Mixed triglycerides

Abstract

To provide compounds that are a source of butyrate having improved organoleptic properties and potential for higher ketone production after oral or enteral intake in human and other mammals.SOLUTION: A composition comprises a compound having the formula (1), (2), (3), or (4) or combinations thereof.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present invention relates to a dietary source of butyric acid-containing triglycerides having improved sensory properties. The present invention also provides butyric acid-containing triglycerides that provide a rich source of ketones.

Background Art

[0002] Salts and esters of butyric acid are called butyrate or butanoate. The ester form of butyric acid is found in many foods, such as milk, especially goat, sheep, cow, camel, and buffalo milk, and milk-derived products, such as butter, and cheeses, such as Parmesan cheese. Butyric acid is also a product of anaerobic fermentation, such as fermentation products produced by the intestinal microbiota. Tributyrin is a triglyceride consisting of three ester functional groups with three butyrate moieties and a glycerol backbone. Under hydrolysis conditions, such as those that occur during digestion, tributyrin can serve as a source of 3 moles of butyric acid per mole of tributyrin.

[0003] In mammals and livestock, many beneficial effects of butyrate have been well documented. At the intestinal level, butyrate functions to regulate trans-epithelial fluid transport, restore mucositis and oxidative status, enhance intestinal barrier function, and act on visceral perception and intestinal motility.

[0004] Butyrates have been shown to improve intestinal structure in piglets with short bowel syndrome (Bartholome et al., J of Parenter Enteral Nutr. 2004;28(4):210-222) and to reduce the proliferation of colon cancer cells in human cell lines (Lupton, J Nutr., 2004;134(2):479-482). The role of dietary fiber in colon cancer may be due to the production of volatile fatty acids such as butyric acid from fermentable fiber (Lupton, J Nutr., 2004;134(2):479-482). Short-chain fatty acids, including but not limited to acetic acid, propionic acid, and butyric acid, are produced by colon bacteria that feed on or ferment non-digestible fiber and / or prebiotics. Butyric acid also benefits colon cells by increasing energy production. Butyrate has also been shown to reduce the incidence of diarrhea (Berni Canani et al., Gastroenterol., 2004;127(2):630-634), improve inflammatory bowel disease (Scarpellini et al., Dig Liver Dis., 2007;1(1):19-22), and improve small intestinal health (Kotunia et al., J Physiol Pharmacol. 1994;55(2):59-68).

[0005] Butyrates are also known to stimulate the massive production of ketones upon ingestion (Saint-Pierre et al., 2016;32 Journal of Functional Foods 32:170-175). Ketones are an alternative energy source (other than carbohydrates, proteins, and fats) that can effectively reach peripheral organs such as the brain. Ketones can directly produce acetyl-CoA in mitochondria to support ATP production and can be used in place of glucose in nerve tissue (Tetrick et al, 2010, Comparative Medicine 60:486-490). Ketones may also have a protective effect against free radical damage to neurons (Vanltallie TB et al, 2003, Ketones: metabolism's ugly duckling. Nutr. Rev. 61:327-41).

[0006] Several studies have suggested that ketone administration after ischemic injury may reduce the impact of ischemic injury on the brain. In fact, ketone supplementation is considered a potential treatment for traumatic brain injury (White and Venkatesh, 2011, Critical Care 15:219). Furthermore, several studies have suggested that neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease may benefit from ketone administration. For example, Reger et al, (2004, Neurobiol Aging. 25:311-4.14) found that elevated serum ketone levels improved cognitive scores in Alzheimer's patients.

[0007] Butyric acid and triptyline are both generally considered safe (GRAS) food additives (21 CFR 582.60 and 21 CFR 184.1903, respectively) and are natural components of many dairy products. However, butyric acid has negative sensory qualities, such as vomit-like, fecal-like, and cheese-like odor characteristics. Triptyline also has negative sensory qualities, particularly a high degree of bitterness. These unpleasant taste and odor characteristics can make oral administration of compositions containing these compounds particularly difficult, especially in child populations.

[0008] Medium-chain triglycerides (MCTs) and medium-chain fatty acids (MCFAs) are also sources of ketones. Octanoic acid (C8) is the most efficient MCFA for producing blood ketones in humans (Vanderberghe et al.; 2017 Curr.Dev.Nutr.1(4)). However, high doses (more than 10g) are associated with undesirable gastrointestinal intolerances such as diarrhea and stomach cramps, limiting the amount that can be taken at one time, and consequently limiting the amount of blood ketones produced.

[0009] Providing a source of food-grade butyrate with improved sensory properties compared to available products would be beneficial.

[0010] [Overview of the prefecture] The present invention provides a compound that is a source of butyrate, having improved sensory properties and showing promise in enhancing ketone production after oral or enteral administration in humans and other mammals. In particular, the present invention provides a novel triglyceride (TG) comprising a mixture of butyrate and medium-chain fatty acids (MCFAs). The compound has improved odor and / or taste compared to butyric acid, butyrate, and / or triptyline. The compound can be used as a food ingredient of butyric acid. The compound may be used, for example, in nutritional compositions and dietary supplements, and may be used as a source of ketones. The compound may also simultaneously result in increased blood concentrations of butyrate and ketones.

[0011] Fatty acids are detached from triglycerides in the gastrointestinal tract by naturally occurring lipases. Compared to butyrates, this compound does not require the addition of further mineral salts to the final formulation.

[0012] According to a first aspect of the present invention, a composition comprising a compound having the following formula or a combination thereof is provided.

[0013] [ka] [In the formula, n1, n2, n3, n4, n5, and n6 are independently between 4 and 10.]

[0014] In one embodiment, n1=n2 and / or n5=n6. In a further embodiment, n1=n2=n3=n4=n5=n6.

[0015] The composition may include a compound having formula (1) and a compound having formula (2).

[0016] The composition may include a compound having formula (1) and a compound having formula (3).

[0017] The composition may include a compound having formula (1) and a compound having formula (4).

[0018] The composition may include a compound having formula (2) and a compound having formula (3).

[0019] The composition may include a compound having formula (2) and a compound having formula (4).

[0020] The composition may include a compound having formula (3) and a compound having formula (4).

[0021] The composition may include a compound having formula (1), a compound having formula (2), and a compound having formula (3).

[0022] The composition may contain a compound having formula (1), a compound having formula (2), and a compound having formula (4).

[0023] The composition may contain a compound having formula (1), a compound having formula (3), and a compound having formula (4).

[0024] The composition may contain a compound having formula (2), a compound having formula (3), and a compound having formula (4).

