Additive for animal nutrition

Abstract

The present invention relates to the use of a compound corresponding to the formula: [Chemical Formula 1] R1C (O)-[O-(CH2) n-CH (R2)-C (O)] kOR3 wherein R1 is selected from a C1-11 alkyl group; r2 is selected from a C1-20 alkyl group, CmH2m-OR4, CmH2m-NHR4, wherein R4 is selected from H and C (O) C1-11 alkyl and m is equal to 0 or represents an integer from 1 to 11; r3 is selected from H and a C1-20 alkyl group; n is equal to 0 or represents an integer from 1 to 10; and k represents an integer from 1 to 10; or a salt of the compound.

Description

Technical Field

[0001] The present invention relates to the use of compounds as sources of organic acids and as animal nutritional additives in animal nutrition. Background Art

[0002] Animal production depends on the use of suitable and high-quality feed. Additives are compounds that are added to this feed to impart improved properties, both from the point of view of the feed itself and for the animals thus fed, or even from the point of view of the food obtained from the latter. Among animal nutritional additives, there are some compounds that have a favorable effect on the preservation, presentation, handling and palatability of this feed. There are also nutritional compounds (such as vitamins, amino acids, trace elements), as well as agents that improve the digestibility and bioavailability of substances contained in the feed or in additives.

[0003] European regulations [EC Regulation No. 1831 / 2003] prohibiting the use of antibiotics have encouraged the development of natural alternatives with antimicrobial properties. Organic acids, which have long been used for food preservation, are an alternative and are increasingly being used in animal nutrition, in particular butyric acid, lactic acid, propionic acid, acetic acid and formic acid. Because of their nutritional and health effects, they are used as additives in animal nutrition, for the preservation of animal feed and its bacterial purification, and also in animal feed and drinking water. Therefore, butyric acid has nutritional properties and antimicrobial capacity that can act on the gastrointestinal flora of animals. Lactic acid is a bacteriostatic agent used as an additive. A disadvantage encountered by many active molecules is their fragility relative to the environment of the animal digestive system. Therefore, they are released prematurely in the upper intestine, where they cross the intestinal barrier and quickly reach the blood, even before they can exert a beneficial effect on the intestinal flora of the lower intestine.

[0004] Butyric acid, tributyrin or butyric acid triglyceride are available on the market in protected form. They constitute a supply of butyric acid in a form that is at least partially resistant to the aggressive conditions of the stomach.

[0005] Document CN 103082094 A provides a solution with mixed triglycerides, the structure of which is shown below, combining two lactic acid molecules and one butyric acid molecule carried by an esterified glycerol molecule.

[0006] [Chemical formula 10]

[0007]

[0008] And it can gradually release butyrate and lactate in the gastrointestinal tract of animals.

[0009] As with tributyrin, the release of lactic acid and / or butyric acid molecules was observed to occur primarily in the upper intestine, with only a very small fraction of these molecules reaching the lower intestine.

[0010] Administration of butyrate and lactate in the form of triglycerides as described above provides the beginning of a solution.

[0011] But up to now there is a real need for these molecules, and many others, especially of the carboxylic acid type, of small size, which have a favourable effect on the microbiota, in a form that allows them to enter the lower part of the intestine, thereby exerting their favourable effect on the intestinal microbiota. Summary of the invention

[0012] This is the problem solved by the present invention by providing a compound corresponding to the following formula or a salt of said compound:

[0013] [Chemical formula 1]

[0014] R1C(O)-[O-(CH2) n -CH(R2)-C(O)] k OR3,

[0015] in

[0016] R1 is selected from C 1-11 Alkyl groups;

[0017] R2 is selected from C 1-20 Alkyl group; C m H 2m -OR4 and C m H 2m -NHR4, wherein R4 is selected from H and C(O)-C 1-11 alkyl and m is equal to 0 or represents an integer from 1 to 11;

[0018] R3 is selected from H and C 1-20 Alkyl groups;

[0019] n is equal to 0 or represents an integer from 1 to 10; and

[0020] k represents an integer from 1 to 10.

