US-20260124168-A1 - OIL COMPOSITION COMPRISING CAPROIC ACID RESIDUES, UNSATURATED FATTY ACID RESIDUES AND SATURATED FATTY ACID RESIDUES

Abstract

An oil composition comprises from 1% to 20% by weight of caproic acid residues (C6:0); at least 55% by weight of C16 to C18 unsaturated fatty acid resides; and less than 40% by weight of C8 to C24 saturated fatty acid residues; wherein said percentages of fatty acid residues refers to fatty acids bound as acyl groups in glycerides in the oil composition and being based on the total weight of saturated and unsaturated C4 to C24 fatty acid residues bound as acyl groups present in the oil composition; and wherein at least 50% of the caproic acid residues present in the oil composition are present in a triglyceride comprising at least one caproic acid residue and at least one fatty acid residue comprising from 16 to 18 carbon atoms.

Inventors

• Lotte SMOLDERS
• Kim OLOFSSON
• Martin Johansson
• Johanna ROSENQVIST

Assignees

• AAK AB (PUBL)

Dates

Publication Date

20260507

Application Date

20231006

Priority Date

20221006

Claims (20)

1. 1 . An oil composition comprising from 1% to 20% by weight of caproic acid residues (C6:0); at least 55% by weight of C16 to C18 unsaturated fatty acid residues; and less than 40% by weight of CS to C24 saturated fatty acid residues; wherein said percentages of fatty acid residues refers to fatty acids bound as acyl groups in glycerides in the oil composition and being based on the total weight of saturated and unsaturated C4 to C24 fatty acid residues bound as acyl groups present in the oil composition; and wherein at least 50% of the caproic acid residues present in the oil composition are present in a triglyceride comprising at least one caproic acid residue and at least one fatty acid residue comprising from 16 to 18 carbon atoms.
2. 2 . An oil composition according to claim 1 , wherein the oil composition comprises from 2% to 30% by weight of butyric acid residues (C4:0); and wherein at least 50% of the butyric acid residues present in the oil composition are present in a triglyceride comprising at least one butyric acid residue and at least one fatty acid residue comprising from 16 to 18 carbon atoms.
3. 3 . An oil composition according to claim 1 , wherein the oil composition comprises butyric acid (C4:0) in an amount of from 2% to 25% by weight.
4. 4 . An oil composition according to claim 1 , wherein the oil composition comprises butyric acid (C4:0) in an amount of from 7.5% to 30% by weight.
5. 5 . An oil composition according to claim 1 , wherein the oil composition comprises caproic acid (C6:0) in an amount of from 1% to 15% by weight.
6. 6 . An oil composition according to claim 1 , wherein the oil composition comprises caproic acid (C6:0) in an amount of from 2% to 10% by weight.
7. 7 . An oil composition according to claim 1 , wherein the oil composition comprises caproic acid (C6:0) in an amount of from 5% to 20% by weight.
8. 8 . An oil composition according to claim 1 , wherein at least 60% of the caproic acid residues present in the oil composition; and at least 60% of butyric acid residues present in the oil composition are present in a triglyceride comprising at least one butyric acid or caproic acid residue and at least one fatty acid residue comprising from 16 to 18 carbon atoms.
9. 9 . An oil composition according to claim 1 , wherein at least 70% of the caproic acid residues present in the oil composition and at least 70% of the butyric acid residues present in the oil composition are present in a triglyceride comprising at least one butyric acid or caproic acid residue and at least one fatty acid residue comprising from 16 to 18 carbon atoms.
10. 10 . An oil composition according to claim 1 , wherein at least 80% of the caproic acid residues present in the oil composition; and at least 80% of the butyric acid residues present in the oil composition are present in a triglyceride comprising at least one butyric acid or caproic acid residue and at least one fatty acid residue comprising from 16 to 18 carbon atoms.
11. 11 . An oil composition according to claim 1 , wherein at least 20% of the caproic acid residues present in the oil composition; and at least 20% of butyric acid residues present in the oil composition are present in a triglyceride comprising a butyric acid or caproic acid residue and two fatty acid residues comprising from 16 to 18 carbon atoms.
12. 12 . An oil composition according to claim 1 , wherein at least 25% of the caproic acid residues present in the oil composition; and at least 25% of the butyric acid residues present in the oil composition are present in a triglyceride comprising a butyric acid or caproic acid residue and two fatty acid residues comprising from 16 to 18 carbon atoms.
13. 13 . An oil composition according to claim 1 , wherein at least 50% of the caproic acid residues present in the oil composition; and at least 50% of the butyric acid residues present in the oil composition are present in a triglyceride comprising a butyric acid or caproic acid residue and two fatty acid residues comprising from 16 to 18 carbon atoms.
14. 14 . An oil composition according to claim 1 , wherein the oil composition has a weight ratio of butyric acid residues (C4:0) to caproic acid residues (C6:0) of from 1:1 to 6:1.
15. 15 . An oil composition according to claim 1 , wherein the oil composition comprises C16 to C18 unsaturated fatty acid residues in an amount of at least 60% by weight.
16. 16 . An oil composition according to claim 1 , wherein the oil composition comprises fatty acid residues having from 16 to 18 carbon atoms in an amount of from 60% to 95% by weight.
17. 17 . An oil composition according to claim 1 , wherein the oil composition has a weight ratio of fatty acid residues having from 16 to 18 carbon atoms to butyric acid residues (C4:0) and caproic acid residues (C6:0) of from 1:1 to 20:1.
18. 18 . An oil composition according to claim 1 , wherein the oil composition comprises 10% by weight or less of palmitic acid (C16:0).
19. 19 . An oil composition according to claim 1 , wherein the oil composition comprises 10% by weight or less of a total amount of fatty acid residues having from 16 to 17 carbon atoms.
20. 20 . An oil composition according to claim 1 , wherein the oil composition comprises from 10% to 40% by weight of total saturated fatty acids.