[0025] The composition may contain a compound having formula (1), a compound having formula (2), a compound having formula (3), and a compound having formula (4).

[0026] In one embodiment, the compound having formula (1) constitutes at least 2 wt%, 5 wt%, 10 wt%, or 15 wt% of the total triglycerides of the composition. In one embodiment, the compound having formula (1) constitutes 2 - 三十五wt%, 5 - 30 wt%, or 10 - 25 wt% of the total triglycerides of the composition.

[0027] In one embodiment, the compound having formula (2) constitutes at least 2 wt%, 5 wt%, 10 wt%, or 15 wt% of the total triglycerides of the composition. In one embodiment, the compound having formula (2) constitutes 2 - 35 wt%, 5 - 30 wt%, or 10 - 25 wt% of the total triglycerides of the composition.

[0028] In one embodiment, the compound having formula (3) constitutes at least 2 wt%, 5 wt%, 10 wt%, or 15 wt% of the total triglycerides of the composition. In one embodiment, the compound having formula (3) constitutes 2 - 35 wt%, 5 - 30 wt%, or 10 - 25 wt% of the total triglycerides of the composition.

[0029] It should be noted that in the translation of "2 - 三十五wt%", it is assumed that "三十五" is a misspelling and should be "35". If this is not the case, please correct the relevant content according to the actual situation.In one embodiment, the compound having the formula (4) constitutes at least 2 wt%, 5 wt%, 10 wt%, or 15 wt% of the total triglycerides of the composition. In one embodiment, the compound having the formula (4) constitutes 2 to 35 wt%, 5 to 30 wt%, or 10 to 25 wt% of the total triglycerides of the composition.

[0030] The compound having the formula (1), the compound having the formula (2), the compound having the formula (3), and the compound having the formula (4) may constitute at least 50 wt%, 60 wt%, 70 wt%, 80 wt%, 90 wt%, 95 wt%, or 99 wt% of the total triglycerides of the composition.

[0031] In one embodiment, the compound having the formula (1) constitutes at least 2 wt%, 5 wt%, 10 wt%, or 15 wt% of the total butyrate - containing triglycerides in the composition, and / or the compound having the formula (2) constitutes at least 2 wt%, 5 wt%, 10 wt%, or 15 wt% of the total butyrate - containing triglycerides in the composition, and / or the compound having the formula (3) and / or the compound having the formula (4) constitutes at least 2 wt%, 5 wt%, 10 wt%, or 15 wt% of the total butyrate - containing triglycerides in the composition.

[0032] The compound having the formula (1), the compound having the formula (2), the compound having the formula (3), and the compound having the formula (4) may constitute at least 50 wt%, 60 wt%, 70 wt%, 80 wt%, 90 wt%, 95 wt%, or 99 wt% of the total butyrate - containing triglycerides in the composition, and / or may constitute at least 50 wt%, 60 wt%, 70 wt%, 80 wt%, 90 wt%, 95 wt%, or 99 wt% of the total medium - chain fatty acid - containing triglycerides in the composition.

[0033] According to one embodiment of the present invention, a composition is provided that includes a compound having the following formula or a combination thereof.

[0034] [ka]

[0035] The composition may include a compound having formula (5) and a compound having formula (6).

[0036] The composition may include a compound having formula (5) and a compound having formula (7).

[0037] The composition may include a compound having formula (5) and a compound having formula (8).

[0038] The composition may include a compound having formula (6) and a compound having formula (7).

[0039] The composition may include a compound having formula (6) and a compound having formula (8).

[0040] The composition may include a compound having formula (7) and a compound having formula (8).

[0041] The composition may include a compound having formula (5), a compound having formula (6), and a compound having formula (7).

[0042] The composition may include a compound having formula (5), a compound having formula (6), and a compound having formula (8).

[0043] The composition may include a compound having formula (5), a compound having formula (7), and a compound having formula (8).

[0044] The composition may include a compound having formula (6), a compound having formula (7), and a compound having formula (8).

[0045] The composition may include a compound having formula (5), a compound having formula (6), a compound having formula (7), and a compound having formula (8).

[0046] In one embodiment, the compound having formula (5) constitutes at least 2% by weight, 5% by weight, 10% by weight, 15% by weight, 20% by weight, or 25% by weight of the total triglycerides in the composition. In another embodiment, the compound having formula (5) constitutes 5-35% by weight, 10-30% by weight, or 20-30% by weight of the total triglycerides in the composition.

[0047] In one embodiment, the compound having formula (6) constitutes at least 2% by weight, 5% by weight, 10% by weight, 15% by weight, 20% by weight, or 25% by weight of the total triglycerides in the composition. In another embodiment, the compound having formula (6) constitutes 5-35% by weight, 10-30% by weight, or 15-25% by weight of the total triglycerides in the composition.

[0048] In one embodiment, the compound having formula (7) constitutes at least 2% by weight, 5% by weight, 10% by weight, 15% by weight, 20% by weight, or 25% by weight of the total triglycerides in the composition. In another embodiment, the compound having formula (7) constitutes 5-35% by weight, 10-30% by weight, or 10-20% by weight of the total triglycerides in the composition.

[0049] In one embodiment, the compound having formula (8) constitutes at least 2% by weight, 5% by weight, 10% by weight, 15% by weight, 20% by weight, or 25% by weight of the total triglycerides in the composition. In another embodiment, the compound having formula (8) constitutes 5 to 35% by weight, 5 to 20% by weight, or 5 to 15% by weight of the total triglycerides in the composition.

[0050] In one embodiment, the compound having formula (5) constitutes at least 5% by weight of the total triglycerides in the composition, the compound having formula (6) constitutes at least 5% by weight of the total triglycerides in the composition, the compound having formula (7) constitutes at least 5% by weight of the total triglycerides in the composition, and the compound having formula (8) constitutes at least 5% by weight of the total triglycerides in the composition.

[0051] In one embodiment, the compound having formula (5) constitutes at least 25% by weight of the total triglycerides of the composition, the compound having formula (6) constitutes at least 15% by weight of the total triglycerides of the composition, the compound having formula (7) constitutes at least 10% by weight of the total triglycerides of the composition, and the compound having formula (8) constitutes at least 5% by weight of the total triglycerides of the composition.

[0052] In one embodiment, the compound having formula (5) constitutes 20 to 30% by weight of the total triglycerides in the composition, the compound having formula (6) constitutes 15 to 25% by weight of the total triglycerides in the composition, the compound having formula (7) constitutes 10 to 20% by weight of the total triglycerides in the composition, and the compound having formula (8) constitutes 5 to 15% by weight of the total triglycerides in the composition.