[0021] The invention therefore relates to the use of a compound as defined above for the preparation of an additive, premix or roughage for animal nutrition, and to an animal feed additive consisting of such a compound.

[0022] According to one variant, the additive of the invention does not consist of butyryl lactylate, which has the following formula:

[0023] [Chemical formula 2]

[0024]

[0025] It has in fact been demonstrated that, on the one hand, the compound of formula [Chemical Formula 1] manages to reach the intestine of animals by resisting the acidic conditions present throughout the upper part of the gastrointestinal tract and, on the other hand, allowing the molecules carried to exert their benefits at the intestinal level.

[0026] According to the present invention, the application of the compounds of formula [chemical formula 1] is not therapeutic, but nutritional, and they target healthy animals. Taking butyrolactate as an example, once it reaches the intestine, the compound is hydrolyzed and releases butyrate, which will exert many benefits on the intestine. It serves as an energy source for intestinal cells, thereby promoting their regeneration and normal function. In addition, butyrate exerts an anti-inflammatory effect by reducing the production of pro-inflammatory cytokines, which contributes to the balance of the intestinal immune system. It also strengthens the intestinal barrier by promoting the production of protective mucus and improving the tight junction function between epithelial cells. Therefore, butyrate plays a key role in promoting intestinal health and may have a positive impact on overall health.

[0027] Before discussing the various subject matters of the present invention in greater detail, certain terms used herein are defined.

[0028] The salt of the compound of formula [Chemical Formula 1] of the present invention may be a salt of the carboxyl functional group of the compound to obtain a salt of a carboxylic acid functional group, a salt of a hydroxyl functional group, or a salt of an amine functional group. Combinations of these potential possibilities are possible.

[0029] Alkyl refers to C x H 2x+1 Aliphatic radical, which may contain one or more non-aromatic rings; it may be straight chain or branched; branched alkyl radical refers to a straight chain alkyl radical in which one or more carbon atoms are replaced by an alkyl group as defined above, and which itself may be straight chain or branched.

[0030] In the definition of R2 in the above formula [Chemical Formula 1], it should be understood that when it represents C m H 2m -OR4 or C m H 2m -NHR4 group, the bond to the carbon carrying R2 is established at C m H 2m -OR4 or C m H 2m -C of NHR4 group m On carbon.

[0031] The compounds of the present invention correspond to the formula [Chemical Formula 1] as defined above, wherein one or more asymmetric carbon atoms may be present; according to the present invention, it should be understood that the term "compound" includes all enantiomers of the compound (alone or in the form of a mixture).

[0032] Animal nutrition premixes are mixtures of additives or a mixture of one or more additives with animal feed ingredients or water used as a carrier, which are not intended for direct feeding to animals.

[0033] Therefore, the present invention relates to the use of a compound in the preparation of an additive, premix or roughage for animal nutrition, and an additive for animal nutrition consisting of a compound (the compound corresponds to the above formula [Chemical Formula 1]) or a salt thereof.

[0034] According to one variant of the invention, the use is for feeding livestock. According to an embodiment of the use, the compound or its salt is intended for feeding monogastric livestock.

[0035] When the compound of formula [chemical formula 1] is in the form of a salt, it is advantageously a salt selected from alkali metal salts, alkaline earth metal salts, transition metal salts, ammonium salts and ammonium derivative salts. Advantageously, salts of Li, Na, K, Ca, Zn, Cu, Ni, Fe, Mn, Mg and Ag are selected.

[0036] It was unexpectedly found that the structure of the compound of formula [Chemical Formula 1] is stable to the hostile environment of the animal digestive system and allows the active molecules to be released in the lower part of the intestine, where they will exert a beneficial effect on the intestinal microflora.

[0037] Another advantage of the compound of formula [chemical formula 1] of the present invention is that it combines several identical or different molecules of interest in animal nutrition. For example, it can carry butyrate, valerate and lactate molecules, which are molecules well known for their benefits to intestinal microorganisms.

