194940-15-3

Usage

Uses

Used in Pharmaceutical Development:
4-Hydroxycinnamamide is used as a pharmaceutical agent for its potential neuroprotective properties, offering a promising avenue for the treatment of neurological disorders. Its antioxidant and anti-inflammatory activities contribute to its potential therapeutic effects in this area.
Used in Food Additive Industry:
Leveraging its antimicrobial properties, 4-Hydroxycinnamamide is used as a preservative in the food industry to extend the shelf life of various products by inhibiting the growth of harmful microorganisms.
Used in Anticancer Research:
4-Hydroxycinnamamide is used as an anti-cancer agent in ongoing research, exploring its potential to target and inhibit the growth of cancer cells. Its ability to modulate various cellular pathways involved in cancer progression makes it a subject of interest for developing novel cancer therapies.
Used in Cosmetics Industry:
Due to its antioxidant properties, 4-Hydroxycinnamamide is used in the cosmetics industry as an ingredient to protect the skin from oxidative stress and environmental damage, potentially reducing the signs of aging and promoting skin health.

Upstream product

• 3943-97-3 methyl p-hydroxycinnamate 
• 3943-97-3 methyl 4-hydroxycinnamate 
• 14482-11-2 (E)-p-methoxycinnamonitrile 
• 7400-08-0 p-Coumaric Acid 
• 82575-52-8 3-(4-hydroxyphenyl)prop-2-ene nitrile 

Downstream Products

• 23838-70-2 3-(4-hydroxyphenyl)propanoic acid amide 

Relevant academic research and scientific papers

A modification of the Hammett equation for predicting ionisation constants of p-vinyl phenols

Currently there are several compounds used as drugs or studied as new chemical entities, which have an electron withdrawing group connected to a vinylic double bond in a phenolic or catecholic core structure. These compounds share a common feature - current computational methods utilizing the Hammett type equation for the prediction of ionisation constants fail to give accurate prediction of pKa's for compounds containing the vinylic moiety. The hypothesis was that the effect of electron-withdrawing substituents on the pKa of p-vinyl phenols is due to the delocalized electronic structure of these compounds. Thus, this effect should be additive for multiple substituents attached to the vinylic double bond and quantifiable by LFER-based methods. The aim of this study was to produce an improved equation with a reduced tendency to underestimate the effect of the double bond on the ionisation of the phenolic hydroxyl. To this end a set of 19 para-substituted vinyl phenols was used. The ionisation constants were measured potentiometrically, and a training set of 10 compounds was selected to build a regression model (r2 = 0.987 and S.E. = 0.09). The average error with an external test set of six compounds was 0.19 for our model and 1.27 for the ACD-labs 7.0. Thus, we have been able to significantly improve the existing model for prediction of the ionisation constants of substituted p-vinyl phenols.

METHODS OF REDUCING VIRULENCE IN BACTERIA

A method of reducing virulence in a bacterium comprising at least one of a GacS/GacA-type system, a HrpX/HrpY-type system, a T3SS-type system, and a Rsm-type system, the method comprising contacting the bacterium with an effective amount of a compound described herein.

Isolation and Activity of N-p-Coumaroyltyramine, an α-Glucosidase Inhibitor in Welsh Onion (Allium fistulosum)

A phenolic amide, N-p-coumaroyltyramine (1), was isolated as an α-glucosidase inhibitor from methanol extracts of Welsh onion (Allium fistulosum). The inhibitory activity of 1 against a yeast enzyme was as high as Ki 8.4 × 10-7 M. From a structure-activity relationship study of 1 and its related compounds, the occurrence of α-glucosidase inhibitory activity required a p-coumaramide structure, with an amide hydrogen and alkyl or aralkyl substituent on the amide part.

Participation of an Extended p-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl 4-Hydroxycinnamates

The alkaline hydrolysis of 4-hydroxycinnamate esters of acidic phenols follows an E1cB mechanism and involves the participation of an "extended" p-oxo ketene intermediate.The apparent bimolecular rate constant (kaKa/Kw) for the hydrolysis of the 2,4-dinitrophenyl ester is some 2500-fold larger than that determined from the Hammett relationship for the BAc2 alkaline hydrolysis of substituted 2,4-dinitrophenyl cinnamates.The positive value of entropy of activation for the hydrolysis of 2,4-dinitrophenyl 4'-hydroxycinnamate and trapping experiments with nitrogen nucleophiles are consistent with the dissociative pathway.A change from a E1cB to a BAc2 mechanism is expected for esters with leaving groups having pKa higher than ca. 6.7.The higher E1cB reactivity of 2,4-dinitrophenyl 4'-hydroxycinnamate compared to that of the corresponding 4'-hydroxybenzoate is due to the vinylene group that further favors the dissociative route, probably increasing the stability of the unsaturated intermediate.

COMPARATIVE REACTIVITY OF NITRILES OF PARA-SUBSTITUTED CINNAMIC ACIDS IN THE ALKYLATION OF BENZENE IN THE PRESENCE OF ALUMINUM CHLORIDE

The relative rate constants for the reactions of the nitriles of p-methoxy, p-methyl, and p-chlorocinnamic acids with benzene in the presence of aluminum chloride were determined by the method of competing reactions in relation to cinnamonitrile.The negative sign of ρ indicates that the electrophilic stage of complex formation between the unsaturated nitrile and aluminum chloride has a deciding role in the alkylation process.