Description
May 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 Properties
3-Methyl-2-cyclohexen-1-one is a nonaromatic cyclic ketone with a medicinal, phenolic, mild cherry aroma
Chemical Properties
CLEAR VERY SLIGHTLY YELLOW TO BROWN LIQUID
Occurrence
Reported 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
Uses
3-Methyl-2-cyclohexenone is an insect sex pheromone of the Douglas-fir beetle. It can be used as a starting material:
- In the total synthesis of (?)-ar-tenuifolene, a naturally occurring aromatic sesquiterpene.
- To synthesize an organic building block 2-trimethylsilyl-3-methyl-cyclohexenone.
- In the total synthesis of natural diterpenoids (+)-taiwaniaquinone H and (+)-dichroanone.
Uses
3-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.
Definition
ChEBI: 3-Methyl-2-cyclohexen-1-one is a cyclic olefin.
Preparation
By 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 values
Aroma characteristics at 2.0%: sweet, nutty, phenolic, walnut, fruity, almond and benzoin
Taste threshold values
Taste 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/ja00496a044The Journal of Organic Chemistry, 42, p. 1349, 1977
DOI: 10.1021/jo00428a017Tetrahedron Letters, 17, p. 3, 1976