[0038] Therefore, according to an advantageous embodiment of the invention which can be considered alone or in combination, the latter relates to the aforementioned use and the aforementioned additive, respectively to the following compounds:

[0039] - a compound of formula [Chemical Formula 1], wherein R1 is selected from methyl, ethyl, propyl, butyl, pentyl and hexyl groups;

[0040] - a compound of formula [Chemical Formula 1], wherein R2 is selected from methyl, ethyl, propyl, butyl, pentyl and hexyl groups; OH; and OC(O)-methyl, OC(O)-ethyl, OC(O)-propyl, OC(O)-butyl, OC(O)-pentyl and OC(O)-hexyl groups;

[0041] - a compound corresponding to formula [Chemical Formula 1], wherein n ranges from 0 to 2 and k ranges from 1 to 5.

[0042] -butyryl lactic acid corresponding to the formula:

[0043] [Chemical formula 2]

[0044]

[0045] According to one variant, butyrolactic acid is only involved in the use according to the invention,

[0046] - corresponds to the compound of the formula

[0047] [Chemical formula 3]

[0048] R1C(O)-[O-CH2-CH(R2)-C(O)OR3

[0049] Wherein R2 is selected from C m H 2m -OR4, wherein m ranges from 0 to 2 and R4 is selected from H and C(O)-C 1-6 alkyl;

[0050] -Compounds corresponding to the following formula:

[0051] [Chemical formula 4]

[0052] CH3(CH2)2C(O)-O-(CH2) n′ -CH(R2)-COOH,

[0053] wherein R2 is selected from OH; CH2CH2OH; and OC(O)CH2CH2CH3; and n' is equal to 0 or 1;

[0054] - a compound corresponding to any of the following formulae:

[0055] [Chemical formula 5]

[0056]

[0057] [Chemical formula 6]

[0058]

[0059] and

[0060] [Chemical formula 7]

[0061]

[0062] The present invention also relates to the aforementioned use and the aforementioned additive, according to which the compound consists of any salt of the compound defined below, or is present in the form of the compound, the salt or any mixture of the compound and the salt.

[0063] The invention is of course not limited to these compounds, but they make it possible to support that the structure [Formula 1] is suitable for optimized release, for example, for butyric acid on the one hand and for hydroxylated carboxylic acids (such as lactic acid, 2,4-dihydroxybutyric acid) on the other hand.

[0064] The invention also relates to any presentation and any use of this additive in animal nutrition, as described below.

[0065] An object of the present invention is therefore an animal feed premix comprising an additive mixture, said premix comprising at least one additive according to the invention as described above, and optionally vegetable or mineral raw materials.

[0066] Another object of the present invention is a feed or roughage for animal nutrition comprising at least one additive according to the invention or an inventive premixture according to the invention as described above.

[0067] The invention further relates to the use of the compound corresponding to the following formula or its salt in animal nutrition:

[0068] [Chemical formula 1]

[0069] R1C(O)-[O-(CH2) n -CH(R2)-C(O)] k OR3,

[0070] in

[0071] R1 is selected from C 1-11 Alkyl groups;

[0072] R2 is selected from C 1-20 Alkyl group; C m H 2m -OR4;C m H 2m -NHR4; wherein R4 is selected from H and C(O)-C 1-11 alkyl and m is 0 or an integer from 1 to 11;

[0073] R3 is selected from H and C 1-20 Alkyl groups;

[0074] n is 0 or an integer from 1 to 10; and

[0075] k is an integer from 1 to 10.

[0076] In the method useful according to the present invention, the compound is selected from the following compounds:

[0077] The compound corresponding to the following formula

[0078] [Chemical formula 2]

[0079]

[0080] The compound corresponding to the following formula

[0081] [Chemical formula 3]

[0082] R1C(O)-[O-CH2-CH(R2)-C(O)OR3,

[0083] in

[0084] R2 is selected from C m H 2m -OR4, wherein m ranges from 0 to 2 and R4 is selected from H and C(O)-C 1-6 alkyl;

[0085] The compound corresponding to the following formula

[0086] [Chemical formula 4]

[0087] CH3(CH2)2C(O)-O-(CH2) n′ -CH(R2)-COOH,

[0088] wherein R2 is selected from OH; CH2CH2OH; and OC(O)CH2CH2CH3 and n' is equal to 0 or 1,

[0089] and salts of said compounds.

