1-Benzopyran-2-on
2H-Chromen-2-one · COUMARINE · 2H-1-BENZOPYRAN-2-ONE · CUMARIN · 1,2-BENZOPYRONE · CHROMEN-2-ONE · Kumarin · coumarin powder
Identifikatoren & physikalische Daten
| CAS No. | 91-64-5 |
|---|---|
| Summenformel | C9H6O2 |
| Durchschnittliche Molmasse | 146,14 g/mol |
| Monoisotopische Masse | 146,03677943 g/mol |
| SMILES | O=c1ccc2ccccc2o1 |
| InChIKey | ZYGHJZDHTFUPRJ-UHFFFAOYSA-N |
| PubChem CID | 323 |
| ChEMBL | CHEMBL6466 |
| ChEBI | CHEBI:28794 |
| EC No. | 202-086-7 |
| DTXSID | DTXSID7020348 |
| Lokaler Name | 1-Benzopyran-2-on |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 196 |
| Schmelzpunkt | 68-73 °C (lit.) |
| Siedepunkt | 298 °C (lit.) |
| Dichte | 0.935 |
| Dampfdruck | 0.01 mm Hg ( 47 °C) |
| Brechungsindex | 1.5100 (estimate) |
| Flammpunkt | 162 °C |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | 1.7g/l1.7 g/L (20 ºC) |
| Aggregatzustand | Crystals or Crystalline Powder |
| Farbe | White |
| Geruch | at 10.00 % in dipropylene glycol. sweet hay tonka new mown hay |
| Geruchsart | tonka |
| Biologische Quelle | synthetic |
| Merck | 14,2562 |
| BRN | 383644 |
| Henry-Konstante | 9.9×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Hauptanwendungen | color filter, organic electroluminescent devices, liquid crystal displays, field emission displays, inks, nickel plating, detergents, deodorant for shoes, petroleum products, cigarettes, personal care products, cosmetics, sunscreen cream, perfumes, nucleic acid sequencing, antiinflammatory agent, treatment of cancer, neurotransmission disorders, bleeding disorders, cerebrovascular disease, thrombosis, hemorrhoids, rheumatic disease, arthritic disease, epilepsy, vaginitis, painkiller, teeth whitening agent, skin whitening agent, wound healing promoter |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H |
| InChIKey | ZYGHJZDHTFUPRJ-UHFFFAOYSA-N |
| SMILES | O=C1Oc2ccccc2C=C1 |
| LogP (Verteilungskoeffizient) | 1.39 at 25℃ |
| CAS Datenbank | 91-64-5(CAS DataBase Reference) |
| NIST chemische Informationen | Coumarin(91-64-5) |
| EPA chemische Informationen | Coumarin (91-64-5) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 1 |
|---|---|
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29322010 |
| RTECS-Nr. | GN4200000 |
| R-Sätze (R) | 22-40-36/37/38-20/21/22-43 |
| Toxizität | LD50 orally in rats, guinea pigs: 680, 202 mg/kg (Jenner) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36-36/37-26 |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralSkin Sens. 1 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 91-64-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Coumarin is a naturally occurring Benzopyrone compound. It is found in a large number of plants belonging to many different families including tonka beans, woodruff, lavender oil, cassia, melilot (sweet clover), and other plants. It is found in edible plants such as strawberries, cinnamon, peppermint, green tea, carrots, and celery, as well as in partially fermented tea, red wine, beer, and other foodstuffs. Concentrations range from 87 000 ppm in cassia and 40 000 ppm in cinnamon to 20 ppm in peppermint and 5 ppb in tangerines.
Occurrence
Found in many plants and essential oils such as cassia, melilot, orchid, lavender and balsam of Peru (Spth, 1937; Gildemeister & Hoffman, 1966).
Verwenden
coumarin is considered a blood thinner, it can also increase blood flow. Some sources cite anti-oxidant capacities, as well. It is a specific plant constituent and is what creates the fragrance of freshly mowed hay. Coumarin is found in such plants as cherries, lavender, licorice, and sweet clover.
Herstellung & Synthese
synthetische
Coumarin is currently produced by Perkin synthesis from salicylaldehyde. In the presence of sodium acetate, salicylaldehyde reacts with acetic anhydride to produce coumarin and acetic acid. The reaction is carried out in the liquid phase at elevated temperature.A process for the production of coumarin from hexahydrocoumarin by dehydrogenation has also been elaborated.Since the odor of coumarin is relatively weak, strong-smelling by-products (e.g., vinylphenol) must be removed. Many purification methods have been reported and patented.