Likewise the per substance indication of harmonised C&L, Seveso directive, or notified C&L regulatory context will be made available as soon as possible. trans-Cinnamic acid is a weakly acidic compound (based on its pKa). CA treatment restored altered lipid peroxidation and antioxidant status in AIA rat models (Pragasam et al., 2012). Treated cells were incubated for 24 h at 37 °C and then reduced glutathione (GSH) levels were measured in cell lysate. Endogenous antioxidant enzymatic defense is a very important source to neutralize the oxygen free radical-mediated lipid peroxidation.46 Free radical scavenging enzymes such as catalase, SOD, and GPx are the first line of cellular defense against oxidative injury, decomposing O2 and H2O2 before their interaction to form the more reactive hydroxyl radical. showed that dose-dependent CGA administration inhibits RANKL-mediated osteoclast differentiation. Cinnamic acid undergoes reduction with sodium amalgam and water to give 3-phenylpropanoic acid. Therefore, CA may be a promising anticancer agent. CGA efficiently inhibited CD80/86 costimulatory signals, which led to decreased T-cell production and elevated Th2 cytokine levels (such as IL-4 and IL-10), which in turn antagonized Th1 cytokine (IL-2, interferon-gamma [IFN-gamma] and IL-12) production (Chauhan et al., 2012). By continuing you agree to the use of cookies. Fig. QTc interval increased from a baseline of 409 to 556 milliseconds. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. It covers their hazardous properties, classification and labelling, and information on how to use them safely. Shikimate is the central intermediate to a large range of secondary metabolites in plants and microorganisms. Another study confirmed antistaphylococcal activity of caffeic acid with MICs of 62.5–250 μg/mL reported (Luis, Silva, Sousa, Duarte, & Domingues, 2013). At the time of the event, the patient also had severe anemia (hemoglobin 6 g/dL). Against these pathogens, MICs are too high for viable systemic use, as a topical or targeted agent, it may have some clinical merits. It does not require a co-factor. The patient was discontinued from study drug. slightly soluble in water, or freely soluble in many organic solvents. There are many phenolic compounds found in plants including cinnamic acids, such as caffeic acid and benzoic acids such as gallic acid, many of which have multiple health benefits including anticancer and antibacterial activities. POP Regulation data should be completely available by the 12th November. (, By heating benzaldehyde with malonic acid in alcoholic ammonia solution. Cinnamic acid undergoes decarboxylation with soda -lime to yield styrene. This website uses cookies to ensure you get the best experience on our websites. Similarly, LAQ824, another cinnamic acid hydroxamate inhibitor of HDAC that blocks the HERG K+, also increases QTc in phase 1 studies. Many studies suggested that antioxidant enzymes are critical in protecting against tumor-promoting agents. Structure, properties, spectra, suppliers and links for: Cinnamic acid, 621-82-9. It undergoes electrophilic substitution reactions to form. Please upgrade your Internet Explorer to a newer version. I’m Mubashir Abid, 22 years old. Figure 1. The results summarize that CA initiates the cancer cell death by decreasing cell proliferation and antioxidant status, increasing intracellular ROS, altering mitochondrial membrane potential, lipid peroxidation, and apoptosis in HeLa and ME-180 cervical carcinoma cell lines. Beilstein/REAXYS Number 1905952 . Data also suggest that at concentrations of 1000 μg/mL, biofilm formation by S. aureus, E. coli, and P. aeruginosa was inhibited by gallic acid and was able to reduce the mass of existing biofilms (Borges, Saavedra, & Simoes, 2012). Please note that it may take a week or two to have everything fully in place, and please be aware in the meantime that the Registration status may be incorrect and the CLP regulatory context may be incompletely shown. Chlorogenic acid (5-caffeoylquinicacid) (Figure 2) is perhaps the most important cinnamic acid observed in fruits, contributing 25% of the dry weight of the bilberry (Vaccinium) fruit. Depletion of GSH can lead to tumor cell death in vitro, especially in melanocytic cells that generate high levels of oxyradicals. 3.4 shows the chemical structures of cinnamic acid derivatives: rosmarinic acid (3), chlorogenic acid (4), and p-coumaric acid (5). It behaves as an α, β-unsaturated acid and a benzene derivative. Molecular Weight 148.16 . Much love! Cinnamic acid reacts with bromine in carbon tetrachloride to give dibromocinnamic acid. The per substance REACH registration status will be made available as soon as possible thereafter. Moreover, in an in vivo model, lipopolysaccharide (LPS)-induced bone erosion is markedly attenuated by CGA treatment (Kwak et al., 2013). In humans, trans-cinnamic acid is safely converted to hippuric acid which is excreted in the urine. (See COFFEE | Green Coffee; FRUITS OF TEMPERATE CLIMATES | Fruits of the Ericacae.). Registration, Evaluation, Authorisation and Restriction of Chemicals, Chemical Agents Directive and Carcinogens or Mutagens Directive, Substances of very high concern identification, Recommendation for the Authorisation List, Getting started with EU chemicals legislation, Classification of substances and mixtures, Harmonised classification and labelling (CLH). The abundance of transcription factors (NF-κB-p65, and p–NF–κB-p65, NFATc-1, and c-Fos) and MAP kinases (JNK, p-JNK, and ERK1/2) expression was downregulated in CA-administered arthritic rats (Neog et al., 2017). MDL number MFCD00004369. CGA inhibited the phosphorylation of p38, Akt, ERK, and IκB degradation and suppressed the messenger RNA (mRNA) expression of NFATc1, TRAP, and OSCAR in RANKL-treated bone marrow macrophages (BMMs). They have a wide distribution among fruits, vegetables, and beverages (e.g., tea, coffee) (Lende et al., 2011). Limited availability; the plant is reputed to be over-exploited and vulnerable in parts of India. Among all the doses tested, 50 μg/ml of CA significantly decreased GSH levels in HeLa and ME-180 cells. Moreover, RosA preferentially induced the apoptotic death of CD4+CD25+ and CD4+CD45RO+ T cells compared with T-cell subsets (Hur et al., 2007). RosA stimulated the apoptosis of T cells in RA patients. It is sparingly soluble in water. In summary, the ECG changes observed to date with HDI treatment appear to be clinically insignificant; however, additional studies may be needed to rule out any long-term cardiac effects.

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