Loganic acidCAS# 22255-40-9 |
- 8-Epiloganic acid
Catalog No.:BCC8956
CAS No.:82509-41-9
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 22255-40-9 | SDF | Download SDF |
| PubChem ID | 89640 | Appearance | White-beige powder |
| Formula | C16H24O10 | M.Wt | 376.4 |
| Type of Compound | Iridoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in methan | ||
| Chemical Name | (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid | ||
| SMILES | CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O | ||
| Standard InChIKey | JNNGEAWILNVFFD-CDJYTOATSA-N | ||
| Standard InChI | InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1 | ||
| 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 | Loganic acid( 0.7% solution) has a strong intraocular pressure (IOP)-hypotensive effect, it exhibits both sides effect on superoxide generation. Loganic acid also has protective effects on atherosclerosis risk factors in hypercholesterolemic rabbits, it shows significant anti-inflammatory effects decreasing TNF-α and IL-6 activity in serum. |
| Targets | PPAR | TNF-α | IL Receptor |
| In vitro | Anti-inflammatory effect of three iridoids in human neutrophils.[Pubmed: 22417122]Nat Prod Res. 2013;27(10):911-5.To verify the anti-inflammatory potency of iridoids, three iridoids (two natural, Loganic acid: LA; geniposide: GE; and an artefact, 7(S)-n-butyl morroniside: BM) were investigated in vitro on the inhibition of superoxide generation in human neutrophils.
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| In vivo | The protective effect of the Cornus mas fruits (cornelian cherry) on hypertriglyceridemia and atherosclerosis through PPARα activation in hypercholesterolemic rabbits.[Pubmed: 25444446 ]Phytomedicine. 2014 Nov 15;21(13):1774-84.
Cornelian cherry (Cornus mas L.) fruits have been used in traditional cuisine and in folk medicine in various countries. This study was conducted to evaluate the constituents and impact of cornelian cherry (C. mas L.) fruits lyophilisate on lipid levels, PPARα protein expression, atheromatous changes in the aorta, oxido-redox state, and proinflammatory cytokines in hypercholesterolemic rabbits.
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| Animal Research | Application of Cornelian Cherry Iridoid-Polyphenolic Fraction and Loganic Acid to Reduce Intraocular Pressure.[Pubmed: 26124854 ]Evid Based Complement Alternat Med. 2015;2015:939402.One of the most common diseases of old age in modern societies is glaucoma. It is strongly connected with increased intraocular pressure (IOP) and could permanently damage vision in the affected eye. As there are only a limited number of chemical compounds that can decrease IOP as well as blood flow in eye vessels, the up-to-date investigation of new molecules is important.
The chemical composition of the dried Cornelian cherry (Cornus mas L.) polar, iridoid-polyphenol-rich fraction was investigated.
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| Structure Identification | Yao Xue Xue Bao. 2007 May;42(5):566-70.Content of gentiopicroside and loganic acid in Radix gentianae and their fingerprints[Pubmed: 17703785]
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Loganic acid Dilution Calculator
Loganic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6567 mL | 13.2837 mL | 26.5675 mL | 53.135 mL | 66.4187 mL |
| 5 mM | 0.5313 mL | 2.6567 mL | 5.3135 mL | 10.627 mL | 13.2837 mL |
| 10 mM | 0.2657 mL | 1.3284 mL | 2.6567 mL | 5.3135 mL | 6.6419 mL |
| 50 mM | 0.0531 mL | 0.2657 mL | 0.5313 mL | 1.0627 mL | 1.3284 mL |
| 100 mM | 0.0266 mL | 0.1328 mL | 0.2657 mL | 0.5313 mL | 0.6642 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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[Content of gentiopicroside and loganic acid in Radix gentianae and their fingerprints].[Pubmed:17703785]
Yao Xue Xue Bao. 2007 May;42(5):566-70.
To develop a HPLC-DAD-ESI-TOF/MS analysis method for the determination of gentiopicroside and Loganic acid in Radix gentianae samples and for the research of their fingerprints. The samples were extracted using ASE for 10 min under 100 degrees C and 9.65 MPa, and divided into water phase and chloroform phase and analyzed them with HPLC-DAD-ESI-TOF/MS method respectively. Based on this method, the HPLC fingerprints of Radix gentianae were established. Comparing the spectrogram and mass spectrum of the chromatogram peak with the reference value, three compounds in water phase were identified as gentiopicroside, asafetida acid and Loganic acid. There is no report of the compounds in chloroform phase. The content of gentiopicroside and Loganic acid in samples of different groups were determined, separately. The fingerprints were compared by the software of the similarity evaluation system for chromatographic fingerprint. The water phase fingerprint congruence coefficients of samples from six different areas were above 0.90, however, the chloroform phase fingerprint congruence coefficients were within 0.62 -0.99. This method can be used for determination of potent component in Radix gentianae and its quality control. Radix gentianae from different producing areas have the largest diversities, and the diversities embodied in the content of chloroform phase compounds.
