HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
6-Methyl-2H-1-benzopyran-2-on
6-Methyl · 2H-1-BENZOPYRAN-2-ONE, 6-METHYL- · FEMA 2699 · Toncarine · METHYL COUMARIN · 6-METHYL-2H-CHROMEN-2-ONE · 6-MC · 6-methyl-coumari
Identifikatoren & physikalische Daten
| CAS No. | 92-48-8 |
|---|---|
| Summenformel | C10H8O2 |
| Durchschnittliche Molmasse | 160,17 g/mol |
| Monoisotopische Masse | 160,05242949 g/mol |
| SMILES | Cc1ccc2oc(=O)ccc2c1 |
| InChIKey | FXFYOPQLGGEACP-UHFFFAOYSA-N |
| PubChem CID | 7092 |
| ChEMBL | CHEMBL443436 |
| ChEBI | CHEBI:563586 |
| EC No. | 202-158-8 |
| DTXSID | DTXSID9025588 |
| Lokaler Name | 6-Methyl-2H-1-benzopyran-2-on |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 220 |
| Geruch | Somewhat dry, herbaceous (tonka-like) odoralso characterized as a delicate fig or date sweetness.Coconut odor |
| Geschmack | Almost bitter taste above 50 ppm, turning sweet and vanilla-like at lower levels.Sweet, coconut tasteVanilla flavor |
| Color/Form | White, crystalline solidWhite needles from benzene |
| Löslichkeit | Insoluble (NTP, 1992)Very slightly sol in hot waterinsol in petroleum ethersol in oils.soluble in alcohol /both alpha and beta forms/Very soluble in ethanol, ether, benzeneslightly soluble in chloroformInsoluble in watersoluble in oilssoluble (in ethanol)DMSO : ≥ 125 mg/mL (780.42 mM) |
| Flammpunkt | 266 °F (NTP, 1992)303°C/725mm |
| Siedepunkt | 577 °F at 725 mmHg (NTP, 1992)304 °C303 °C/725 mmHg (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 167 to 169 °F (NTP, 1992)76.5 °CExists as alpha and beta forms, melting point(alpha): 90 °C, melting point (beta): 82 °Cboth forms are soluble in alcoholcombustible73-76 °C (lit.) |
| Physical Description | 6-methylcoumarin appears as white crystals with a flavor of vanilla. Insoluble in water. (NTP, 1992)White solid[HSDB]White crystal solidcoconut-like aroma |
| Kovats Retention Index | 15451564157415881618255125602630 |
| Other Experimental Properties | Congealing point: >73.5 °CUV: 375 (Sadtler Research Laboratories Spectral Collection) /Coumarin, 3-methyl/ |
| Dichte | 1.0924 (rough estimate) |
| Brechungsindex | 1.5300 (estimate) |
| FEMA | 2699 | 6-METHYLCOUMARIN |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | powder to crystal |
| Farbe | White to Almost white |
| Geruch | at 1.00 % in dipropylene glycol. coconut creamy powdery coumarinic tonka cinnamyl vanilla floral earthy |
| Geruchsart | coconut |
| Biologische Quelle | synthetic |
| JECFA Number | 1172 |
| BRN | 4222 |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMINGFRAGRANCE |
| InChI | 1S/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3 |
| InChIKey | FXFYOPQLGGEACP-UHFFFAOYSA-N |
| SMILES | Cc1ccc2OC(=O)C=Cc2c1 |
| LogP (Verteilungskoeffizient) | 1.85 |
| CAS Datenbank | 92-48-8(CAS DataBase Reference) |
| NIST chemische Informationen | 2H-1-Benzopyran-2-one, 6-methyl-(92-48-8) |
| EPA chemische Informationen | 6-Methylcoumarin (92-48-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H319 (95%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1613 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.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. |
|---|---|
| Regulatorische Informationen | Chemical: 2H-1-Benzopyran-2-one, 6-methyl-Hazard Traits - Fragrance AllergenAuthoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance AllergensReport - if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)2H-1-Benzopyran-2-one, 6-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Coumarins: Human health tier II assessment |
| Brandgefahren | This chemical is combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: This compound may cause photo-allergic reactions.ACUTE/CHRONIC HAZARDS: This compound is a mild irritant. (NTP, 1992) |
| Gefahrenübersicht | Emergency treatment: CoumarinAfter an ingestion of 4 grams of coumarin, a patient developed muscle paralysis but no cardiovascular effectsCauses liver toxicity in rats, but humans are relatively resistantNot active as an anti-coagulant[HSDB] Causes seizures at lethal doses in mice |
Anwendungen & Verwendung
Occurrence
Has apparently not been reported to occur in nature
Verwenden
6-Methylcoumarin is a synthetic fragrance in cosmetics, toiletries and soaps. It mainly used to prepare flavors such as coconut, vanilla and caramel.
Herstellung & Synthese
synthetische
6-methylcoumarin is synthesized from p-cresol and fumaric acid. Preheat 72% sulfuric acid to 80 °C, add a mixture of fumaric acid and p-cresol, keep the reaction at 160-170 °C for 3-4 hours, cool, pour into crushed ice to precipitate a precipitate, and filter. The filtrate was extracted with benzene, and after adding benzene, the obtained crude product was subjected to vacuum distillation to obtain 6-methylcoumarin. synthesis of 6-methylcoumarin: By heating 6-methyl coumarin-3-carboxylic acid to 300 to 340°C; by condensation of p-cresol-disulfonic acid with fumaric acid in the presence of H2SO4; by condensation of p-homosalicyclic aldehyde with malonic acid in the presence of aniline, followed by heating for the lactone; from salicylaldehyde with propionic acid anhydride and sodium propionate.