2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyron
luteoline · cyanidenon · FLACITRAN · digitoflavone · 3',4',5,7-Tetrahydroxyflavone · 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-on · LUTEOLOL · Rose extract P.E
Identifikatoren & physikalische Daten
| CAS No. | 491-70-3 |
|---|---|
| Summenformel | C15H10O6 |
| Durchschnittliche Molmasse | 286,24 g/mol |
| Monoisotopische Masse | 286,04773803 g/mol |
| SMILES | O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12 |
| InChIKey | IQPNAANSBPBGFQ-UHFFFAOYSA-N |
| PubChem CID | 5280445 |
| ChEMBL | CHEMBL151 |
| ChEBI | CHEBI:15864 |
| EC No. | 207-741-0 |
| DTXSID | DTXSID4074988 |
| Lokaler Name | 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyron |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 107 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 447 |
| LogP (Verteilungskoeffizient) | 2.53 |
| Schmelzpunkt | 329.5 °C~330 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 158.43 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 348.61°C (rough estimate) |
| Dichte | 1.2981 (rough estimate) |
| Brechungsindex | 1.4413 (estimate) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Methanol (Slightly, Heated)Soluble in aqueous alkaline solutions (1.4 mg/ml), ethanol (~5 mg/ml), dimethyl sulfoxide (7 mg/ml), 1eq. Sodium hydroxide (5 mM), dimethylformamide (~20 mg/ml), water (1 mg/ml) at 25°C and methanol. |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 6.50±0.40(Predicted) |
| Farbe | yellow |
| Merck | 14,5614 |
| BRN | 292084 |
| Hauptanwendungen | food and beverages |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| InChI | 1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H |
| InChIKey | IQPNAANSBPBGFQ-UHFFFAOYSA-N |
| SMILES | Oc1cc(O)c2C(=O)C=C(Oc2c1)c3ccc(O)c(O)c3 |
| LogP (Verteilungskoeffizient) | 2.40 |
| CAS Datenbank | 491-70-3(CAS DataBase Reference) |
| EPA chemische Informationen | Luteolin (491-70-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.9% (1 of 54) of reports.WarningH315 (98.1%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (98.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (96.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 54 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 54 reports by companies.There are 9 notifications provided by 53 of 54 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (98.1%)Eye Irrit. 2 (98.1%)STOT SE 3 (96.3%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29329990 |
| RTECS-Nr. | LK9275210 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-36/37/39 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Luteolin is a flavone derived from Honeysuckle(Lonicera japonica Thunb). Luteolin is widely distributed in nature. It can be isolated from a variety of natural herbs, vegetables, and fruits. At present, luteolin is found mainly in honeysuckle, chrysanthemum, Schizonepeta, Ajuga, artichokes, Scutellaria, and Callicarpa nudiflora natural herbs.[3] Dietary sources include celery, broccoli, green pepper, parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano. It can also be found in the seeds of the palm Aiphanes aculeata.Fig 2 Source of Luteolin[4]
History
At present, luteolin does not have the application of the proprietary medicine, but as one of the main active ingredients of medicinal plants, there is a long history of application. In northern and southern dynasties, honeysuckle with sweet taste, nontoxic, can treat swelling, lose weight, and prolong life under long-term use. In Tang dynasty, honeysuckle was used for treatment of abdominal distension, hot toxic blood dysentery, and water dysentery. It was showed that the clinical application of honeysuckle had made significant progress. During the Song and Yuan dynasties, honeysuckle was widely used for the treatment of diseases such as sore and ulcer. To the Ming dynasty, there were many treatises about honeysuckle. For example, it is said in Compendium of Materia Medica: honeysuckle cure all rheumatism QI and all sorts of swollen poison, ulcer,scab, and heat dissipation detoxify. The prescription has also expanded its scope of application. Up to the Qing dynasty, the application of honeysuckle can not only inherit the theory of the predecessors but also put forward some original ideas and innovation in some respects. In recent years, through the in-depth study of pharmacological effects, it is found that luteolin has significant effects on antitumor, cardioprotection, neuroprotection,respiratory system, immune regulation, anti-inflammatory, spasmolysis, expectorant, anti-allergic, enzyme activities, antioxidant, diuretic, and other aspects.
Verwenden
Luteolin has been used:to induce and elucidate the apoptotic pathway in renal cell carcinoma 786-O cellsas an additive in M9 minimal medium to induce nodF gene expressionas a reference standard to qualitatively and quantitatively analyse luteolin using reverse phase-high performance liquid chromatography with diode array detector (RP-HPLC-DAD)as a reaction supplement for β-galactosidase assayto elucidate the anti-inflammatory efficacy of luteolin in pseudorabies virus infected RAW264.7 cell line by measuring the anti-inflammatory mediators production and also cell viability and cytotoxicity assay