Aroma
Intensely floral and fresh odor with fruity
and somewhat Myrrh-like undertone. 2-Pentyl-3-methyl-2-cyclopenten-1-one is
often described as the "closest to ci&Jasmone
in odor". In proper dilution it has a pleasant,
sweet, herbaceous-floral taste which is easily twisted towards a fruity note in presence of
traces of fruity chemicals. It has an excellent
softening effect upon the overly "chemical"
fruit materials.
Uses in Perfume
2-Pentyl-3-methyl-2-cyclopenten-1-one is widely used in perfume compositions, not
only for artificial Jasmin and Bergamot, but
in general as a floralizer in the more fruityfloral fragrance types: Ylang, Lily, Tuberose,
Magnolia, etc. and it introduces a pleasant
undertone in Citrus type fragrances.
Chemical Properties
2-Pentyl-3-methyl-2-cyclopenten-1-one is a colorless,
slightly viscous liquid with a typical jasmine odor, resembling that of the naturally
occurring (Z)-jasmone. Dihydrojasmone is produced by an acid-catalyzed
rearrangement of 4-methyl-??-decalactone, which is readily obtained by
radical addition of 2-octanol to acrylic acid.
Dihydrojasmone is used in perfumery in jasmine bases and, more generally, in
floral and fruity fragrances.
Chemical Properties
3-Methyl-2-(n-pentanyl)-2-cyclopenten-1-one has a fresh, fruity, jasmine odor with woody and herbal nuances.
Occurrence
Has apparently not been reported to occur in nature.
Preparation
Hexyl bromide plus levulinic ester yields a lactone, which is reacted with polyphosphoric acid or phosphorus pentoxide
to produce hydrojasmone.
Definition
ChEBI: 3-methyl-2-pentylcyclopent-2-en-1-one is a cyclic ketone.
Taste threshold values
Taste characteristics at 10 ppm: sweet, floral, green, herbal with a citrus nuance.
Synthesis Reference(s)
Canadian Journal of Chemistry, 56, p. 2301, 1978
DOI: 10.1139/v78-379Journal of the American Chemical Society, 92, p. 7428, 1970
DOI: 10.1021/ja00728a029
