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Improved citral and citronellal derivatives

A technology of citral and citronellal, which is applied in the field of flavoring agents and spices, and can solve the problems of citral being unstable and unusable

Inactive Publication Date: 2008-01-09
FLEXITRAL INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Citral is unstable in bleach and cannot be used

Method used

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  • Improved citral and citronellal derivatives
  • Improved citral and citronellal derivatives
  • Improved citral and citronellal derivatives

Examples

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Embodiment 1

[0085] Example 1: Preparation and aroma profile of cyclopropanated citral or citronellal derivatives

[0086] Cyclopropanation of citral to produce citral-6,7-cyclopropane

[0087] The following experiments are based on known methods for cyclopropanation of olefins and were performed multiple times with various stoichiometric equivalents of the cyclopropanation reagent. The best results for the synthesis of the monocyclopropanated citral derivatives described above were obtained using the amounts indicated below. Attempts to increase the relative amounts of reagents resulted in the formation of considerable amounts of by-products. However, this response has not been optimized. The use of substoichiometric diethylzinc and diiodomethane reactants is feasible if the separation of citral and citral-6,7-cyclopropane is optimized. However, since this separation was not optimized, the cyclopropanation reaction was carried to completion. Due to the reported explosive potential...

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PUM

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Abstract

Improved citral and citronellal derivatives, and fragrance and flavorings including the derivatives, that have a longer useful shelf life than citral and citronellal and / or fragrances and flavoring including citral and citronellal, are disclosed. In particular, the derivatives maintain the fragrance characteristics of citral and citronellal, while lowering the allergic properties, and lemony flavors and fragrances with a longer shelf-life than citral and citronellal, are disclosed. Also disclosed are methods of making the derivatives, and articles of manufacture including the derivatives. The derivatives replace the aldehyde group in citral or citronellal with a hydroxy group. In one embodiment, the derivatives also replaced one or more double bonds in citral or the double bond in citronellal with a cyclopropyl group, which can be unsubstituted, or substituted with one or two alkyl, preferably methyl, groups, or with an oxirane or thiirane ring, or combinations thereof. The alkyl groups in the cycloprohyl groups can optionally be substituted, for example, with electron donating groups, electron withdrawing groups, groups which increase the hydrophilicity or hydrophobicity, and the like. Examples of suitable articles of manufacture include candles, air fresheners, perfumes, desinfectant 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.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to Provisional Application Serial No. 60 / 638,964, filed December 22,2004. technical field [0003] The present invention relates generally to the field of flavors and fragrances. More specifically, the present invention relates to citral and citronellal derivatives that impart lemony or fresh rose scents to beverages and other food products, as well as perfumes and other aromatic products, while overcoming the stability limitations of native citral or citronellal compounds. Background technique [0004] The odor profile of citronellal is sweet, floral, rosey, waxy, citrusy, and green. Citral (3,7-dimethyl-2,6-octadienal) is the main component of lemon flavor and has the sweet-sour characteristic of natural lemon. Mainly for historical reasons, lemon flavor has been associated with freshness and cleanliness in beverages and household products, and in fragrances and flavorings in gener...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/05C07D331/02C07D303/14A23L27/00A23L27/20
CPCC07C33/05C07D331/02C07C2101/02C07C31/13C07C31/1333C07C2601/02C07C303/14C07C331/02A61K31/336
Inventor 卢卡·图莱
Owner FLEXITRAL INC
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