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
2000-03-24
2002-04-02
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
C426S089000, C426S096000, C426S516000, C560S040000
Reexamination Certificate
active
06365216
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to the formation of particles of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester (neotame) by, for example, extrusion and/or spheronization with and without binders. Neotame is converted from a light powder to dustless, free-flowing particles suitable for use in a variety of applications. This invention also relates to food products sweetened with the neotame particles, as well as to methods of preparing such food products.
2. Related Background Art
It is known that N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-phenylalanine 1-methyl ester (neotame) is an extremely potent sweetening agent (about 8000X sweeter than sugar) that has the formula
Clearly, the use of a high potency sweetener such as N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester requires consideration of the ability to deliver the sweetener in a given application. Thus, effective means for delivering neotame in desired compositions are very useful.
Extrusion is a well known technique used in a number of industries for a variety of purposes. For example, food compositions are routinely extruded in order to obtain desired shapes and forms; similarly, other materials such as agricultural compositions and plastics are extruded. In addition, extrusion apparatuses can be used as delivery means for a wide range of products.
Spheronization is a well known technique used in the pharmaceutical industry to provide rounded particles that can be uniformly coated. For example, WO 95/22319 discloses a process for preparing fine particle pharmaceutical formulations by combining dry components with an extrusion aid (typically a pharmaceutically acceptable oil or wax), wetting the mixture, extruding and then spheronizing. This procedure results in fine particle formulations which exhibit improved uniformity of particle size and performance characteristics such as drug release.
WO 93/07859 generally discloses a method of preparation for pharmaceutical pellets comprising melt spheronization, i.e., extrusion under temperatures appropriate to melt the active pharmaceutical agent and necessary excipients and subsequent spheronization.
Spheronization has also been employed in the sweetener industry. WO 89/00819 discloses self-stabilized compositions of dipeptide sweeteners and their salts and complexes, which exhibit heat stability and a sustained release mechanism that insures uniform dissolution and dispersion within baked products. The compositions are produced by spheronizing a dipeptide sweetener, aspartame in particular, with or without a suitable binding agent to produce dense, non-porous spherical granules of narrow particle size distribution. The compositions may be coated with a hydrophobic coating.
Particles of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester formed by either extrusion or spheronization are not disclosed or suggested by the aforementioned art.
SUMMARY OF THE INVENTION
The present invention is directed to a process for forming particles of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester. This process comprises the steps of (a) mixing N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and a plasticizer to form a wet mass; (b) extruding said wet mass to form extrudates; and (c) drying said extrudates to form said particles of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester. In a preferred embodiment of the present invention, water is used as the plasticizer.
In certain preferred embodiments of the present invention, a binder is incorporated in the wet mass prior to the extruding step. In other preferred embodiments, the wet mass is heated prior to the extruding step.
In further preferred embodiments of the present invention, spheres are formed from the extrudates prior to drying.
This invention is further directed to extruded or spheronized particles of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester made according to the processes of the present invention.
Additional embodiments of the present invention are directed to food products sweetened with such particles of neotame and to methods of sweetening food products with the particles of neotame of this invention such as extruded neotame, spheronized neotame or the like.
DETAILED DESCRIPTION
N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester (neotame) is a high potency dipeptide sweetener (about 8000X sweeter than sucrose) that has the formula
The chemical synthesis of neotame is disclosed in U.S. Pat. No. 5,480,668, U.S. Pat. No. 5,510,508 and U.S. Pat. No. 5,728,862, the disclosure of each of which is incorporated by reference herein. Thus, the starting material may be readily prepared by one of ordinary skill without undue experimentation.
Generally, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester exists as a light, somewhat dusty powder. Extrusion and optional spheronization can be used as particle formation techniques to form relatively dustless, free flowing particles of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester. Such particles can be regarded as “extrudates” or “spheres”, depending upon their processing and characteristics.
As used herein, the term “particles” includes, for example, “granules” such as “extrudates”, “spheres” and the like, which have been, for example, “granulated”, (e.g., “extruded”, “spheronized” or the like). Also as used herein, the terms “extrudates” or “extruded neotame” refer to preferably cylindrical, free-flowing, relatively non-dusty, mechanically strong granules of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester. Further, as used herein, the terms “spheres” or “spheronized neotame” refer to relatively spherical, smooth, free-flowing, relatively non-dusty, mechanically strong granules. While spheres typically have a smoother surface and may be stronger/harder than extrudates, extrudates offer a cost advantage in that less processing is required. The spheres and extrudates of this invention may be further processed, if desired, to form various other particles, such as, for example, by grinding or chopping.
Any form of neotame may be used in the extrudates and spheres of this invention. For example, salts and metal complexes of neotame may be used, such as disclosed in U.S. Pat. No. 6,291,004, U.S. Pat. No. 6,180,156, U.S. Pat. No. 6,129,942, and U.S. Pat. No. 6,146,680, all filed Sep. 4, 1998, and all of which are incorporated by reference herein. The anhydrous form of neotame is suitable for use in this invention, as well as the various crystalline forms of neotame. Other exemplary forms of neotame that may be useful in this invention include cyclodextrin
eotame complexes such as disclosed in U.S. Provisional Patent Application No. 60/100,867 and co-crystallized neotame disclosed in U.S. Pat. No. 6,214,402, both filed Sep. 17, 1998, and the disclosure of both of which are incorporated by reference herein.
One embodiment of the present invention is directed to a process by which particles of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester are formed with the use of a binder.
In the first step of this process, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, a plasticizer and a binder are mixed to form a wet mass.
Suitable plasticizers include, without limitation, water, glycerol and mixtures thereof. Water is a particularly preferred plasticizer.
Suitable binders include, without limitation, polyvinylpyrollidone (PVP), maltodextrins, microcrystalline cellulose, starches, hydroxypropylmethyl cellulose (HPMC), methylcellulose, hydroxypropyl cellulose (HPC), gum arabic, gelatin, xanthan gum and mixtures thereof. The binder is generally present in the wet mass in an amount of about 0.01-45% b
Bishay Ihab E.
Dron Aditi
Fotos Jim
Trione Michael J.
Fitzpatrick ,Cella, Harper & Scinto
Hoster Jeffrey M
The NutraSweet Company
Wong Leslie
LandOfFree
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