-p-cresol Diacetate; α-Cyclohexylidene-α-(p-hydroxyphenyl)-p-cresol Diacetate; Cyclofenil; 4-(Cyclohexylidenemethylene)-bis-phenol; Cyclofenil; 4,4′-Cyclohexylidenemethylenediphenol

Database IDs

• CAS Number: 2624-43-3
• EC Number: 220-089-1
• MDL Number: MFCD00190153
• PubChem SID: 162247329
• PubChem CID: 2898

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.8576446
• LogD (pH = 7.4): 4.8576446
• Log P: 4.8576446
• Molar Refractivity: 113.5181 cm^3
• Polarizability: 40.758526 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; DMSO: ≥10 mg/mL; Methanol
• Apperance: white solid; White Solid
• Melting Point: 133-135°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: GO7550000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H24O4

DETAILS

Sigma Aldrich - C3490

Biochem/physiol Actions
Cyclofenil is a selective estrogen receptor β antagonist.

Toronto Research Chemicals - C987835

Cyclofenil is a weak nonsteroidal estrogen with ovulation induction properties. Mammalian hormone.

REFERENCES

• Miquel, et al.: J. Med. Chem., 6, 774 (1963)