Tomato based sauce containing allulose

Abstract

The invention relates to a tomato based sauce, preferably a ketchup, comprising allulose and vinegar, wherein the sauce has a pH value of at most 5.0, preferably within the range of from 3.2 to 4.6, more preferably 3.2 to 4.2; wherein the content of allulose in the sauce is at least 0.5 wt.-%, relative to the total weight of the sauce; and wherein the content of fructose in the sauce, if any, is at most 7.0 wt.-%, relative to the total content of monosaccharides and disaccharides. The invention further relates to a process for preparing the tomato based sauce, preferably a ketchup.

Description

Tomato based sauce containing allulose

[0001] Priority is claimed of European patent application no. 25 152359.3 that was filed on 16 January 2025.

[0002] The invention relates to a tomato based sauce, preferably a ketchup, comprising allulose and vinegar, wherein the sauce has a pH value of at most 5.0, preferably within the range of from 3.2 to 4.6, more preferably 3.2 to 4.2, still more preferably 3.2 to 3.7; wherein the content of allulose in the sauce is at least 0.5 wt.-%, relative to the total weight of the sauce; and wherein the content of fructose in the sauce, if any, is at most 7.0 wt.-%, relative to the total content of monosaccharides and disaccharides. The invention further relates to a process for preparing the tomato based sauce, preferably a ketchup.

[0003] The red color of tomato ketchup is an important property. Many ketchups are commercialized in transparent bottles so that the red color is directly visible. The red color of tomato ketchup is essentially based upon lycopene, is a bright red tetraterpene. Lycopene gives tomatoes, pink grapefruit, watermelon, and guava their red color. It has been estimated that 80% of the lycopene in the US diet comes from tomatoes and tomato products like tomato sauce, tomato paste, and ketchup (see Linus Pauling Institute, Micronutrient Information Center, Oregon State University).

[0004] Degradation of lycopene upon storage of ketchup results in an undesirable color change. For this and other reasons, chemical stability of lycopene under various storage conditions has been subject to extensive research.

[0005] Lycopene belongs to the carotenoid family and mostly exists in nature as all-trans form. Heat, light, oxygen, and different food matrices are factors that have an effect on lycopene isomerization and autooxidation. After oxidation, the lycopene molecule splits causing loss of color (see Stability of lycopene during food processing and storage, Food Ingredients Brasil, No. 5, 2008, 32-42).

[0006] A. Rajchl et al., Journal of Food Engineering 99 (2010) 465-470 relates to the stability of nutritionally important compounds and shelflife prediction of tomato ketchup. The samples were stored at different temperature and during the storage the content of total lycopene and ascorbic acid was observed as well as the color parameters (a*, AE). The obtained data were processed using the pseudo first order (total lycopene, ascorbic acid and a*) and zero order kinetics (AE).

[0007] R.K. Saini et al., Journal of Agricultural and Food Chemistry, J. Agric. Food Chem. 2020, 68, 3, 712-726 review chemical stability of lycopene in processed products, especially the effects of processing methods and modem preservation strategies. Some effects of pH are also discussed and degradation of lycopene is typically more pronounced at acidic pH than at neutral pH.

[0008] J. Kim et al., Foods 2020, 9, 971, 1-15 relates to the improvement of the stability of lycopene from chemical degradation in model beverage emulsions, especially the impact of hydrophilic groups size of emulsifiers and antioxidant polarity.

[0009] Allulose (psicose) is a low-calorie epimer of fructose that has utility as a low -calorie sweetener in food and beverages. The sweetness of allulose is estimated to be 70% of the sweetness of sucrose. It has been suggested to replace sucrose by allulose in various foods including ketchup.

[0010] The pH value of ketchup depends upon many factors including but not limited to the pH value of the tomato source that is used as starting material, the pH value of the vinegar that is used as a starting material, the pH value of the carbohydrate source that is used as starting material, and the like.

[0011] US 2018 0243325 Al relates to a composition for preventing or treating lipid-related metabolic diseases. It is stated that tomato ketchups including 0.2 - 1.0 wt.-% of D-psicose were prepared

[0012] US 2019 0328018 Al relates to a ketchup comprising a tomato concentrate, saccharides comprising allulose, vinegar, sodium chloride and purified water, wherein the tomato concentrate is present in an amount of 10 parts by weight to 80 parts by weight and the saccharides are present in an amount of 10 parts by weight to 40 parts by weight relative to 100 parts by weight of the ketchup. The ketchup is said to have improved preservability due to reduction in viscosity change, dehydration prevention and / or enhancement in microbial stability. The ketchup may comprise food ingredients (vitamins, electrolytes, flavors, colorants, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, pH regulators, stabilizers, preservatives, glycerin, and carbonating agents).

[0013] US 20200157594 Al, US 2021 0002318 Al, US 2021 0246156 Al, US 20220017557 Al, and US 2022 0380824 Al relate to high-purity steviol glycosides. The steviol glycosides can be combined e.g. allulose. The steviol glycosides can be used to prepare consumable products including ketchups.

[0014] US 2023 0139835 Al relates to a crystalline allulose with a defined particle size distribution, to a process for the production thereof, as well as to the use thereof. The crystalline allulose can be used for preparing oral preparations including ketchup.

[0015] Y. Xia et al., Foods 2021, 10, 2186, 2-21 reviews research advances of D-allulose and provide an overview of physiological functions, enzymatic biotransformation technologies, and production processes. The authors suggest that due to its neutral sweetness, reductive properties, and high browning reactivity, D-allulose is suitable not only for baked goods, but also for sauces, ketchup, confectionery, beverages, and other products.

[0016] Z. Chen et al., Frontiers in Microbiology, 2022, 13, 881037, 1-12 relates to recent advantages regarding the physiological functions and biosynthesis of D-allulose. It is disclosed that allulose is capable of acting as scavenger of reactive oxygen species (ROS) to protect 6-hydroxydopamineinduced apoptosis or prevent testicular injury.

[0017] H. Daniel et al., British Journal of Nutrition (2022), 128, 172-178 relates to allulose in human diet, the knowns and the unknowns. It is stated that the content of allulose in conventional ketchup with no added allulose is about 40 mg / 100 g.

