Retrofractamide CCAS# 96386-33-3 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 96386-33-3 | SDF | Download SDF |
PubChem ID | 25255091 | Appearance | Powder |
Formula | C20H27NO3 | M.Wt | 329.4 |
Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | (2E,8E)-9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,8-dienamide | ||
SMILES | CC(C)CNC(=O)C=CCCCCC=CC1=CC2=C(C=C1)OCO2 | ||
Standard InChIKey | PAXQNYHJDFKFEU-FIFLTTCUSA-N | ||
Standard InChI | InChI=1S/C20H27NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h7-13,16H,3-6,14-15H2,1-2H3,(H,21,22)/b9-7+,10-8+ | ||
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. |
Retrofractamide C Dilution Calculator
Retrofractamide C Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 3.0358 mL | 15.1791 mL | 30.3582 mL | 60.7165 mL | 75.8956 mL |
5 mM | 0.6072 mL | 3.0358 mL | 6.0716 mL | 12.1433 mL | 15.1791 mL |
10 mM | 0.3036 mL | 1.5179 mL | 3.0358 mL | 6.0716 mL | 7.5896 mL |
50 mM | 0.0607 mL | 0.3036 mL | 0.6072 mL | 1.2143 mL | 1.5179 mL |
100 mM | 0.0304 mL | 0.1518 mL | 0.3036 mL | 0.6072 mL | 0.759 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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Chemical Composition of Leaves, Stem, and Roots of Peperomia pellucida (L.) Kunth.[Pubmed:35335210]
Molecules. 2022 Mar 11;27(6):1847.
Peperomia pellucida is a species known in the Amazon as "erva-de-jabuti" that has been used in several therapeutic applications based on folk medicine. Herein, we describe the classes, subclasses, and the main compounds of the leaves, stems, and roots from P. pellucida by ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry associated with molecular networks, mirror plot on the GNPS library, and machine learning. These data show compounds that were annotated for the first time in the Peperomia genus, such as 2',4',5'-trihydroxybutyrophenonevelutin, dehydroRetrofractamide C, and retrofractamide B.
Retrofractamide C Derived from Piper longum Alleviates Xylene-Induced Mouse Ear Edema and Inhibits Phosphorylation of ERK and NF-kappaB in LPS-Induced J774A.1.[Pubmed:32899525]
Molecules. 2020 Sep 5;25(18):4058.
Many studies have reported the biological activities of Retrofractamide C (RAC). However, few studies have investigated the anti-inflammatory effect of RAC. In the present study, we investigated the anti-inflammatory effect of RAC using lipopolysaccharide (LPS)-induced J774A.1 cells and a xylene-induced mouse ear edema model. Treatment with RAC decreased LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) secretion and inducible NO synthase (iNOS) and cyclooxygenase 2 (COX2) protein expression. It also downregulated the LPS-induced production of interleukin-1beta (IL-1beta) and interleukin-6 (IL-6) but not tumor necrosis factor alpha (TNF-alpha). In the LPS-induced signaling pathway, RAC inhibited the phosphorylation of extracellular signal-regulated kinase (ERK) and nuclear factor kappa light chain enhancer of activated B cells (NF-kappaB) but not c-Jun N-terminal kinase (JNK) or p38. In a xylene-induced mouse ear edema model, RAC treatment alleviated edema formation and inflammatory cell infiltration. In conclusion, the present study indicates that RAC has the potential to have anti-inflammatory effects and could be a prospective functional food.
Activation of TRPV1 and TRPA1 by black pepper components.[Pubmed:20460725]
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ACAT inhibition of alkamides identified in the fruits of Piper nigrum.[Pubmed:17188313]
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In this study, via a bioactivity-guided fractionation of MeOH extracts of the fruits of Piper nigrum, alkamide (5) and five previously-identified alkamides were isolated. Their structures were elucidated via spectroscopic analysis ((1)H, (13)C NMR and ESI-MS), as follows: retrofractamide A (1), pipercide (2), piperchabamide D (3), pellitorin (4), dehydroRetrofractamide C (5) and dehydropipernonaline (6). The IC(50) values determined for the compounds were 24.5 (1), 3.7 (2), 13.5 (3), 40.5 (4), 60 (5) and 90 microM (6), according to the results of an ACAT enzyme assay system using rat liver microsomes. These compounds all inhibited cholesterol esterification in HepG2 cells.
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Pharmacological inhibition of acyl CoA:diacylglycerol acyltransferase (DGAT, EC 2.3.1.20) has emerged as a potential therapy for the treatment of obesity and type 2 diabetes. Bioassay-guided isolation of CHCl3 extracts of the fruits of Piper longum and Piper nigum (Piperaceae), using an in vitro DGAT inhibitory assay, lead to isolation of a new alkamide named (2E,4Z,8E)-N-[9-(3,4-methylenedioxyphenyl)-2,4,8-nonatrienoyl]piperidine (2), together with four known alkamides: Retrofractamide C (1), pipernonaline (3), piperrolein B (4), and dehydropipernonaline (5). Compounds 2-5 inhibited DGAT with IC50 values of 29.8 (2), 37.2 (3), 20.1 (4), and 21.2 (5) microM, respectively, but the IC50 value for 1 was more than 900 microM. This finding indicates that compounds possessing piperidine groups (2-5) can be potential DGAT inhibitors.