US009491963B2 (12) United States Patent (10) Patent No.: US 9,491.963 B2 Prakash et al. (45) Date of Patent: Nov. 15, 2016 (54) SWEETNESS ENHANCERS, COMPOSITIONS 200,657 R 58 FErakash et cal al. THEREOF, AND METHODS FOR USE 2009/0311686 A1 12/2009 Slack et al. (71) Applicant: Its co-col Company, Atlanta, GA FOREIGN PATENT DOCUMENTS EP O154235 6, 1991 (72) Inventors: Indra Prakash, Alpharetta, GA (US); JP 6O199364 10, 1985 Grant E. DuBois, Roswell, GA (US); E. 206.6 2: Josef Klucik, Marietta, GA (US); JP 2009,534018 9, 2009 Rafael I. San Miguel, Smyrna, GA WO WO9934689 7, 1999 (US); Rudolf Johann Fritsch, Atlanta, WO WO 2007 121604 11/2007 GA (US); Venkata Sai Prakash WO 2008049256 A1 + 5/2008 Chaturvedula, Gilbert, AZ (US) W. W. 3.35 539. WO 2009085762 A1 T 2009 (73) Assignee: The Coca-Cola Company, Atlanta, GA WO WO 2010 135378 t 11 2010 (US) WO WO 2011009081 1, 2011 WO WO 2011028671 3, 2011 (*) Notice: Subject to any disclaimer, the term of this past is,. adjusted under 35 OTHER PUBLICATIONS M YW- y U days. International Preliminary Report on Patentability for PCT/US2010/ (21) Appl. No.: 14/689,170 062210 (Jul. 4, 2012). International Search Report for PCT/US2010/062210 (mailed Apr. (22) Filed: Apr. 17, 2015 26, 2011). Prakash et al., “Development of rebiana, a natural, non-caloric (65) Prior Publication Data sweetener.” vol. 46, S75-S82, Epub May 16, 2008. US 2015/0216219 A1 Aug. 6, 2015 it cited by third party Primary Examiner — Johann R Richter Related U.S. Application Data Assistant Examiner — Yanzhi Zhang (74) Attorney, Agent, or Firm — King & Spalding (63) Continuation of application No. 12/979.917, filed on Dec. 28, 2010, now Pat. No. 9,012,520. (57) ABSTRACT (60) Provisional application No. 61/290,370, filed on Dec. Disclosed herein are Sweetener compositions comprising at 28, 2009. least one Sweetener and at least one Sweetness enhancer chosen from terpenes (such as sesquiterpenes, diterpenes, (51) Int. Cl. and triterpenes), flavonoids, amino acids, proteins, polyols, A2.3L 2/60 (2006.01) other known natural Sweeteners (such as cinnamaldehydes, A2.3L I/09 (2006.01) selligueians, hematoxylins), secodammarane glycosides, A2.3L. I./22 (2006.01) and analogues thereof, wherein the at least one Sweetness A2.3L I/236 (2006.01) enhancer is present in the composition in an amount at or (52) U.S. Cl below the sweetness detection threshold level of the Sweet CPC.A23L 2.60 (2013.01), A23L 109 (2013.01); E. 2 t 1929, it 2, are methods for enhancing sweetness of a composition, ( .01): ( .01): comprising combining at least one Sweetener and at least I/2366 (2013.01) one Sweetness enhancer chosen from terpenes (such as (58) Field of Classification Search sesquiterpenes, diterpenes, and triterpenes), flavonoids, CPC ........................... CO7H 15/256; A23L 1/2366 amino acids, proteins, polyols, other known natural Sweet USPC ...... 5 14/777; 426/548, 66 CS (such aS cinnamaldehydes, selligueians, hematoxy See application file for complete search history. lins), secodammarane glycosides, and analogues thereof, wherein the at least one Sweetness enhancer is present in the (56) References Cited composition in an amount at or below the Sweetness detec tion threshold level of the at least one Sweetness enhancer, U.S. PATENT DOCUMENTS and the at least one Sweetener and the at least one Sweetness 4,612,942 A it 9/1986 Dobberstein enhancer are different. 4,990,354 A 2f1991 Bakal et al. 6,368,651 B1 it 4/2002 Gerlat 24 Claims, 1 Drawing Sheet U.S. Patent Nov. 15, 2016 US 9,491.963 B2 Control 8% HFSS + Rubuscoside 8%, HSS Sweet Tastelrtensity Sweet Taste Intensity US 9,491,963 B2 1. 2 SWEETNESS ENHANCERS, COMPOSITIONS doside A and polypodoside B; mogrosides, such as mogro THEREOF, AND METHODS FOR USE side IV and mogroside V: abrusoside A and abrusoside B: cyclocariosdies, such as cyclocarioside A and cyclocarioside This application claims the benefit of priority to U.S. B; pterocaryoside A and pterocaryoside B; flavanoids. Such Provisional Application No. 61/290,370 filed on Dec. 28, as phyllodulcin, phloridzin, neoastilbin, and dihydroquerce 2009, which is incorporated in its entirety herein. tin acetate and its derivatives; amino acids, Such as glycine The present disclosure relates to compositions having and monatin; proteins, such as thaumatins (thaumatin I. enhanced Sweetness comprising at least one Sweetener and thaumatin II, thaumatin III, and thaumatin IV), monellin, at least one Sweetness enhancer chosen from terpenes (such mabinlins (mabinlin I and mabinlin II), braZZein, miraculin, as sesquiterpenes, diterpenes, and triterpenes), flavonoids, 10 and curculin, polyols such as erythritol; cinnamaldehyde; amino acids, proteins, polyols, other known natural Sweet selligueains, such as selligueain A and selligueain