[0090] According to one variant of the invention, the use is intended for feeding livestock. According to an embodiment of the use, the compound or its salt is intended for feeding monogastric livestock.

[0091] In animal nutrition, the compound of the invention or a salt thereof also has the advantage of being effective in any state.

[0092] Thus, compounds of the invention such as butyrylactic acid can be incorporated into the drinking water of livestock without the risk of hydrolysis in water to lactic acid and free butyric acid. In fact, butyrylactic acid is soluble in water, while tributyrin is not.

[0093] The compound of the present invention, such as liquid butyryl lactic acid, can be distributed in the form of a dry product after being dispersed on a support (especially an inorganic support), such as a silica or calcium carbonate support. According to one embodiment, the compound of the present invention, such as butyryl lactic acid, can be dispersed or adsorbed on silica particles, wherein the weight ratio of butyryl lactic acid ranges from 50 to 80%, and the weight ratio of silica particles ranges from 20 to 50%.

[0094] In another variation, the compounds of the invention may also be administered in another solid form. For example, butyryl lactate (such as the calcium salt) is solid. Therefore, it may be distributed in the form of a dry product having a high butyric acid content, the butyric acid content contained in butyryl lactate may be between about 1% by weight and about 60% by weight.

[0095] Furthermore, butyric acid has a very unpleasant odour which creates handling problems, whereas the compounds of the present invention are odourless. As shown in the following examples, butyrylactic acid has been observed to have palatability which contributes to the nutritional properties of the feed provided.

[0096] Therefore, the present invention relates to the use of the compound of [Chemical Formula 1], such as butyrylactic acid, for the preparation of an additive, premix or roughage for animal nutrition, for its palatability (ie its ability to attract animals to eat it).

[0097] Another subject of the present invention is a method for making the compounds of the present invention. This method uses reactive distillation. Thus, a mixture of carboxylic acid molecules of interest is obtained and reactive distillation is performed to obtain the compounds of formula [Chemical Formula 1] of the present invention.

[0098] Therefore, the present invention further relates to a process for preparing a compound of the present invention or a salt of the compound as defined above, comprising the following steps:

[0099] - Mix at least two carboxylic acid molecules corresponding to the following formulas

[0100] [Chemical formula 8]

[0101] R1COOH

[0102] Wherein R1 is selected from C 1-11 Alkyl groups;

[0103] [Chemical formula 9]

[0104] OH(CH2) n -CH(R2)COOH

[0105] wherein n is equal to 0 or represents an integer from 1 to 10, and R2 is selected from C 1-20 Alkyl group; C m H 2m -OR4;C m H 2m -NHR4, wherein R4 is selected from H and C(O)-C 1-11 Alkyl and m is equal to 0 or represents an integer from 1 to 11;

[0106] In the presence of a catalyst,

[0107] - subjecting the mixture thus obtained to a reactive distillation, and

[0108] - Obtaining a compound of formula [Chemical Formula 1] corresponding to any one of the above definitions or a salt of the compound.

[0109] In a typical reaction, the carboxylic acid molecule of interest is mixed with a suitable catalyst, and the mixture is heated to a temperature that can vary from 25°C to 150°C. The catalyst used is homogeneous or heterogeneous; when the catalyst is heterogeneous, it can be in a fixed bed (the reaction medium passes over the catalyst) or in a slurry (the catalyst is mixed with the reaction medium). A condenser or distillation column can be connected to the reaction vessel so that water, any by-products and / or unreacted reagents can be removed from the vessel during the reaction. In addition, a vacuum can be applied to the reaction mixture to expel the water, the by-products and / or unreacted reagents more quickly, thereby completing the reaction more quickly. A third compound that helps remove water from the reaction mixture, such as toluene, can be added.

