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Dihydrocaffeic acid Sale

(Synonyms: 二氢咖啡酸; 3,4-Dihydroxy-benzenepropanoic acid) 目录号 : GC38319

A polyphenol with diverse biological activities

Dihydrocaffeic acid Chemical Structure

Cas No.:1078-61-1

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100mg
¥450.00
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产品描述

Dihydrocaffeic acid is a polyphenol that has diverse biological activities, including antioxidant, neuroprotective, and enzyme inhibitory properties.1,2 Dihydrocaffeic acid scavenges ABTS and 2,2-diphenyl-1-picrylhydrazyl radicals and increases the survival of RGC-5 mouse retinal ganglion cells under hypoxic conditions and in the presence of S-nitroso-N-acetyl-D,L-penicillamine in a concentration-dependent manner.1 It also decreases endothelial nitric oxide synthase (eNOS) activity in EA.hy926 human endothelial cells in a concentration-dependent manner.3 In vivo, dihydrocaffeic acid (30 mg/kg) decreases infarct size in a rat model of transient ischemia induced by middle cerebral artery occlusion (MCAO).2

1.Jang, H., Choi, Y., Ahn, H.R., et al.Effects of phenolic acid metabolites formed after chlorogenic acid consumption on retinal degeneration in vivoMol. Nutr. Food Res.59(10)1918-1929(2015) 2.Lee, K., Lee, B.J., and Bu, Y.Protective effects of dihydrocaffeic acid, a coffee component metabolite, on a focal cerebral ischemia rat modelMolecules20(7)11930-11940(2015) 3.Huang, J., De Paulis, T., and May, J.M.Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cellsJ. Nutr. Biochem.15(12)722-729(2004)

Chemical Properties

Cas No. 1078-61-1 SDF
别名 二氢咖啡酸; 3,4-Dihydroxy-benzenepropanoic acid
Canonical SMILES O=C(O)CCC1=CC=C(O)C(O)=C1
分子式 C9H10O4 分子量 182.17
溶解度 DMSO: 250 mg/mL (1372.34 mM) 储存条件 Store at -20°C
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1 mM 5.4894 mL 27.4469 mL 54.8938 mL
5 mM 1.0979 mL 5.4894 mL 10.9788 mL
10 mM 0.5489 mL 2.7447 mL 5.4894 mL
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Research Update

Dihydrocaffeic Acid-Decorated Iron Oxide Nanomaterials Effectively Inhibit Human Calcitonin Aggregation

ACS Omega 2022 Aug 22;7(35):31520-31528.PMID:36092590DOI:10.1021/acsomega.2c04206.

To date, more than 30 human peptides or proteins have been found to form amyloid fibrils, most of which are associated with human diseases. However, currently, no cure for amyloidosis exists. Therefore, development of therapeutic strategies to inhibit amyloid formation is urgently required. Although the role of some amyloidogenic proteins has not been identified in certain diseases, their self-assembling behavior largely affects their bioactivity. Human calcitonin (hCT) is a hormone peptide containing 32 amino acids and is secreted by the parafollicular cells of the thyroid gland in the human body. It can regulate the concentration of calcium ions in the blood and block the activity of osteoclasts. Therefore, calcitonin has also been considered a therapeutic peptide. However, the aggregation of hCT hinders this process, and hCT has been replaced by salmon calcitonin in drug formulations. Recently, iron oxide nanomaterials have been developed as potential materials for various applications owing to their high biocompatibility, low toxicity, and ease of functionalization. In this study, nanoparticles (NPs) were prepared using a simple chemical coprecipitation method. We first demonstrated that dopamine-conjugated Fe3O4 inhibited hCT aggregation, similar to what we found when carbon dots were used as core materials in the previous study. Later, we continued to simplify the preparation process, that is, the mixing of Dihydrocaffeic acid (DCA) and iron oxide NPs, to maintain their stability and inhibitory effect against hCT aggregation. Furthermore, DCA-decorated Fe3O4 can dissociate preformed hCT amyloid fibrils. This appears to be one of the most promising ways to stabilize hCT in solution and may be helpful for amyloidosis treatment.

pH/Glucose Dual Responsive Metformin Release Hydrogel Dressings with Adhesion and Self-Healing via Dual-Dynamic Bonding for Athletic Diabetic Foot Wound Healing

ACS Nano 2022 Feb 22;16(2):3194-3207.PMID:35099927DOI:10.1021/acsnano.1c11040.

