5-Hydroxy-2-methyl-1,4-naphthochinon
plumagin · Plumbagine · 5-Hydroxy-2-methylnaphthalene-1,4-dione · plumbapin · PLUMBAGAN · PLUMBAGIN · Plumbaein · plumbagone
Identifikatoren & physikalische Daten
| CAS No. | 481-42-5 |
|---|---|
| Summenformel | C11H8O3 |
| Durchschnittliche Molmasse | 188,18 g/mol |
| Monoisotopische Masse | 188,04734412 g/mol |
| SMILES | CC1=CC(=O)c2c(O)cccc2C1=O |
| InChIKey | VCMMXZQDRFWYSE-UHFFFAOYSA-N |
| PubChem CID | 10205 |
| ChEMBL | CHEMBL295316 |
| ChEBI | CHEBI:8273 |
| EC No. | 207-569-6 |
| DTXSID | DTXSID8075413 |
| Lokaler Name | 5-Hydroxy-2-methyl-1,4-naphthochinon |
Chemische & physikalische Eigenschaften
| XLogP | 2,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 54,4 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 316 |
| SpringerMaterials Properties | Chemical shift |
| Collision Cross Section | 124.1 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]134.5 Ų [M+H]+ [CCS Type: TW |
| Schmelzpunkt | 76-78 °C(lit.) |
| Siedepunkt | 283.17°C (rough estimate) |
| Dichte | 1.354 |
| Brechungsindex | 1.6310 (estimate) |
| Lagerbedingungen | -20°C |
| Löslichkeit | very faint turbidity in hot Methanol |
| pKa (Säurekonstante) | 6.70±0.20(Predicted) |
| Aggregatzustand | Crystals or Crystalline Powder |
| Farbe | Orange |
| Biologische Quelle | Plumbago indica |
| Merck | 7538 |
| Stabilität | Hygroscopic |
| Hauptanwendungen | food and beverages |
| InChI | InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3 |
| InChIKey | VCMMXZQDRFWYSE-UHFFFAOYSA-N |
| SMILES | C1(=O)C2=C(C(O)=CC=C2)C(=O)C=C1C |
| LogP (Verteilungskoeffizient) | 2.450 (est) |
| EPA chemische Informationen | 1,4-Naphthalenedione, 5-hydroxy-2-methyl- (481-42-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P264, P264+P265, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2923 8/PG 2 |
| Zollcode | 29146990 |
| RTECS-Nr. | QL8500000 |
| R-Sätze (R) | 25-34-36/37/38 |
| Toxizität | LD50 i.p. in mice: ~0.015 g/kg (Debray) |
| Gefahrensymbole | T |
| hazard_note | Toxic |
| Sicherheitshinweise (S) | 22-26-36/37/39-45-37/39-28A |
| Gefahrenklasse | 6.1(a)Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
Plumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells. It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells. Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner. It can be protective against peroxide stress or deprivation of glucose or oxygen.
Verwenden
Plumbagin from Plumbago indica has been used: as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblastsas an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiaeas a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples