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United States Patent Office Patented June 12, 1973 2 3,739,064 Ser

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United States Patent Office Patented June 12, 1973 2 3,739,064 Ser 3,739,064 United States Patent Office Patented June 12, 1973 2 3,739,064 Ser. No. 76,974, filed Sept. 30, 1970, and Rizzi and Neely, DHYDROCHALCONE SWEETENING AGENTS entitled Sweetening Compositions Containing Aglyconic George P. Rizzi, Springfield Township, Hamilton County, Dihydrochalcones Ser. No. 76,973, filed Sept. 30, 1970. Ohio, assignor to The Procter & Gamble Company, Accordingly, it is an object of this invention to pro Cincinnati, Ohio 5 vide sweetening compositions containing hesperetin dihy No Drawing. Fied Sept. 30, 1970, Ser. No. 76,972 drochalcone and certain homologs thereof having en nt. Cl. A61k 7/16; A23 1/26 hanced sweetness. Another object of this invention is to U.S. C. 424-49 9 Cains provide artificial sweetening compositions containing solu bilized hesperetin dihydrochalcone and solubilized homo ABSTRACT OF THE DISCLOSURE O logs thereof. Still another object is to provide a method Hesperetin dihydrochalcone, and certain homologs for enhancing the sweetness of hesperetin dihydro thereof, are dissolved in appropriate organic solvents and chalcone and the homologs thereof. These and other ob aqueous-organic solvents to provide novel Sweetening jects are obtained by the present invention as will become compositions useful in flavoring edible products. apparent from the following disclosure. SUMMARY OF THE INVENTION The Sweetening compositions of this invention comprise BACKGROUND OF THE INVENTION hesperetin dihydrochalcone and certain homologs of This invention relates to compositions for imparting hesperetin dihydrochalcone dissolved in certain solvents sweetness to food substances without the use of natural 20 as hereinafter defined. In its process aspects this inven sugars. This invention also relates to a method for en tion comprises a method for potentiating the sweetness of hancing the minimal natural sweetness of hesperetin certain aglyconic dihydrochalcones, and a method for dihydrochalcone, and certain homologs thereof, by disso Sweetening foods, beverages, dentifrices, chewing gums, lution in an appropriate organic solvent or in mixtures mouthwashes and other ingestible compositions. of organic solvents and water (aqueous-organic solvents) 25 More specifically, this invention provides sweetening thereby rendering these aglyconic dihydrochalcones Suit compositions comprising from about a 5x10-4 molar to able for use as artificial sweetening agents. about a 2.0 molar concentration of a compound of the Various dihydrochalcone derivatives of naturally oc formula curring compounds, for example, those described by Horowitz and Gentili in U.S. Pat. 3,087,821, have been 30 gh QH used as artificial sweetening agents. Of greatest utility as sweeteners are compounds of the general structure EO --CH-CH-KY-ORO t H oH (II) RO- -OH -OR, 35 wherein R is a member selected from the group consisting of methyl, ethyl, isopropyl, propyl and butyl, dissolved in a solvent selected from the group consisting of ingestible polar, organic liquids and mixtures of ingestible polar on-on organic liquids and water, said mixtures containing at E (I) 40 least about 0.15% by weight of said ingestible polar, wherein R is lower alkyl and R' is a sugar. These flava organic liquids. none glycosides are derivable from compounds found In addition, this invention provides a process for en in naturally-occurring sources such as grapefruit and other hancing the sweetness of compounds of Formula FI hav citrus fruits. Especially important among these sweeten- 4 ing as group R a member selected from the group con ing agents are compounds wherein R' is the neohesperi sisting of methyl, ethyl, isopropyl, propyl and butyl, com dosyl radical. Horowitz and Gentili teach that partial hy prising dissolving said compounds in a solvent selected drolysis of the neohesperidosyl group, with the removal from the group consisting of ingestible polar, organic of the rhamnose moiety, results in the formation of glu liquids, and mixtures of ingestible polar, organic liquids cosyl dihydrochalcone compounds having an intense and water containing at least about 0.15% by weight sweetness comparable to that of saccharin. The art fur 50 of said ingestible polar, organic liquids. ther teaches that it is necessary that the dihydrochalcones Finally, this invention provides a process for sweetening have a sugar substituent in their structures to exhibit any ingestible materials which comprises dissolving therein a useful degree of sweetness. Complete removal of the Sugar dihydrochalcone compound of Formula II having as group group (R') from compounds of structure (I) having sub- 55 R a member selected from the group consisting of methyl, stituent R as methyl and