[0053] Compounds having formula (5), compound having formula (6), compound having formula (7), and compound having formula (8) may constitute at least 50%, 60%, 70%, 80%, 90%, 95%, or 99% by weight of the total triglycerides in the composition.

[0054] In one embodiment, the compound having formula (5) constitutes at least 5% by weight of the total butyrate-partially-containing triglycerides in the composition. In another embodiment, the compound having formula (5) constitutes at least 10% by weight, 20% by weight, or 30% by weight of the total butyrate-partially-containing triglycerides in the composition.

[0055] In one embodiment, the compound having formula (6) constitutes at least 5% by weight of the total butyrate-containing triglycerides in the composition. In another embodiment, the compound having formula (6) constitutes at least 10% by weight, 15% by weight, or 20% by weight of the total butyrate-containing triglycerides in the composition.

[0056] In one embodiment, the compound having formula (7) constitutes at least 5% by weight, 10% by weight, or 15% by weight of the total butyrate-containing triglycerides in the composition.

[0057] In one embodiment, the compound having formula (8) constitutes at least 5% by weight or 10% by weight of the total butyrate-containing triglycerides in the composition.

[0058] The compounds having formula (5), formula (6), formula (7), and formula (8) may constitute at least 50% by weight, 60% by weight, 70% by weight, 80% by weight, 90% by weight, 95% by weight, or 99% by weight of the total butyrate-containing triglycerides in the composition, and / or may constitute at least 50% by weight, 60% by weight, 70% by weight, 80% by weight, 90% by weight, 95% by weight, or 99% by weight of the total octanoate-containing triglycerides in the composition.

[0059] In preferred embodiments, triptyline constitutes less than 10% by weight of the total triglycerides in the composition, preferably less than 8% by weight, and more preferably less than 5% by weight of the total triglycerides in the composition.

[0060] The composition of the present invention may be a nutritional composition.

[0061] The composition may be a dietary supplement. The dietary supplement may be in the form of capsules, tablets, sachets, powders, or liquid shots.

[0062] In another embodiment, the present invention provides a composition for providing a source of butyric acid having improved functional properties.

[0063] In another embodiment, the present invention provides compositions for use in improving or maintaining gastrointestinal health.

[0064] In another embodiment, the present invention provides compositions for use in increasing ketone concentration, preferably blood ketone concentration.

[0065] In another embodiment, the present invention provides compositions for treating diseases treatable by ketone concentration, preferably blood ketone concentration.

[0066] In another embodiment, compositions of the present invention are provided for treating diseases associated with low ketone concentrations, preferably low blood ketone concentrations. In one embodiment, compositions of the present invention are provided for use in the treatment or prevention of neurological disorders, metabolic disorders, cancer, and / or myocardial ischemia.

[0067] In one embodiment, the present invention provides a composition for use in the treatment or prevention of one or more diseases selected from the list consisting of cerebral energy deficiency, migraine, memory impairment, age-related memory impairment, brain injury, stroke, amyloid lateral sclerosis, multiple sclerosis, cognitive impairment, post-intensive care cognitive impairment, age-related cognitive impairment, Alzheimer's disease, Parkinson's disease, Huntington's disease, congenital metabolic disorders (such as glucose transporter 1 deficiency syndrome and pyruvate dehydrogenase complex deficiency), depression, schizophrenia, epilepsy, narcolepsy, diabetes mellitus, obesity, non-alcoholic fatty liver disease, and polycystic ovary syndrome.

[0068] In one embodiment, a composition of the present invention is provided for use in the treatment or prevention of epilepsy.

[0069] In another embodiment, a compound having formula (1) is provided. In one embodiment, n1=n2=6. In this embodiment, the compound having formula (1) corresponds to the compound having formula (5).

[0070] In another embodiment, a compound having formula (2) is provided. In one embodiment, n3 = 6. In this embodiment, the compound having formula (2) corresponds to the compound having formula (6).

[0071] In another embodiment, a compound having formula (3) is provided. In one embodiment, n4=6. In this embodiment, the compound having formula (3) corresponds to the compound having formula (7).

[0072] In another embodiment, a compound having formula (4) is provided. In one embodiment, n5=n6=6. In this embodiment, the compound having formula (4) corresponds to the compound having formula (8).

[0073] In another embodiment, the use of compounds having formula (1), formula (2), formula (3), and / or formula (4), preferably compounds having formula (5), formula (6), formula (7), and / or formula (8), as defined herein, is provided for a source of butyrate having improved functional properties.

[0074] In another embodiment, compounds having formula (1), formula (2), formula (3), or formula (4), or combinations thereof, preferably compounds having formula (5), formula (6), formula (7), or formula (8), or combinations thereof, are provided for use in increasing blood ketone concentration, preferably blood ketone concentration.

[0075] In another embodiment, compounds having formula (1), formula (2), formula (3), or formula (4), preferably compounds having formula (5), formula (6), formula (7), or formula (8), or combinations thereof, are provided for use in improving or maintaining gastrointestinal (GI) health and / or for increasing blood ketone concentrations.

[0076] In another embodiment, compounds having formula (1), formula (2), formula (3), or formula (4), or combinations thereof, preferably compounds having formula (5), formula (6), formula (7), or formula (8), or combinations thereof, are provided for use as pharmaceuticals.

[0077] In another embodiment, compounds having formula (1), formula (2), formula (3), or formula (4), or combinations thereof, preferably compounds having formula (5), formula (6), formula (7), or formula (8), or combinations thereof, are provided for treating diseases treatable by increasing blood ketone concentration.

[0078] In another embodiment, compositions of the present invention are provided for treating diseases associated with low ketone concentrations, preferably low blood ketone concentrations. In one embodiment, compounds having formula (1), formula (2), formula (3), or formula (4), or combinations thereof, preferably compounds having formula (5), formula (6), formula (7), or formula (8), or combinations thereof, are provided for use in the prevention or treatment of neurological diseases, metabolic diseases, cancer, and / or myocardial ischemia.

[0079] In one embodiment, compounds having formula (1), formula (2), formula (3), and / or formula (4), preferably having formula (5), formula (6), formula (7), and / or formula (8), are provided for use in the treatment or prevention of one or more diseases selected from the list consisting of cerebral energy deficiency, migraine, memory impairment, age-related memory impairment, brain injury, stroke, amyloid lateral sclerosis, multiple sclerosis, cognitive impairment, post-intensive care cognitive impairment, age-related cognitive impairment, Alzheimer's disease, Parkinson's disease, Huntington's disease, congenital metabolic disorders (such as glucose transporter 1 deficiency syndrome and pyruvate dehydrogenase complex deficiency), depression, schizophrenia, epilepsy, narcolepsy, diabetes mellitus, obesity, non-alcoholic fatty liver disease, and polycystic ovary syndrome.

