Patents Assigned to The NutraSweet Company
  • Patent number: 6627431
    Abstract: A chemoenzymatic method is disclosed for preparing N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester via the enzymatic regioselective hydrolysis of neotame esters using lipases or esterases.
    Type: Grant
    Filed: May 12, 2000
    Date of Patent: September 30, 2003
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Robert Y. Zhao
  • Patent number: 6573409
    Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and sulfuric acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hvdrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.
    Type: Grant
    Filed: May 19, 2000
    Date of Patent: June 3, 2003
    Assignee: The Nutrasweet Company
    Inventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
  • Patent number: 6506434
    Abstract: The present invention relates to a process for coating N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester onto a carrier. The invention also relates to N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester coated carrier compositions.
    Type: Grant
    Filed: August 4, 2000
    Date of Patent: January 14, 2003
    Assignee: The NutraSweet Company
    Inventors: Allan Towb, Douglas Nolte
  • Patent number: 6465677
    Abstract: The synthesis of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester via conversion under reducing conditions of novel imidazolidinone(s) is disclosed.
    Type: Grant
    Filed: November 17, 1999
    Date of Patent: October 15, 2002
    Assignee: The NutraSweet Company
    Inventors: Vladislav Orlovski, Indra Prakash, Mike G. Scaros, Christine M. V. Moore
  • Patent number: 6423864
    Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is crystallized in order to give highly pure product in high yield. In a preferred embodiment of the present invention, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is crystallized directly from an aqueous methanol reaction mixture.
    Type: Grant
    Filed: November 24, 1999
    Date of Patent: July 23, 2002
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Christine M. V. Moore, Kurt Wachholder
  • Patent number: 6368651
    Abstract: This invention relates to the use of at least one taste modifying ingredient to modify at least one taste characteristic imparted by N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, or neotame, compositions containing the same, and use of modified forms of neotame that possess an improved taste, wherein at least one taste characteristic imparted by neotame is positively affect by the modification of neotame.
    Type: Grant
    Filed: May 10, 2000
    Date of Patent: April 9, 2002
    Assignee: The NutraSweet Company
    Inventors: Paula A. Gerlat, Gale C. Walters, Ihab E. Bishay, Indra Prakash, Tammy C. Jarrett, Nitin Desai, Harold A. Sawyer, Claire-Lise T. Bechert
  • Patent number: 6365216
    Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is converted from a light powder to relatively dustless, free-flowing particles with and without the use of binders using extrusion and spheronization processes. These particles are suitable for use in a variety of applications. Food products sweetened with extruded or spheronized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and methods of sweetening food products with such N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester are also disclosed.
    Type: Grant
    Filed: March 24, 2000
    Date of Patent: April 2, 2002
    Assignee: The NutraSweet Company
    Inventors: Aditi Dron, Ihab E. Bishay, Jim Fotos, Michael J. Trione
  • Patent number: 6358714
    Abstract: The present invention provides materials and methods for production of D-phenylalanine by recombinant expression in a microorganisms of a D-aminotransferase gene and optionally a dadX gene in optional combination with eliminating or reducing expression of L-transaminase genes.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: March 19, 2002
    Assignee: The Nutrasweet Company
    Inventors: Ian Fotheringham, Paul P. Taylor, Roberta K. Yoshida
  • Patent number: 6291004
    Abstract: Dipeptide sweeteners are disclosed that are basic salts of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester represented by the formula wherein Xm+ is selected from the group consisting of Na+, K+, Al3+, Fe2+, Fe3+, Ca2+, Mg2+, NH4+ and Zn2+; Qs− absent or a physiologically acceptable counter anion; and m−s=n. Also disclosed is a liquid low-calorie sweetener containing such basic salts.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: September 18, 2001
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Kurt L. Wachholder
  • Patent number: 6225493
    Abstract: This invention relates to the purification of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester by resolving a mixture of the alpha- and beta-isomers of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester using metal ions.
    Type: Grant
    Filed: August 21, 2000
    Date of Patent: May 1, 2001
    Assignee: The Nutrasweet Company
    Inventors: Indra Prakash, Joseph P. Haar, Jr., Robert Y. Zhao
  • Patent number: 6214402
    Abstract: This disclosure relates to the co-crystallization of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester with sugar in various ratios. The sugar co-crystallized sweetener is very soluble in water and has no dusting problems.
