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C7870

Sigma-Aldrich

Chalcone 4 hydrate

≥98% (HPLC)

Synonym(s):

(E)-1-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one hydrate

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About This Item

Empirical Formula (Hill Notation):
C16H13ClO3 · xH2O
CAS Number:
1202866-96-3
Molecular Weight:
288.73 (anhydrous basis)
MDL number:
MFCD12912407
UNSPSC Code:
51111800
PubChem Substance ID:
329775154
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

storage condition

protect from light

color

yellow

solubility

DMSO: >20 mg/mL

storage temp.

−20°C

SMILES string

O.COc1cc(ccc1O)\C=C\C(=O)c2ccc(Cl)cc2

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/b8-2+;

InChI key

PXVQKTVKTBMRIW-VOKCZWNHSA-N

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.

Features and Benefits

This compound is featured on the Chemokine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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