Improved aromachemical derivatives, and fragrances and flavorings including the derivatives, that have a longer useful
shelf life than the aromachemicals from which they can be derived, are disclosed. In particular, the derivatives maintain the fragrance characteristics of the aromachemicals, while lowering the allergic properties, increasing the stability, and / or increasing the
odor intensity. Also disclosed are methods of making the derivatives, and articles of manufacture including the derivatives. In one embodiment, the derivatives are prepared by replacing one or more double bonds in
citral with a
thioether, cyclopropyl, oxirane, or
thiirane group. The
cyclopropane ring can be unsubstituted, or substituted with one or two lower
alkyl, preferably methyl groups. The
alkyl groups can optionally be substituted, for example, with
electron donating groups,
electron with drawing groups, groups which increase the hydrophilicity or hydrophobocity, and the like. In another embodiment, the derivatives are prepared by replacing the
aldehyde group in the
essential oil with a
nitrile, methyl
ether or
acetal group. The
acetal groups can provide the compounds with a
long lasting flavor or fragrance, where the acetals slowly hydrolyze to provide the
aldehyde group in the parent
essential oil. In some embodiments, both the
aldehyde and at least one of the
double bond functional groups are both derivatized as described herein. Examples of suitable articles of manufacture include candles, air fresheners, perfumes,
disinfectant compositions,
hypochlorite (
bleach) compositions, beverages such as beer and soda, denture
cleanser tablets and flavored orally-delivered products such as lozenges, candies, and the like.