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3-Methyl-2-cyclohexen-1-one

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3-Methyl-2-cyclohexen-1-one Basic information
3-Methyl-2-cyclohexen-1-one Chemical Properties
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3-Methyl-2-cyclohexen-1-one Usage And Synthesis
  • DescriptionMay be prepared by acid hydrolysis and decarboxylation of the corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-l-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric acid.
  • Chemical Properties3-Methyl-2-cyclohexen-1-one is a nonaromatic cyclic ketone with a medicinal, phenolic, mild cherry aroma
  • Chemical PropertiesCLEAR VERY SLIGHTLY YELLOW TO BROWN LIQUID
  • OccurrenceReported found in oil of Mentha pulegium, cocoa, coffee, filbert, sweet corn, dried bonito, katsuobushi, wild rice and clam. Also produced by some animals in vivo
  • Uses3-Methyl-2-cyclohexen-1-one was used in the synthesis of 19-nor-1α, 25-dihydroxyvitamin D(3) derivatives. It was also used in sex pheromone of the Douglas-fir beetle. Used in nut flavor.
  • PreparationBy acid hydrolysis and decarboxylation of the corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-1-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric acid.
  • Aroma threshold valuesAroma characteristics at 2.0%: sweet, nutty, phenolic, walnut, fruity, almond and benzoin
  • Taste threshold valuesTaste characteristics at 50 ppm: nutty, musty, phenolic and woody with grain-like nuances.
  • Synthesis Reference(s)Journal of the American Chemical Society, 101, p. 494, 1979 DOI: 10.1021/ja00496a044
    The Journal of Organic Chemistry, 42, p. 1349, 1977 DOI: 10.1021/jo00428a017
    Tetrahedron Letters, 17, p. 3, 1976
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