[0080] In one embodiment, compounds having formula (1), formula (2), formula (3), or formula (4), or combinations thereof, preferably compounds having formula (5), formula (6), formula (7), or formula (8), or combinations thereof, are provided for the treatment of epilepsy.

[0081] In another embodiment, a method is provided for increasing ketone concentration, preferably blood ketone concentration, comprising administering a compound or composition defined herein to a subject requiring treatment.

[0082] In another embodiment, a method is provided for treating a treatable disease by increasing ketone concentration, preferably blood ketone concentration, comprising administering a compound or composition defined herein to a subject requiring treatment.

[0083] In another embodiment, a method is provided for treating or preventing a disease associated with low ketone concentrations, preferably low blood ketone concentrations, comprising administering a compound or composition as defined herein to a subject requiring treatment.

[0084] In another embodiment, a method is provided for treating or preventing neurological disorders, metabolic disorders, cancer, and / or myocardial ischemia, comprising administering a compound or composition as defined herein to a subject requiring treatment.

[0085] In one embodiment, a method is provided for treating or preventing one or more diseases selected from the list consisting of cerebral energy deficiency, migraine, memory impairment, age-related memory impairment, brain injury, stroke, amyloid lateral sclerosis, multiple sclerosis, cognitive impairment, post-intensive care cognitive impairment, age-related cognitive impairment, Alzheimer's disease, Parkinson's disease, Huntington's disease, congenital metabolic disorders (such as glucose transporter 1 deficiency syndrome and pyruvate dehydrogenase complex deficiency), depression, schizophrenia, epilepsy, narcolepsy, diabetes mellitus, obesity, non-alcoholic fatty liver disease, and polycystic ovary syndrome, comprising administering a compound or composition defined herein to a subject in need of treatment.

[0086] In another embodiment, the present invention provides a composition comprising transesterification of triphyline with one or more triglycerides selected from the list consisting of trihexanoin, triheptanoin, tricapryline, trinonanoin, tricaprine, triundecanoin, and toridodecanoin, or a method for producing a compound having formula (1), formula (2), formula (3), or formula (4) as defined herein.

[0087] According to one embodiment, a method is provided for producing a composition of the present invention or a compound having formula (5), formula (6), formula (7), or formula (8) as defined herein, comprising transesterification of triptyline with tricapryline. [Brief explanation of the drawing]

[0088] [Figure 1] The average values ​​of total plasma ketones (BHB and AcAc) up to 4 hours after ingestion of the C4C8 butyrate-modified triglyceride "MCT C4 / C8" or "MCT" according to the present invention are shown. [Figure 2] This shows the plasma BHB, AcAc, and total ketone concentrations over 4 hours after ingestion of the C4C8 butyrate-modified triglyceride "MCT C4 / C8" according to the present invention. [Figure 3]Figure 3 shows the plasma concentrations of propionic acid, butyric acid, and hexanoic acid over 4 hours after ingestion of the C4C8 butyrate triglyceride "MCT C4 / C8" according to the present invention. [Modes for carrying out the invention]

[0089] Triglycerides Triglycerides (also called triacylglycerols) are triesters derived from glycerol and three fatty acids.

[0090] Fatty acids can be either unsaturated or saturated. Fatty acids that are not bound to other molecules are called free fatty acids (FFAs).

[0091] The term "fatty acid portion" refers to the portion of the triglyceride derived from a fatty acid in the esterification reaction with glycerol. The triglycerides used in this invention include at least one butyric acid (C4) portion and at least one medium-chain fatty acid portion (C6, C7, C8, C9, C10, C11, or C12).

[0092] The medium-chain fatty acid portion may contain 6 to 12 carbon atoms. Therefore, the medium-chain fatty acid portion may be hexanoate (caproic acid), heptanoate (enanthic acid), octanoate (caprylic acid), nonanoate (pelargonic acid), decanoate (capric acid), undecanoate (undecylic acid), or dodecanoate (lauric acid).

[0093] When one or more medium-chain fatty acid moieties are present in a triglyceride, the medium-chain fatty acid moieties may contain the same or different numbers of carbon atoms.

[0094] In some embodiments, one or more medium-chain fatty acid portions contain 6 to 10 carbon atoms. In preferred embodiments, one or more medium-chain fatty acid portions contain 8 carbon atoms (the medium-chain fatty acid portions are octanoates).

[0095] The triglycerides of the present invention can be synthesized, for example, by esterification of medium-chain fatty acids (e.g., hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, and / or dodecanoic acid) and butyric acid with glycerol. When the medium-chain fatty acid portion is an octanoate, the triglycerides can be synthesized, for example, by esterification of octanoic acid and butyric acid with glycerol.

[0096] Alternatively, the triglycerides of the present invention may be synthesized, for example, by transesterification between tributyline and trihexanoin, triheptanoin, tricapryline, trinonanoin, tricaprine, triundecanoin, and / or toridodecanoin. When the medium-chain fatty acid portion is an octanoate, the triglycerides may be synthesized, for example, by transesterification between tributyline and tricapryline (trioctanoin).

[0097] As an example, the following shows how to obtain compounds having formula (5), formula (6), formula (7), and formula (8).

[0098] [ka]

[0099] A single butyrate-partially-containing triglyceride may be used herein. Alternatively, a mixture of different butyrate-partially-containing triglycerides may be used.

[0100] composition The present invention provides compositions comprising a butyrate-partially-containing triglyceride as referred to herein. The compositions may be, for example, nutritional compositions or dietary supplements.

[0101] The term "nutritional composition" refers to a composition that provides nutrition to a subject.

[0102] In some specific embodiments, the nutritional composition according to the present invention is an "enteral nutrition composition," i.e., a food product in which the gastrointestinal tract is involved in the administration of the composition. Intragastric delivery may involve the use of a nasogastric tube or an oral gastric tube that leads directly to the stomach. Such tubes can be used particularly in hospitals or clinics.