    Type: Grant
    Filed: September 17, 1998
    Date of Patent: April 10, 2001
    Assignee: The NutraSweet Company
    Inventors: Jim Fotos, Ihab E. Bishay, Indra Prakash, Kurt Wachholder, Nitin Desai
  • Patent number: 6180157
    Abstract: A process for preparing an agglomerate of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and a carrier including the steps of: (a) providing a premix solution comprising N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and a binding agent; (b) fluidizing a carrier; and (c) applying the premix solution of step (a) onto said fluidized carrier to form an agglomerate of said N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and said carrier. Also the novel agglomerates prepared by the process of this invention.
    Type: Grant
    Filed: February 18, 1999
    Date of Patent: January 30, 2001
    Assignee: The NutraSweet Company
    Inventors: Jim Fotos, Ihab Bishay
  • Patent number: 6180156
    Abstract: Dipeptide sweeteners are disclosed that are salts of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester represented by the formula wherein X− is selected from the group consisting of Cl−, HSO4−, H2PO3−, citrate, HCO3−, furmarate, malate, maleiate, tartarate, acetate, benzoate or gluconate. Also disclosed is a liquid low-calorie sweetener containing such salts.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: January 30, 2001
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Kurt L. Wachholder
  • Patent number: 6146680
    Abstract: Dipeptide sweeteners are disclosed that are metal complexes of N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine 1-methyl ester represented by the formula ##STR1## wherein X.sup.p+ is selected from the group consisting of Al.sup.3+, Fe.sup.2+, Fe.sup.3+, Ca.sup.2+, Mg.sup.2+ and Zn.sup.2+ ; Y.sup.q- is selected from the group consisting of Cl.sup.-, SO.sub.4.sup.2-, PO.sub.4.sup.3- and CH.sub.3 COO.sup.- ; x is a number from 1 to 4 and pn=qm. Also disclosed is a liquid low-calorie sweetener containing such metal complexes.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: November 14, 2000
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Zhi Guo
  • Patent number: 6129942
    Abstract: Dipeptide sweeteners are disclosed that are sweetener salts of N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine 1-methyl ester represented by the formula ##STR1## wherein X.sup.m- is a conjugate base derived by deprotonation of an acidic sweetener, preferably saccharin, acesulfame, cyclamic acid and glycyrrhizic acid; and m=n. Also disclosed is a liquid low-calorie sweetener containing such basic salts.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: October 10, 2000
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Zhi Guo
  • Patent number: 6077962
    Abstract: This invention relates to the chemical synthesis of N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine 1-methyl ester using peptide coupling methods. The coupling reaction is conducted by condensation of an activated derivative of novel N-neohexyl-L-aspartic acid with L-phenylalanine or L-phenylalanine methyl ester or by enzymatic coupling of N-neohexyl-L-aspartic acid with L-phenylalanine or L-phenylalanine methyl ester. This invention also relates to novel N-(3,3-dimethylbutyl)-L-aspartic acid, derivatives thereof and the preparation thereof. The activated derivative of N-neohexyl-L-aspartic acid may be an anhydride, mixed anhydride, active ester or an intermediate activated derivative thereof.
    Type: Grant
    Filed: December 24, 1998
    Date of Patent: June 20, 2000
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Marie-Christine D. Chapeau
  • Patent number: 6048999
    Abstract: This invention provides sweetener blends comprising N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine 1-methyl ester and another sweetener. The sweetener blends of this invention exhibit isobole synergy.
    Type: Grant
    Filed: January 25, 1999
    Date of Patent: April 11, 2000
    Assignee: The NutraSweet Company
    Inventors: Laurie L. Pajor, Kernon M. Gibes
  • Patent number: 5994593
    Abstract: 3,3-Dimethylbutyraldehyde is synthesized via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane in the presence of water and a base and is purified via an aldehyde/bisulfite adduct.
    Type: Grant
    Filed: September 17, 1998
    Date of Patent: November 30, 1999
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Zhi Guo
  • Patent number: 5977415
    Abstract: This invention provides a method for preparing 3,3-dimethylbutyraldehyde from a tert-butyl cation precursor and vinyl chloride. The tert-butyl cation precursor is contacted with vinyl chloride in the presence of an inorganic acid, and the product is allowed to react with water to form 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: August 20, 1998
    Date of Patent: November 2, 1999
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Zhi Guo
  • Patent number: 5973209
    Abstract: A method is disclosed for preparing 3,3-dimethylbutyraldehyde by using silica gel to isomerize 3,3-dimethyl-1,2-epoxybutane, which in turn may be prepared by oxidation of dimethylbutene. Also disclosed is a method for oxidizing dimethylbutene with dimethyldioxirane to form 3,3-dimethyl-1,2-epoxybutane. The methods provide an economical means of preparing 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: July 11, 1997
    Date of Patent: October 26, 1999
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Marie-Christine D. Chapeau