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Methyl cyclopentenolone

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Methyl cyclopentenolone Basic information
Methyl cyclopentenolone Chemical Properties
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Methyl cyclopentenolone Usage And Synthesis
  • Chemical PropertiesMethyl cyclopentenolone occurs in beechwood tar and has a caramel-like (burnt sugar) odor. It has been identified as a flavor component in food. Crystals of the compound usually contain 1 mol of water. Synthetic routes of production are of limited importance in comparison with isolation from beechwood tar. Homologs of cyclotene such as 3-ethyl-2-hydroxy-2-cyclopenten-1-one, C7H10O2, Mr 126.16, 2-hydroxy-3,4-dimethyl-2-cyclopenten-1-one, C7H10O2, Mr 126.16, and 2-hydroxy-3,5-dimethyl-2-cyclopenten-1-one, C7H10O2, Mr 126.16, are also used as flavor ingredients and have similar caramel-like properties.
    Cyclotene and its homologs are frequently used in flavor compositions for its caramel note, for example, in beverages and in confectionery.
  • Chemical PropertiesOff-white solid
  • OccurrenceReported to be found during the dry distillation of wood and in the corresponding tar oil. It has also been identified in fenugreek (FenaroWs Handbook of Flavor Ingredients, 1975).
  • UsesMethyl Cyclopentenolone is a flavoring agent that is a white crys- talline powder. it has a nutty odor suggesting a maple-licorice aroma when diluted. it is soluble in alcohol and propylene glycol, slightly soluble in most fixed oils, and sparingly soluble in water. it is obtained by synthesis. it is also termed 3-methyl-cyclopentane-1,2-dione.
  • PreparationBy ketonic hydrolysis of the corresponding dicarboxylic ester (Arctander, 1969)
  • Toxicity evaluationThe acute oral LD50 value in guinea-pigs was reported as 1.4 g/kg (Dow Chemical Company, 1953) and that in rats as > 1.85 g/kg, while the acute dermal LD50 value in guinea-pigs exceeded 2 g/kg (Moreno, 1976). Methylcyclopentenolone was lethal to mice and rats at ip doses of 0.5-1 g/kg (Shugaev, 1959), and at a concentration of 7 χ 10-4 m was toxic to cultured human leucocytes (Withers, 1966).
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