[0103] "Dietary supplements" may be used to supplement an individual's nutrition (although typically used as such, dietary supplements may be added to any type of composition intended for consumption). This may be in the form of, for example, tablets, capsules, lozenges, or liquids. Dietary supplements may further contain protective hydrophilic colloids (such as gums, proteins, modified starches), binders, membrane-forming agents, encapsulating agents / materials, wall / shell materials, matrix compounds, coatings, emulsifiers, surfactants, solubilizers (such as oils, fats, waxes, lecithin), adsorbents, carriers, fillers, co-compounds, dispersants, wetting agents, processing aids (solvents), flowing agents, taste masking agents, bulking agents, gelling agents, and gel-forming agents. Dietary supplements may also contain conventional pharmaceutical additives and adjuvants, excipients, and diluents, including, but not limited to, water, gelatin of any origin, vegetable gum, lignin sulfonate, talc, sugar, starch, gum arabic, vegetable oil, polyalkylene glycol, flavoring agents, preservatives, stabilizers, emulsifiers, buffers, lubricants, colorants, wetting agents, and fillers. If the composition is a nutritional supplement, it may be provided in the form of a unit dose.

[0104] The nutritional composition of the present invention may contain a protein source, a carbohydrate source, and / or a lipid source. However, in some embodiments, particularly when the nutritional composition of the present invention is a nutritional supplement or fortifier, only lipids (or a lipid source) may be present.

[0105] For example, protein sources may be based not only on soybeans, but also on whey, casein, and mixtures thereof. With respect to whey protein, the protein source may be based on acidic whey, sweet whey, or mixtures thereof, and may contain α-lactalbumin and β-lactoglobulin in any desired proportion.

[0106] The protein may be either completely hydrolyzed or partially hydrolyzed. If a hydrolyzed protein is required, the hydrolysis process may be carried out as desired, as is known in the art. For example, a hydrolyzed whey protein can be prepared by enzymatically hydrolyzing the whey fraction in one or more steps.

[0107] In one embodiment, the protein in the composition is a plant-derived protein.

[0108] The nutritional composition according to the present invention may contain a carbohydrate source. Any carbohydrate source may be used, such as lactose, sucrose, sucrose, maltodextrin, starch, and mixtures thereof. The nutritional composition according to the present invention may also contain vitamins and minerals considered essential for a daily diet in nutritionally significant amounts. Minimum requirements for specific vitamins and minerals have been established. Examples of minerals, vitamins, and other nutrients optionally present in the composition according to the present invention include vitamin A, vitamin B1, vitamin B2, vitamin B3, vitamin B6, vitamin B12, vitamin E, vitamin K, vitamin C, vitamin D, folic acid, inositol, niacin, biotin, pantothenic acid, choline, calcium, phosphorus, iodine, iron, magnesium, copper, zinc, manganese, chlorine, potassium, sodium, selenium, chromium, molybdenum, taurine, and L-carnitine. Minerals are usually added in salt form. The presence and amount of specific minerals and other vitamins will vary depending on the target population. If necessary, the nutritional composition of the present invention may contain emulsifiers and stabilizers, such as soy, lecithin, and citrate esters of mono and diglycerides. The nutritional composition of the present invention may also contain other substances that may have beneficial effects, such as lactoferrin, osteopontin, TGFβ, slgA, glutamine, nucleotides, and nucleosides.

[0109] The composition of the present invention may further contain at least one indigestible oligosaccharide (e.g., a prebiotic).

[0110] Prebiotics are typically indigestible, meaning they are not broken down or absorbed in the stomach or small intestine. Therefore, prebiotics remain intact when they enter the large intestine, where they are selectively fermented by beneficial bacteria. Examples of prebiotics include certain oligosaccharides such as fructooligosaccharides (FOS), inulin, xylooligosaccharides (XOS), polydextrose, or any mixture thereof. In certain embodiments, the prebiotics may be fructooligosaccharides and / or inulin. In certain embodiments, the prebiotics may be a combination of FOS and inulin, for example, the combination in a product marketed by BENEO-Orafti under the trademark name Orafti® Oligofructose (formerly Raftilose®), or the combination in a product marketed by BENEO-Orafti under the trademark name Orafti® Inulin (formerly Raftiline®). Another example is a combination of 70% short-chain fructooligosaccharides and 30% inulin, which is registered by Nestle as the trademark "Prebio1". The nutritional compositions of the present invention may also contain at least one milk oligosaccharide, which may be BMO (bovine milk oligosaccharide) and / or HMO (human milk oligosaccharide). The compositions of the present invention may further contain at least one probiotic (i.e., a probiotic strain), such as a probiotic strain.

[0111] The most commonly used probiotic microorganisms are primarily bacteria and yeasts of the genera Lactobacillus, Streptococcus, Enterococcus, Bifidobacterium, Clostridium, and Saccharomyces.

[0112] In some specific embodiments, the probiotic is a probiotic strain. In some specific embodiments, the probiotic strain is Bifidobacterium and / or Lactobacillus.

[0113] In some specific embodiments, the microorganisms are derived from feces. The compositions of the present invention may be, for example, in solid (e.g., powder), liquid, or gelatinous form.

[0114] The compositions of the present invention may be in the form of, for example, tablets, sugar-coated tablets, capsules, gel caps, powders, granules, solutions, emulsions, suspensions, coated particles, spray-dried particles, pills, or shots (for example, small amounts of liquid that can be easily consumed, for example, in one or more mouthfuls).

[0115] The composition may be in the form of a pharmaceutical composition and may contain one or more pharmaceutically acceptable suitable carriers, diluents, and / or excipients.

[0116] Examples of such excipients suitable for the compositions described herein can be found in "Handbook of Pharmaceutical Excipients," 2nd Edition, (1994), edited by A. Wade and P.J. Weller.

[0117] Acceptable carriers or diluents for therapeutic use are known in the pharmaceutical field and are described, for example, in Remington's Pharmaceutical Sciences, Mack Publishing Co. (ARGennaro edit. 1985).

[0118] The pharmaceutical composition may contain, or in addition to, any suitable binder, lubricant, suspending agent, coating agent, and / or solubilizer as a carrier, excipient, or diluent. Examples of suitable binders include starch, gelatin, natural sugars such as glucose, anhydrous lactose, fluid lactose, and β-lactose, corn sweeteners, natural and synthetic gums such as acacia, tragacanth, or sodium alginate, carboxymethylcellulose, and polyethylene glycol.

[0119] Examples of suitable lubricants include sodium oleate, sodium stearate, magnesium stearate, sodium benzoate, sodium acetate, and sodium chloride.

[0120] Preservatives, stabilizers, dyes, and even flavorings may be included in the composition. Examples of preservatives include sodium benzoate, sorbic acid, and esters of p-hydroxybenzoic acid. Antioxidants and suspending agents may also be used.

[0121] treatment In this specification, all references to “treatment” are understood to include curative, palliative, and preventive treatments. Treatment may also include slowing the progression of disease severity.

