1-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one hydrate

• ChemBase ID: 154280
• Molecular Formular: C16H15ClO4
• Molecular Mass: 306.7409
• Monoisotopic Mass: 306.06588664
• SMILES: COc1cc(ccc1O)/C=C/C(=O)c1ccc(cc1)Cl.O
• Canonical SMILES: COc1cc(/C=C/C(=O)c2ccc(cc2)Cl)ccc1O.O
• InChI: InChI=1S/C16H13ClO3.H2O/c1-20-16-10-11(3-9-15(16)19)2-8-14(18)12-4-6-13(17)7-5-12;/h2-10,19H,1H3;1H2
• InChIKey: PXVQKTVKTBMRIW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one hydrate
• IUPAC Traditional name: 1-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one hydrate
• Synonyms: (E)-1-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one hydrate; Chalcone 4 hydrate

Database IDs

• CAS Number: 1202866-96-3
• MDL Number: MFCD12912407
• PubChem SID: 162248419
• PubChem CID: 71311831

CALCULATED PROPERTIES

• Acid pKa: 9.503661
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.0330906
• LogD (pH = 7.4): 4.0297484
• Log P: 4.0331335
• Molar Refractivity: 80.1259 cm^3
• Polarizability: 30.319565 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: protect from light
• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H13ClO3 · xH2O

DETAILS

Sigma Aldrich - C7870

Biochem/physiol Actions
Chalcone 4 is a potent, selective inhibitor of the chemokine CXCL12 via direct binding. It is also a small molecule anti-ligand (or neutraligand) of CXCR4 and CXCR7. The chemokine CXCL12 (stromal cell-derived factor-1) and its receptors play pivotal roles in inflammatory responses, normal vascular and neuronal development, as well as in infectious diseases and cancer. Chalcone 4 binds to and activates the chemokine receptors CXCR4 and CXCR7 and stimulates a rapid receptor-mediated intracellular calcium mobilization and signaling through a Pertussis toxin sensitive Gi protein. Chalcone 4 potently and selectively inhibits CXCL12 binding to CXCR4 and CXCR7, and consequent CXCL12-evoked calcium cellular responses. Chalcone 4 binds to the chemokine CXCL12, but not to its receptors.