4501-31-9

Usage

Uses

Used in Antioxidant Applications:
4-Hydroxycinnamic acid is used as an antioxidative active compound for its ability to neutralize free radicals and protect cells from oxidative damage. This property makes it a valuable ingredient in the food, pharmaceutical, and cosmetic industries, where it can extend the shelf life of products and maintain their quality.
Used in Photoisomerization:
In the field of chemistry, 4-Hydroxycinnamic acid is used as a compound that undergoes geometric isomerization when exposed to light. This property is of interest in the development of smart materials and systems that can change their properties in response to external stimuli, such as light.
Used in Dimerization:
4-Hydroxycinnamic acid is also used in the formation of different dimers in the crystalline state. This application is relevant in the synthesis of complex organic molecules and the development of new materials with unique properties.
Used in Pharmaceutical Industry:
4-Hydroxycinnamic acid can be used as a building block for the synthesis of various pharmaceutical compounds due to its versatile chemical structure and reactivity. It may also have potential applications in the development of new drugs targeting specific diseases or conditions.
Used in Cosmetic Industry:
Due to its antioxidative properties, 4-Hydroxycinnamic acid can be used in the cosmetic industry as an ingredient in skincare products, hair care products, and other personal care items. It can help protect the skin and hair from oxidative stress and environmental damage, promoting overall health and appearance.

InChI:InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-

Upstream product

• 7400-08-0 p-Coumaric Acid 
• 29588-94-1 N-phthaloyl-L-tyrosine 
• 3943-97-3 methyl p-hydroxycinnamate 
• 1225064-68-5 kankanoside H₂ 
• 1899-30-5 trans-3-p-coumaroylquinic acid 
• 117405-49-9 E-4-O-β-D-glucopyranosyl-p-coumaric acid 
• 87099-71-6 3-O-trans-p-coumaroyl-D-quinic acid 
• 1108200-72-1 4-O-(trans-p-coumaroyl)quinic acid 
• 117405-48-8 4-O-β-D-glucopyranosyl-Z-4-hydroxycinnamic acid 
• 1392307-47-9 1,2',3',4',6'-penta-O-acetyl-3-O-(Z)-p-coumaroylsucrose 

Downstream Products

• 123-07-9 4-Ethylphenol 
• 672341-24-1 cis-p-coumaroylsuccinimide 
• 632323-91-2 N-(2-(tert-butoxycarbonylamino)ethoxyethyl) N_α-cis-p-coumaroyl-D-arginine amide 
• 632323-92-3 (R)-5-Guanidino-2-[(Z)-3-(4-hydroxy-phenyl)-acryloylamino]-pentanoic acid [2-(2-amino-ethoxy)-ethyl]-amide 
• 929713-60-0 4-methoxybenzyl 3-{4-[(4-methoxybenzyl)oxy]phenyl}-4-nitrobutanoate 
• 929713-61-1 4-methoxybenzyl 3-{4-[(4-methoxybenzyl)oxy]phenyl}-3-(1,2-oxazol-3-yl)propanoate 
• 1356600-14-0 3-(4-hydroxyphenyl)-3-(1,2-oxazol-3-yl)propanoic acid 
• 1356600-16-2 methyl 3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}-3-(1,2-oxazol-3-yl)propanoate 
• 1356598-73-6 3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}-3-(1,2-oxazol-3-yl)propanoic acid 
• 1356600-15-1 methyl 3-(4-hydroxyphenyl)-3-(1,2-oxazol-3-yl)propanoate 
• 1356600-13-9 4-methoxybenzyl (2Z)-3-{4-[(4-methoxybenzyl)oxy]phenyl}prop-2-enoate 
• 5676-64-2 (Z)-3-(4-methoxyphenyl)acrylic acid 
• 19310-29-3 3-(4-methoxyphenyl)acrylic acid methyl ester 
• 61240-27-5 3-(4'-hydroxyphenyl)-(Z)-propenoic acid methyl ester 

Relevant academic research and scientific papers

Xanthones, triterpenes and a biphenyl from Kielmeyera coriacea

Analysis of the dichloromethane extracts of Kielmeyera coriacea leaves and stems by high performance liquid chromatography coupled with a photodiode array detector (LC-UV) and thermospray liquid chromatography-mass spectrometry (TSP/LC-MS) revealed the presence of several xanthones. Phytochemical investigation of these extracts resulted in the isolation and identification of ten xanthones, one biphenyl and two triterpenes. Their structures were established by chemical and spectroscopic methods (UV, EI- MS, D/CI-MS, 1H NMR, 13C NMR, HMQC and HMBC). One xanthone and two triterpenes are new compounds. Four xanthones and the biphenyl exhibited antifungal activity against the plant pathogenic fungus Cladosporium cucumerinum, while two prenylated xanthones inhibited the growth of Candida albicans.

