Improved citral derivatives, and fragrances and flavorings including the
derivatives, that have a longer useful shelf life than citral and/or
fragrances and flavorings including citral, are disclosed. In particular,
the derivatives maintain the fragrance characteristics of citral, while
lowering the allergic properties, and lemony flavors and fragrances with
a longer shelf-life than citral, are disclosed. 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 cyclopropyl group,
which 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 citral 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 citral. 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.