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4-Hydroxycinnamamide

CAS# 194940-15-3

4-Hydroxycinnamamide

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Quality Control of 4-Hydroxycinnamamide

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Chemical structure

4-Hydroxycinnamamide

3D structure

Chemical Properties of 4-Hydroxycinnamamide

Cas No. 194940-15-3 SDF Download SDF
PubChem ID 16637983 Appearance Powder
Formula C9H9NO2 M.Wt 163.2
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (E)-3-(4-hydroxyphenyl)prop-2-enamide
SMILES C1=CC(=CC=C1C=CC(=O)N)O
Standard InChIKey DSMLJOHWFORNLY-ZZXKWVIFSA-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-Hydroxycinnamamide

The herbs of Berberis pruinosa.

Biological Activity of 4-Hydroxycinnamamide

Description1. 4-Hydroxycinnamamide has antioxidant activity. 2. 4-Hydroxycinnamamide derivatives are specific inhibitors of tyrosine-specific protein kinases.
TargetsEGFR | Calcium Channel | Sodium Channel | ATPase | Potassium Channel | AMPK | p38MAPK

4-Hydroxycinnamamide Dilution Calculator

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4-Hydroxycinnamamide Molarity Calculator

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Preparing Stock Solutions of 4-Hydroxycinnamamide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.1275 mL 30.6373 mL 61.2745 mL 122.549 mL 153.1863 mL
5 mM 1.2255 mL 6.1275 mL 12.2549 mL 24.5098 mL 30.6373 mL
10 mM 0.6127 mL 3.0637 mL 6.1275 mL 12.2549 mL 15.3186 mL
50 mM 0.1225 mL 0.6127 mL 1.2255 mL 2.451 mL 3.0637 mL
100 mM 0.0613 mL 0.3064 mL 0.6127 mL 1.2255 mL 1.5319 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-Hydroxycinnamamide

Specific inhibitors of tyrosine-specific protein kinases: properties of 4-hydroxycinnamamide derivatives in vitro.[Pubmed:2706625]

Cancer Res. 1989 May 1;49(9):2374-8.

Inhibition by seven synthetic 4-Hydroxycinnamamide derivatives, ST 271, ST 280, ST 458, ST 494, ST 633, ST 638, and ST 642, of tyrosine-specific protein kinases (tyrosine kinase) of oncogene or proto-oncogene products (p130gag-v-fps, p70gag-actin-v-fgr, pp60v-src, pp60c-src) and epidermal growth factor (EGF) receptor kinase were investigated. ST 638 (alpha-cyano-3-ethoxy-4-hydroxy-5-phenylthiomethylcinnamamide) strongly inhibited more of the tyrosine kinases than any of the other compounds. The susceptibilities of these tyrosine kinases to ST 638 increased in the following order: EGF receptor greater than p70gag-actin-v-fgr greater than pp60c-src greater than p130gag-v-fps, pp60v-src, with 50% inhibitory concentration values of 1.1, 4.2, 18, 70, and 87 microM, respectively. The phosphorylation of the tyrosine residues in particulate fractions from RR1022 cells expressing pp60v-src was inhibited by ST 638 in a dose-dependent way, while it had a negligible effect on the phosphorylations of threonine and serine residues. Kinetic analysis showed that ST 638 competitively inhibited the phosphorylation of an exogenous substrate by the EGF receptor kinase with a Ki of 2.1 microM. ST 638 noncompetitively inhibited autophosphorylation by EGF receptor kinase. These results indicate that ST 638 is a potent and specific inhibitor of tyrosine kinases in vitro, and that its inhibitory activity is caused by competing with the substrate protein for the tyrosine kinase binding site.

Synthesis and evaluation of 4-hydroxyphenylacetic acid amides and 4-hydroxycinnamamides as antioxidants.[Pubmed:12182869]

Bioorg Med Chem Lett. 2002 Sep 16;12(18):2599-602.

