501-98-4

Basic information

• Product Name: p-coumaric acid
• Synonyms: (e)-3-(4-hydroxyphenyl)-2-propenoicacid;(E)-p-Coumaric acid;(e)-p-coumaricacid;(E)-p-Hydroxycinnamic acid;(e)-p-hydroxycinnamicacid;2-Propenoic acid, 3-(4-hydroxyphenyl)-, (E)-;3-(4-hydroxyphenyl)-,(E)-2-Propenoicacid;Cinnamic acid, p-hydroxy-, (E)-
• CAS NO: 501-98-4
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.16
• EINECS: 231-000-0
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives;Antioxidant;Auxins;Biochemistry;Plant Growth Regulators;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 501-98-4.mol

Chemical Properties

• Melting Point: 214 °C (dec.)(lit.)
• Boiling Point: 231.61°C (rough estimate)
• Flash Point: 177.284 °C
• Appearance: Off-white to beige or greenish/Powder
• Density: 1.1403 (rough estimate)
• Vapor Pressure: 7.19E-05mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: ethanol: soluble50mg/mL
• PKA: 4.65±0.10(Predicted)
• Water Solubility: soluble
• Merck: 14,2560
• BRN: 2207383
• CAS DataBase Reference: p-coumaric acid(CAS DataBase Reference)
• NIST Chemistry Reference: p-coumaric acid(501-98-4)
• EPA Substance Registry System: p-coumaric acid(501-98-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: GD9095000
• Hazardous Substances Data: 501-98-4(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
4-Hydroxycinnamic acid is used as an antioxidant for reducing the risk of cancer by potentially reducing the formation of carcinogenic nitrosamines.
Used in Proteomics Research:
In the field of proteomics, 4-Hydroxycinnamic acid is used as an aromatic phytochemical, contributing to the study and analysis of proteins.
Used in Western Blotting:
4-Hydroxycinnamic acid is utilized as a component of chemiluminescent substrates for protein detection in western blotting, a widely used technique for the detection and quantification of specific proteins in a sample.

Preparation

Synthesis of p-Coumaric acid: take o-acetylsalicyloyl chloride as raw material, in the presence of magnesium chloride, react with diethyl malonate in acetonitrile solvent, then add triethylamine, and react at 0°C for 1 h to obtain ( 2-acetoxybenzoyl) diethyl malonate product, then heated to 50°C in potassium hydroxide/methanol solution, reacted for 3h, and cyclized to obtain p-Coumaric acid.

Biochem/physiol Actions

p-Coumaric acid is mainly a plant metabolite which exhibits antioxidant and anti-inflammatory properties. It also shows bactericidal activity by damaging bacterial cell membrane and by interacting with bacterial DNA. In western blot, p-coumaric is also used as an enhancer in chemiluminescent substrate.Hydroxycinnamic acid found in many fruits and vegetables.

Purification Methods

Crystallise p-coumaric acid from H2O (charcoal). It forms needles from concentrated aqueous solutions as the anhydrous acid, but from hot dilute solutions the monohydrate acid separates on slow cooling. The acid (33g) has been crystallised from 2.5L of H2O (1.5g charcoal) yielding 28.4g of recrystallised acid, m 207o. It is insoluble in *C6H6 or pet ether. The UV in 95% EtOH has max 223 and 286nm ( 14,450 and 19000 M-1cm-1). [UV Wheeler & Covarrubias J Org Chem 28 2015 1963, Corti Helv Chim Acta 32 681 1949, Beilstein 10 IV 1005.]

InChI:InChI=1/C9H8O3/c1-6(9(11)12)7-2-4-8(10)5-3-7/h2-5,10H,1H2,(H,11,12)

Upstream product

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

Downstream Products

• 632323-91-2 N-(2-(tert-butoxycarbonylamino)ethoxyethyl) N_α-cis-p-coumaroyl-D-arginine amide 
• 7400-08-0 p-Coumaric Acid 
• 672341-24-1 cis-p-coumaroylsuccinimide 
• 123-07-9 4-Ethylphenol 
• 69033-81-4 4-propoxy-cis-cinnamic acid 
• 5676-64-2 (Z)-3-(4-methoxyphenyl)acrylic acid 
• 2373-79-7 4-ethoxy-cis-cinnamic acid 
• 55379-96-9 4-butoxy-cis-cinnamic acid 

Relevant articles and documents

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).

Structures of acylated sucroses from the flower buds of Prunus mume

Seven new acylated sucroses, mumeoses P-V, were isolated from the flower buds of Prunus mume, cultivated in Zhejiang province, China. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. Moreover, mumeoses C, D,

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.

Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis

The methanolic extract from the flower buds of Prunus mume, cultivated in Zhejiang Province, China, showed an inhibitory effect on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the methanolic extract, five acylated sucroses, mumeoses A-E, and three acylated quinic acid analogs, 5- O-(E)-p-coumaroylquinic acid ethyl ester, and mumeic acid-A and its methyl ester, were isolated together with 13 known compounds. The chemical structures of the compounds were elucidated on the basis of chemical and physicochemical evidence. Inhibitory effects of the isolated compounds on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were also investigated. Acylated quinic acid analogs substantially inhibited melanogenesis. In particular, 5-O-(E)-feruloylquinic acid methyl ester exhibited a potent inhibitory effect [inhibition (%): 21.5 ± 1.0 (P 97% at 10 μM]. It is concluded that acylated quinic acid analogs are promising therapeutic agents for the treatment of skin disorders.

Triacylated peonidin 3-sophoroside-5-glucosides from the purple flowers of Moricandia ramburii Webb.

Triacylated peonidin 3-sophoroside-5-glucosides were isolated from the purple flowers of Moricandia ramburii Webb. (Family: Brassicaceae), and determined to be peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p- coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (1), peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(cis-p-coumaroyl)-glucoside] -5-O-[6-O-(malonyl)-glucoside] (2) and peonidin 3-O-[2-O-(2-O-(trans-sinapoyl)- glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (3), respectively, by chemical and spectroscopic methods. In addition, one known acylated cyanidin glycoside, cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)- 6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (4), was also identified in the flowers. Peonidin glycosides have not been reported hitherto in floral tissues in to Brassicaceae.

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.