replacement of said sugar group ethyl, isopropyl, propyl and butyl at a concentration of with hydrogen yields the aglycone, hesperetin dihydro at least about 5X 104 molar. This latter process prefer chalcone, which is characterized as being only moderately ably comprises the steps of: (a) dissolving a dihydro sweet. Because of its low level of sweetness, hesperetin chalcone compound of Formula II in a solvent selected dihydrochalcone has not heretofore been employed as 60 from the group consisting of ingestible polar, organic a sweetening agent. Surprisingly, however, it has now liquids, and mixtures of ingestible polar, organic liquids been discovered that hesperetin dihydrochalcone, when and water containing at least about 0.15% by weight of solubilized in the presence of an organic solvent as here said ingestible polar, organic liquids; and (b) adding inbelow described, exhibits an enhanced and useful degree the Solution of step (a) to an ingestible material until the of sweetness approximately 100 times that of sucrose. By 65 final concentration of the dihydrochalcone dissolved the practice of this invention, then, hesperetin dihydro therein is at least 5X 104 molar. chalcone and certain of its homologs are rendered useful When R in the above Formula II is methyl, the com as sweetening agents. Moreover, certain of these dihydro pound is hesperetin dihydrochalcone, which is preferred chalcones are found to enhance the natural sweetness of for use herein. Hesperetin dihydrochalcone can be pre various sugars and sugar alcohols, as is disclosed in the 70 pared from hesperidin by hydrolysis in aqueous mineral concurrently filed applications of Rizzi, entitled Sugar acid, followed by catalytic hydrogenation, as hereinafter Compositions Containing Aglyconic Dihydrochalcones, detailed. Alternatively, hesperetin dihydrochalcone gluco 3,739,064 3 4. side, prepared by the method of Horowitz, U.S. Pat. without ill effects. For example, many of the organic 3,429,873, can be subjected to further hydrolysis with acids are found in oxidized fat mixtures and acetic acid is removal of the 3-D-glucose moiety and recovery of the a well-known constituent of vinegar. As hereinafter noted, aglycone, hesperetin dihydrochalcone. Likewise, U.S. Pat. organic acid esters are major components of most natural 3,375,242 describes a process for condensing naringin ly-occurring flavor oils. Mercaptains are found in vegeta with isovanillin to yield neohesperidin chalcone which, on bles such as the onion and garlic, while a variety of hydrogenation and complete hydrolysis of the sugar, yields polar, organic liquids are known to be present in the so hesperetin dihydrochalcone. Hesperetin dihydrochalcone called "fusel oil' component of alcoholic beverages. Many prepared by any of these methods is suitable for use in of these polar, organic liquids cause no ill effects if in the practice of the present invention. O gested occasionally and in low concentrations, but some When R in Formula II is ethyl, the compound is homo should be avoided if repeated use is anticipated. Accord hesperetin dihydrochalcone which is also preferred herein. ingly, there are certain preferred polar, organic liquids When R is propyl, the compound is bis-homohesperetin which can be employed herein singly, in combination one dihydrochalcone. When R is any of the indicated groups with another and with water, to enhance the sweetness of other than methyl, the compounds are homologs of 5 the hesperetin and hesperetin-like dihydrochalcones used hesperetin dihydrochalcone and are referred to herein herein and thereby provide sweetening compositions. after as "hesperetin-like' dihydrochalcones. These homo These preferred, polar, liquid, organic compounds are logs can be prepared in much the same fashion as hespere Sometimes hereinafter referred to as ingestible organic tin dihydrochalcone as will be seen hereinafter. solvents. Preferred, ingestible, polar, organic liquid sol Admixture of the dihydrochalcones having the general 20 vents suitable for use herein, singly, in admixtures and Formula II with pure water results in solutions which with water for the preparation of artificial sweetening are almost imperceptibly sweet. Likewise, the solid dihy compositions containing hesperetin dihydrochalcone and drochalcones of the above formula are not detectably the hesperetin-like dihydrochalcones include the ingestible sweet to the average taster. However, when solubilized by members of the hereinafter disclosed classes of polar, admixture with the proper solvent, as hereinbelow de 25 organic liquids, especially those detailed in the list of per tailed, in the concentration ranges herein noted, these di mitted food additives periodically prepared and issued hydrochalcones are found to exhibit a sweetness level by the United States Food & Drug Administration and pub approximately
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