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HCID 89640Erstellt: 4. November 2026
[1S-(1α,4aα,6α,7α,7aα)]-1-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carbonsure
Loganate · Norloganin · loganicaci · Loganic acid · Margannic acid · Loganic acid-RM · LOGANIC ACID hplc · LOGANIC ACID WITH HPLC
https://huagongshe.com/de/chemical/89640
Identifikatoren & physikalische Daten
| CAS No. | 22255-40-9 |
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| Summenformel | C16H24O10 |
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| Durchschnittliche Molmasse | 376,36 g/mol |
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| Monoisotopische Masse | 376,13694696 g/mol |
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| SMILES | C[C@@H]1[C@H]2[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C(C(=O)O)[C@H]2C[C@@H]1O |
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| InChIKey | JNNGEAWILNVFFD-CDJYTOATSA-N |
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| PubChem CID | 89640 |
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| ChEMBL | CHEMBL1081585 |
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| ChEBI | CHEBI:30632 |
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| EC No. | 244-875-9 |
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| DTXSID | DTXSID80944913 |
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| Lokaler Name | [1S-(1α,4aα,6α,7α,7aα)]-1-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carbonsure |
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Chemische & physikalische Eigenschaften
| XLogP | -1,7 |
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| Polarare Oberfläche (TPSA) | 166 |
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| H-Brücken-Donoren | 6 |
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| H-Brücken-Akzeptoren | 10 |
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| Frei drehbare Bindungen | 4 |
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| Schwere Atome | 26 |
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| Formalladung | 0 |
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| Komplexität | 565 |
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| Lipide | Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102] |
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| Siedepunkt | 646.3±55.0 °C(Predicted) |
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| Dichte | 1.60±0.1 g/cm3(Predicted) |
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| Lagerbedingungen | -20°C |
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| Löslichkeit | Soluble in methan |
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| Aggregatzustand | powder |
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| pKa (Säurekonstante) | 4.55±0.70(Predicted) |
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| Farbe | White-beige |
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| Hauptanwendungen | metabolomicsvitamins, nutraceuticals, and natural products |
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| InChIKey | JNNGEAWILNVFFD-CDJYTOATSA-N |
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| SMILES | C[C@H]1[C@@H](O)C[C@H]2[C@@H]1[C@@H](OC=C2C(O)=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O |
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| LogP (Verteilungskoeffizient) | -2.411 (est) |
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Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
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| Lagerklasse | 11 - Combustible Solids |
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Anwendungen & Verwendung
Beschreibung
Loganic acid is an iridoid glycoside that has been found in C. mas and has diverse biological activities, including antidiabetic, antiadipogenic, anti-atherosclerotic, and anti-inflammatory properties. Loganic acid (1 μM) stimulates glucagon-like peptide-1 (GLP-1) secretion by NCI H716 human enteroendocrine colorectal cancer cells. It inhibits dexamethasone-, 3-isobutyl-1-methylxanthine-, and insulin-induced differentiation of mouse 3T3-L1 fibroblasts into adipocytes when used at a concentration of 10 μg/ml. Loganic acid (20 mg/kg per day) decreases the plasma atherogenic index, a ratio of triglyceride to HDL cholesterol, and the cardiac risk ratio, a ratio of total cholesterol to HDL cholesterol, in a rabbit model of atherosclerosis induced by a cholesterol-rich diet. It also decreases IL-6, TNF-α, and oxidized LDL (oxLDL) plasma levels in the same model.
![Molekülstruktur von [1S-(1α,4aα,6α,7α,7aα)]-1-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carbonsure](/img/chemical/89640.png)