Description

FIELD OF THE INVENTION The invention relates to oil compositions and nutritional products comprising said compositions. The invention also relates to methods of supplementing the diet of individuals with said nutritional products and oil compositions. BACKGROUND OF THE INVENTION It is known that short chain fatty acids (SCFA) are a desirable component of the diet of mammals. Short chain fatty acids are fatty acid molecules containing typically six or less carbon atoms. Examples of SCFA include acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid and caproic acid. SCFA are reported as being associated with various health and wellbeing benefits. For example, SCFA have been reported as being associated with healthy gastrointestinal function and intestinal absorption, a healthy immune system, reduced chronic inflammation and improved metabolism. It has also been suggested that circulating SCFA may be associated with improved weight and appetite regulation thereby potentially being used as an obesity preventative. Circulating SCFA levels are also reported as being associated with regulation of blood sugar levels and the prevention of insulin resistance meaning that SCFA could potentially be used to prevent or ameliorate the development of type II diabetes. Blaak et al., Short chain fatty acids in human gut and metabolic health, Beneficial Microbes, 2020; 11(5): 411-455 discloses that actetate, butyrate and propionate may play a role in the pathophysiology of gastrointestinal health, obesity and type II diabetes. Canfora et al., Short-chain fatty acids in control of body weight and insulin sensitivity, Endocrinology, Volume 11, October 2015 also discusses the link between actetate, butyrate and propionate and obesity and type II diabetes. Whilst SCFA in general are known to be associated with the positive effects discussed above, the prior art is mainly focused upon the study of the in vivo effects of butyric acid (C4:0), propionic acid (C3:0) and acetic acid (C2:0), with the principal focus being on butyric acid (C4:0). For example, Steliou et al., Butyrate Histone Deacetylase Inhibitors, BioResearch Open Access, Volume 1, Number 4, August 2012 discusses how butyrate is a histone deacetylase inhibitor that can potentially be used to treat diet induced obesity and prevent insulin resistance. Ivanov et al., The role of prenatal melatonin in the regulation of childhood obesity, Biology, 2020, 9, 72 discloses that butyrate may regulate obesity by being active on the p-opioid receptor. Lin et al., Butyrate and propionate protect against diet-induced obesity and regulate gut hormones via free fatty acid receptor 3-independent mechanisms, Plos One, April 2012, Volume 7, Issue 4, e35240 discusses how butyrate and propionate protect against diet induced obesity and insulin resistance and that these SCFA may have a major impact upon therapies for diabetes type II and obesity. Whilst the art has investigated the potential and mechanism of action of butyric acid (and to a lesser extent propionic and acetic acid) as a supplement for promotion of the abovementioned health benefits, caproic acid (C6:0) has to date not been focused upon. It is known in the art that where butyric acid is to be provided as an orally administered nutritional supplement, providing the fatty acid in a free fatty acid form is not desirable since the butyric acid is broken down in the stomach and does not reach the systemic circulation where it can promote the health benefits discussed above. Providing the butyric acid in the form of a salt such as sodium butyrate is also undesirable since it has an unpleasant flavour and odour meaning that it is less organoleptically acceptable for consumers when orally ingested. In order to alleviate these problems, several attempts have been made to provide the butyric acid in the form of a plant derived triglyceride oil. However, in order to provide a butyrate-containing triglyceride oil with sufficient organoleptic properties for oral consumption, it has been found necessary to subject the plant derived triglycerides to a deodorization process step in order to remove odiferous compounds that impart an unpleasant smell, colour or taste to the triglycerides. Deodorization is a normal process step in the refining of plant derived triglyceride oils once they have been extracted from plant sources. Deodorization steps typically involve subjecting the triglyceride oil to high temperatures of from 100° C. to 260° C. whilst under vacuum. It has been appreciated by the inventors of the present invention that when deodorization of butyrate-containing triglyceride oils (and also acetate or propionate-containing triglyceride oils) is carried out, significant quantities of the triglyceride oil are lost during the deodorization step. During deodorization, the oils are typically heated to high temperatures. This heating process can cause the triglycerides to evaporate which reduces the yield of the deodoriza