[0018] It is an object of the invention to provide tomato based sauces that have advantages compared to the tomato based sauces of the prior art. The tomato based sauces should have reduced calorific value at excellent sensory properties and taste and should have a storage stability such that the visual appearance, especially the red color, does not significantly change over time. A tomato based sauce according to the invention that has been stored for 3 months at room temperature should preferably not be visually distinguishable from a freshly prepared tomato based sauce.

[0019] This object has been achieved by the subject-matter of the patent claims.

[0020] It has been surprisingly found that allulose influences the color change (color distances AE) of tomato based sauce upon storage. At identical pH values of the allulose-containing tomato ketchups, allulose syrups that are used as starting materials in the preparation and that have different pH values in their neat state lead to different color changes upon storage of the allulose-containing tomato ketchups made therefrom.

[0021] Further, it has been surprisingly found that the color change of tomato based sauce upon storage is particularly pronounced when the allulose syrups (starting materials) in their neat state have a pH value of about 4, whereas the color change is less pronounced at lower pH values as well at higher pH values of the allulose syrups in their neat state.

[0022] Still further, it has been surprisingly found that the effect of allulose on color change (color distances AE) of tomato based sauce upon storage is not a function of long term impact of pH value on allulose syrups in their neat state. While the pH value of the allulose syrups in their neat state obviously has an influence on color change upon storage, this influence does not result from long term changes of the composition of the allulose syrups in their neat state under different pH conditions, e.g. degradation, formation of byproducts, and the like.

[0023] Yet further, it has been surprisingly found that the pH value of the tomato based sauce also influences the color change (color distances AE) of tomato based sauce upon storage. Allulose-containing ketchups made having different pH values lead to different color changes of the allulose-containing tomato ketchups upon storage. The color change of the allulose-containing ketchups upon storage is less pronounced at a pH value of allulose-containing ketchup of about 4, whereas the color change is more pronounced at lower pH values as well at higher pH values of the allulose-containing ketchups.

[0024] Furthermore, it has been surprisingly found that the purity of the allulose syrups in their neat state also influences the color change (color distances AE) of tomato based sauce upon storage. At comparable pH values of allulose syrups in their neat state and identical pH values of allulose-containing ketchups, allulose syrups made from highly pure crystalline allulose are significantly less prone to colorchange upon storage than those provided by allulose syrups made from purified reaction products of enzymatic conversions of fructose not involving crystallization of allulose and redissolution of crystalline allulose in water.

[0025] A first aspect of the invention relates to a tomato based sauce, preferably a ketchup, comprising allulose; and vinegar; wherein the sauce has a pH value of at most 5.0, preferably within the range of from 3.2 to 4.6, more preferably 3.2 to 4.2, still more preferably 3.2 to 3.7; wherein the content of allulose in the sauce is at least 0.5 wt.-%, relative to the total weight of the sauce; and wherein the content of fructose in the sauce, if any, is at most 7.0 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0026] Preferably, the sauce has a pH value of at most 3.7.

[0027] As vinegar is aqueous, the tomato based sauce according to the invention comprises water. Vinegar typically contains about 4-8 wt.-% acetic acid and about 92-96 wt.-% water.

[0028] Preferably, the sauce has a pH value of at most 4.9, preferably at most 4.8, more preferably at most 4.7, still more preferably at most 4.6, yet more preferably at most 4.5, even more preferably at most 4.4, most preferably at most 4.3, and in particular at most 4.2.

[0029] Preferably, the sauce has a pH value of at most 4.1, preferably at most 4.0, more preferably at most 3.9, still more preferably at most 3.8, yet more preferably at most 3.7, even more preferably at most 3.6, most preferably at most 3.5, and in particular at most 3.4.

[0030] Preferably, the sauce has a pH value of at least 3.0, preferably at least 3.1, more preferably at least 3.2, still more preferably at least 3.3, yet more preferably at least 3.4, even more preferably at least 3.5, most preferably at least 3.6, and in particular at least 3.7.

[0031] In particularly preferred embodiments, the sauce has a pH value within the range of from 3.2 to 4.6, preferably 3.2 to 4.2 more preferably 3.2 to 3.7.

[0032] In preferred embodiments, the sauce has a pH value within the range of 3.1 to 4.7, preferably 3.2 to 4.6, more preferably 3.3 to 4.5, still more preferably 3.4 to 4.4, yet more preferably 3.5 to 4.3, even more preferably 3.6 to 4.2, most preferably 3.7 to 4.1, and in particular 3.8 to 4.0.

[0033] In other preferred embodiments, the sauce has a pH value within the range of 3.2 to 3.7.

[0034] Preferably, the sauce has an allulose content of at least 1.0 wt.-%, preferably at least 2.0 wt.-%, more preferably at least 3.0 wt.-%, still more preferably at least 4.0 wt.-%, yet more preferably at least 5.0 wt.-%, even more preferably at least 6.0 wt.-%, most preferably at least 7.0 wt.-%, and in particular at least 8.0 wt.-%, relative to the total weight of the sauce.

[0035] Preferably, the sauce has an allulose content of at most 25 wt.-%, preferably at most 22.5 wt.-%, more preferably at most 20 wt.-%, still more preferably at most 17.5 wt.-%, yet more preferably atmost 15 wt.-%, even more preferably at most 12.5 wt.-%, most preferably at most 10 wt.-%, and in particular at most 7.5 wt.-%, relative to the total weight of the sauce.

[0036] Preferably, the sauce has an allulose content of at least 10 wt.-%, preferably at least 20 wt.-%, more preferably at least 30 wt.-%, still more preferably at least 40 wt.-%, yet more preferably at least 50 wt.-%, even more preferably at least 60 wt.-%, most preferably at least 70 wt.-%, and in particular at least 80 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0037] Preferably, the sauce has an allulose content of at least 96.5 wt.-%, preferably at least 97.0 wt.-%, more preferably at least 97.5 wt.-%, still more preferably at least 98.0 wt.-%, yet more preferably at least 98.5 wt.-%, even more preferably at least 99.0 wt.-%, most preferably at least 99.5 wt.-%, and in particular at least 99.8 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0038] While it is contemplated that the sauce may contain one or more monosaccharides other than allulose; preferably glucose, fructose, tagatose, or mixtures thereof, their content, if any, is preferably limited.

