(6E)-6-(bromomethylidene)-3-(naphthalen-1-yl)oxan-2-one

• ChemBase ID: 134403
• Molecular Formular: C16H13BrO2
• Molecular Mass: 317.17722
• Monoisotopic Mass: 316.00989166
• SMILES: c1ccc2c(c1)cccc2C1CC/C(=C\Br)/OC1=O
• Canonical SMILES: Br/C=C/1\CCC(C(=O)O1)c1cccc2c1cccc2
• InChI: InChI=1S/C16H13BrO2/c17-10-12-8-9-15(16(18)19-12)14-7-3-5-11-4-1-2-6-13(11)14/h1-7,10,15H,8-9H2/b12-10+
• InChIKey: BYUCSFWXCMTYOI-ZRDIBKRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6E)-6-(bromomethylidene)-3-(naphthalen-1-yl)oxan-2-one
• IUPAC Traditional name: (6E)-6-(bromomethylidene)-3-(naphthalen-1-yl)oxan-2-one
• Synonyms: BEL; E-6-(Bromoethylene)tetrahydro-3-(1-naphthyl)-2H-pyran-2-one; Bromoenol lactone

Database IDs

• CAS Number: 88070-98-8
• MDL Number: MFCD00270871
• PubChem SID: 162228679; 24278257
• PubChem CID: 5940264

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.9624982
• LogD (pH = 7.4): 3.9624982
• Log P: 3.9624982
• Molar Refractivity: 78.4111 cm^3
• Polarizability: 31.255398 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: degassed ethanol: soluble (Dilute in aqueous medium immediately prior to use and store on ice for no more than 12 hours.); DMSO: soluble (Dilute in aqueous medium immediately prior to use and store on ice for no more than 12 hours.)
• Absorption Wavelength: λmax 224 nm

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - B1552

Biochem/physiol Actions
Potent, irreversible inhibitor of calcium-independent phospholipase A2 and of magnesium-dependent phosphatidate phosphohydrolase from P388D macrophages (IC50 = 8 μM); enzyme activated irreversible chymotrypsin inhibitor (Ki = 636 nM).