Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Noncarbohydrate sweetener or composition containing same
Reexamination Certificate
1998-09-17
2001-04-10
Wong, Leslie (Department: 1761)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Noncarbohydrate sweetener or composition containing same
C426S549000, C426S590000, C426S658000, C560S040000
Reexamination Certificate
active
06214402
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a water-soluble, non-dusting, sugar co-crystallized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester (neotame) composition. This invention also relates to a process for producing a water-soluble, non-dusting sugar co-crystallized neotame composition, as well as to beverages, fluid dairy products, condiments, baked goods, frostings, bakery fillings, candy, chewing gum or table-top sweeteners prepared with the sugar co-crystallized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester compositions and methods of preparing the same.
2. Related Background Art
U.S. Pat. No. 4,362,757 describes a crystallized sugar product containing a heat-sensitive, acidic, or high invert sugar substance. Such crystallized sugar products are said to be dry, granular, free-flowing, non-caking and readily dispersible in water. The crystallized sugar products are formed via a two-step process: preparing a premix of dry granular or transformed sugar base with a heat-sensitive, acidic or high invert sugar substance; and then co-crystallizing by concentrating a sugar syrup, adding a predetermined amount of premix and subjecting the mixture to impact beating.
The use of high potency dipeptide sweeteners, such as neotame (about 8000× sweeter than sucrose), requires consideration of the ability to deliver the sweetener and the solubility of the sweetener. Thus, effective means for delivering such a high potency sweetener such as neotame in desired compositions would be very useful. In particular, it is highly desirable to provide a means for uniformly dispersing a high potency dipeptide sweetener such as neotame so as to avoid “hot spots” of high intensity sweetener.
SUMMARY OF THE INVENTION
This invention relates to the co-crystallization of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester with sugar in various ratios resulting in increased solubility and enhanced delivery characteristics. In addition, the products of this invention provide for the uniform dispersion of neotame in any application, thus avoiding “hot spots”.
The sugar co-crystallized sweetener composition of this invention comprises sugar and N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester. The composition of this invention can be used, for example, as a sweetener for incorporation in processed foods and beverages or as a table-top sweetener.
In a preferred embodiment of the sugar co-crystallized sweetener composition of the present invention, the N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is present in an amount from 0.001% to 50% by weight of the final product. More preferably this range is from 0.001% to 5%, and most preferably this range is from 0.001% to 2.5%.
Without being bound to theory, it is believed that the sugar co-crystallized sweetener composition may comprise agglomerates.
In yet another preferred embodiment of this invention, the sugar co-crystallized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester composition additionally comprises another sweetener, which is selected from a natural sweetener, a high intensity sweetener, or a mixture thereof.
The present invention is also directed to a process for preparing a sugar co-crystallized sweetener composition comprising the steps of mixing sugar with water with agitation, heating the resultant mixture to about 120° C., seeding the mixture with a premix comprised of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and sugar, removing the mixture from the heat and allowing the mixture to cool with vigorous agitation.
The present invention is also directed to a method of sweetening beverage, dessert, condiment, candy, chewing gum and table-top sweetener compositions by adding a sugar co-crystallized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester composition in an amount effective to sweeten such a composition.
This invention is also directed to compositions such as beverages, fluid dairy products, condiments, baked goods, frostings, bakery fillings, candy and chewing gum containing the sugar co-crystallized sweetener composition of this invention in an amount effective to sweeten the compositions.
The invention also includes table-top sweeteners comprised of the sugar co-crystallized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester composition of this invention.
DETAILED DESCRIPTION
The sugar used in the present invention is sucrose of formula, C
12
H
22
O
11
. For purposes of this invention, the term “sugar” is used to refer to sucrose in its dry or syrup form.
The N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester used in the present invention has the formula
Salts and complexes of neotame are also suitable for use in the present invention.
The N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester may be prepared through a variety of methods. One such method comprises the steps of (i) treating a mixture of aspartame and 3,3-dimethylbutyraldehyde in an organic solvent with hydrogen in the presence of a hydrogenation catalyst at a temperature and pressure effective to form an organic solvent solution of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester; (ii) filtering the organic solvent solution to remove the hydrogenation catalyst; and (iii) forming an aqueous/organic solvent solution from the organic solvent solution to precipitate the N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester from the aqueous/organic solvent solution. Preferably, the aqueous/organic solvent solution has an amount of organic solvent of about 17% to about 30% by weight of the aqueous/organic solvent solution. A particularly preferred organic solvent for use in this method is methanol. The precipitate is recovered using standard filtration techniques to provide highly purified N-[N-3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester. This method of preparation is described in U.S. Pat. No. 5,728,862, the entire disclosure of which is incorporated by reference herein. Further, the entire disclosures of U.S. Pat. Nos. 5,480,668 and 5,510,508, also related to the synthesis and purification of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, are incorporated by reference herein.
One aspect of the present invention is a process for preparing a sugar co-crystallized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester composition. In the first step of this process, a sugar syrup is obtained. This can be accomplished by obtaining a commercially available sugar syrup or by mixing sugar with water with agitation. Agitation can be provided by any conventional means. Typically, a sugar syrup which is about 67% sucrose and 33% water is commercially available. However, other sugar syrups with different sucrose concentrations may also be used for purposes of the present invention.
In the second step of the process, water is removed to produce a supersaturated sugar syrup. This is most readily accomplished through heating the syrup with agitation, though any conventional method would suffice. The resulting syrup is maintained at a temperature not less than about 120° C. in order to prevent premature crystallization. The solids content of the resulting syrup is from 95-98% by weight of the syrup.
A dry premix comprising N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester or salt thereof and sugar is prepared. The weight ratio of neotame to sugar in this premix ranges from about 0.001:1 to about 1:1. Other components, such as flavors or other high potency sweeteners in extremely small amounts, may be added in this step, so long as the amount added does not adversely affec
Bishay Ihab E.
Desai Nitin
Fotos Jim
Prakash Indra
Wachholder Kurt
Fitzpatrick ,Cella, Harper & Scinto
The NutraSweet Company
Wong Leslie
LandOfFree
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