ChemicalBook > Product Catalog > Food Additives > Food flavorings > Artificial flavor > 6-Methylcoumarin
6-Methylcoumarin Chemical Properties
- Melting point:73-76 °C(lit.)
- Boiling point:303 °C725 mm Hg(lit.)
- Density 1.0924 (rough estimate)
- FEMA 2699 | 6-METHYLCOUMARIN
- refractive index 1.5300 (estimate)
- Flash point:303°C/725mm
- JECFA Number1172
- BRN 4222
- CAS DataBase Reference92-48-8(CAS DataBase Reference)
- NIST Chemistry Reference2H-1-Benzopyran-2-one, 6-methyl-(92-48-8)
- EPA Substance Registry System6-Methylcoumarin (92-48-8)
- Hazard Codes Xn
- Risk Statements 22-42/43
- Safety Statements 22-36/37-45
- WGK Germany 3
- RTECS GN7792000
- TSCA Yes
- HS Code 29321900
- Hazardous Substances Data92-48-8(Hazardous Substances Data)
- ToxicityThe 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).
6-Methylcoumarin Usage And Synthesis
- Description6-Methylcoumarin has a somewhat dry, herbaceous (tonka-like) odor. It is also characterized as a delicate fig or date sweetness. It has an almost bitter taste above 50 ppm, turning sweet and vanillalike at lower levels. 6-Methylcoumarin may be prepared by heating 6-methyl coumarin-3-carboxylic acid to 300 - 340°C; by condensation of p-cresol-disulfonic acid with fumaric acid in the presence of H2S04; by condensation of p-homosalicyclic aldehyde with malonic acid in the presence of aniline, followed by heating to form the lactone; from salicylaldehyde with propionic anhydride and sodium propionate.
- Chemical Properties6-Methylcoumarin 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.
- Chemical PropertiesWHITE TO ALMOST WHITE CRYSTALLINE POWDER
- OccurrenceHas apparently not been reported to occur in nature
- Uses6-Methylcoumarin is a synthetic fragrance in cosmetics, toiletries and soaps.
- UsesPerfumes, flavoring.
- DefinitionChEBI: A member of the class of coumarins that is coumarin in which the hydrogen at position 6 is replaced by a methyl group.
- PreparationBy 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.
- Aroma threshold valuesAroma characteristics at 1.0%: sweet vanilla cake, creamy, coconut, coumarin-like and powdery, with herbaceous hay and tonka-like nuances.
- Taste threshold valuesTaste characteristics at 5 ppm: coconut, sweet vanilla, dairy creamy, hay-like with anisic and coumarin nuances.
- Synthesis Reference(s)Tetrahedron, 62, p. 6918, 2006 DOI: 10.1016/j.tet.2006.04.080
- General DescriptionWhite crystals with a flavor of vanilla. Insoluble in water.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileKetones, 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 Hazard6-Methylcoumarin is combustible.
- Safety ProfilePoison by subcutaneous route. Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
6-Methylcoumarin Preparation Products And Raw materials
- Coumarin 338 Coumarin 2 Coumarin 153 4-CHLOROMETHYL-6-METHYL-CHROMEN-2-ONE 7-ACETOXY-6-(2,3-DIBROMOPROPYL)-4,8-DIMETHYLCOUMARIN 6-Methylcoumarin Basic Violet 1 Acetonitrile 7-HYDROXY-4-METHYLCOUMARIN DICUMAROL Methyl acetate Methyl acrylate Methylparaben Kresoxim-methyl Coumarin 4-Methylcumarin Paraquat dichloride Methanol
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