[0110] The reaction can be monitored, for example, by TLC and / or GC and / or HPLC. If the reaction is complete, the reaction can be stopped by cooling the reaction mixture. If necessary, after the reaction and before or after purification, neutralize and filter the catalyst. The compound thus obtained may be further purified by distillation or not by distillation.

[0111] As mentioned above, for animal feed, the compound can be used as it is, dispersed on a support or in the form of a corresponding salt. The salt obtained can be optionally purified by washing, recrystallization, extraction with a solvent to obtain a product with higher purity. BRIEF DESCRIPTION OF THE DRAWINGS

[0112] The invention is illustrated in the following examples, which relate to the synthesis of the compounds of the invention and their use as additives for animal nutrition and support the invention of the invention. Figure 1 ] which shows the amount of butyric acid released (in % by weight relative to the weight of tributyrin or butyryl lactylate administered) in the stomach and intestines, which define the upper part of the gastrointestinal system, and in the cecum, which defines the lower part of the gastrointestinal system. DETAILED DESCRIPTION

[0113] Example 1: Preparation of butyryllactylate from lactic acid and butyric acid in the presence of sulfuric acid as a catalyst

[0114] 1068.7 g (12 mol) of butyric acid (99%) was added to 151.9 g (1.52 mol) of 90% (w / w) aqueous lactic acid solution (90% w / w). 8 g (0.0775 mol) of sulfuric acid (95% w / w) was then added to the mixture. The temperature of the mixture was raised to 110°C and the butyric acid / water azeotropic mixture was continuously distilled. Vacuum was applied if necessary. After 5 hours, the reaction mixture was cooled and 20.50 g (0.1538 mol) of aqueous sodium hydroxide solution (30% w / w) was added. The resulting precipitate was filtered. Excess water and butyric acid were removed by evaporation to obtain 222.8 g of butyryl lactic acid.

[0115] Example 2: Preparation of butyryl lactate by wet method

[0116] 946.6 g (0.63 moles) of a 5% w / w aqueous solution of calcium hydroxide were added to 208.9 g (1.26 moles) of the butyryl lactylic acid mixture prepared in Example 1. Solid butyryl lactylate was obtained by evaporation or spray drying of the obtained solution.

[0117] Example 3: Dry preparation of butyryl lactate

[0118] 63.06 g (0.63 mole) of solid calcium carbonate was mixed with 208.9 g (1.26 mole) of the butyrylactic acid mixture prepared in Example 1. A neutralization reaction was performed in an extruder to obtain a solid butyrylactic acid calcium salt.

[0119] Example 4: Preparation of butyryl lactylate on silica

[0120] 208.9 g (1.26 moles) of butyryl lactylic acid prepared in Example 1 were dispersed on 112.5 g of suitable silica. The resulting preparation was dried to obtain solid butyryl lactylate.

[0121] Example 5: Preparation of butyryllactylate from lactic acid and butyric acid in the presence of a heterogeneous catalyst

[0122] 20.5 g (0.2303 mol) of butyric acid (99%) was added to 5.2 g (0.0556 mol) of lactic acid (98% w / w). 2 g of sulfonic acid resin was then added to the mixture. The temperature of the mixture was raised to 110°C and the butyric acid / water azeotrope was continuously distilled. Vacuum was applied if necessary. After 20 hours, the reaction mixture was cooled and the resin was filtered. Excess butyric acid was removed by evaporation to obtain 7.69 g of liquid butyryl lactic acid.

[0123] Example 6: Preparation of butyryl lactylate from lactic acid and methyl butyrate by transesterification

[0124] 22.45 g (0.22 mol) of methyl butyrate was added to 5 g (0.0544 mol) of L-lactic acid. 0.281 g (0.0027 mol) of sulfuric acid (95% w / w) was added to the mixture. The temperature of the mixture was raised to 90°C. If necessary, vacuum was applied. After 6 hours, the reaction mixture was cooled and the excess methyl butyrate was removed by distillation to obtain butyryl lactic acid.

