3,5-bis[(2-fluorophenyl)methylidene]piperidin-4-one hydrochloride

• ChemBase ID: 154506
• Molecular Formular: C19H16ClF2NO
• Molecular Mass: 347.7862464
• Monoisotopic Mass: 347.08884826
• SMILES: c1cc(c(cc1)F)/C=C/1\C(=O)/C(=C\c2c(cccc2)F)/CNC1.Cl
• Canonical SMILES: O=C1/C(=C\c2ccccc2F)/CNC/C/1=C/c1ccccc1F.Cl
• InChI: InChI=1S/C19H15F2NO.ClH/c20-17-7-3-1-5-13(17)9-15-11-22-12-16(19(15)23)10-14-6-2-4-8-18(14)21;/h1-10,22H,11-12H2;1H
• InChIKey: ILMJCEBAMHGBAA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-bis[(2-fluorophenyl)methylidene]piperidin-4-one hydrochloride
• IUPAC Traditional name: 3,5-bis[(2-fluorophenyl)methylidene]piperidin-4-one hydrochloride
• Synonyms: (3E,5E)-3,5-bis[(2-fluorophenyl)methylene]-4-piperidinone; EF-24

Database IDs

• CAS Number: 342808-40-6
• PubChem SID: 162248645
• PubChem CID: 71311883

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.3290873
• LogD (pH = 7.4): 4.151803
• Log P: 4.184382
• Molar Refractivity: 87.8944 cm^3
• Polarizability: 32.650917 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: yellow powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-50
• Safety Statements: 61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H15F2NO

DETAILS

Sigma Aldrich - E8409

Biochem/physiol Actions
EF-24 is a IKK inhibitor and curcumin analog. EF-24 is more potent and bioavailable than curcumin, with 10-fold greater potency in cell death induction. It is also more efficacious in anti-cancer screens and less toxic than Cisplatin. EF-24 inhibits HIF-1alpha posttranscriptional activity and induces microtubule stabilization, in contrast to Curcumin. EF-24 up-regulates PTEN expression via inhibition of ubiquitination. EF-24 induces cell death through direct inhibition of IkappaB kinase (IKK), resulting in suppression in NFκB activity.