The protective effect of the Cornus mas fruits (cornelian cherry) on hypertriglyceridemia and atherosclerosis through PPARalpha activation in hypercholesterolemic rabbits.[Pubmed:25444446]
Phytomedicine. 2014 Nov 15;21(13):1774-84.
Cornelian cherry (Cornus mas L.) fruits have been used in traditional cuisine and in folk medicine in various countries. This study was conducted to evaluate the constituents and impact of cornelian cherry (C. mas L.) fruits lyophilisate on lipid levels, PPARalpha protein expression, atheromatous changes in the aorta, oxido-redox state, and proinflammatory cytokines in hypercholesterolemic rabbits. The HPLC-MS method was used for determining active constituents in cornelian cherry. In a subsequent in vivo study the protective effect of the cornelian cherry on diet-induced hyperlipidemia was studied using a rabbit model fed 1% cholesterol. Cornelian cherry (100mg/kg b.w.) or simvastatin (5mg/kg b.w.) were administered orally for 60 days. Two iridoids - Loganic acid and cornuside - and five anthocyanins were identified as the main constituents of the cornelian cherry. The administering of the cornelian cherry led to a 44% significant decrease in serum triglyceride levels, as well as prevented development of atheromatous changes in the thoracic aorta. Cornelian cherry significantly increased PPARalpha protein expression in the liver, indicating that its hypolipidemic effect may stem from enhanced fatty acid catabolism. Simvastatin treatment did not affect PPAR-alpha expression. Moreover, the cornelian cherry had a significant protective effect on diet-induced oxidative stress in the liver, as well as restored upregulated proinflammatory cytokines serum levels. In conclusion, we have shown Loganic acid to be the main iridoid constituent in the European cultivar of the cornelian cherry, and proven that the cornelian cherry could have protective effects on diet-induced hypertriglicerydemia and atherosclerosis through enhanced PPARalpha protein expression and via regulating oxidative stress and inflammation.
Anti-inflammatory effect of three iridoids in human neutrophils.[Pubmed:22417122]
Nat Prod Res. 2013;27(10):911-5.
To verify the anti-inflammatory potency of iridoids, three iridoids (two natural, Loganic acid: LA; geniposide: GE; and an artefact, 7(S)-n-butyl morroniside: BM) were investigated in vitro on the inhibition of superoxide generation in human neutrophils. All compounds showed inhibitory effect on fMLP-induced superoxide generation in a concentration-dependent manner with the following order: BM>LA>GE. BM exhibits potent inhibitory activity on superoxide anion induced by PMA, while LA and GE showed weak effect. When AA was used as stimulus, the generation of superoxide anion was suppressed by BM in a concentration-dependent manner. LA and GE exhibit both sides effect on superoxide generation.
Application of Cornelian Cherry Iridoid-Polyphenolic Fraction and Loganic Acid to Reduce Intraocular Pressure.[Pubmed:26124854]
Evid Based Complement Alternat Med. 2015;2015:939402.
One of the most common diseases of old age in modern societies is glaucoma. It is strongly connected with increased intraocular pressure (IOP) and could permanently damage vision in the affected eye. As there are only a limited number of chemical compounds that can decrease IOP as well as blood flow in eye vessels, the up-to-date investigation of new molecules is important. The chemical composition of the dried Cornelian cherry (Cornus mas L.) polar, iridoid-polyphenol-rich fraction was investigated. Loganic acid (50%) and pelargonidin-3-galactoside (7%) were found as the main components. Among the other constituents, iridoid compound cornuside and the anthocyans cyanidin 3-O-galactoside, cyanidin 3-O-robinobioside, and pelargonidin 3-O-robinobioside were quantified in the fraction. In an animal model (New Zealand rabbits), the influence of Loganic acid and the polyphenolic fraction isolated from Cornelian cherry fruit was investigated. We found a strong IOP-hypotensive effect for a 0.7% solution of Loganic acid, which could be compared with the widely ophthalmologically used timolol. About a 25% decrease in IOP was observed within the first 3 hours of use.
