 | This article's lead section contains information that is not included elsewhere in the article.(June 2023) |
SN2 Palmitate is a structured triglyceride where palmitic acid is bonded to the middle position (sn-2) of the glycerol backbone. Structured triglycerides are achieved through an enzymatic process using vegetable oils. Current usage of structured triglycerides is mainly for infant formula providing a human milk fat substitute.
Fats in human breast milk provides about 50% of the energy needed for the development and growth of a newborn infant. About 98% of the fats provided by human milk are in the form of triglycerides, which themselves are molecules consisting of mixtures of three fatty acids bonded to sn-1, sn-2, and sn-3 positions of a glycerol backbone. [1] The human mammary gland provides the baby with a unique fat composition where the fatty acids arranged in specific combinations, different from the triglycerides in other human tissues and plasma, [2] or from common dietary fats and oils. Palmitic acid (C16:0) is the major saturated fatty acid in human milk, accounting for 17-25% of the total fatty acids, [2] with over 70% of 16:0 is esterified at the milk triglyceride sn-2 position. [2] [3] The major unsaturated fatty acid in human milk is oleic acid (18:1n-9) and this is mostly esterified at the triglyceride sn-1,3 (outer) positions. The positioning of palmitic acid at the sn-2 position is conserved in all women, regardless of race or nutrition, unlike the general fatty acid profile of human milk.
The development of the sn-2 Palmitate structured triglycerides enables the mimicking of both the composition as well as the structure of human milk fat. Vegetable oils that are commonly used as source for infant formula fat have the opposite structure where the palmitic is located mainly at sn-1 and sn-3 positions. Enzymatic process on vegetable oils enables changing the position of palmitic acid to the sn-2 position. [4] [5] [6] [7] [8] Clinical studies in preterm and term infants, as well as preclinical animal model studies, show that enrichment of infant formula with sn-2 Palmitate results in increased fat absorption, reduced calcium soaps formation and stool hardness, increased calcium retention and larger skeletal mineral deposition. [4] [5] [6] [8] [9]
Triglyceride digestion by endogenous lipases leads to hydrolysis of fatty acids from the triacylglyceride sn-1,3 positions, to release two fatty acids and one sn-2 monoglyceride into the intestinal lumen. [10] The fatty acids configuration on the triglyceride has a major contribution to the efficacy of this nutrient absorption. While the unsaturated and short chain saturated free fatty acids are well absorbed regardless of their position, [11] the absorption of free long chain saturated fatty acids, i.e. palmitic acid and longer, is relatively low. [12] The main cause for this low absorption is their melting point above body temperature (~630 C), and thus high tendency to create complexes with dietary minerals, such as calcium or magnesium [13] which are secreted into feces leading to loss of both fatty acids (energy) and calcium. These complexes, also known as fatty acids soaps, are insoluble and therefore indigestible and positively related to stool hardness. [14]
Litmanovitz et al. applied the bone speed of sound (SOS) ultrasound technology in a randomized, controlled, double-blind clinical study of bone parameters in term infants and showed that infants fed formula containing sn-2 Palmitate (INFAT®) had higher bone SOS compared to infants fed formula with standard vegetable oil blends at age of 12 weeks. [15] The bone SOS measures for infants fed the sn-2 Palmitate formula were also comparable to those of the group of breast-fed infants [15]
The intestinal microflora is an essential “organ” which serves numerous important functions, including protection against pathogens and modulation of inflammatory and immune responses, provision of metabolic intermediates and some vitamins, and regulation of intestinal epithelial proliferation and intestinal maturation. [16] [17] [18] Yaron et al. showed that infants fed formula containing sn-2 Palmitate had higher numbers of Lactobacilli and Bifidobacteria after 6 weeks of feeding than infants fed a control formula with standard vegetable oils. [19] Another recent experimental study published by Lu et al. has used the MUC2 deficient mice to address the possible role of milk palmitic acid content and positioning in triglycerides on intestinal inflammation.
"Stereo-specific positioning of fatty acids in human milk triglycerides involves preferential positioning of the saturated fatty acid palmitic acid (16:0) at the sn-2 position, rather than at the sn-1,3 positions, as is typical of human tissue and plasma lipids, and vegetable oils common in human diets." Early infant crying is considered to reflect basic, instinctive responses governed by neurochemical mechanisms similar to those that control feeding and drinking (i.e., spontaneous behaviors). Term infants fed formula with sn-2 Palmitate for the 12 weeks after birth demonstrated lower crying duration during the day and night compared to infants fed a standard vegetable oil [20]
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.
In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.
Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.
A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.
Essential fatty acids, or EFAs, are fatty acids that humans and other animals must ingest because the body requires them for good health but cannot synthesize them.
Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent FA in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C and a pKa of 4.50.
Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. It is a major component of the oil from the fruit of oil palms, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats. Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4). Palmitic acid is the most common SFA found in plants, animals, and many microorganisms. Major sources of C16:0 are palm oil, palm kernel oil, coconut oil, and milk fat.
Malabsorption is a state arising from abnormality in absorption of food nutrients across the gastrointestinal (GI) tract. Impairment can be of single or multiple nutrients depending on the abnormality. This may lead to malnutrition and a variety of anaemias.