[0122] The treatment of both humans and animals falls within the scope of this invention.

[0123] Gastrointestinal (GI) health The compounds and compositions defined herein are sources of butyrate / butyric acid and may therefore be used to improve or maintain gastrointestinal (GI) health.

[0124] Butyrate has been well documented for its numerous beneficial effects on GI health. At the intestinal level, butyrate functions to regulate transepithelial fluid transport, restore mucositis and oxidative conditions, strengthen the epithelial protective barrier, and regulate visceral sensation and bowel motility.

[0125] Fatty acids such as butyrate are the primary energy source for colonic mucosal cells (Reodriger, Gut. 1980;21:793-798), and are most important for colonic cells in the distal colon. The strong nutritional effect of butyrate on the small intestinal mucosa has been observed in experimental animals (Guilteau et al., 2 J Anim Feed Sci 2004;13, Suppl. 1:393-396). A decrease in intestinal butyrate concentration leads to atrophy of the colonic mucosa, which is usually explained by a decrease in the usefulness of the matrix to colonic cells. On the other hand, administration of butyrate into the colonic lumen induces weight gain, increased DNA synthesis, and increased depth of intestinal crypts (Kripke et al., J Parenter Enter Nutr. 1989;13:109-116).

[0126] High concentrations of butyrate, achieved through the fermentation of insoluble dietary fiber or after rectal administration of butyrate, may inhibit the early and late stages of tumorigenesis in the colon by regulating the transcription, expression, and activation of key proteins in the apoptosis cascade (Aviv-Green et al., J Nutr..2002;132(7):1812-18).

[0127] Chapman et al. (Gut 1994;35(1):73-76) showed that inflamed colonic mucosa captures far greater amounts of butyrate compared to glutamine or glucose. Multiple experiments in rats have shown that butyrate perfusion significantly reduces inflammation and the extent of colonic wall ulceration (Andoh et al., J Parenter Enter Nutr. 1999;23(5):70-73).

[0128] Clinical observations of patients with ulcerative colitis have demonstrated the effectiveness of butyrate enemas (Han et al., Gastroenterol Clin North Am. 1999;28:423-443; Scheppach et al., Gastroenterol Suppl. 1997;222:53-57).

[0129] The direct anti-inflammatory activity of butyrates may be related to the inhibition of nuclear factor κB (NFκB) translocation and binding to DNA, as well as the inhibition of transcription and production of inflammatory cytokines (Segain et al., Gut. 2000; 47: 397-403).

[0130] In one embodiment, the compounds and compositions defined herein may be used to treat inflammatory bowel diseases, such as Crohn's disease or ulcerative colitis.

[0131] Ketones As described above, the compounds and compositions of the present invention contain C4 and medium-chain fatty acids and are a rich source of ketones.

[0132] In the body, ketones are primarily produced by the liver through ketone body synthesis from fatty acids. In ketone body synthesis, medium-chain fatty acids are broken down by enzymatic β-oxidation, producing acetyl-CoA and "ketone bodies" (water-soluble molecules containing a ketone group). Octanoates are the most efficient medium-chain fatty acids for ketone production through the synthesis of C4 ketones. The three primary ketone bodies are acetacetate, β-hydroxybutyrate, and acetone. Therefore, in some embodiments, the compounds and compositions of the present invention are sources of acetacetate, β-hydroxybutyrate, and / or acetone.

[0133] Ketone body production can occur in response to the inability to utilize blood glucose, for example, during fasting, starvation, on a low-carbohydrate diet, during prolonged exercise, and in untreated type 1 diabetes mellitus. Specifically, ketone body production is promoted by a low-carbohydrate diet or a "ketogenic diet." In one embodiment, the composition according to the present invention is intended for use as part of a low-carbohydrate diet or a ketogenic diet.

[0134] In addition to being a source of fatty acids for ketone production, buttyrates can stimulate fatty acid oxidation and ketone production (Cavaleri, F. and Bashar, E., 2018. Journal of Nutrition and Metabolism).

[0135] In one embodiment, the compound or composition according to the present invention is intended for use in introducing ketones into a body fluid of interest.

[0136] In one embodiment, the compound or composition according to the present invention is for use in increasing blood ketone concentrations and / or for use in treating diseases that can be treated by increasing blood ketone concentrations.

[0137] Ketone bodies are transported from the liver to other tissues, particularly the brain. For example, ketones are transported to the brain by monocarboxylic acid transporter 1 (MCT1), where they are primarily metabolized by neurons. Ketone bodies become an energy source by being converted back into acetyl-CoA. The brain obtains some of its energy needs from ketone bodies when available glucose is lower than normal. The heart can also effectively utilize ketone bodies.

[0138] The free fatty acids and ketones produced from the triglycerides described herein can serve as an alternative energy source to glucose and can supply or replenish energy in cells such as muscle cells, cardiomyocytes, or nerve cells. Therefore, in metabolic conditions such as cancer, trauma, and ischemia, ketone bodies can be beneficial by providing an additional energy source to tissues that may be susceptible to cell death (Baranano, K. Wand, Hartman, AL, 2008. Current treatment options in neurology, 10(6), p. 410). For example, a ketogenic diet (one method that promotes ketone body production) is a treatment for drug-resistant epilepsy and may have therapeutic effects on various neurological disorders (Gano, L., Patel, M. and Rho, JM, 2014. Journal of lipid research, pp. jlr-R048975).

[0139] Brain tissue consumes a large amount of energy relative to its volume. In an average healthy subject, the brain obtains most of its energy from the oxygen-dependent metabolism of glucose. Typically, most of the brain's energy is used to assist in signal transduction by neurons or nerve cells, and the remaining energy is used to maintain cellular health. For example, energy deficiency in the brain caused by impaired glucose utilization can lead to increased neuronal activity, seizures, and cognitive impairment.

[0140] Therefore, the compounds and compositions of the present invention can be used to treat deficiencies in neurological conditions or diseases. The compounds and compositions of the present invention can be used to treat deficiencies in brain energy and / or conditions associated with such deficiencies.

[0141] Examples of brain energy deficiency states or diseases include migraines, memory impairment, age-related memory impairment, brain injury, neurorehabilitation, stroke and post-stroke, amyloid lateral sclerosis, multiple sclerosis, cognitive impairment, post-intensive care cognitive impairment, age-related cognitive impairment, Alzheimer's disease, Parkinson's disease, Huntington's disease, congenital metabolic disorders (such as glucose transporter 1 deficiency syndrome and pyruvate dehydrogenase complex deficiency), bipolar disorder, schizophrenia, and / or epilepsy.

