3-(2,4-dichlorophenyl)-7-hydroxy-4H-chromen-4-one

• ChemBase ID: 154354
• Molecular Formular: C15H8Cl2O3
• Molecular Mass: 307.12822
• Monoisotopic Mass: 305.98504948
• SMILES: c1cc2c(cc1O)occ(c2=O)c1ccc(cc1Cl)Cl
• Canonical SMILES: Clc1ccc(c(c1)Cl)c1coc2c(c1=O)ccc(c2)O
• InChI: InChI=1S/C15H8Cl2O3/c16-8-1-3-10(13(17)5-8)12-7-20-14-6-9(18)2-4-11(14)15(12)19/h1-7,18H
• InChIKey: QMSGNLMBWFRALO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2,4-dichlorophenyl)-7-hydroxy-4H-chromen-4-one
• IUPAC Traditional name: 3-(2,4-dichlorophenyl)-7-hydroxychromen-4-one
• Synonyms: 3-(2,4-Dichlorophenyl)-7-hydroxy-4H-chromen-4-one; DCHC

Database IDs

• CAS Number: 302953-06-6
• MDL Number: MFCD01848896
• PubChem SID: 162248493
• PubChem CID: 5397220

CALCULATED PROPERTIES

• Acid pKa: 6.4748917
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.198676
• LogD (pH = 7.4): 3.292925
• Log P: 4.2420926
• Molar Refractivity: 77.3307 cm^3
• Polarizability: 29.663162 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: yellow solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H8Cl2O3

DETAILS

Sigma Aldrich - D5569

Biochem/physiol Actions
DCHC is a SIRT1 activator. It increases peroxisome proliferator-activated receptor gamma co-activator 1α (PGC1α) expression, resulting in mitochondrial biogenesis. DCHC activates SIRT1 at low micromolar concentrations (5-10 μM) and increases SIRT1 activity at 100 μM. It is different from 5,7,4′-T in that it induces the activation of recombinant SIRT1, but does not increase SIRT1 expression.