[0125] Example 7: Preparation of butyryl lactylate from methyl lactate and butyric acid by transesterification

[0126] 2.02 g (0.0192 mol) of methyl lactate was added to 6.79 g (0.0763 mol) of butyric acid. 0.11 g (0.0011 mol) of sulfuric acid (95% w / w) was added to the mixture. The temperature of the mixture was raised to 110°C. If necessary, vacuum was applied. After 6 hours, the reaction mixture was cooled and the excess butyric acid was removed by distillation to obtain butyryl lactic acid.

[0127] Example 8: Preparation of butyryl lactylate from lactic acid and butyrate sodium salt

[0128] 3.01 g (0.0268 mol) of sodium butyrate was added to 0.449 g (0.0049 mol) of D,L-lactic acid. 1.74 g (0.0169 mol) of sulfuric acid (95% w / w) was added to the mixture. The temperature of the mixture was raised to 110°C and the butyric acid / water azeotropic mixture was continuously distilled. Vacuum was applied if necessary. After 5 hours, the reaction mixture was cooled and the resulting precipitate was filtered. Excess water and butyric acid were removed by evaporation to obtain 0.509 g of liquid butyryl lactic acid.

[0129] Example 9: Effect of butyryl lactylate - comparison with tributyrin

[0130] Experimental testing was performed in the following in vitro model.

[0131] 1) Upper digestive tract model:

[0132] The method developed by Menezez and Blackburn was used to simulate the chicken digestive tract [Menezes-Blackburn D, Gabler S, Greiner R. "Performance of Seven Commercial Phytases in an in Vitro Simulation of Poultry Digestive Tract." J Agric Food Chem. 2015 Jul 15; 63 (27): 6142-9]. It consists of three compartments simulating the upper part of the digestive tract: crop (stirred at pH 5, 40 ° C for 30 minutes), forestomach / gizzard (stirred at pH 3, 40 ° C for 45 minutes with the addition of pepsin), intestine (stirred at pH 6.5, 40 ° C for 60 minutes with the addition of pancreatic enzymes and bile extract). The butyrate protection rate and release rate (quantification of released butyric acid and residual butyrate) of each molecule (50 mM butyric acid equivalent of the present invention or tributyrin of the prior art) were evaluated in each compartment in turn.

[0133] 2) In vitro model: lower digestive tract (cecal fermentation):

[0134] Twelve 21-day-old broiler chickens (Ross PM33) were caged, fed and watered ad libitum, euthanized, and their cecal contents were collected and pooled. All experiments were performed in accordance with the EU animal protection guidelines and regulations governing the ethical treatment of animals, and the researchers were licensed by the French government to conduct animal experiments. The facilities of the Centre for Nutritional Expertise and Research comply with Convention C 03 159 4 of 6 November 2008 on experimentation on live vertebrate animals (European Regulation 24 / 11 / 86 86 / 609 EEC; Ministerial Decree of 19 April 1988).

[0135] The cecal contents were mixed with anaerobic buffer (5% w / v) prepared according to Theodorou et al. [Theodorou, Michael K., et al. "A simple gas production method using a pressure transducer to determine the fermentation kinetics of ruminant feeds." Animal feed science and technology 48.3-4 (1994): 185-197], and the microbial suspension was then transferred to a Hungate tube containing 50 mM butyrate equivalents of each candidate (butyrylactic acid of the present invention or tributyrin of the prior art) and incubated at 40°C under constant stirring for 24 hours.

[0136] To ensure that none of the treatments had an adverse effect on the activity and viability of the microorganisms, gas production was measured dynamically throughout the fermentation using a pressure sensor according to the method of Theodorou et al.

[0137] At the end of the fermentation, butyric acid and residual butyrate were quantified.

[0138] Example 10: Test results

[0139] The results are shown in the figure.

[0140] It was observed that butyrolactate does not release butyric acid in the stomach and has an improved intestinal release profile with balanced release in the upper and lower intestine, unlike tributyrin which shows significant gastric loss and complete release at the beginning of the small intestine.

[0141] These results demonstrate the efficacy of compounds of the invention compared to tributyrin.

[0142] Example 11: Evaluation of the palatability of butyryl lactylate

[0143] The evaluation was performed by in vivo testing in broiler chickens and piglets in the post-weaning stage.