Saponification value or saponification number represents the number of milligrams of potassium hydroxide (KOH) or sodium hydroxide (NaOH) required to saponify one gram of fat under the conditions specified. It is a measure of the average molecular weight of all the fatty acids present in the sample in form of triglycerides. The higher the saponification value, the lower the fatty acids average length, the lighter the mean molecular weight of triglycerides and vice versa. Practically, fats or oils with high saponification value are more suitable for soap making.
Jojoba oil is the liquid produced in the seed of the Simmondsia chinensis (jojoba) plant, a shrub, which is native to southern Arizona, southern California, and northwestern Mexico. The oil makes up approximately 50% of the jojoba seed by weight. The terms "jojoba oil" and "jojoba wax" are often used interchangeably because the wax visually appears to be a mobile oil, but as a wax it is composed almost entirely (~97%) of mono-esters of long-chain fatty acids (wax ester) and alcohols, accompanied by only a tiny fraction of triglyceride esters. This composition accounts for its extreme shelf-life stability and extraordinary resistance to high temperatures, compared with true vegetable oils.
Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. It is present in all tissues but, in general, found in higher concentrations in the liver. It is biosynthesized from palmitic acid by the action of the enzyme Stearoyl-CoA desaturase-1.
Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1-monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2-monoacylglycerols where the fatty acid is attached to the secondary alcohol.
Medium-chain triglycerides (MCTs) are triglycerides with two or three fatty acids having an aliphatic tail of 6–12 carbon atoms, i.e. medium-chain fatty acids (MCFAs). Rich food sources for commercial extraction of MCTs include palm kernel oil and coconut oil.
Lipid metabolism is the synthesis and degradation of lipids in cells, involving the breakdown and storage of fats for energy and the synthesis of structural and functional lipids, such as those involved in the construction of cell membranes. In animals, these fats are obtained from food and are synthesized by the liver. Lipogenesis is the process of synthesizing these fats. The majority of lipids found in the human body from ingesting food are triglycerides and cholesterol. Other types of lipids found in the body are fatty acids and membrane lipids. Lipid metabolism is often considered as the digestion and absorption process of dietary fat; however, there are two sources of fats that organisms can use to obtain energy: from consumed dietary fats and from stored fat. Vertebrates use both sources of fat to produce energy for organs such as the heart to function. Since lipids are hydrophobic molecules, they need to be solubilized before their metabolism can begin. Lipid metabolism often begins with hydrolysis, which occurs with the help of various enzymes in the digestive system. Lipid metabolism also occurs in plants, though the processes differ in some ways when compared to animals. The second step after the hydrolysis is the absorption of the fatty acids into the epithelial cells of the intestinal wall. In the epithelial cells, fatty acids are packaged and transported to the rest of the body.
Vaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food.
Diacylglycerol oil is a cooking oil in which the ratio of triglycerides, also known as Triacylglycerols (TAGs), to diacylglycerols (DAGs) is shifted to contain mostly DAG, unlike conventional cooking oils, which are rich in TAGs. Vegetable DAG oil, for example, contains 80% DAG and is used as a 1:1 replacement for liquid vegetable oils in all applications.
Fatty acid desaturase 2 (FADS2) is encoded by the FADS2 gene, the associated enzyme is sometimes known as FADS2 as well. Its main associated enzyme is Delta 6 desaturase (D6D) however the human enzyme been shown to also catalyze some delta-8 and delta-4 desaturases despite naming conventions.
Lipase inhibitors belong to a drug class that is used as an antiobesity agent. Their mode of action is to inhibit gastric and pancreatic lipases, enzymes that play an important role in the digestion of dietary fat. Lipase inhibitors are classified in the ATC-classification system as A08AB . Numerous compounds have been either isolated from nature, semi-synthesized, or fully synthesized and then screened for their lipase inhibitory activity but the only lipase inhibitor on the market is orlistat . Lipase inhibitors have also shown anticancer activity, by inhibiting fatty acid synthase.
Milk fat globule membrane (MFGM) is a complex and unique structure composed primarily of lipids and proteins that surrounds milk fat globule secreted from the milk producing cells of humans and other mammals. It is a source of multiple bioactive compounds, including phospholipids, glycolipids, glycoproteins, and carbohydrates that have important functional roles within the brain and gut.
Viscoleo is a thin or low-viscosity vegetable oil. It is specifically a proprietary form of fractionated coconut oil and a medium-chain triglyceride (MCT) oil. It is prepared from the dried, solid endosperm of the fruit Cocos nucifera via hydrolysis, fractionation, and purification. Viscoleo is composed of the medium-chain fatty acids caprylic acid (C8) (55–60%), capric acid (C10) (40%), lauric acid (C12) (1–5%), and caproic acid (C6) (0.5%). It is used as an oil vehicle for several depot antipsychotics including clopentixol decanoate, flupentixol decanoate, pipotiazine palmitate, zuclopentixol acetate, and zuclopentixol decanoate. Injectable antipsychotics using Viscoleo as a carrier may be absorbed more rapidly and have shorter durations than preparations using sesame oil.