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4-(Dimethylamino)cinnamic acid

CAS# 1552-96-1

4-(Dimethylamino)cinnamic acid

2D Structure

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3D structure

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4-(Dimethylamino)cinnamic acid

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Chemical Properties of 4-(Dimethylamino)cinnamic acid

Cas No. 1552-96-1 SDF Download SDF
PubChem ID 1540638 Appearance White cryst.
Formula C11H13NO2 M.Wt 191.23
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (E)-3-[4-(dimethylamino)phenyl]prop-2-enoic acid
SMILES CN(C)C1=CC=C(C=C1)C=CC(=O)O
Standard InChIKey CQNPVMCASGWEHM-VMPITWQZSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 4-(Dimethylamino)cinnamic acid

The barks of Cinnamomum cassia Presl

Biological Activity of 4-(Dimethylamino)cinnamic acid

Description4-(Dimethylamino)cinnamic acid (DMACA) could be as charge transfer (ICT) probe.
In vitro

Interaction of cinnamic acid derivatives with serum albumins: a fluorescence spectroscopic study.[Pubmed: 21247795]

Spectrochim Acta A Mol Biomol Spectrosc. 2011 Mar;78(3):942-8.

Cinnamic acid (CA) derivatives are known to possess broad therapeutic applications including anti-tumor activity. The present study was designed to determine the underlying mechanism and thermodynamic parameters for the binding of two CA based intramolecular charge transfer (ICT) fluorescent probes, namely, 4-(dimethylamino) cinnamic acid (DMACA) and trans-ethyl p-(dimethylamino) cinnamate (EDAC), with albumins by fluorescence spectroscopy.
METHODS AND RESULTS:
Stern-Volmer analysis of the tryptophan fluorescence quenching data in presence of the added ligand reveals fluorescence quenching constant (κ(q)), Stern-Volmer constant (K(SV)) and also the ligand-protein association constant (K(a)). The thermodynamic parameters like enthalpy (ΔH) and entropy (ΔS) change corresponding to the ligand binding process were also estimated. The results show that the ligands bind into the sub-domain IIA of the proteins in 1:1 stoichiometry with an apparent binding constant value in the range of 10(4) dm(3) mol(-1).
CONCLUSIONS:
In both the cases, the spontaneous ligand binding to the proteins occur through entropy driven mechanism, although the interaction of DMACA is relatively stronger in comparison with EDAC. The temperature dependence of the binding constant indicates the induced change in protein secondary structure.

Protocol of 4-(Dimethylamino)cinnamic acid

Structure Identification
Photochem Photobiol Sci. 2008 Sep;7(9):1063-70.

Fluorimetric studies on the binding of 4-(dimethylamino)cinnamic acid with micelles and bovine serum albumin.[Pubmed: 18754053]

The constrained photophysics of intramolecular charge transfer (ICT) probe 4-(Dimethylamino)cinnamic acid (DMACA) was studied in different surfactant systems as well as in presence of model water soluble protein bovine serum albumin (BSA).
METHODS AND RESULTS:
Binding of the probe in ionic micelles like sodium dodecyl sulfate (SDS) and cetyl trimethyl ammonium bromide (CTAB) causes an increase in ICT fluorescence intensity, whereas, in non-ionic TritonX-100 (TX-100) the intensity decreases with a concomitant increase in emission from locally excited (LE) state. The observations were explained in terms of the different binding affinity, location of the probe and also the nature of specific hydrogen bonding interaction in the excited state nonradiative relaxation process of DMACA. The ICT fluorescence emission yield decreases in BSA due to the locking in of the probe buried in the hydrophobic pocket of the protein structure. SDS induced uncoiling of protein and massive cooperative binding between BSA and SDS is manifested by the release of probe molecules in relatively free aqueous environment.

4-(Dimethylamino)cinnamic acid Dilution Calculator

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Preparing Stock Solutions of 4-(Dimethylamino)cinnamic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.2293 mL 26.1465 mL 52.2931 mL 104.5861 mL 130.7326 mL
5 mM 1.0459 mL 5.2293 mL 10.4586 mL 20.9172 mL 26.1465 mL
10 mM 0.5229 mL 2.6147 mL 5.2293 mL 10.4586 mL 13.0733 mL
50 mM 0.1046 mL 0.5229 mL 1.0459 mL 2.0917 mL 2.6147 mL
100 mM 0.0523 mL 0.2615 mL 0.5229 mL 1.0459 mL 1.3073 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 4-(Dimethylamino)cinnamic acid

Interaction of cinnamic acid derivatives with serum albumins: a fluorescence spectroscopic study.[Pubmed:21247795]

Spectrochim Acta A Mol Biomol Spectrosc. 2011 Mar;78(3):942-8.

Cinnamic acid (CA) derivatives are known to possess broad therapeutic applications including anti-tumor activity. The present study was designed to determine the underlying mechanism and thermodynamic parameters for the binding of two CA based intramolecular charge transfer (ICT) fluorescent probes, namely, 4-(dimethylamino) cinnamic acid (DMACA) and trans-ethyl p-(dimethylamino) cinnamate (EDAC), with albumins by fluorescence spectroscopy. Stern-Volmer analysis of the tryptophan fluorescence quenching data in presence of the added ligand reveals fluorescence quenching constant (kappa(q)), Stern-Volmer constant (K(SV)) and also the ligand-protein association constant (K(a)). The thermodynamic parameters like enthalpy (DeltaH) and entropy (DeltaS) change corresponding to the ligand binding process were also estimated. The results show that the ligands bind into the sub-domain IIA of the proteins in 1:1 stoichiometry with an apparent binding constant value in the range of 10(4) dm(3) mol(-1). In both the cases, the spontaneous ligand binding to the proteins occur through entropy driven mechanism, although the interaction of DMACA is relatively stronger in comparison with EDAC. The temperature dependence of the binding constant indicates the induced change in protein secondary structure.

Fluorimetric studies on the binding of 4-(dimethylamino)cinnamic acid with micelles and bovine serum albumin.[Pubmed:18754053]

Photochem Photobiol Sci. 2008 Sep;7(9):1063-70.

The constrained photophysics of intramolecular charge transfer (ICT) probe 4-(Dimethylamino)cinnamic acid (DMACA) was studied in different surfactant systems as well as in presence of model water soluble protein bovine serum albumin (BSA). Binding of the probe in ionic micelles like sodium dodecyl sulfate (SDS) and cetyl trimethyl ammonium bromide (CTAB) causes an increase in ICT fluorescence intensity, whereas, in non-ionic TritonX-100 (TX-100) the intensity decreases with a concomitant increase in emission from locally excited (LE) state. The observations were explained in terms of the different binding affinity, location of the probe and also the nature of specific hydrogen bonding interaction in the excited state nonradiative relaxation process of DMACA. The ICT fluorescence emission yield decreases in BSA due to the locking in of the probe buried in the hydrophobic pocket of the protein structure. SDS induced uncoiling of protein and massive cooperative binding between BSA and SDS is manifested by the release of probe molecules in relatively free aqueous environment.

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