[0142] A "neurological condition" refers to a disorder of the nervous system. Neurological conditions can result from damage to the brain, spine, or nerves caused by illness or trauma. Examples of symptoms of a neurological condition include paralysis, muscle weakness, poor coordination, loss of sensation, seizures, confusion, pain, and altered levels of consciousness. Assessment of responses to touch, pressure, vibration, limb position, heat, cold, pain, and reflexes can determine whether a person has a nervous system disorder.

[0143] In one embodiment, the neurological condition is a result of traumatic brain injury.

[0144] The terms "cognitive impairment" and "cognitive disorder" refer to disorders that impair cognition, particularly those that primarily affect learning, memory, perception, and / or problem-solving. Cognitive impairment may occur in patients after intensive care. Cognitive impairment can also occur as part of aging.

[0145] The term "cognition" refers to the entire set of mental abilities and processes, including knowledge, attention, long-term and working memory, judgment and evaluation, reasoning and "calculation," problem-solving and decision-making, language comprehension and language creation.

[0146] The level and improvement of cognition can be readily assessed by those skilled in the art using any suitable neurological and cognitive tests known in the art, including cognitive tests designed to assess information processing speed, executive function, and memory.Examples of suitable tests include the Mini Mental State Examination (MMSE), the Cambridge Neuropsychological Test Automated Battery (CANTAB), the Alzheimer's Disease Assessment Scale-cognitive test (ADAScog), the Wisconsin Card Sorting Test, the Verbal and Figurative Fluency Test and Trail Making Test, the Wechsler Memory Scale (WMS), the immediate and delayed Visual Reproduction Test (Trahan et al. Neuropsychology, 1988 19(3) p.173-89), and the Rey Auditory Verbal Learning Test (RAVLT) (Ivnik, RJ. et al. Psychological Assessment: A Journal of Consulting and Clinical). Psychology, 1990(2): p.304-312), electroencephalography (EEG), magnetoencephalography (MEG), positron emission tomography (PET), single-photon emission computed tomography (SPECT), magnetic resonance imaging (MRI), functional magnetic resonance imaging (fMRI), computed tomography, and long-term enhancement are examples of such methods.

[0147] In addition to cancer (astrocytoma, prostate cancer, and gastric cancer), the ketogenic diet may also have therapeutic effects on metabolic diseases such as glucose transporter 1 (GLUT-1) deficiency, pyruvate dehydrogenase (PDH) deficiency, phosphofructokinase (PFK) deficiency, and glycogen storage diseases including McArdle's disease (Baranano, KWand Hartman, AL, 2008. Current treatment options in neurology, 10(6), p.410). The ketogenic diet has also been shown to be an effective strategy for managing type 2 diabetes (Azar, ST, Beydn, HMand Albadri, MR, 2016. J Obes Eat Disord, 2(2)).

[0148] Therefore, the compounds and compositions of the present invention can be used to treat glucose transporter 1 (GLUT-1) deficiency, pyruvate dehydrogenase (PDH) deficiency, phosphofructokinase (PFK) deficiency; and glycogen storage disorders such as McArdle disease and diabetes. The compounds and compositions of the present invention can also be used to treat cancer and myocardial ischemia.

[0149] Administration Preferably, the compounds and compositions described herein are administered enterally.

[0150] Enteral administration may be oral, gastric, and / or rectal.

[0151] Generally speaking, the administration of the combinations or compositions described herein may be, for example, administered orally or via another route into the gastrointestinal tract, and may also be administered by enteral nutrition.

[0152] In preferred embodiments, administration is by oral infusion.

[0153] The subject may be mammals such as humans, dogs, cats, horses, goats, cattle, sheep, pigs, deer, and primates. Preferably, the subject is humans.

[0154] Further preferred features and embodiments of the present invention are described as non-limiting examples. [Examples]

[0155] Unless otherwise stated, the implementation of this invention utilizes prior art in chemistry, molecular biology, microbiology, recombinant DNA, and immunology, which are within the scope of the skills of those skilled in the art. Such art is described in the literature. For example, J. Sambrook, EFFritsch, and T. Maniatis, 1989, Molecular Cloning: A Laboratory Manual, Second Edition, Books 1-3, Cold Spring Harbor Laboratory Press; Ausubel, FMet al. (1995 and periodic supplements; Current Protocols in Molecular Biology, ch.9,13, and 16, John Wiley&Sons, New York, NY); B. Roe, J. Crabtree, and A. Kahn, 1996, DNA Isolation and Sequencing: Essential Techniques, John Wiley&Sons; JMPolak and James O'D. McGee, 1990, In Situ Hybridization: Principles and Practice; Oxford University Press; Approach,Irl Press;DMJLilley and JEDahlberg,1992,Methods of See Enzymology: DNA Structure Part A: Synthesis and Physical Analysis of DNA Methods in Enzymology, Academic Press; and EMShevach and W. Strober, 1992 and periodic supplements, Current Protocols in Immunology, John Wiley & Sons, New York, NY. Each of these general texts is incorporated herein by reference.

[0156] Example 1 - Preparation of butyrate triglycerides (TAGs) The composition containing butyrate-modified TAG was produced by chemical transesterification between triptyline and tricapryline in the presence of a sodium methoxide catalyst.

[0157] The following steps were used: reaction Tricaprylin (Neobee 895 from Stepan) and triplylin were sequentially added to a multipurpose reactor L2600 at room temperature. One liter of tricaprylin was set aside to facilitate the addition of sodium methoxide. Degassing was performed under nitrogen agitation. The reactor was heated to 60°C. Sodium methoxide suspended in 1 liter of tricaprylin was added (whipped and stirred before addition). The mixture was heated to 80°C in an inert atmosphere (nitrogen) for 3 hours (time counted from 60°C). Post-processing The mixture was cooled to below 60°C. The mixture was washed with deionized water (approximately 8 L) until a neutral pH was obtained (removal of sodium methoxide). After the first wash, the reactor was emptied and washed with warm water if any sodium methoxide fragments were adhering to the walls. After the final wash and removal of the aqueous layer, the crude oil was vacuum-dried (at 60°C and 60 mBar, until all remaining water was gone). purification • Add 3% Tonsil Supreme 110 FF to the suspension. Stir and heat at 70°C for 40 minutes under vacuum (60 mbar). • Nitrogen supplementation. Filtration of bleaching land on a Buchner filter (Filtrox 8-20μm). 16.48 kg of crude product. Deodorization • 8 kg of the decolorized product was added to 6 L of L800 deodorant. Heat at 142°C for 3 hours under a pressure of 0.8 mbar while injecting steam (water volume / hour = 30 mL / hour) (145°C for 1 mbar, 149°C for 1.2 mbar, and 154°C for 1.5 mbar). Samples will be taken at 1 hour, 2 hours, and at the end of the deodorization process. Cool to 60°C (1 hour 15 minutes). • Nitrogen replenishment. ·filtration. 6.07 kg was obtained.

