N-trans-FeruloyltyramineCAS# 66648-43-9 |
- Cis-N-Feruloyltyramine
Catalog No.:BCN3729
CAS No.:80510-09-4
Quality Control & MSDS
3D structure
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| Cas No. | 66648-43-9 | SDF | Download SDF |
| PubChem ID | 5280537 | Appearance | White powder |
| Formula | C18H19NO4 | M.Wt | 313.4 |
| Type of Compound | Phenylpropanoids | Storage | Desiccate at -20°C |
| Synonyms | Alfrutamide; Moupinamide | ||
| Solubility | Soluble in DMSO and methan | ||
| Chemical Name | (E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide | ||
| SMILES | COC1=C(C=CC(=C1)C=CC(=O)NCCC2=CC=C(C=C2)O)O | ||
| Standard InChIKey | NPNNKDMSXVRADT-WEVVVXLNSA-N | ||
| Standard InChI | InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | N-trans-Feruloyltyramine(NTF) is a platelet aggregation inhibitor, which has hepatoprotective, and antioxidative effects, NTF is likely to inhibit COX enzymes, thereby suppressing P-selectin expression on platelets;NTF inhibits melanogenesis in a dose-dependent manner. |
| Targets | NO | PGE | AP-1 | NOS | COX | TNF-α | JNK | Beta Amyloid | Caspase |
| In vitro | N-trans-feruloyltyramine inhibits LPS-induced NO and PGE2 production in RAW 264.7 macrophages: Involvement of AP-1 and MAP kinase signalling pathways.[Pubmed: 25843058]Chem Biol Interact. 2015 Jun 25;235:56-62.Mitogen-activated protein kinase (MAPK) signalling pathway can regulate inflammatory and immune responses. N-trans-Feruloyltyramine (FLA) is an active phenylpropanoid compound.
It possesses antioxidant, antimicrobial, anti-melanogenesis, and anticancer activities. However, the precise molecular mechanisms underlying FLA modulation of cytokine expression in LPS-stimulated RAW 264.7 macrophages have not been fully investigated. In this study, we examined the mechanisms underlying the immunomodulative effects of FLA isolated from Arcangelisia gusanlung.
Antioxidant and enzyme inhibition activities and chemical profiles of Polygonum sachalinensis F.Schmidt ex Maxim (Polygonaceae).[Pubmed: 19698767]Fitoterapia. 2010 Mar;81(2):124-31.Polygonum sachalinensis is a widespread invasive plant in Europe. Chemical profiles of its different organs were studied by HPLC-UV-ESI/MS.
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| Kinase Assay | N-trans-feruloyltyramine as a melanin biosynthesis inhibitor.[Pubmed: 17917275]Biol Pharm Bull. 2007 Oct;30(10):1972-4.In this study, we examined the effect of N-trans-Feruloyltyramine (FA) on melanogenesis in mouse B16 melanoma cells.
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| Cell Research | Protective role of N-trans-feruloyltyramine against β-amyloid peptide-induced neurotoxicity in rat cultured cortical neurons.[Pubmed: 22387154]Neurosci Lett. 2012 Apr 4;513(2):229-32.Enhanced oxidative stress and inflammation play important roles in the pathogenesis of Alzheimer's disease (AD). Amyloid β-peptide (Aβ), a major component of amyloid plaques, is considered to have a causal role in the development and progress of AD by being the initiator of a pathological cascade leading to oxidative stress.
The present study investigated the effect of N-trans-Feruloyltyramine (NTF) purified from Polyalthia suberosa, an alkaloid shown to protect against oxidative stress and cell death. |
N-trans-Feruloyltyramine Dilution Calculator
N-trans-Feruloyltyramine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.1908 mL | 15.9541 mL | 31.9081 mL | 63.8162 mL | 79.7703 mL |
| 5 mM | 0.6382 mL | 3.1908 mL | 6.3816 mL | 12.7632 mL | 15.9541 mL |
| 10 mM | 0.3191 mL | 1.5954 mL | 3.1908 mL | 6.3816 mL | 7.977 mL |
| 50 mM | 0.0638 mL | 0.3191 mL | 0.6382 mL | 1.2763 mL | 1.5954 mL |
| 100 mM | 0.0319 mL | 0.1595 mL | 0.3191 mL | 0.6382 mL | 0.7977 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Protective role of N-trans-feruloyltyramine against beta-amyloid peptide-induced neurotoxicity in rat cultured cortical neurons.[Pubmed:22387154]
Neurosci Lett. 2012 Apr 4;513(2):229-32.
