4-(2-{3-bromo-4-[2-(4-hydroxyphenyl)ethenyl]phenyl}ethenyl)phenol

• ChemBase ID: 153840
• Molecular Formular: C22H17BrO2
• Molecular Mass: 393.27318
• Monoisotopic Mass: 392.04119178
• SMILES: c1cc(ccc1/C=C/c1ccc(c(c1)Br)/C=C/c1ccc(cc1)O)O
• Canonical SMILES: Oc1ccc(cc1)/C=C/c1ccc(c(c1)Br)/C=C/c1ccc(cc1)O
• InChI: InChI=1S/C22H17BrO2/c23-22-15-18(2-1-16-5-11-20(24)12-6-16)4-10-19(22)9-3-17-7-13-21(25)14-8-17/h1-15,24-25H
• InChIKey: OXPHQQMZTXMEGO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{3-bromo-4-[2-(4-hydroxyphenyl)ethenyl]phenyl}ethenyl)phenol
• IUPAC Traditional name: 4-(2-{3-bromo-4-[2-(4-hydroxyphenyl)ethenyl]phenyl}ethenyl)phenol
• Synonyms: (trans,trans)-1-bromo-2,5-bis-(4-hydroxy)styrylbenzene; K114

Database IDs

• CAS Number: 872201-12-2
• MDL Number: MFCD11045294
• PubChem SID: 162247979
• PubChem CID: 44828481

CALCULATED PROPERTIES

• Acid pKa: 9.19461
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 6.8144627
• LogD (pH = 7.4): 6.807649
• Log P: 6.81455
• Molar Refractivity: 108.5522 cm^3
• Polarizability: 40.545856 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble >10 mg/mL
• Apperance: white to beige powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H413
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H17BrO2

DETAILS

Sigma Aldrich - K1015

Biochem/physiol Actions
K114 is a fluorescent, amyloid-specific dye, an analogue of Congo Red and BSB that recognizes amyloid lesions and allows the quantitative monitoring of the formation of amyloid fibrils assembled from the Aβ peptide, α-synuclein, and tau. The affinity for fibrils ranges 20-30 nM. Unlike the other compounds K114 has minimal fluorescence in aqueous buffers, but fluoresces brightly in the presence of amyloid fibrils. K114 can be used to monitor in vitro amyloid fibril formation by fluorescence emission at 550 nm.