HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
(S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron
NARIGENIN · naringenine · (s)-naringenin · 5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMAN-4-ONE · (2S)-Naringenin · (S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroMan-4-one · naringetol · 5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
Identifikatoren & physikalische Daten
| CAS No. | 480-41-1 |
|---|---|
| Summenformel | C15H12O5 |
| Durchschnittliche Molmasse | 272,25 g/mol |
| Monoisotopische Masse | 272,06847348 g/mol |
| SMILES | O=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O)cc(O)c21 |
| InChIKey | FTVWIRXFELQLPI-ZDUSSCGKSA-N |
| PubChem CID | 439246 |
| ChEMBL | CHEMBL9352 |
| ChEBI | CHEBI:17846 |
| EC No. | 207-550-2 |
| DTXSID | DTXSID1022392 |
| Lokaler Name | (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 87 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 363 |
| Stoffklassen | Antioxidant |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Polyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214] |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | 2.52 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 251 °C247-250 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 166.9 Ų [M+H]+ |
| Siedepunkt | 335.31°C (rough estimate) |
| Dichte | 1.2066 (rough estimate) |
| Brechungsindex | 1.6000 (estimate) |
| FEMA | 4797 | (+/-)-NARINGENIN |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly, Sonicated) |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 7.52±0.40(Predicted) |
| Farbe | Beige-brown |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| InChI | InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1 |
| InChIKey | FTVWIRXFELQLPI-ZDUSSCGKSA-N |
| SMILES | [C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C(=O)C1 |
| LogP (Verteilungskoeffizient) | 2.520 |
| CAS Datenbank | 480-41-1(CAS DataBase Reference) |
| EPA chemische Informationen | 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- (480-41-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (99.3%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 305 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (99.3%) |
| Toxizitätsübersicht | A 2022 review notes that Naringenin has protective effects against toxicities produced by various natural toxins, pharmaceuticals, heavy metals, and environmental chemicals, and that the effects are mainly mediated via suppression of lipid peroxidation, oxidative stress (one example is lead), and inflammatory factors (one example is daunorubicin), and the activation of PI3K/Akt and MAPK survival signaling pathways. |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29329990 |
| R-Sätze (R) | 36/37/38-22 |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 26-36-37/39 |
| Gefahrenklasse | IRRITANT |
Anwendungen & Verwendung
Verwenden
The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions