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    • 7. 发明授权
    • Citral derivatives
    • 柠檬醛衍生物
    • US07704941B2
    • 2010-04-27
    • US11861610
    • 2007-09-26
    • Luca Turin
    • Luca Turin
    • A61K8/40C07C255/46
    • C11D3/50A23L27/203A23L27/2052C07C45/69C07C47/11C07C47/225C07C47/293C07C47/34C07C47/45C11B9/003C11B9/0076
    • 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.
    • 公开了改进的柠檬醛衍生物,以及包括衍生物的香料和调味剂,其具有比柠檬醛和/或香料和调味剂(包括柠檬醛)更长的有用的保质期。 特别地,衍生物保持柠檬醛的香味特性,同时降低过敏性质,并且具有比柠檬醛更长的保质期的柠檬香精和香料。 还公开了制备衍生物的方法和包括衍生物的制品。 在一个实施方案中,衍生物通过用环丙基取代柠檬醛中的一个或多个双键来制备,所述环丙基可以是未取代的,或被一个或两个低级烷基,优选甲基取代。 烷基可以任选地被取代,例如具有给电子基团,具有拉伸基团的电子,增加亲水性或疏水性的基团等。 在另一个实施方案中,通过用腈,甲醚或缩醛基代替柠檬醛中的醛基来制备衍生物。 缩醛基团可为化合物提供持久的风味或香味,其中缩醛缓慢水解以在柠檬醛中提供醛基。 在一些实施方案中,醛和至少一个双键官能团都如本文所述被衍生化。 合适的制造方法的实例包括蜡烛,空气清新剂,香料,消毒剂组合物,次氯酸盐(漂白剂)组合物,饮料如啤酒和苏打,义齿清洁剂片剂和调味的口服递送产品如锭剂,糖果等。