4-Hydroxyphenylacetic acid amides and 4-Hydroxycinnamamides were synthesized and their antioxidant and neuroprotective activities were evaluated. Among the prepared compounds, 8b, and exhibited potent inhibition of lipid peroxidation in rat brain homogenates, and marked DPPH radical scavenging activities. Furthermore, and exhibited neuroprotective action against the oxidative damage induced by the exposure of primary cultured rat cortical cells to H(2)O(2), xanthine/xanthine oxidase, or Fe(2+)/ascorbic acid. Based on these results, we found that was the most potent antioxidant among the compounds tested.

Specific inhibitors of tyrosine-specific protein kinase, synthetic 4-hydroxycinnamamide derivatives.[Pubmed:2820397]

Biochem Biophys Res Commun. 1987 Aug 31;147(1):322-8.

Several newly synthesized 4-Hydroxycinnamamide derivatives such as 3-(3',5'-di-isopropyl-4'-hydroxybenzylidene)-2-oxindol (ST 280), 3-(3',5'-di-methylthiomethyl-4'-hydroxybenzylidene)-2-oxindole (ST 458), alpha-cyano-3-ethoxy-4-hydroxy-5-phenylthiomethylcinnamamide (ST 638) and 3-(3'-ethoxy-4'-hydroxy-5'-phenylthiomethylbenzylidene)-2-pyrol idinone (ST 642) were found to inhibit tyrosine-specific protein kinase activity of the epidermal growth factor (EGF) receptor with IC50 values of 0.44 microM, 0.44 microM, 0.37 microM and 0.85 microM, respectively. None of them showed inhibitory effect on the enzyme activities of serine- and/or threonine-specific protein kinases such as cAMP-dependent protein kinase, Ca2+/phospholipid-dependent protein kinase C, casein kinase I and casein kinase II. In addition, none of them had effect on Na+/K+-ATPase or 5'-nucleotidase. The results suggest that the compound ST 280, ST 458, ST 638 and ST 642 are potent and specific inhibitors of tyrosine-specific protein kinase.

Development of 3-hydroxycinnamamide-based HDAC inhibitors with potent in vitro and in vivo anti-tumor activity.[Pubmed:25462271]

Eur J Med Chem. 2015 Jan 7;89:628-37.

Inhibition of histone deacetylases (HDACs) has diverse effects on cell function, such as causing differentiation, growth arrest and apoptosis in nearly all types of tumor cell lines. In our previous work, we have designed and synthesized a novel series of 4-Hydroxycinnamamide-based and 3-hydroxycinnamamide-based HDAC inhibitors (HDACIs), among which, 3-hydroxycinnamamide-based HDACIs 1a-1c exhibited moderate inhibition against HDACs. In this article, we report the development of a more potent class of 3-hydroxycinnamamide-based HDACIs, compound 7o exhibited much higher pan-HDAC inhibitory activity than positive control SAHA. In addition, compound 7h showed excellent in vitro growth inhibitory activity against more than ten cell lines and induced U937 cells apoptosis in micromolar concentration. In vivo assay in U937 xenograft model identified compound 7h as a potent, orally active HDACI.

A possible involvement of tyrosine kinase in TRH-induced prolactin secretion in GH3 cells.[Pubmed:8147889]

Biochem Biophys Res Commun. 1994 Mar 30;199(3):1447-52.

Thyrotropin-releasing hormone (TRH) is a well-known regulatory factor of prolactin (PRL) secretion and synthesis in lactotrophs. Recently we have found that TRH stimulates early tyrosine phosphorylation of MAP kinase in GH3 cells. Then we investigated whether tyrosine phosphorylation in TRH action is involved in TRH-stimulated PRL secretion by GH3 cells, using a 4-Hydroxycinnamamide derivative (ST638), a tyrosine kinase inhibitor. TRH-stimulated tyrosine phosphorylation of MAP kinase and PRL secretion were remarkably inhibited by ST638 treatment. These results suggest that tyrosine phosphorylation of MAP kinase is strongly associated with TRH-stimulated PRL secretion.

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