6-Methylcoumarin CAS 92-48-8
Introduction：Basic information about 6-Methylcoumarin CAS 92-48-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
6-Methylcoumarin Basic information
| Product Name: | 6-Methylcoumarin |
| Synonyms: | 6-MC;6-Methyl-1,2-benzopyrone;6-methyl-2h-1-benzopyran-2-on;6-methyl-2H-1-Benzopyran-2-one;6-Methyl-2-oxo-2H-benzopyran;6-Methyl-2-oxochronene;6-Methyl-chromen-2-one;6-methyl-coumari |
| CAS: | 92-48-8 |
| MF: | C10H8O2 |
| MW: | 160.17 |
| EINECS: | 202-158-8 |
| Product Categories: | Building Blocks;Heterocyclic Building Blocks;Alphabetical Listings;Flavors and Fragrances;M-N;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Coumarins;Miscellaneous;Pharmaceutical Raw Materials |
| Mol File: | 92-48-8.mol |
6-Methylcoumarin Chemical Properties
| Melting point | 73-76 °C (lit.) |
| Boiling point | 303 °C/725 mmHg (lit.) |
| density | 1.0924 (rough estimate) |
| FEMA | 2699 | 6-METHYLCOUMARIN |
| refractive index | 1.5300 (estimate) |
| Fp | 303°C/725mm |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | DMSO : ≥ 125 mg/mL (780.42 mM) |
| form | powder to crystal |
| color | White to Almost white |
| Odor | at 1.00 % in dipropylene glycol. coconut creamy powdery coumarinic tonka cinnamyl vanilla floral earthy |
| Odor Type | coconut |
| biological source | synthetic |
| JECFA Number | 1172 |
| BRN | 4222 |
| Major Application | flavors and fragrances |
| Cosmetics Ingredients Functions | PERFUMING FRAGRANCE |
| 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 | 1.85 |
| CAS DataBase Reference | 92-48-8(CAS DataBase Reference) |
| NIST Chemistry Reference | 2H-1-Benzopyran-2-one, 6-methyl-(92-48-8) |
| EPA Substance Registry System | 6-Methylcoumarin (92-48-8) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-42/43 |
| Safety Statements | 22-36/37-45 |
| WGK Germany | 3 |
| RTECS | GN7792000 |
| TSCA | TSCA listed |
| HS Code | 29321900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Resp. Sens. 1 Skin Sens. 1 |
| Hazardous Substances Data | 92-48-8(Hazardous Substances Data) |
| toxicity | The acute oral LD50 value in rats was reported to be 1.68 g/kg (1.43-1.93 g/kg) (Moreno, 1973). The acute dermal LD50 value in rabbits exceeded 5 g/kg (Moreno, 1973). |
| Chemical Properties | 6-methylcoumarin is a white to almost white crystalline powder with has a somewhat coconut-like odor. the odor is also characterized as having a delicate fig or date sweetness. it has an almost bitter taste above 50 ppm, turning sweet and vanilla-like at lower levels. soluble in benzene, hot ethanol and non-volatile oil, insoluble in hot water. |
| Occurrence | Has apparently not been reported to occur in nature |
| Uses | 6-Methylcoumarin is a synthetic fragrance in cosmetics, toiletries and soaps. It mainly used to prepare flavors such as coconut, vanilla and caramel. |
| Preparation | 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. |
| Definition | ChEBI: 6-methylcoumarin is a member of the class of coumarins that is coumarin in which the hydrogen at position 6 is replaced by a methyl group. It has a role as a fragrance and an allergen. |
| Aroma threshold values | Aroma characteristics at 1.0%: sweet vanilla cake, creamy, coconut, coumarin-like and powdery, withherbaceous hay and tonka-like nuances. |
| Taste threshold values | Taste characteristics at 5 ppm: coconut, sweet vanilla, dairy creamy, hay-like with anisic and coumarinnuances. |
| Synthesis Reference(s) | Tetrahedron, 62, p. 6918, 2006 DOI: 10.1016/j.tet.2006.04.080 |
| General Description | 6-methylcoumarin appears as white crystals with a flavor of vanilla. Insoluble in water. (NTP, 1992) |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | Ketones, such as 6-Methylcoumarin, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. |
| Fire Hazard | 6-Methylcoumarin is combustible. |
| Biochem/physiol Actions | Taste at 5 ppm |
| Safety Profile | Poison bysubcutaneous route. Moderately toxic byingestion. A skin irritant. Mutation datareported. Combustible liquid. When heatedto decomposition it emits acrid smoke andirritating fumes. |
6-Methylcoumarin Preparation Products And Raw materials
| Raw materials | Sulfurous Acid-->Salicylaldehyde-->Fumaric acid-->Propionic anhydride-->Sodium propionate-->Coumarin-3-carboxylic acid-->Phenol, 2-ethenyl-4-methyl--->ethyl (E)-3-(2-hydroxy-5-methylphenyl)acrylate-->MONOTHIOLPHENYL MALONATE-->3-OXO-PROPIONIC ACID ETHYL ESTER |
| Preparation Products | 3,4-dihydro-6-methyl-2H-1-benzopyran-2-one |
