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Usage

Uses

Used in Scientific Research:
2-Hydroxycinnamic acid is used as a research compound for its biological activity, particularly in the study of its potential anti-cancer effects. Its antioxidant properties and natural occurrence in plants make it a valuable subject for investigation in various scientific fields.
Used in Antioxidant Applications:
In the field of nutrition and health, 2-Hydroxycinnamic acid is used as a natural antioxidant, helping to protect cells from damage caused by free radicals. Its presence in various plants suggests that it may play a role in the overall health benefits associated with a diet rich in fruits and vegetables.
Used in Pharmaceutical Development:
2-Hydroxycinnamic acid is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure and biological activity make it a promising candidate for the development of new drugs, particularly in the area of cancer therapy.
Used in Cosmetics and Personal Care Products:
Due to its antioxidant properties, 2-Hydroxycinnamic acid is used in cosmetics and personal care products to protect the skin from oxidative stress and environmental damage. It may be incorporated into creams, lotions, and other formulations to help maintain skin health and appearance.
Used in Food Industry:
2-Hydroxycinnamic acid may be used in the food industry as a natural preservative or flavor enhancer, taking advantage of its antioxidant properties to extend the shelf life of certain products or to impart a specific taste profile. Its natural occurrence in plants makes it an attractive option for consumers seeking products with minimal artificial additives.

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

Upstream product

• 141-82-2 malonic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 
• 90-02-8 salicylaldehyde 
• 105-53-3 diethyl malonate 
• 533-58-4 2-Iodophenol 
• 79-10-7 acrylic acid 
• 95-56-7 2-hydroxybromobenzene 
• 6099-03-2 3-(2'-methoxyphenyl)propenoic acid 
• 91-64-5 coumarin 

Downstream Products

• 63408-36-6 9,9-diphenyl-3a,9-dihydro-3H-9λ⁵-benzo[d][1,2]oxaphospholo[2,3-b][1,2]oxaphosphol-2-one 
• 20883-98-1 methyl 2-coumarate 
• 121-69-7 N,N-dimethyl-aniline 
• 90-02-8 salicylaldehyde 
• 3943-94-0 3-(2-hydroxy-phenyl)-acrylic acid ethyl ester 
• 444154-66-9 (2E)-3-(2-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 444154-78-3 (2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropioic acid 
• 444154-68-1 ethyl (2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionate 
• 444154-84-1 N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine 
• 444154-81-8 N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester 
• 60125-23-7 2'-hydroxycinnamaldehyde 
• 51764-86-4 2-hydroxycinnamyl alcohol 
• 161258-31-7 Cum-Phe-Ala-Arg-OH 
• 95123-55-0 2-(2-vinylphenoxy)acetic acid 

Relevant academic research and scientific papers

Palladium nanoparticles immobilized on amphiphilic and hyperbranched polymer-functionalized magnetic nanoparticles: An efficient semi-heterogeneous catalyst for Heck reaction

To address the obstacles facing the use of palladium-based homogeneous and heterogeneous catalysts in C─C cross-coupling reactions, a novel semi-heterogeneous support was developed based on hyperbranched poly(ethylene glycol)-block-poly(citric acid)-functionalized Fe3O4 magnetic nanoparticles (Fe3O4@PCA-b-PEG). Because of the surface modification of the Fe3O4 nanoparticles with amphiphilic and hyperbranched polymers (PCA-b-PEG), these hybrid materials are not only soluble in a wide range of solvents (e.g. water, ethanol and dimethylformamide) but also are able to trap Pd2+ ions via complex formation of free carboxyl groups of the PCA dendrimer with metal ions. The reduction of trapped palladium ions in the dendritic shell of Fe3O4@PCA-b-PEG leads to immobilized palladium nanoparticles. The morphology and structural features of the catalyst were characterized using various microscopic and spectroscopic techniques. The catalyst was effectively used in the palladium-catalysed Mizoroki–Heck coupling reaction in water as a green solvent. In addition, the catalyst can be easily recovered from the reaction mixture by applying an external magnetic field and reused for more than ten consecutive cycles without much loss in activity, exhibiting an example of a sustainable and green methodology.