[0039] The content of fructose in the sauce, if any, is at most 7.0 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0040] Preferably, the sauce has a fructose content, if any, of at most 6.5 wt.-%, preferably at most 6.0 wt.-%, more preferably at most 5.5 wt.-%, still more preferably at most 5.0 wt.-%, yet more preferably at most 4.5 wt.-%, even more preferably at most 4.0 wt.-%, most preferably at most 3.5 wt.-%, and in particular at most 3.0 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0041] Preferably, the sauce has a fructose content, if any, of at most 2.5 wt.-%, preferably at most 2.0 wt.-%, more preferably at most 1.5 wt.-%, still more preferably at most 1.0 wt.-%, yet more preferably at most 0.8 wt.-%, even more preferably at most 0.6 wt.-%, most preferably at most 0.4 wt.-%, and in particular at most 0.2 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0042] Preferably, the sauce has a glucose content, if any, of at most 6.5 wt.-%, preferably at most 6.0 wt.-%, more preferably at most 5.5 wt.-%, still more preferably at most 5.0 wt.-%, yet more preferably at most 4.5 wt.-%, even more preferably at most 4.0 wt.-%, most preferably at most 3.5 wt.-%, and in particular at most 3.0 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0043] Preferably, the sauce has a glucose content, if any, of at most 2.5 wt.-%, preferably at most 2.0 wt.-%, more preferably at most 1.5 wt.-%, still more preferably at most 1.0 wt.-%, yet more preferably at most 0.8 wt.-%, even more preferably at most 0.6 wt.-%, most preferably at most 0.4 wt.-%, and in particular at most 0.2 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0044] Preferably, the sauce contains one or more disaccharides; preferably sucrose.

[0045] Preferably, the sauce has a sucrose content of at least 2.5 wt.-%, preferably at least 5.0 wt.-%, more preferably at least 10 wt.-%, still more preferably at least 15 wt.-%, yet more preferably at least20 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 40 wt.-%, and in particular at least 50 wt.-%, relative to the total content of monosaccharides and disaccharides.

[0046] Preferably, the sauce has a water content of at least 22.5 wt.-%, preferably at least 25 wt.-%, more preferably at least 27.5 wt.-%, still more preferably at least 30 wt.-%, yet more preferably at least 32.5 wt.-%, even more preferably at least 35 wt.-%, most preferably at least 37.5 wt.-%, and in particular at least 40 wt.-%, relative to the total weight of the sauce.

[0047] Preferably, the sauce has a water content of at most 54 wt.-%, preferably at most 52 wt.-%, more preferably at most 50 wt.-%, still more preferably at most 48 wt.-%, yet more preferably at most 46 wt.-%, even more preferably at most 42 wt.-%, most preferably at most 40 wt.-%, and in particular at most 38 wt.-%, relative to the total weight of the sauce.

[0048] Any water that is contained in the vinegar which is used for preparing the sauce is included in this water content.

[0049] Preferably, the sauce has a vinegar content (including the water that is intrinsically contained in the vinegar) of at least 3.0 wt.-%, preferably at least 3.5 wt.-%, more preferably at least 4.0 wt.-%, still more preferably at least 4.5 wt.-%, yet more preferably at least 5.0 wt.-%, even more preferably at least 5.5 wt.-%, most preferably at least 6.0 wt.-%, and in particular at least 6.5 wt.-%, relative to the total weight of the sauce.

[0050] Preferably, the sauce has a vinegar content (including the water that is intrinsically contained in the vinegar) of at most 12 wt.-%, preferably at most 11 wt.-%, more preferably at most 10 wt.-%, still more preferably at most 9.0 wt.-%, yet more preferably at most 8.0 wt.-%, even more preferably at most 7.0 wt.-%, most preferably at most 6.0 wt.-%, and in particular at most 5.0 wt.-%, relative to the total weight of the sauce.

[0051] Preferably, the sauce has a content of acetic acid of at least 0.15 wt.-%, preferably at least 0.18 wt.-%, more preferably at least 0.2 wt.-%, still more preferably at least 0.23 wt.-%, yet more preferably at least 0.25 wt.-%, even more preferably at least 0.28 wt.-%, most preferably at least 0.3 wt.-%, and in particular at least 0.33 wt.-%, relative to the total weight of the sauce.

[0052] Preferably, the sauce has a content of acetic acid of at most 0.6 wt.-%, preferably at most 0.55 wt.-%, more preferably at most 0.5 wt.-%, still more preferably at most 0.45 wt.-%, yet more preferably at most 0.4 wt.-%, even more preferably at most 0.35 wt.-%, most preferably at most 0.3 wt.-%, and in particular at most 0.25 wt.-%, relative to the total weight of the sauce.

[0053] Preferably, the sauce contains starch; preferably wherein the starch is selected from wheat starch, rice starch, potato starch, maize starch, and peas starch.

[0054] Preferably, the content of starch is at least 0.6 wt.-%, preferably at least 0.9 wt.-%, more preferably at least 1.2 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 1.8 wt.-%,even more preferably at least 2.1 wt.-%, most preferably at least 2.4 wt.-%, and in particular at least 2.7 wt.-%, relative to the total weight of the sauce.

[0055] Preferably, the content of starch is atmost 5.4 wt.-%, preferably atmost 5.1 wt.-%, more preferably at most 4.8 wt.-%, still more preferably at most 4.5 wt.-%, yet more preferably at most 4.2 wt.-%, even more preferably at most 3.9 wt.-%, most preferably at most 3.6 wt.-%, and in particular at most 3.3 wt.-%, relative to the total weight of the sauce.

[0056] Preferably, the freshly prepared tomato based sauce after storage for 12 weeks at 23°C and 50% r.h. has a color distance AE value according to DIN EN ISO / CIE 11664-4:2020-03 of at most 3.50.