In view of the lack of a specific drug-sustained release system that is responsive to chronic wounds of the type II diabetic foot, and the demands for frequent movement at the foot wound, pH/glucose dual-responsive metformin-released adhesion-enhanced self-healing easy-removable antibacterial antioxidant conductive hemostasis multifunctional phenylboronic acid and benzaldehyde bifunctional polyethylene glycol-co-poly(glycerol sebacic acid)/Dihydrocaffeic acid and l-arginine cografted chitosan (PEGS-PBA-BA/CS-DA-LAG, denoted as PC) hydrogel dressings were constructed based on the double dynamic bond of the Schiff-base and phenylboronate ester. It was further demonstrated that the PC hydrogel promotes wound healing by reducing inflammation and enhancing angiogenesis in a rat type II diabetic foot model. In addition, the addition of metformin (Met) and graphene oxide (GO), as well as their synergy, were confirmed to better promote wound repair in vivo. In summary, adhesion-enhanced self-healing multifunctional PC/GO/Met hydrogels with stimuli-responsive metformin release ability and easy removability have shown a promoting effect on the healing of chronic athletic diabetic wounds and provide a local-specific drug dual-response release strategy for the treatment of type II diabetic feet.

Boronate-ester crosslinked hyaluronic acid hydrogels for Dihydrocaffeic acid delivery and fibroblasts protection against UVB irradiation

Carbohydr Polym 2020 Nov 1;247:116845.PMID:32829875DOI:10.1016/j.carbpol.2020.116845.

Herein, we exploit the dynamic nature and pH dependence of complexes between phenylboronic acid and diol-containing molecules to control the release of an anti-photoaging agent, Dihydrocaffeic acid (DHCA), from a dynamic covalent hydrogel (HG). The HG is prepared by reversible formation of boronate ester crosslinks between hyaluronic acid (HA) modified with saccharide (GLU) residues and HA functionalized with 3-aminophenylboronic acid (APBA), part of which is involved in complexation with DHCA. The hydrogel exhibited increased dynamic moduli and a lower relaxation time at pH 7.4 in comparison to pH 6, and greater amount of DHCA was incorporated at pH 7.4. Moreover, this hydrogel prolonged DHCA release at pH 7.4 through drug reversible complexation/decomplexation, while the rate of release was fastest in acidic (skin) conditions. Very interestingly, the incorporation of DHCA into the network enhances its protection against UVB-induced L929 fibroblast death. Therefore, this smart hydrogel can contribute to photoaging prevention.

The colonic metabolites Dihydrocaffeic acid and dihydroferulic acid are more effective inhibitors of in vitro platelet activation than their phenolic precursors

Food Funct 2017 Mar 22;8(3):1333-1342.PMID:28229135DOI:10.1039/c6fo01404f.

Cardiovascular disease (CVD) is the major cause of morbidity and mortality worldwide. The consumption of a healthy diet rich in polyphenols has been inversely associated with the development of CVD. This study evaluated the effects of green coffee bean extract (GCBE) and yerba mate phenolic extract (YMPE), the main phenolic and methylxanthine constituents (5-caffeoylquinic acid, 3,5-dicaffeoylquinic acid, caffeine, and theobromine), and their main metabolites (caffeic acid, ferulic acid, Dihydrocaffeic acid (DHCA) and dihydroferulic acid (DHFA)) on platelet activation in vitro. Upon incubation with different doses (0.01-100 μg mL-1 or μM) of each compound, adenosine 5'-diphosphate-induced P-selectin expression and fibrinogen binding were determined using whole blood flow cytometry. Platelet P-selectin expression was significantly decreased by YMPE and all phenolic and methylxanthine constituents at physiological concentrations, compared with control, whereas fibrinogen binding on platelets was significantly increased. The colonic metabolites (DHCA and DHFA) had stronger inhibitory effects on P-selectin expression than their phenolic precursors, suggesting an increase in the efficacy to modulate platelet activation with the metabolism of the phenolic compounds.

Effect of Dihydrocaffeic acid on UV irradiation of human keratinocyte HaCaT cells

Arch Biochem Biophys 2008 Aug 15;476(2):196-204.PMID:18267100DOI:10.1016/j.abb.2008.01.019.

Dihydrocaffeic acid, a dietary constituent and a microbial metabolite of flavonoids, is an antioxidant, but few biological effects have been examined. After its production by microflora in the colon, Dihydrocaffeic acid is absorbed and found in plasma as a combination of free and metabolized forms. Excess solar UV radiation provokes damage and initiates immune response and inflammation in skin, sometimes leading to cancer. Dihydrocaffeic acid reduced the cytotoxicity and pro-inflammatory cytokine production (interleukin-6 and -8) in HaCaT cells, a keratinocyte model, following UV radiation. The effect of Dihydrocaffeic acid may result from a combination of direct radical scavenging of the reactive oxygen species formed or reinforcement of the antioxidant potential of the keratinocytes, as well as a direct interference with the pathway involved in cytokine stimulation. The minimum structure required for such an effect appears to consist of a propionate side chain attached to a catechol moiety, as indicated by the efficacy of caffeic acid, but not of the methyl and glucuronide conjugates of Dihydrocaffeic acid. The data obtained suggest that Dihydrocaffeic acid is a potential candidate for photo-protection by interfering with the events initiated after UV exposure in keratinocytes.