Curcumin recognizes a unique binding site of tubulin

Although curcumin is known for its anticarcinogenic properties, the exact mechanism of its action or the identity of the target receptor is not completely understood. Studies on a series of curcumin analogues, synthesized to investigate their tubulin binding affinities and tubulin self-assembly inhibition, showed that: (i) curcumin acts as a bifunctional ligand, (ii) analogues with substitution at the diketone and acetylation of the terminal phenolic groups of curcumin are less effective, (iii) a benzylidiene derivative, compound 7, is more effective than curcumin in inhibiting tubulin self-assembly. Cell-based studies also showed compound 7 to be more effective than curcumin. Using fluorescence spectroscopy we show that curcumin binds tubulin 32 ? away from the colchicine-binding site. Docking studies also suggests that the curcumin-binding site to be close to the vinblastine-binding site. Structure-activity studies suggest that the tridented nature of compound 7 is responsible for its higher affinity for tubulin compared to curcumin.

Linear polystyrene-stabilized PdO nanoparticle-catalyzed mizoroki-heck reactions in water

Linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs) were prepared by thermal decomposition of Pd(OAc)2 in the presence of polystyrene. X-ray diffraction (XRD) and transmission electron microscopy (TEM) indicated the production of PdO nanoparticles. The loading of palladium was determined by inductively coupled plasma-atomic emission spectroscopy (ICP-AES). PS-PdONPs exhibited high catalytic activity for Mizoroki-Heck reactions under air in water and could be recycled without loss of activity.

Coumarinyl-substituted sulfonamides strongly inhibit several human carbonic anhydrase isoforms: Solution and crystallographic investigations

We investigated a series of coumarinyl-substituted aromatic sulfonamides as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms with medical applications, the cytosolic hCA I, and II, and the transmembrane, tumor-associated hCA IX and XII. Compounds incorporating 7-methoxy-coumarin-4- yl-acetamide-tails and benzenesulfonamide and benzene-1,3-disulfonamide scaffolds showed medium potency inhibition of hCA I (KIs of 73-131 nM), effective hCA II inhibition (KIs of 9.1-36 nM) and less effective hCA IX and XII inhibition (KIs of 55-128 nM). Only one compound, the derivatized 4-amino-6-trifluoromethyl-benzene-1,3-disulfonamide with the coumarinyl tail, showed effective inhibition of the transmembrane isoforms, with KIs of 5.9-14.2 nM, although it was less effective as hCA I and II inhibitor (KIs of 36-120 nM). An X-ray crystal structure of hCA II in complex with 4-(7-methoxy-coumarin-4-yl-acetamido)- benzenesulfonamide (KI of 9.1 nM against hCA II) showed the intact inhibitor coordinated to the zinc ion from the enzyme active site by the sulfonamide moiety, and participating in a edge-to-face stacking with Phe131, in addition to other hydrophobic and hydrophilic interactions with water molecules and amino acid residues from the active site. Thus, sulfonamides incorporating coumarin rings have a distinct inhibition mechanism compared to the coumarins, and may lead to compounds with interesting inhibition profiles against various α-CAs found in mammals or parasites, such as Plasmodium falciparum.

7,8-Disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones i and II in the low nanomolar/subnanomolar range

Two series of disubstituted coumarins incorporating ether and acetyl/propionyl moieties in positions 6,7- and 7,8- of the heterocyclic ring were synthesized investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). All these

A facile method for synthesis of amine-functionalized mesoporous zirconia and its catalytic evaluation in Knoevenagel condensation

Amine-functionalized mesoporous zirconia was prepared by a co-condensation method using silane (aminopropyltrimethoxysilane, APTES) and zirconium butoxide. The materials were characterized by X-ray diffraction, BET surface area analysis, 13C magic angle spinning-nuclear magnetic resonance (NMR), Fourier-transfer infrared spectroscopy (FTIR), transmittance electron micrography (TEM), and CHN analysis. FTIR and NMR results revealed the successful grafting of organic amines onto the surface of zirconia. The catalytic activities were investigated for liquid phase Knoevenagel condensation of various aromatic aldehydes with diethyl malonate. The catalysts showed excellent yield of products at room temperature in solvent-free condition.

Hydroxyapatite supported caesium carbonate as a new recyclable solid base catalyst for the Knoevenagel condensation in water

The Knoevenagel condensation between aromatic aldehydes and malononitrile, ethyl cyanoacetate or malonic acid with hydroxyapatite supported caesium carbonate in water is described. HAP-Cs2CO3 was found to be a highly active, stable and recyclable catalyst under the reaction conditions.

Preparation of coumarins

Coumarin compounds may be produced by the conversion of o-hydroxycinnamates or o-hydroxycinnamic acids in the presence of catalysts comprising compounds containing metals of Group VIII of the Periodic Table.