[0057] Preferably, the freshly prepared tomato based sauce after storage for 12 weeks at 23°C and 50% r.h. has a color distance AE value according to DIN EN ISO / CIE 11664-4:2020-03 of most 3.40, preferably at most 3.30, more preferably at most 3.20, still more preferably at most 3.10, yet more preferably at most 3.00, even more preferably at most 2.90, most preferably at most 2.80, and in particular at most 2.70.

[0058] Preferably, the freshly prepared tomato based sauce after storage for 12 weeks at 23°C and 50% r.h. has a color distance AE value according to DIN EN ISO / CIE 11664-4:2020-03 of most 2.60, preferably at most 2.50, more preferably at most 2.40, still more preferably at most 2.30, yet more preferably at most 2.20, even more preferably at most 2.10, most preferably at most 2.00, and in particular at most 1.90.

[0059] Preferably, the sauce is selected from the group consisting of ketchup, barbecue sauce, chili sauce, habanero sauce, steak sauce, cocktail sauce, pasta sauce, pizza sauce, sriracha sauce, burger sauce, tacco sauce, salsa, pesto and the like; preferably ketchup.

[0060] Preferably, the sauce comprises a tomato component selected from the group consisting of tomatoes, tomato puree, tomato sauce, tomato paste, tomato concentrate, tomato extract, tomato powder, tomato juice, tomato sauce, and the like; preferably tomato paste or tomato concentrate.

[0061] Preferably, the sauce is made from an allulose syrup.

[0062] Preferably, the allulose syrup in its neat state has an allulose content of at least 95.0 wt.-%, preferably at least 96.0 wt.-%, more preferably at least 97.0 wt.-%, still more preferably at least 98.0 wt.-%, yet more preferably at least 98.5 wt.-%, even more preferably at least 99.0 wt.-%, most preferably at least 99.5 wt.-%, and in particular at least 99.8 wt.-%, relative to the dry solid content.

[0063] Preferably, the allulose syrup in its neat state has a dry solids content of at least 73 wt.-%, preferably at least 74 wt.-%, more preferably at least 75 wt.-%, still more preferably at least 76 wt.-%, yet more preferably at least 77 wt.-%, even more preferably at least 78 wt.-%, most preferably at least 79 wt.-%, and in particular at least 80 wt.-%, relative to the total weight of the allulose syrup.

[0064] Preferably, the allulose syrup in its neat state has been made from allulose and water and neither acid nor base has been added.

[0065] Preferably, the allulose syrup in its neat state essentially consists of allulose and water.

[0066] Preferably, the allulose syrup in its neat state has a pH value of at least 3.3, preferably at least 3.4, more preferably at least 3.5, still more preferably at least 3.6, yet more preferably at least 3.7, even more preferably at least 3.8, most preferably at least 3.9, and in particular at least 4.0.

[0067] Preferably, the allulose syrup in its neat state has a pH value of at least 4.1, preferably at least 4.2, more preferably at least 4.3, still more preferably at least 4.4, yet more preferably at least 4.5, even more preferably at least 4.6, most preferably at least 4.7, and in particular at least 4.8.

[0068] Preferably, the allulose syrup in its neat state has a pH value of at least 4.9, preferably at least 5.0, more preferably at least 5.1, still more preferably at least 5.2, yet more preferably at least 5.3, even more preferably at least 5.4, most preferably at least 5.5, and in particular at least 5.6.

[0069] Preferably, the allulose syrup in its neat state has a pH value of at least 5.7, preferably at least 5.8, more preferably at least 5.9, still more preferably at least 6.0, yet more preferably at least 6.1, even more preferably at least 6.2, most preferably at least 6.3, and in particular at least 6.4.

[0070] Preferably, the allulose syrup in its neat state has a pH value of at least 6.5, preferably at least 6.6, more preferably at least 6.7, still more preferably at least 6.8, yet more preferably at least 6.9, even more preferably at least 7.0, most preferably at least 7.1, and in particular at least 7.2.

[0071] Preferably, the allulose syrup in its neat state has a pH value of at most 5.0, preferably at most 4.9, more preferably at most 4.8, still more preferably at most 4.7, yet more preferably at most 4.6, even more preferably at most 4.5, most preferably at most 4.4, and in particular at most 4.3.

[0072] Preferably, the allulose syrup in its neat state has a pH value of at most 4.2, preferably at most 4.1, more preferably at most 4.0, still more preferably at most 3.9, yet more preferably at most 3.8, even more preferably at most 3.7, most preferably at most 3.6, and in particular at most 3.5.

[0073] Preferably, the allulose syrup in its neat state has a pH value of at most 3.4, preferably at most 3.3, more preferably at most 3.2, still more preferably at most 3.1, yet more preferably at most 3.0, even more preferably at most 2.9, most preferably at most 2.8, and in particular at most 2.7.

[0074] Preferably, the sauce according to the invention is obtainable by a process comprising preparing said sauce from an allulose syrup having a pH value in its neat state of less than 3.3 or greater than 4.9.

[0075] Preferably, the sauce according to the invention is obtainable by a process comprising preparing said sauce from an allulose syrup according to the invention as described above.

[0076] Another aspect of the invention relates to a process for the preparation of a tomato based sauce according to the invention as described above, said process comprising the steps of(a) providing an allulose syrup; preferably as defined above;(b) mixing the allulose syrup with the remaining ingredients of the sauce; and(c) optionally, adjusting the pH value of the thus obtained tomato based sauce.

[0077] Preferably, the process according to the invention does not involve adding purified water. Thus, preferably, the total content of water that is finally contained in the tomato based sauce originates from other starting material such as vinegar and allulose syrup.

[0078] Another aspect of the invention relates to a tomato based sauce that is obtainable by the process according to the invention as described above.

[0079] Another aspect of the invention relates to the use of an allulose syrup; preferably as described above; for preparing a tomato based sauce according to the invention as described above.EXAMPLES

[0080] The following examples further illustrate the invention but are not to be construed as limiting its scope.