[0144] 1) Testing in broiler chickens

[0145] The chickens were kept under normal housing conditions.

[0146] They were divided into several groups, each receiving for five days a feed containing a butyrate source incorporated directly into the standard diet (STD). Several sources of butyrate were compared: butyrylactic acid of the present invention and two protected forms of commercially available butyrate, fat-encapsulated butyrate and tributyrin.

[0147] Growth performance and feed consumption were measured at the beginning and end of the study.

[0148] The results are shown in Table 1 below.

[0149] Table 1: Effect of butyrate source compared to standard diet on broiler chickens (%)

[0150]

[0151] BWG: Weight gain

[0152] FI: Feed intake

[0153] FCR: Feed Conversion Ratio

[0154] Table 1 shows that the weight gain of the birds fed the existing protected butyrate sources (fat coated and tributyrin) was lower than that of the birds fed the standard diet, -5% and -9% (BWG) respectively. This lower growth was associated with a decrease in consumption of -15% and -3% (FI).

[0155] Despite being in a protective form, it was noted that the feed containing fat-coated butyrate had a strong and unpleasant rancid odor, and this unpleasant odor could explain the reduction in consumption.

[0156] In contrast, animals fed the diet containing butyrylactate ate more feed, +2.8% FI compared to the standard diet, and as a result their growth (BWG) increased by +10%. The higher consumption of the diet containing butyrylactate than the standard diet allows us to conclude that butyrylactate encourages animals to eat more.

[0157] 2) Testing of piglets after weaning

[0158] The animals were kept under normal housing conditions.

[0159] They were divided into four different groups and each group received a standard diet (STD) containing a butyrate source for about 10 days (from 36 to 49 days of age). Several sources of butyrate were compared: butyrylactic acid of the present invention and two protected forms of butyrate available on the market, encapsulated butyrate (fat-encapsulated) and tributyrin.

[0160] Growth performance and feed consumption were measured at the beginning and end of the study.

[0161] The results are shown in Table 2 below.

[0162] Table 2: Effects of butyrate sources on piglets compared with standard controls (%)

[0163]

[0164] BWG: Weight gain

[0165] FI: Feed intake

[0166] FCR: Feed Conversion Ratio

[0167] Table 2 shows that both sources of protected butyrate (fat-coated and tributyrin) had an adverse effect on animal performance. Animal growth (BWG) decreased by -31% in the fat-coated butyrate group and by -17% in the tributyrin group compared to the standard group. Feed efficiency (FCR) also decreased, by +26% and +3.3%, respectively. This performance decrease was associated with a significant decrease in consumption, by -13% and -14%, respectively.

[0168] It was noted that the feed containing fat-encapsulated butyrate and the feed containing tributyrin had a strong odor, which resulted in lower consumption. In fact, by emitting an unpleasant odor, the animals were forced to spend less time at the feeder.

[0169] Butyrylactate, on the other hand, has a beneficial effect. Piglets that received a feed containing it ate more feed than piglets that received a standard commercial feed: +16% FI. This increase in consumption was beneficial for their growth (BWG), which was +21% higher. Feed efficiency was not affected and even improved by -4% (FCR) with the feed containing butyrylactate. It therefore encouraged the animals to eat. This proves that butyrylactate has appetizing properties. In addition, it has an effect on digestive health, since the increase in consumption leads to an improvement in BWG and FCR, so this excess consumption is valuable for the animals.

[0170] This example demonstrates the appetizing effect of butyryllactate compared to other sources of butyrate, promoting growth in animals without reducing feed efficiency.

Claims

1. Use of a compound or a salt of said compound in the preparation of an additive, premix or feed or roughage for animal nutrition, said compound corresponding to the following formula: [Chemical formula 1] R1C(O)-[O-(CH2) n -CH(R2)-C(O)] k OR3, in R1 is selected from C 1-11 Alkyl groups; R2 is selected from C 1-20 Alkyl group; C m H 2m -OR4;C m H 2m -NHR4, wherein R4 is selected from H and C(O)-C 1-11 Alkyl and m is equal to 0 or represents an integer from 1 to 11; R3 is selected from H and C 1-20 Alkyl groups; n is equal to 0 or represents an integer from 1 to 10; and k represents an integer from 1 to 10.