[0158] The components of triglycerides are shown in Table 1 below. These triglycerides are represented by the three fatty acids they contain. These fatty acids are represented by their lipid ratios, with butyrate being 4:0 and caprylic acid being 8:0.

[0159] The central fatty acid is located at the sn-2 position of the triglyceride. For example, 8:0-4:0-8:0 is a triglyceride that has both a butyrate at the sn-2 position and octanoates at the sn-1 and sn-3 positions.

[0160] TAG profiles and positional isomers were analyzed by liquid chromatography connected to a high-resolution mass spectrometer. The proportion of each lipid was evaluated by liquid chromatography connected to an evaporative light scattering detector (ELSD).

[0161] The C4C8 triglyceride composition had good sensory properties (mild taste, odorless).

[0162] [Table 1]

[0163] [Table 2]

[0164] Example 2 - Administration of butyrate-modified triglycerides (TAGs) (in vivo) After an overnight fast, at zero hour, 15 healthy volunteers were orally administered 15 g of the C4C8 butyrate triglyceride "MCT C4 / C8" from Example 1, emulsified in 70 mL of 5% milk protein aqueous solution. Another 15 healthy volunteers were orally administered 15 g of "MCT," a mixture of medium-chain triglycerides with a C8:C10 ratio of approximately 58:42, emulsified in 70 mL of 5% milk protein aqueous solution. A standard breakfast was provided at 30 minutes and consumed over 15 minutes. Blood samples were collected intravenously at regular intervals over 4 hours, and the plasma was analyzed for C3, C4, C8, 3-hydroxybutyrate (BHB), and acetoacetate (AcAc) by UPLC-MSMS.

[0165] Figure 1 shows the average plasma total ketone (BHB and AcAc) concentrations up to 4 hours for 15 patients in each treatment group: the C4C8 butyrate triglyceride "MCT C4 / C8" group and the MCT group. As can be seen from Figure 1, a higher plasma ketone Cmax was observed in the C4C8 butyrate triglyceride treatment group.

[0166] Figures 2 and 3 show the 4-hour plasma concentrations of C3, C4, C8, BHB, AcAc, and total ketones for one individual from the C4C8 butyrate triglyceride "MCT C4 / C8" treatment group. The total ketone concentration is the sum of 3-hydroxybutyrate and acetacetate as measured by ULC-MSMS.

Claims

1. The compound comprises a compound having formula (1), a compound having formula (2), a compound having formula (3), and a compound having formula (4). The compound having formula (1) constitutes at least 2% by weight of the total triglycerides in the composition, the compound having formula (2) constitutes at least 2% by weight of the total triglycerides in the composition, the compound having formula (3) constitutes at least 2% by weight of the total triglycerides in the composition, and the compound having formula (4) constitutes at least 2% by weight of the total triglycerides in the composition. The compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 50% by weight of the total triglycerides of the composition. Tributyline constitutes less than 10% by weight of the total triglycerides in the composition. A composition for use in improving or maintaining gastrointestinal health. 【Chemistry 1】 [In the formula, n1, n2, n3, n4, n5, and n6 are independently between 4 and 10.]

2. The composition according to claim 1, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 60% by weight of the total triglycerides of the composition.

3. The composition according to claim 1 or 2, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 70% by weight of the total triglycerides of the composition.

4. The composition according to any one of claims 1 to 3, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 80% by weight of the total triglycerides of the composition.

5. The composition according to any one of claims 1 to 4, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 90% by weight of the total triglycerides of the composition.

6. The composition according to any one of claims 1 to 5, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 95% by weight of the total triglycerides of the composition.

7. The composition according to any one of claims 1 to 6, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 99% by weight of the total triglycerides of the composition.

8. A composition according to any one of claims 1 to 7, comprising a compound having the following formula or a combination thereof. 【Chemistry 2】

9. The composition according to claim 8, wherein the composition comprises the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8).

10. The composition according to claim 8 or 9, wherein the compound having formula (5) constitutes at least 2% by weight of the total triglycerides of the composition, the compound having formula (6) constitutes at least 2% by weight of the total triglycerides of the composition, the compound having formula (7) constitutes at least 2% by weight of the total triglycerides of the composition, and the compound having formula (8) constitutes at least 2% by weight of the total triglycerides of the composition.

11. The composition according to any one of claims 8 to 10, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 50% by weight of the total triglycerides of the composition.

12. The composition according to any one of claims 8 to 10, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 60% by weight of the total triglycerides of the composition.

13. The composition according to any one of claims 8 to 10, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 70% by weight of the total triglycerides of the composition.

14. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 50% by weight of the total butyrate-containing triglycerides in the composition.

15. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 60% by weight of the total butyrate-containing triglycerides in the composition.

16. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 70% by weight of the total butyrate-containing triglycerides in the composition.

17. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 80% by weight of the total butyrate-containing triglycerides in the composition.

18. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 90% by weight of the total butyrate-containing triglycerides in the composition.

19. The composition according to any one of claims 8 to 18, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 50% by weight of the total octanoate-containing triglycerides in the composition.

20. The composition according to any one of claims 8 to 18, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 60% by weight of the total octanoate-containing triglycerides in the composition.

21. The composition according to any one of claims 8 to 18, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 70% by weight of the total octanoate-containing triglycerides in the composition.

22. The composition according to any one of claims 1 to 21, wherein triptyline constitutes less than 8% by weight of the total triglycerides in the composition.

23. The composition according to any one of claims 1 to 21, wherein triptyline constitutes less than 5% by weight of the total triglycerides in the composition.

24. The composition according to any one of claims 1 to 23, wherein the composition is a nutritional composition.

25. The composition according to any one of claims 1 to 24, which is a dietary supplement in the form of a capsule, tablet, sachet, powder, or liquid shot.

26. A method for producing the composition according to any one of claims 1 to 25, comprising transesterification of tributyline with one or more triglycerides selected from the list consisting of trihexanoin, triheptanoin, tricapryline, trinonanoin, tricaprine, triundecanoin, and toridodecanoin.

27. The manufacturing method according to claim 26, wherein the triglyceride is tricaprylin.

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