[0081] The term "syrup pH" refers to the pH value of the allulose syrup before it is mixed with the allulose-free crude tomato ketchup. The term "ketchup pH" refers to the pH value of the mixture of the allulose-free crude tomato ketchup and the allulose syrup.Example 1 - allulose syrup obtained by enzymatic conversion of fructose:

[0082] Allulose syrup was prepared by enzymatic conversion of fructose. The reaction product was subsequently purified by moving bed chromatography and ion exchange chromatography. The allulose fraction was concentrated yielding an allulose syrup having a pH value of 4.12. The allulose syrup had a dry solids content of 70 wt.-%, relative to the total weight of the allulose syrup, and a purity of allulose amounting to about 95 wt.-%, relative to the dry solids content of the allulose syrup.

[0083] Unlike the allulose syrups employed in Example 2 below, the allulose syrups employed in Example 1 were made from purified reaction products of enzymatic conversions of fructose not involving crystallization of allulose and redissolution of crystalline allulose in water. Thus, the purity of allulose in the allulose syrups employed in Example 1 was lower than in Example 2.

[0084] Allulose-free crude tomato ketchup was made from the following ingredients in the following amounts:

[0085] The pH-adapted allulose syrups were then mixed with allulose-free crude tomato ketchup to provide allulose-containing tomato ketchup. In each case, 247.2 g of allulose syrup were homogenized and heated with 552.8 g of allulose-free crude tomato ketchup. The allulose content in the resultant mixture, i.e. the allulose-containing tomato ketchup, was 32.84 wt.-%, relative to the total weight of the ketchup. In each case, the time from adjusting the pH value of the allulose syrup to the time of mixing the pH-adapted allulose syrups with allulose-free crude tomato ketchup to provide allulose-containing tomato ketchup was less than 1 hour.

[0086] a) In a first series of experiments (samples 1-1, 1-2, 1-4, 1-6 and 1-7), the influence of the pH value of the allulose syrup that was employed as a starting material for the preparation of the allulose-containing tomato ketchup was investigated. For that purpose, the pH value of two allulose syrup samples was decreased by adding hydrochloric acid (pH 2.51 and pH 3.24), and the pH value of two allulose syrup samples was increased by adding sodium hydroxide (pH 5.08 and pH 6.49), whereas one further allulose syrup sample had the initial pH value of 4.12. Therefore, a total of fife different allulose syrups was prepared having different pH values, namely pH 2.51, 3.24, 4.12, 5.08, and 6.49. In each case, the pH value of the allulose-containing tomato ketchup (ketchup pH) was adjusted to the same pH value by adding the appropriate amount of vinegar, namely about pH 3.9.

[0087] b) In a second series of experiments (samples 1-3, 1-4 and 1-5), the influence of the pH value of the allulose-containing tomato ketchup (ketchup pH) was investigated. For each sample, an allulose syrup having a pH value (syrup pH) of pH 4.12 was employed. The pH value of the allulose-containing tomato ketchup (ketchup pH) was adjusted to different pH values by the appropriate amount of vinegar, namely pH 3.74, 3.91, and 4.55.

[0088] For each mixture, the CIELAB color space was measured before storage. The mixtures were stored for 12 weeks at 23°C and 50% r.h. For each mixture, the CIELAB color space was again measured after storage.

[0089] The color distances AE were calculated after storage relative to the starting allulose syrup from the data of the CIELAB color space in accordance with DIN EN ISO / CIE 11664-4:2020-03 (AE*ab= [(AL*)2+(Aa*)2+(Ab*)2]1 / 2) using a Minolta CR-10 colorimeter, wherein L refers to perceptual lightness, a refers to green-magenta opponent colors, and b refers to blue-yellow opponent colors. For the measurement, 50 g of each sample was weighed and measured with a gap setting of 8 mm.

[0090] The experimental results are compiled in the table here below:

[0091] In each case, the pH value of the allulose-containing ketchup did not change upon storage.

[0092] The experimental results ofthe first series of Example 1 (samples 1-1, 1-2, 1-4, 1-6 and 1-7) are visualized in Figure 1. The experimental results ofthe second series of Example 1 (samples 1-3, 1-4 and 1-5) are visualized in Figure 2.Example 2 - allulose syrup prepared by dissolving crystalline allulose in water:

[0093] An allulose syrup was prepared by mixing 300 g of water and 700 g of highly pure crystalline allulose with one another. The initial pH value of the thus obtained allulose syrup was 6.75. The pH value was adjusted to pH values of about 3.0, about 3.8 and about 5.0 (syrup pH) by adding the following amounts of hydrochloric acid:

[0094] The pH-adapted allulose syrups were then mixed with allulose-free crude tomato ketchup. In analogy to the first series of experiments in Example 1, the pH value of the allulose-containing tomato ketchup (ketchup pH) was adjusted to the same pH value by adding the appropriate amount of vinegar, namely about pH 3.9.

[0095] In analogy to Example 1, for each mixture the CIELAB color space was measured before storage. The mixtures were stored for 12 weeks at 20°C and a humidity of 50% r.h. For each mixture, the CIELAB color space was again measured after storage and the AE value was determined.

[0096] The experimental results are compiled in the table here below:

[0097] The experimental results of Example 2 are additionally visualized in Figure 1.Conclusions:

[0098] The above experimental data lead at least to the following conclusions:(a) Allulose influences the color change (color distances AE) of tomato based sauce upon storage. Samples 1-1, 1-2, 1-4, 1-6, and 1-7 demonstrate that under the experimental conditions at identical pH values of the allulose -containing tomato ketchups amounting to about pH 3.9, allulose syrups having different pH values in their neat state lead to different color changes upon storage of the allulose-containing tomato ketchups made therefrom.(b) The color change of tomato based sauce upon storage is particularly pronounced when the allulose syrups in their neat state have a pH value of about 4, whereas the color change is less pronounced at lower pH values as well at higher pH values of the allulose syrups in their neat state. Samples 1-1, 1-4, and 1-7 demonstrate that under the experimental conditions at identical pH values of the allulose-containing tomato ketchups amounting to about pH 3.9, allulose syrups having a pH value of 2.51 in their neat state (sample 1-1) or allulose syrups having a pH value of 6.49 in their neat state (sample 1-7) provide allulose-containing ketchups that are significantly less prone to color change upon storage than those provided by allulose syrups having a pH value of 4.12 in their neat state (sample 1-5).(c) The effect of allulose on color change (color distances AE) of tomato based sauce upon storage is not a function of long term impact of pH value on allulose syrups in their neat state. The pH values of all allulose syrups in their neat state were all freshly adjusted, and the thus prepared pH-adapted allulose syrups were quickly employed to prepare the allulose-containing ketchups. Thus, while the pH value of the allulose syrups in their neat state obviously has an influence on color change upon storage, this influence cannot result from long term changes of the composition of the allulose syrups in their neat state under different pH conditions, e.g. degradation, formation of byproducts, and the like.(d) The pH value of the tomato based sauce also influences the color change (color distances AE) of tomato based sauce upon storage. Samples 1-3, 1-4, and 1-5 demonstrate that under the experimental conditions at identical pH values of the allulose syrups in their neat state amounting to pH 4.12, allulose-containing ketchups made therefrom having different pH values lead to different color changes ofthe allulose-containing tomato ketchups upon storage. Samples 1-3, 1-4, and 1-5 demonstrate that under the experimental conditions the color change of the allulose-containing ketchups upon storage is less pronounced at a pH value of allulose-containing ketchup of about 4, whereas the color change is more pronounced at lower pH values as well at higher pH values of the allulose- containing ketchups.(e) The purity of the allulose syrups in their neat state also influences the color change (color distances AE) of tomato based sauce upon storage. A comparison of highly pure samples 2-1, 2-2, and 2-3 against less pure samples 1-1, 1-2, 1-4, 1-6, and 1-7 demonstrates that under the experimental conditions, at comparable pH values of allulose syrups in their neat state and identical pH values of allulose-containing ketchups, allulose syrups made from highly pure crystalline allulose are signif-icantly less prone to color change upon storage than those provided by allulose syrups made from purified reaction products of enzymatic conversions of fructose not involving crystallization of allulose and redissolution of crystalline allulose in water.Example 3 - pH value of ketchup according to US 20190328018 Al:

[0099] Two ketchup samples were prepared in accordance with Example 5 of US 2019 0328018. As onion concentrate was not available when the samples were prepared, onion concentrate was omitted. However, it is not believed that the presence of onion concentrate does significantly alter the pH value of the resultant ketchup.

[0100] Both samples were mixed from the ingredients, heated to 85°C and stirred for 20 minutes (18 minutes at 3000 rpm, 1 minute at 4000 rpm, and 1 minute at 5000 rpm). The composition of both samples as well as the measured pH value is compiled in the table here below:

Claims

Patent claims:

1. A tomato based sauce comprising allulose and vinegar, wherein the sauce has a pH value of at most 5.0; wherein the content of allulose in the sauce is at least 0.5 wt.-%, relative to the total weight of the sauce; and wherein the content of fructose in the sauce, if any, is at most 7.0 wt.-%, relative to the total content of monosaccharides and disaccharides.

2. The sauce according to claim 1, wherein the sauce has a pH value of at most 4.9, preferably at most 4.8, more preferably at most 4.7, still more preferably at most 4.6, yet more preferably at most 4.5, even more preferably at most 4.4, most preferably at most 4.3, and in particular at most 4.2.

3. The sauce according to claim 1 or 2, wherein the sauce has a pH value of at most 4.1, preferably at most 4.0, more preferably at most 3.9, still more preferably at most 3.8, yet more preferably at most 3.7, even more preferably at most 3.6, most preferably at most 3.5, and in particular at most 3.4.

4. The sauce according to any of the preceding claims, wherein the sauce has a pH value of at least 3.0, preferably at least 3.1, more preferably at least 3.2, still more preferably at least 3.3, yet more preferably at least 3.4, even more preferably at least 3.5, most preferably at least 3.6, and in particular at least 3.7.

5. The sauce according to any of the preceding claims, wherein the sauce has a pH value within the range of 3.1 to 4.7, preferably 3.2 to 4.6, more preferably 3.3 to 4.5, still more preferably 3.4 to 4.4, yet more preferably 3.5 to 4.3, even more preferably 3.6 to 4.2, most preferably 3.7 to 4.1, and in particular 3.8 to 4.0.

6. The sauce according to any of the preceding claims, which has an allulose content of at least 1.0 wt.-%, preferably at least 2.0 wt.-%, more preferably at least 3.0 wt.-%, still more preferably at least 4.0 wt.-%, yet more preferably at least 5.0 wt.-%, even more preferably at least 6.0 wt.-%, most preferably at least 7.0 wt.-%, and in particular at least 8.0 wt.-%, relative to the total weight of the sauce.

7. The sauce according to any of the preceding claims, which has an allulose content of at most 25 wt.-%, preferably at most 22.5 wt.-%, more preferably at most 20 wt.-%, still more preferably at most 17.5 wt.-%, yet more preferably at most 15 wt.-%, even more preferably at most 12.5 wt.- %, most preferably at most 10 wt.-%, and in particular at most 7.5 wt.-%, relative to the total weight of the sauce.

8. The sauce according to any of the preceding claims, which has an allulose content of at least 10 wt.-%, preferably at least 20 wt.-%, more preferably at least 30 wt.-%, still more preferably atleast 40 wt.-%, yet more preferably at least 50 wt.-%, even more preferably at least 60 wt.-%, most preferably at least 70 wt.-%, and in particular at least 80 wt.-%, relative to the total content of monosaccharides and disaccharides.

9. The sauce according to any of the preceding claims, which has an allulose content of at least 96.5 wt.-%, preferably at least 97.0 wt.-%, more preferably at least 97.5 wt.-%, still more preferably at least 98.0 wt.-%, yet more preferably at least 98.5 wt.-%, even more preferably at least 99.0 wt.-%, most preferably at least 99.5 wt.-%, and in particular at least 99.8 wt.-%, relative to the total content of monosaccharides and disaccharides.

10. The sauce according to any of the preceding claims, which contains one or more monosaccharides other than allulose; preferably glucose, fructose, tagatose, or mixtures thereof.

