6-Methylcoumarin

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;Pharmaceutical Raw Materials;Coumarins;Miscellaneous;Chemical Synthesis;Heterocyclic Building Blocks
Mol File:92-48-8.mol
6-Methylcoumarin Structure
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
Odorat 1.00 % in dipropylene glycol. coconut creamy powdery coumarinic tonka cinnamyl vanilla floral earthy
Odor Typecoconut
JECFA Number1172
BRN 4222
LogP1.85
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)
Safety Information
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).
MSDS Information
ProviderLanguage
6-Methyl-2H-chromen-2-one English
ACROS English
SigmaAldrich English
ALFA English
6-Methylcoumarin Usage And Synthesis
Chemical Properties6-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.
OccurrenceHas apparently not been reported to occur in nature
Uses6-Methylcoumarin is a synthetic fragrance in cosmetics, toiletries and soaps. It mainly used to prepare flavors such as coconut, vanilla and caramel.
Preparation6-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.
DefinitionChEBI: 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 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 Description6-methylcoumarin appears as white crystals with a flavor of vanilla. Insoluble in water. (NTP, 1992)
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.
Biochem/physiol ActionsTaste at 5 ppm
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.
Methylparaben Paraquat dichloride Methyl Acetonitrile Coumarin 7-ACETOXY-6-(2,3-DIBROMOPROPYL)-4,8-DIMETHYLCOUMARIN Basic Violet 1 7-HYDROXY-4-METHYLCOUMARIN 4-CHLOROMETHYL-6-METHYL-CHROMEN-2-ONE Kresoxim-methyl Methanol 4-Methylcumarin Coumarin 153 Methyl acrylate 6-Methylcoumarin Methyl acetate DICUMAROL Coumarin 2

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