2. The use according to claim 1 for animal nutrition of monogastric livestock.

3. An animal feed additive consisting of a compound having the following formula or a salt of said compound: [Chemical formula 1] R1C(O)-[O-(CH2) n -CH(R2)-C(O)] k OR3, in R1 is selected from C 1-11 Alkyl groups; R2 is selected from C 1-20 Alkyl group; C m H 2m -OR4;C m H 2m -NHR4, wherein R4 is selected from H and C(O)-C 1-11 Alkyl and m is 0 or represents an integer from 1 to 11; R3 is selected from H and C 1-20 Alkyl groups; n is 0 or an integer representing 1 to 10; and k represents an integer from 1 to 10; The compound is different from the compound having the formula [Chemical formula 2] 4. The use according to claim 1 or 2, or the additive according to claim 3, characterized in that It consists of a compound corresponding to formula [Chemical Formula 1] or a salt of the compound, wherein R1 is selected from methyl, ethyl, propyl, butyl, pentyl, and hexyl groups.

5. The use according to any one of claims 1, 2 and 4, or the additive according to claim 3 or 4, characterized in that: The compound corresponds to the formula [Chemical Formula 1], wherein R2 is selected from methyl, ethyl, propyl, butyl, pentyl and hexyl groups; OH; and OC(O)-methyl, OC(O)-ethyl, OC(O)-propyl, OC(O)-butyl, OC(O)-pentyl and OC(O)-hexyl groups, or a salt of the compound.

6. The use according to any one of claims 1, 2, 4, and 5, or the additive according to any one of claims 3, 4, and 5, characterized in that: n ranges from 0-2 and k ranges from 1-5.

7. The use according to any one of claims 1, 2, 4 to 6, characterized in that The compound corresponds to the following formula: [Chemical formula 2] or a salt of the compound.

8. The use according to any one of claims 1, 2, 4 to 6, or the additive according to any one of claims 3, 4 to 6, characterized in that It consists of a compound corresponding to the following formula or a salt of said compound composition: [Chemical formula 3] R1C(O)-[O-CH2-CH(R2)-C(O)OR3, in R2 is selected from C m H 2m -OR4, wherein m ranges from 0 to 2 and R4 is selected from H and C(O)-C 1-6 alkyl.

9. The use according to any one of claims 1, 2, 4 to 8, or the additive according to any one of claims 3, 4 to 6, 8, characterized in that The compound corresponds to the following formula: [Chemical formula 4] CH3(CH2)2C(O)-O-(CH2) n′ -CH(R2)-COOH, wherein R2 is selected from OH; CH2CH2OH; and OC(O)CH2CH2CH3 and n' is equal to 0 or 1, or a salt of said compound.

10. The use according to any one of claims 1, 2, 4 to 9, or the additive according to any one of claims 3 to 6, 8, 9, characterized in that The salt of any one of the compounds of Formula 1, Formula 2, Formula 3 and Formula 4 is selected from alkali metal salts, alkaline earth metal salts, transition metal salts, ammonium salts and salts of ammonium derivatives.

11. The use according to claim 10, or the additive according to claim 10, characterized in that The salt of the compound is selected from salts of Li, Na, K, Ca, Zn, Cu, Ni, Fe, Mn, Mg and Ag.

12. The use according to any one of claims 1, 2, 4 to 11, or the additive according to any one of claims 3 to 6, 8 to 11, for improving the palatability of the compound of formula [Chemical Formula 1].

13. A premix for animal feed comprising an additive mixture, characterized in that It comprises an additive according to any one of claims 3, 4 to 6, 8 to 10, and optionally plant or mineral raw materials.

14. A food or roughage for animal nutrition, characterized in that It comprises at least one additive according to any one of claims 3, 4 to 6, 8 to 10, or a premix according to claim 13.

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