11. The sauce according to any of the preceding claims, which has a fructose content of at most 6.5 wt.-%, preferably at most 6.0 wt.-%, more preferably at most 5.5 wt.-%, still more preferably at most 5.0 wt.-%, yet more preferably at most 4.5 wt.-%, even more preferably at most 4.0 wt.-%, most preferably at most 3.5 wt.-%, and in particular at most 3.0 wt.-%, relative to the total content of monosaccharides and disaccharides.

12. The sauce according to any of the preceding claims, which has a fructose content of at most 2.5 wt.-%, preferably at most 2.0 wt.-%, more preferably at most 1.5 wt.-%, still more preferably at most 1.0 wt.-%, yet more preferably at most 0.8 wt.-%, even more preferably at most 0.6 wt.-%, most preferably at most 0.4 wt.-%, and in particular at most 0.2 wt.-%, relative to the total content of monosaccharides and disaccharides.

13. The sauce according to any of the preceding claims, which has a glucose content of at most 6.5 wt.-%, preferably at most 6.0 wt.-%, more preferably at most 5.5 wt.-%, still more preferably at most 5.0 wt.-%, yet more preferably at most 4.5 wt.-%, even more preferably at most 4.0 wt.-%, most preferably at most 3.5 wt.-%, and in particular at most 3.0 wt.-%, relative to the total content of monosaccharides and disaccharides.

14. The sauce according to any of the preceding claims, which has a glucose content of at most 2.5 wt.-%, preferably at most 2.0 wt.-%, more preferably at most 1.5 wt.-%, still more preferably at most 1.0 wt.-%, yet more preferably at most 0.8 wt.-%, even more preferably at most 0.6 wt.-%, most preferably at most 0.4 wt.-%, and in particular at most 0.2 wt.-%, relative to the total content of monosaccharides and disaccharides.

15. The sauce according to any of the preceding claims, which contains one or more disaccharides;preferably sucrose.

16. The sauce according to any of the preceding claims, which has a sucrose content of at least 2.5 wt.-%, preferably at least 5.0 wt.-%, more preferably at least 10 wt.-%, still more preferably at least 15 wt.-%, yet more preferably at least 20 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 40 wt.-%, and in particular at least 50 wt.-%, relative to the total content of monosaccharides and disaccharides.

17. The sauce according to any of the preceding claims, wherein the freshly prepared tomato based sauce after storage for 12 weeks at 23°C and 50% r.h. has a color distance AE value according to DIN EN ISO / CIE 11664-4:2020-03 of at most 3.50.

18. The sauce according to any of the preceding claims, wherein the freshly prepared tomato based sauce after storage for 12 weeks at 23°C and 50% r.h. has a color distance AE value according to DIN EN ISO / CIE 11664-4:2020-03 of most 3.40, preferably at most 3.30, more preferably at most 3.20, still more preferably at most 3.10, yet more preferably at most 3.00, even more preferably at most 2.90, most preferably at most 2.80, and in particular at most 2.70.

19. The sauce according to any of the preceding claims, wherein the freshly prepared tomato based sauce after storage for 12 weeks at 23°C and 50% r.h. has a color distance AE value according to DIN EN ISO / CIE 11664-4:2020-03 of most 2.60, preferably at most 2.50, more preferably at most 2.40, still more preferably at most 2.30, yet more preferably at most 2.20, even more preferably at most 2.10, most preferably at most 2.00, and in particular at most 1.90.

20. The sauce according to any of the preceding claims, which is selected from the group consisting of ketchup, barbecue sauce, chili sauce, habanero sauce, steak sauce, cocktail sauce, pasta sauce, pizza sauce, sriracha sauce, burger sauce, tacco sauce, salsa, pesto and the like; preferably ketchup.

21. The sauce according to any of the preceding claims, which comprises a tomato component selected from the group consisting of tomatoes, tomato puree, tomato sauce, tomato paste, tomato concentrate, tomato extract, tomato powder, tomato juice, tomato sauce, and the like; preferably tomato paste or tomato concentrate.

22. The sauce according to any of the preceding claims, which is made from an allulose syrup.

23. The sauce according to claim 22, wherein the allulose syrup in its neat state has an allulose content of at least 95.0 wt.-%, preferably at least 96.0 wt.-%, more preferably at least 97.0 wt.-%, still more preferably at least 98.0 wt.-%, yet more preferably at least 98.5 wt.-%, even more preferably at least 99.0 wt.-%, most preferably at least 99.5 wt.-%, and in particular at least 99.8 wt.-%, relative to the dry solid content.

24. The sauce according to claim 22 or 23, wherein the allulose syrup in its neat state has a dry solids content of at least 73 wt.-%, preferably at least 74 wt.-%, more preferably at least 75 wt.-%, still more preferably at least 76 wt.-%, yet more preferably at least 77 wt.-%, even more preferably at least 78 wt.-%, most preferably at least 79 wt.-%, and in particular at least 80 wt.-%, relative to the total weight of the allulose syrup.

25. The sauce according to any of claims 22 to 24, wherein the allulose syrup in its neat state has been made from allulose and water and neither acid nor base has been added.

26. The sauce according to any of claims 22 to 25, wherein the allulose syrup in its neat state essentially consists of allulose and water.

27. The sauce according to any of claims 22 to 26, wherein the allulose syrup in its neat state has a pH value of at least 3.3, preferably at least 3.4, more preferably at least 3.5, still more preferably at least 3.6, yet more preferably at least 3.7, even more preferably at least 3.8, most preferably at least 3.9, and in particular at least 4.0.

28. The sauce according to claim 27, wherein the allulose syrup in its neat state has a pH value of at least 4.1, preferably at least 4.2, more preferably at least 4.3, still more preferably at least 4.4, yet more preferably at least 4.5, even more preferably at least 4.6, most preferably at least 4.7, and in particular at least 4.8.

29. The sauce according to claim 28, wherein the allulose syrup in its neat state has a pH value of at least 4.9, preferably at least 5.0, more preferably at least 5.1, still more preferably at least 5.2, yet more preferably at least 5.3, even more preferably at least 5.4, most preferably at least 5.5, and in particular at least 5.6.