Photo-isomerization upshifts the pka of the photoactive yellow protein chromophore to contribute to photocycle propagation

The influence of chromophore structure on the protonation constant of the Photoactive Yellow Protein chromophore is explored with isolated para-coumaric acid (pCA) and thiomethyl-para-coumaric acid model chromophores in solution. pH titration coupled with visible absorption spectra of the trans and photogenerated cis conformer of isolated pCA demonstrates that the isomerization of the chromophore increases the pKa of the phenolate group by 0.6 units (to 10.1 ± 0.22). Formation of the pCA thioester reduces the pKa of the phenolic group by 0.3 units (from 9.5 ± 0.15 to 9.2 ± 0.16). Unfortunately, a macroscopic cis-TMpCA population was not achieved via photoexcitation. Both trends were explained with electronic structure calculations including a Natural Bond Orbital analysis that resolves that the pKa upshift for the cis configuration is attributed to increased Columbic repulsion between the coumaryl tail and the phenolate moieties. This structurally induced pKa upshift after isomerization is argued to aid in the protonation of the chromophore within the PYP protein environment and the subsequent propagation of the photocycle response and in vivo photo-activity.

FOUR ACYLATED FLAVONOL GLYCOSIDES FROM LEAVES OF STRYCHNOS VARIABILIS

Four new acylated flavonol glycosides have been isolated and identified from the leaves of Strychnos variabilis: quercetin 3-(4"-trans-p-coumaroyl)robinobioside-7-glucoside (variabiloside A) and its cis derivative (variabiloside B), kaempferol 3-(4"-trans-p-coumaroyl)robinobioside-7-glucoside (varibiloside C) and its cis derivative (variabiloside D).Key Word Index - Strychnos variabilis; Loginiaceae; acylated flavonol glycosides; variabilosides A, B, C, and D; DCCC.

Photo-induced phase transition from multilamellar vesicles to wormlike micelles

A novel complex fluid system of tetradecyldimethylamine oxide (C 14DMAO) mixed with para-coumaric acid (PCA) in water was investigated. The phase behavior was determined in detail; one observed sequentially the L1-phase (micelles), two-phase L1/L α, Lα-phase (vesicles), and L α/precipitates with increasing PCA concentration at constant concentration of C14DMAO. The samples in the regions of micelles and vesicles were characterized by rheological measurements and cryo-TEM observations. Fascinatingly, we found a phase transition from vesicles to wormlike micelles performed via UV-light irradiation. The properties and structures after UV-light irradiation were determined by rheological measurements and cryo-TEM observations to demonstrate the phase transition. To the best of our knowledge, this transition is rarely reported, which could provide a better understanding of the phase transition via light irradiation and find potential applications in drug delivery, biochemistry, and the oilfield industry.

Nonaqueous photorheological fluids based on light-responsive reverse wormlike micelles

Fluids whose flow properties can be altered by light are an emerging class of functional materials, with potential applications in microscale actuators and valves. While many such photorheological (PR) fluids have been developed over the years, most are based on specialized organized molecules that require synthesis. We have instead sought to develop PR fluids using inexpensive chemical components that are commercially available, and this approach has been successfully applied to aqueous systems. Here, we demonstrate a simple class of nonaqueous PR fluids based on the phospholipid, lecithin, and the organic derivative, para-coumaric acid (PCA). The combination of lecithin with the trans form of PCA results in reverse wormlike micelles, which are long, flexible chains that undergo entanglement, thereby giving rise to viscoelastic fluids. Upon UV irradiation, trans-PCA is photoisomerized to its cis form, which has a lower polarity and hydrogen-bonding tendency. This causes a significant reduction in the length of the micellar chains, and in turn, the fluid viscosity drops more than 1000-fold. We show that photoresponsive reverse micelles can be formed in a range of organic solvents including cyclohexane, n-alkanes, alkenes, and fatty acid esters.

Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of: Z-cinnamic acid derivatives

Photoisomerization of a series of substituted E-cinnamic acids in MeCN in their acid forms and as their corresponding protic ionic liquids (PILs) with light of 300 nm is studied. The nature, strength, number, and position effects of substituents on the photochemical behavior of E-cinnamic derivatives are investigated. The photosensitization of the reaction in the presence of Michler's ketone is also studied at 366 nm and it demonstrates that the triplet-excited state is involved in the reaction. As the presence of n-butylamine needed to form the PILs significantly increases the photoproduct yields in all cases, the role of the PILs is also discussed. Thus, understanding of these fundamental aspects has allowed us to establish an excellent and practical synthetic protocol for successfully synthesizing Z-cinnamic acids. This journal is

Four New Flavonoids Isolated from the Aerial Parts of Cadaba rotundifolia Forssk. (Qadab)