Enhanced oxidative stress and inflammation play important roles in the pathogenesis of Alzheimer's disease (AD). Amyloid beta-peptide (Abeta), a major component of amyloid plaques, is considered to have a causal role in the development and progress of AD by being the initiator of a pathological cascade leading to oxidative stress. The present study investigated the effect of N-trans-Feruloyltyramine (NTF) purified from Polyalthia suberosa, an alkaloid shown to protect against oxidative stress and cell death. Pre-treatment of rat primary cortical cell cultures with 25-250muM NTF significantly attenuated 10muM Abeta(1-42)-induced neuronal death in a dose-dependent manner. Apoptotic cell death was demonstrated morphologically as well as by detection of the presence of activated caspase-3 and Bax, levels of which could be reduced by NTF pre-treatment. NTF also reduced production of reactive oxygen species induced by Abeta(1-42). These findings suggest that the protective effect of NTF against Abeta(1-42)-induced neuronal death might be due to its antioxidative property.
N-trans-feruloyltyramine inhibits LPS-induced NO and PGE2 production in RAW 264.7 macrophages: Involvement of AP-1 and MAP kinase signalling pathways.[Pubmed:25843058]
Chem Biol Interact. 2015 Jun 25;235:56-62.
Mitogen-activated protein kinase (MAPK) signalling pathway can regulate inflammatory and immune responses. N-trans-Feruloyltyramine (FLA) is an active phenylpropanoid compound. It possesses antioxidant, antimicrobial, anti-melanogenesis, and anticancer activities. However, the precise molecular mechanisms underlying FLA modulation of cytokine expression in LPS-stimulated RAW 264.7 macrophages have not been fully investigated. In this study, we examined the mechanisms underlying the immunomodulative effects of FLA isolated from Arcangelisia gusanlung. FLA strongly suppressed mRNA expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), but not tumor necrosis factor (TNF)-alpha, thereby inhibiting the production of nitric oxide (NO) and prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Furthermore, FLA also inhibited nuclear translocation of activation protein (AP)-1, and simultaneously decreased the expression and phosphorylation of the c-Jun N-terminal kinase (JNK) protein. These results suggest that the anti-inflammatory effects of FLA might be attributed to downregulation of COX-2 and iNOS via suppression of AP-1 and the JNK signalling pathway in RAW 264.7 macrophages.
Antioxidant and enzyme inhibition activities and chemical profiles of Polygonum sachalinensis F.Schmidt ex Maxim (Polygonaceae).[Pubmed:19698767]
Fitoterapia. 2010 Mar;81(2):124-31.
Polygonum sachalinensis is a widespread invasive plant in Europe. Chemical profiles of its different organs were studied by HPLC-UV-ESI/MS. Seven major constituents quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-arabinopyranoside, lapathoside D, N-trans-Feruloyltyramine, lapathoside C, hydropiperoside, and vanicoside B were isolated and identified. The free radical-scavenging, alpha/beta-glucosidase, and acetylcholinesterase inhibitory activities of crude MeOH extracts and isolated compounds were studied. The structure-activity relationships were discussed. The chemical profiles revealed flavonoids and phenylpropanoids are the major compounds of all the organs of this plant. Quercetin-3-O-arabinopyranoside, lapathoside D, N-trans-Feruloyltyramine, lapathoside C and hydropiperoside were isolated from this species for the first time. In the alpha-glucosidase bioassay, quercetin-3-O-beta-D-galactopyranoside, lapathoside D and N-trans-Feruloyltyramine demonstrated stronger activities than the positive reference acarbose. The trend in scavenging power showed no relation to enzyme inhibition in the test models.
N-trans-feruloyltyramine as a melanin biosynthesis inhibitor.[Pubmed:17917275]
Biol Pharm Bull. 2007 Oct;30(10):1972-4.
In this study, we examined the effect of N-trans-Feruloyltyramine (FA) on melanogenesis in mouse B16 melanoma cells. Melanogenesis was inhibited by FA in a dose-dependent manner. FA exhibited a greater potency than kojic acid as a standard inhibitor of melanogenesis. Moreover, treatment of B16 melanoma cells with FA was found to cause marked decreases in the expression levels of tyrosinase. FA-induced downregulation of tyrosinase resulted in suppression of melanin biosynthesis in murine B16 melanoma cells.