B; and eners (such as cinnamaldehydes, selligueians, and hema hematoxylin. toxylins), secodammarane glycosides, and analogues For example, the Sweetness enhancer is chosen from pine thereof. The disclosure also relates to methods of enhancing rosin diterpenoids, ploridizin, neoastilbin, dihydroquercetin Sweetness of a composition comprising combining at least 15 acetate, glycine, erythritol, cinnamaldehyde, selligueain A, one Sweetener and at least one Sweetness enhancer chosen selligueain B, hematoxylin, rebaudioside A: rebaudioside B: from terpenes (such as sesquiterpenes, diterpenes, and trit rebaudioside C. rebaudioside D, rebaudioside E. dulcoside erpenes), flavonoids, amino acids, proteins, polyols, other A; Steviolbioside; rubusoside, Stevia, Stevioside, Steviol 13 known natural Sweeteners (such as cinnamaldehydes, selli O-B-D-glycoside, mogroside V. Luo Han Guo, Siamenoside, gueians, hematoxylins), secodammarane glycosides, and siamenoside I, monatin and salts thereof (monatin SS, RR, analogues thereof. RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin Although Sweeteners, such as carbohydrate Sweeteners I, thaumatin II, thaumatin III, thaumatin IV, monellin, including fructose, glucose, and Sucrose, are often used in mabinlin I, mabinlin II, brazzein, hernandulcin, phyllodul beverage compositions, these Sweeteners may be expensive cin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osla to purchase and/or may require high transportation and/or 25 din, polypodoside A, polypodoside B, pterocaryoside A, storage space costs when purchased in bulk. Moreover, pterocaryoside B, mukurozioside, mukurozioside IIb, phlo although natural caloric Sweetener compositions such as misoside I, phlomisoside II, periandrin I, periandrin II, Sucrose, fructose, and glucose taste good to most consumers, periandrin III, periandrin VI, periandrin V. cyclocarioside A, they are caloric. In addition, carbohydrate Sweetener pro cyclocarioside B, Suavioside A, Suavioside B, Suavioside G, duction has a high carbon footprint. Therefore, alternative 30 Suavioside H. Suavioside I, Suavioside J, labdane glycosides, non-caloric or low-caloric sweeteners have been widely baiyunoside, gaudichaudioside A, mogroside IV, iso-mogro sought after and used as sugar or sucrose substitutes. Many side, bryodulcoside, bryoside, bryonoside, camosifloside V. non-caloric or low-caloric Sweeteners, however, are prohibi camosifloside VI, scandenoside R6, 11-oxomogroside V. tively expensive. Furthermore, there is a demand, for prod abrusoside A, abrusoside B, abrusoside C, abrusoside D, ucts that comprise natural products, such as natural Sweet 35 abrusoside E. gypenoside XX, glycyrrhizin, apioglycyr eners or natural Sweetness enhancers. rhizin, araboglycyrrhizin, pentadin, perillaldehyde, rebau Accordingly, it may be desirable to identify compounds dioside F; steviol; 13-(2-O-(3-O-O-D-glucopyranosyl)-3- capable of enhancing or increasing the perception of Sweet D-glucopyranosyl-3-O-B-D-glucopyranosyl-B-D- ness of Such Sweeteners, such as natural and synthetic glucopyranosyl)oxykaur-16-en-18-oic acid B-D- Sweeteners. By combining Such compounds with Sweeten 40 glucopyranosyl ester, 13-(2-O-B-D-glucopyranosyl-3-O- ers, the amount of sweetener needed to obtain a desired (4-O-O-D-glucopyranosyl)-3-D-glucopyranosyl-3-D- degree of Sweetness may be reduced significantly, thereby glucopyranosyl)oxykaur-16-en-18-oic acid B-D- reducing the calories imparted by natural caloric Sweeteners glucopyranosyl ester, 13-(3-O-B-D-glucopyranosyl-B-D- or reducing the amounts of low-caloric or non-caloric natu glucopyranosyl)oxykaur-16-en-18-oic acid B-D- ral or synthetic sweeteners. Moreover, it may be desirable to 45 glucopyranosyl ester, 13-hydroxy-kaur-16-en-18-oic acid identify natural compounds that may enhance the Sweetness B-D-glucopyranosyl ester, 13-methyl-16-oxo-17-norkauran of synthetic and/or natural Sweeteners. 18-oic acid B-D-glucopyranosyl ester; 13-(2-O-B-D-glu Thus, one aspect of the present disclosure is to address at copyranosyl-3-O-B-D-glucopyranosyl-B-D-glucopyranosyl) least one of the above-identified needs by providing com oxykaur-15-en-18-oic acid B-D-glucopyranosyl ester, 13 positions comprising at least one Sweetener and at least one 50 (2-O-B-D-glucopyranosyl-3-O-B-D-glucopyranosyl-B-D- Sweetness enhancer chosen from terpenes (such as sesquit glucopyranosyl)oxykaur-15-en-18-oic acid; 13-(2-O-B-D- erpenes, diterpenes, and triterpenes), flavonoids, amino glucopyranosyl-3-O-B-D-glucopyranosyl-B-D- acids, proteins, polyols, other known natural Sweeteners glucopyranosyl)oxy-17-hydroxy-kaur-15-en-18-oic acid (such as cinnamaldehydes, selligueains, and hematoxylins), B-D-glucopyranosyl ester, 13-(2-O-B-D-glucopyranosyl-3- secodammarane glycosides,