Cadaba rotundifolia (Forssk.) (family: Capparaceae; common name: Qadab) is one of four species that grow in the Red Sea costal region in the Kingdom of Saudi Arabia. The roots and leaves of C. rotundifolia is traditionally used to treat tumors and abscesses in Sudan. A previous phytochemical study of the roots yielded a quaternary alkaloid, but no report on chemical constituents of the aerial parts of the C. rotundifolia growing in Saudi Arabia has been issued so far. Oxidative stress and advanced glycation end products (AGEs) are thought as causal factors in many degenerative diseases, such as Alzheimer's disease, diabetes, atherosclerosis and aging. In this study, a total of twenty compounds, including four previously undescribed acylated kaempferol glucosides, were isolated from the aerial parts of C. rotundifolia collected in Saudi Arabia. These new compounds were identified as kaempferol 3-O-[2-O-(trans-feruloyl)-3-O-β-d-glucopyranosyl]-β-d-glucopyranoside (1), kaempferol 3-O-β-neohesperidoside-7-O-[2-O-(cis-p-coumaroyl)-3-O-β-d-glucopyranosyl]-β-d-glucopyranoside (2), kaempferol 3-O-[2,6-di-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside-7-O-[6-O-(trans-feruloyl)]-β-d-glucopyranoside (3) and kaempferol 3-O-[2,6-di-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside-7-O-[6-O-(trans-p-coumaroyl)]-β-d-glucopyranoside (4). Their structures were established based on UV-visible, 1D, 2D NMR, and HR-ESI-MS analyses. Of the assayed compounds, 17 and 18 showed potent radical scavenging activity with IC50 values of 14.5 and 11.7 μM, respectively, and inhibitory activity toward AGEs together with compound 7 with IC50 values 96.5, 34.9 and 85.5 μM, respectively.

Flavonoid glycosides from Sedum bulbiferum

The MeOH extract from dried whole Sedum bulbiferum MAKINO (Crassulaceae) plants yielded 34 compounds, including six new flavonoid glycosides and 28 known compounds. The structures of new compounds were established using NMR, Mass spectroscopic analysis an

Stability of Hydroxycinnamic Acid Derivatives, Flavonol Glycosides, and Anthocyanins in Black Currant Juice

The stability of phenolic compounds was followed in black currant juice at ambient temperatures (in light and in dark conditions) and at +4 °C for a year. Analyses were based on high-performance liquid chromatography-diode-array detection-electrospray ionization-mass spectrometry (or tandem mass spectrometry) and high-performance liquid chromatography-diode-array detection-electrospray ionization-quadrupole time-of-flight mass spectrometry methods supported by nuclear magnetic resonance after selective high-performance liquid chromatography isolation. Altogether, 43 metabolites were identified, of which 2-(Z)-p-coumaroyloxymethylene-4-β-d-glucopyranosyloxy-2-(Z)-butenenitrile, 2-(E)-caffeoyloxymethylene-4-β-d-glucopyranosyloxy-2-(Z)-butenenitrile, 1-O-(Z)-p-coumaroyl-β-d-glucopyranose, (Z)-p-coumaric acid 4-O-β-d-glucopyranoside, and (Z)-p-coumaric acid were novel findings in black currant juice. Hydroxycinnamic acid derivatives degraded 20-40% at room temperature during one year of storage, releasing free hydroxycinnamic acids. O-Glucosides of hydroxycinnamic acid compounds were the most stable, followed by O-acylquinic acids, acyloxymethyleneglucosyloxybutenenitriles, and O-acylglucoses. Light induced the isomerization of (E)-coumaric acid compounds into corresponding Z-isomers. Flavonol glycosides stayed fairly stable. Flavonol aglycones were derived mainly from malonylglucosides. Over 90% of anthocyanins were lost at room temperature in a year, practically independent of light. Storage at low temperatures, preferably excluding light, is necessary to retain the original composition of phenolic compounds.

Phenolic glycosides from the twigs of Salix glandulosa

As a part of an ongoing search for bioactive constituents from Korean medicinal plants, the phytochemical investigations of the twigs of Salix glandulosa afforded 12 new phenolic glycosides (1-12) and a known analogue (13). The structures of 1-13 were characterized by a combination of NMR methods (1H and 13C NMR, 1H-1H COSY, HMQC, and HMBC), chemical hydrolysis, and GC/MS. The absolute configuration of 13 [(1R,2S)-2-hydroxycyclohexyl-2′-O-trans-p-coumaroyl-β-d- glucopyranoside] was determined for the first time. Compounds 1-3, 6, and 7 exhibited inhibitory effects on nitric oxide production in lipopolysaccharide- activated murine microglial cells (IC50 values in the range 6.6-20.5 μM).