This invention provides methyl(methylthioalkyl)-1,3-dithiolanes defined according to the generic structure: ##STR2## wherein R.sub.1 and R.sub.2 are the same or different and each represents methyl or hydrogen with the proviso that at least one of R.sub.1 and R.sub.2 is methyl; and wherein m represents an integer of 1 or 2 and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
Artifical flavoring agents for foodstuffs have received increasing attention in recent years. In many areas, such food flavoring agents are preferred over natural flavoring agents at least in part because of the uniform flavor that may be so obtained. For example, natural food flavoring agents such as extracts, essences, concentrates and the like are often subject to wide variation due to changes in the quality, type and treatment of the raw materials. Such variation can be reflected in the end product and results in unreliable flavor characterists and uncertainty as to consumer acceptance and cost. Additionally, the presence of the natural product in the ultimate food may be undesirable because of increased tendency to spoil. This is particularly troublesome in convenience and snack food usage where such products as dips, soups, chips, prepared dinners, canned foods, sauces, gravies and the like are apt to be stored by the consumer for some time prior to use.
The fundamental problem in preparing artifical flavoring agents is that of achieving an nearly as possible a true flavor reproduction. This generally proves to be a difficult task since the mechanism for flavoring development in many foods is not understood. This is notable in products having meaty, hydrolyzed vegetable protein-like, sweet, meat extract-like, mushroom-like, turkey-like, chicken-like, pork-like and butterscotch aroma profiles and oniony, onion/roasted-like, hydrolyzed vegetable protein-like, sweet, meaty, meat extract-like, bready, mushroom-like, turkey-like, chicken-like, pork-like and butterscotch-like taste nuances.
Reproduction of meaty, hydrolyzed vegetable protein-like, sweet, meat extract-like, mushroom-like, turkey-like, chicken-like, pork-like and butterscotch aroma nuances and oniony, onion/roasted, hydrolyzed vegetable protein-like, sweet, meaty, meat extract-like, mushroom-like, turkey-like, chicken-like, pork-like, butterscotch-like and bready taste nuances has been the subject of a long and continuous search by those engaged in the production of foodstuffs. The severe shortage of foods, especially protein foods, in many parts of the world has given rise to the need for utilizing non-meat sources of proteins and making such protein as palatable and as meat-like as possible. Hence, materials which will closely simulate or exactly reproduce the flavor and aroma of mushroom, hydrolyzed vegetable protein, beef broth, pot roast, onion and turkey are required. Furthermore, meat flavors have been enhanced previously by the use of such materials as monosodium glutamate. In many diets monosodium is not desired. Therefore, a need has arisen for a monosodium glutamate replacer.
Moreover, there are a great many meat containing or meat based foods presently distributed in a preserved form. Examples being condensed soups, dry-soup mixes, dry meat, freeze-dried or lyophilized meats, packaged gravies and the like. While these products contain meat or meat extracts, the fragrance, taste and other organoleptic factors are very often impaired by the processing operation and it is desirable to supplement or enhance the flavors of these preserved foods with versatile materials which have either roasted meat or sweet meat or vegetable-like or nut-like nuances.
Various 4-(methylthio)-butanal derivatives including 4-(methylthio)-butanal itself defined according to the structure: ##STR3## and the diethyl acetal thereof are known for augmenting or enhancing the aroma or taste of foodstuffs and other consumable materials as is taught in U.S. Pat. No. 3,904,556 issued on Sept. 9, 1975 (the specification of which is incorporated by reference herein). Thus, the compound 4-(methylthio)-butanal diethyl acetal is taught in said U.S. Pat. No. 3,904,556 to provide a mushroom, heated onion flavor with green, sweet tomato, oniony and garlic nuances. The 4-(methylthio)-butanal itself is taught by said U.S. Pat. No. 3,904,556 to provide a mushroon-like, tomato-like, vegetable-like, cheesy and fruity taste.
Alkanes having 3-methylthio moieties are known in the prior art, for example, that disclosed in Chem.Abstracts, Volume 96:103327h having the structure: ##STR4## This abstract is of Tetrahedron Letters, Volume 22, No. 42, pages 4159-4162, 1981, (Title: "THIOSULFONIUM IONS. METHYLTHIOLATION OF 3-METHYLTHIO-1-BUTENE AND CIS- AND TRANS-1-METHYLTHIO-2-BUTENE": Kim and Caserio).
Chem.Abstracts, Volume 96:20080m which is an abstract of Fischer, Liebigs Ann.Chem., 1981 (10), 1899-1902 discloses the compound having the structure: ##STR5## wherein n is 2, 3 or 4 but does not disclose its organoleptic utilities.
Chem.Abstracts, Volume 84:164792v, (abstract of German Offenlegungsschrift 2,530,273) discloses the compound having the structure: ##STR6## but does not disclose its organoleptic utilities.
U.S. Pat. No. 4,153,442 issued on May 8, 1979; U.S. Pat. No. 4,224,051 issued on Sept. 23, 1980; and U.S. Pat. No. 4,101,307 issued on June 18, 1978 each discloses plant growth regulating material compounds defined according to the generic structure: ##STR7## in which X and Y which may be the same or different and represent oxygen, sulphur or a radical N-B where B is hydrogen, a lower alkyl radical containing 1 to 4 carbon atoms, an optionally substituted aryl radical or an optionally substituted acyl radical containing from 1 to 4 carbon atoms,
R and R.sup.1 which may be the same or different and represent a lower alkyl radical containing from 1 to 4 carbon atoms or an acyl or amido radical containing from 1 to 4 carbon atoms; in addition, they may form with ##STR8## a cycle corresponding to the formula: ##STR9## in which: R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different and represent hydrogen, an alkyl radical containing from 1 to 4 carbon atoms and optionally substituted by a halogen, the radicals NO.sub.2, hydroxy, or alkoxy containing from 1 to 4 carbon atoms, PA1 A represents either a single bond or an alkylene chain containing from 1 to 4 carbon atoms optionally interrupted by an oxygen atom or a group N-B' where B' represents hydrogen, an optionally halogenated or hydroxylated alkyl group, an acyl group, the hydrocarbon portion of these radicals containing from 1 to 4 carbon atoms, or a cycle having in common with the preceding cycle 1 to 2 carbon atoms and containing from 3 to 6 carbon atoms, from 0 to 2 oxygen atoms and/or a group N-B, or a cycle corresponding to the formula ##STR10##
Included in this genetic structure is the genus defined according to the structure: ##STR11## Although the generic structure set forth in the aforementioned U.S. Pat. Nos. 4,153,442, 4,224,051 and 4,101,307 contemplate within the genus a number of the compounds of the instant application, this disclosure is a "shot-gun" disclosure because it does not include the specific compounds of our invention, nor does it set forth the criticality of the compounds of our invention in their uses for their organoleptic properties.
Nagao, et al, Tetrahedron Letters No. 34, Pages 3167-3168 (1979) discloses the genus of compounds defined according to the structure: ##STR12## in a synthetic route to yield certain ketones. In this genus R may be methyl, ethyl, propyl, butyl, tolyl, tolyl methoxy, allyl or phenyl. This genus is not part of the instant invention. Furthermore, the Nagao, et al paper does not disclose the organoleptic uses of such compounds.
Nothing in the prior art, however, discloses the compound having the structure: ##STR13## wherein R.sub.1 and R.sub.2 are the same or different and each represents methyl or hydrogen with the proviso that at least one of R.sub.1 and R.sub.2 is methyl; and wherein m represents an integer of 1 or 2 or their organoleptic utilities.
USPTO Backgrounds
USPTO Backgrounds