3-O-Caffeoylquinic acid methyl esterCAS# 123483-19-2 |
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Quality Control & MSDS
3D structure
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| Cas No. | 123483-19-2 | SDF | Download SDF |
| PubChem ID | 6476139 | Appearance | Powder |
| Formula | C17H20O9 | M.Wt | 368.3 |
| Type of Compound | Phenylpropanoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylate | ||
| SMILES | COC(=O)C1(CC(C(C(C1)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O)O | ||
| Standard InChIKey | MZNIJRAPCCELQX-AWOKGZDASA-N | ||
| 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 | 3-O-Caffeoylquinic acid methyl ester is a natural product from Morus alba L. |
| In vitro | Inhibiting activities of the secondary metabolites of Phlomis brunneogaleata against parasitic protozoa and plasmodial enoyl-ACP Reductase, a crucial enzyme in fatty acid biosynthesis.[Pubmed: 15326547 ]Planta Med. 2004 Aug;70(8):711-7.Anti-plasmodial activity-guided fractionation of Phlomis brunneogaleata (Lamiaceae) led to the isolation of two new metabolites, the iridoid glycoside, brunneogaleatoside and a new pyrrolidinium derivative (2 S,4 R)-2-carboxy-4-( E)- p-coumaroyloxy-1,1-dimethylpyrrolidinium inner salt [(2 S,4 R)-1,1-dimethyl-4-( E)- p-coumaroyloxyproline inner salt]. Moreover, a known iridoid glycoside, ipolamiide, six known phenylethanoid glycosides, verbascoside, isoverbascoside, forsythoside B, echinacoside, glucopyranosyl-(1-->G (i)-6)-martynoside and integrifolioside B, two flavone glycosides, luteolin 7- O-beta- D-glucopyranoside ( 10) and chrysoeriol 7- O-beta- D-glucopyranoside ( 11), a lignan glycoside liriodendrin, an acetophenone glycoside 4-hydroxyacetophenone 4- O-(6'- O-beta- D-apiofuranosyl)-beta- D-glucopyranoside and three caffeic acid esters, chlorogenic acid, 3-O-Caffeoylquinic acid methyl ester and 5- O-caffeoylshikimic acid were isolated.
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| Structure Identification | Yao Xue Xue Bao. 2014 Apr;49(4):504-6.Studies on chemical constituents from fruits of Morus alba L.[Pubmed: 24974468]Chemical investigation of fruits of Mours alba L. lead to the isolation of fifteen compounds by various chromatographies such as silica gel, Sephadex LH-20, RP-C18 column chromatography. |
3-O-Caffeoylquinic acid methyl ester Dilution Calculator
3-O-Caffeoylquinic acid methyl ester Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7152 mL | 13.5759 mL | 27.1518 mL | 54.3036 mL | 67.8794 mL |
| 5 mM | 0.543 mL | 2.7152 mL | 5.4304 mL | 10.8607 mL | 13.5759 mL |
| 10 mM | 0.2715 mL | 1.3576 mL | 2.7152 mL | 5.4304 mL | 6.7879 mL |
| 50 mM | 0.0543 mL | 0.2715 mL | 0.543 mL | 1.0861 mL | 1.3576 mL |
| 100 mM | 0.0272 mL | 0.1358 mL | 0.2715 mL | 0.543 mL | 0.6788 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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Inhibiting activities of the secondary metabolites of Phlomis brunneogaleata against parasitic protozoa and plasmodial enoyl-ACP Reductase, a crucial enzyme in fatty acid biosynthesis.[Pubmed:15326547]
Planta Med. 2004 Aug;70(8):711-7.
Anti-plasmodial activity-guided fractionation of Phlomis brunneogaleata (Lamiaceae) led to the isolation of two new metabolites, the iridoid glycoside, brunneogaleatoside and a new pyrrolidinium derivative (2 S,4 R)-2-carboxy-4-( E)- p-coumaroyloxy-1,1-dimethylpyrrolidinium inner salt [(2 S,4 R)-1,1-dimethyl-4-( E)- p-coumaroyloxyproline inner salt]. Moreover, a known iridoid glycoside, ipolamiide, six known phenylethanoid glycosides, verbascoside, isoverbascoside, forsythoside B, echinacoside, glucopyranosyl-(1-->G (i)-6)-martynoside and integrifolioside B, two flavone glycosides, luteolin 7- O-beta- D-glucopyranoside ( 10) and chrysoeriol 7- O-beta- D-glucopyranoside ( 11), a lignan glycoside liriodendrin, an acetophenone glycoside 4-hydroxyacetophenone 4- O-(6'- O-beta- D-apiofuranosyl)-beta- D-glucopyranoside and three caffeic acid esters, chlorogenic acid, 3-O-Caffeoylquinic acid methyl ester and 5- O-caffeoylshikimic acid were isolated. The structures of the pure compounds were elucidated by means of spectroscopic methods (UV, IR, MS, 1D and 2D NMR, [alpha] (D)) and X-ray crystallography. Compounds 10 and 11 were determined to be the major anti-malarial principles of the crude extract (IC (50) values of 2.4 and 5.9 micrograms/mL, respectively). They also exhibited significant leishmanicidal activity (IC (50) = 1.1 and 4.1 micrograms/mL, respectively). The inhibitory potential of the pure metabolites against plasmodial enoyl-ACP reductase (FabI), which is the key regulator of type II fatty acid synthases (FAS-II) in P. falciparum, was also assessed. Compound 10 showed promising FabI inhibiting effect (IC (50) = 10 micrograms/mL) and appears to be the first anti-malarial natural product targeting FabI of P. falciparum.
[Studies on chemical constituents from fruits of Morus alba L].[Pubmed:24974468]
Yao Xue Xue Bao. 2014 Apr;49(4):504-6.
Chemical investigation of fruits of Mours alba L. lead to the isolation of fifteen compounds by various chromatographies such as silica gel, Sephadex LH-20, RP-C18 column chromatography. Their structures were determined to be: 1-[5-(2-formlfuryl) methyl] dihydrogen 2-hydroxypropane-1, 2, 3-tricarboxylate 2, 3-diethyl ester (1), 1-[2-(furan-2-yl)-2-oxoethyl] pyrrolidin-2-one (2), divaricataester A (3), methyl 1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylate (4), 1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylic acid (5), L-pyroglutamic acid (6), L-pyroglutamic acid ethyl ester (7), 3-O-Caffeoylquinic acid methyl ester (8), 3-O-caffeoylquinic acid ethyl ester (9), 5-O-caffeoylquinic acid methyl ester (10), 5-O-caffeoylquinic acid ethyl ester (11), 4-O-caffeoylquinic acid methyl ester (12), 4-O-caffeoylquinic acid methyl ester (13), 4-O-caffeoylquinic acid (14), 3-O-caffeoylquinic acid (15), respectively, based on the spectral analysis such as NMR, MS etc. Compounds 1-14 were isolated from this genus for the first time, among which 1 was a new compound.