30. The sauce according to claim 29, wherein the allulose syrup in its neat state has a pH value of at least 5.7, preferably at least 5.8, more preferably at least 5.9, still more preferably at least 6.0, yet more preferably at least 6.1, even more preferably at least 6.2, most preferably at least 6.3, and in particular at least 6.4.

31. The sauce according to claim 30, wherein the allulose syrup in its neat state has a pH value of at least 6.5, preferably at least 6.6, more preferably at least 6.7, still more preferably at least 6.8, yet more preferably at least 6.9, even more preferably at least 7.0, most preferably at least 7.1, and in particular at least 7.2.

32. The sauce according to any of claims 22 to 31, wherein the allulose syrup in its neat state has a pH value of at most 5.0, preferably at most 4.9, more preferably at most 4.8, still more preferably at most 4.7, yet more preferably at most 4.6, even more preferably at most 4.5, most preferably at most 4.4, and in particular at most 4.3.

33. The sauce according to claim 32, wherein the allulose syrup in its neat state has a pH value of at most 4.2, preferably at most 4.1, more preferably at most 4.0, still more preferably at most 3.9, yet more preferably at most 3.8, even more preferably at most 3.7, most preferably at most 3.6, and in particular at most 3.5.

34. The sauce according to claim 33, wherein the allulose syrup in its neat state has a pH value of at most 3.4, preferably at most 3.3, more preferably at most 3.2, still more preferably at most 3.1, yet more preferably at most 3.0, even more preferably at most 2.9, most preferably at most 2.8, and in particular at most 2.7.

35. The sauce according to any of the preceding claims, which has a water content of at least 22.5 wt.-%, preferably at least 25 wt.-%, more preferably at least 27.5 wt.-%, still more preferably at least 30 wt.-%, yet more preferably at least 32.5 wt.-%, even more preferably at least 35 wt.-%, most preferably at least 37.5 wt.-%, and in particular at least 40 wt.-%, relative to the total weight of the sauce.

36. The sauce according to any of the preceding claims, which has a water content of at most 54 wt.- %, preferably at most 52 wt.-%, more preferably at most 50 wt.-%, still more preferably at most 48 wt.-%, yet more preferably at most 46 wt.-%, even more preferably at most 42 wt.-%, most preferably at most 40 wt.-%, and in particular at most 38 wt.-%, relative to the total weight of the sauce.

37. The sauce according to any of the preceding claims, which has a vinegar content (including the water that is intrinsically contained in the vinegar) of at least 3.0 wt.-%, preferably at least 3.5 wt.-%, more preferably at least 4.0 wt.-%, still more preferably at least 4.5 wt.-%, yet more preferably at least 5.0 wt.-%, even more preferably at least 5.5 wt.-%, most preferably at least 6.0 wt.- %, and in particular at least 6.5 wt.-%, relative to the total weight of the sauce.

38. The sauce according to any of the preceding claims, which has a vinegar content (including the water that is intrinsically contained in the vinegar) of at most 12 wt.-%, preferably at most 11 wt.- %, more preferably at most 10 wt.-%, still more preferably at most 9.0 wt.-%, yet more preferably at most 8.0 wt.-%, even more preferably at most 7.0 wt.-%, most preferably at most 6.0 wt.-%, and in particular at most 5.0 wt.-%, relative to the total weight of the sauce.

39. The sauce according to any of the preceding claims, which has a content of acetic acid of at least 0.15 wt.-%, preferably at least 0.18 wt.-%, more preferably at least 0.2 wt.-%, still more preferably at least 0.23 wt.-%, yet more preferably at least 0.25 wt.-%, even more preferably at least 0.28 wt.-%, most preferably at least 0.3 wt.-%, and in particular at least 0.33 wt.-%, relative to the total weight of the sauce.

40. The sauce according to any of the preceding claims, which has a content of acetic acid of at most 0.6 wt.-%, preferably at most 0.55 wt.-%, more preferably at most 0.5 wt.-%, still more preferably at most 0.45 wt.-%, yet more preferably at most 0.4 wt.-%, even more preferably at most 0.35 wt.-%, most preferably at most 0.3 wt.-%, and in particular at most 0.25 wt.-%, relative to the total weight of the sauce.

41. The sauce according to any of the preceding claims, which contains starch; preferably wherein the starch is selected from wheat starch, rice starch, potato starch, maize starch, and peas starch.

42. The sauce according to claim 41, wherein the content of starch is at least 0.6 wt.-%, preferably at least 0.9 wt.-%, more preferably at least 1.2 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 1.8 wt.-%, even more preferably at least 2.1 wt.-%, most preferably at least 2.4 wt.-%, and in particular at least 2.7 wt.-%, relative to the total weight of the sauce.

43. The sauce according to claim 41 or 42, wherein the content of starch is at most 5.4 wt.-%, preferably at most 5.1 wt.-%, more preferably at most 4.8 wt.-%, still more preferably at most 4.5 wt.- %, yet more preferably at most 4.2 wt.-%, even more preferably at most 3.9 wt.-%, most preferably at most 3.6 wt.-%, and in particular at most 3.3 wt.-%, relative to the total weight of the sauce.

44. The sauce according to any of the preceding claims, which is obtainable by a process comprising preparing said sauce from an allulose syrup having a pH value in its neat state of less than 3.3 or greater than 4.9.

45. The sauce according to any of the preceding claims, which is obtainable by a process comprising preparing said sauce from an allulose syrup as defined in any of claims 22 to 34.

46. A process for the preparation of a tomato based sauce according to any of the preceding claims, said process comprising the steps of(a) providing an allulose syrup; preferably as defined in any of claims 22 to 34;(b) mixing the allulose syrup with the remaining ingredients of the sauce; and(c) optionally, adjusting the pH value of the thus obtained tomato based sauce.

47. A tomato based sauce that is obtainable by the process according to claim 46.

48. Use of an allulose syrup; preferably as defined in any of claims 22 to 34; for preparing a tomato based sauce according to any of claims 1 to 45 or 47.

Images