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Simple lipid

Simple lipids are a subclass of lipids defined as esters formed between fatty acids and various alcohols, such as glycerol or long-chain monohydric alcohols, without additional molecular components like phosphates or carbohydrates.^[1] They include fats and oils, which are triesters of glycerol (triglycerides), as well as waxes, which involve higher molecular weight alcohols.^[2] These compounds are characteristically hydrophobic, insoluble in water but soluble in nonpolar organic solvents, due to their long hydrocarbon chains.^[3] Fats and oils serve primarily as energy storage molecules in animals and plants, yielding approximately 9 kcal/g upon oxidation—more than twice the energy from carbohydrates or proteins—while also providing thermal insulation and cushioning for organs.^[4] Waxes, in contrast, function as protective coatings, such as in plant cuticles to prevent water loss or in animal secretions for waterproofing, like beeswax in hives.^[2] The physical state of simple lipids varies with fatty acid composition: saturated chains lead to solid fats at room temperature, whereas unsaturated chains result in liquid oils.^[3] Overall, simple lipids play essential roles in biological systems, from nutrient absorption—facilitating fat-soluble vitamins—to structural integrity in diverse organisms.^[3]

Definition and Classification

Definition

Simple lipids are esters formed between fatty acids and various alcohols, without the inclusion of additional functional groups such as phosphorus or carbohydrates.^[1] This composition distinguishes them as a fundamental class within lipid biochemistry, emphasizing their role as straightforward acyl derivatives.^[5] The classification of simple lipids traces back to early 20th-century biochemical efforts, particularly the system proposed by W. R. Bloor in his 1943 monograph Biochemistry of the Fatty Acids and Their Compounds, the Lipids, where he categorized lipids into simple, compound, and derived types based on chemical constitution.^[6] Bloor's framework highlighted simple lipids as those yielding only fatty acids and alcohols upon hydrolysis, providing a foundational nomenclature still referenced in modern lipid studies.^[7] Key characteristics of simple lipids include their pronounced hydrophobic properties, rendering them insoluble in water due to the nonpolar nature of their hydrocarbon chains, while they exhibit high solubility in nonpolar organic solvents such as chloroform, ether, and benzene.^[3] This solubility profile underscores their biological utility in energy storage and structural roles, as they aggregate in aqueous environments to form barriers against polar substances.^[1]

Classification

Lipids are broadly classified into three main categories based on their chemical composition and the products obtained upon hydrolysis: simple lipids, compound lipids, and derived lipids.^[1] Simple lipids are esters composed solely of fatty acids and alcohols, yielding only these two types of components upon hydrolysis.^[8] In contrast, compound lipids, such as phospholipids and glycolipids, produce fatty acids, alcohols, and additional groups like phosphoric acid or carbohydrates upon hydrolysis.^[1] Derived lipids, including steroids and fatty acids themselves, arise from the hydrolysis or further modification of simple or compound lipids and often lack ester linkages.^[1] Within the category of simple lipids, the primary types are neutral fats, also known as triacylglycerols, and waxes.^[8] Neutral fats consist of three fatty acid molecules esterified to a glycerol molecule, while waxes are esters of a single fatty acid with a long-chain alcohol.^[8] This classification emphasizes their role as non-polar, hydrophobic molecules that do not ionize in aqueous solutions.^[1] Simple lipids are further subdivided based on the degree of saturation in their fatty acid chains and their biological origins. Saturated simple lipids contain fatty acids with no carbon-carbon double bonds, resulting in straight-chain structures, whereas unsaturated simple lipids feature one or more cis double bonds, leading to kinked chains that affect packing and fluidity.^[8] Regarding origins, simple lipids from animal sources, such as lard or butter, tend to be more saturated and solid at room temperature, while those from plant sources, like olive or corn oil, are often more unsaturated and liquid.^[8] Waxes, though less common, occur in both animal (e.g., beeswax) and plant (e.g., carnauba wax) origins, serving protective functions.^[8]

Chemical Structure

Fatty Acids

Fatty acids are long-chain carboxylic acids consisting of a hydrocarbon chain attached to a carboxyl group, serving as the primary building blocks for simple lipids through esterification. The general formula for most fatty acids is CH₃(CH₂)ₙCOOH, where n represents the number of methylene groups and typically ranges from 4 to 22 or more, resulting in even-numbered carbon chains that are usually unbranched in naturally occurring forms. Fatty acids are classified as saturated or unsaturated based on the presence of carbon-carbon double bonds in their hydrocarbon chain. Saturated fatty acids contain no double bonds, with all carbon atoms linked by single bonds, such as palmitic acid (C16:0, hexadecanoic acid), a 16-carbon chain abundant in palm oil. Unsaturated fatty acids have one or more double bonds; monounsaturated types feature a single double bond, exemplified by oleic acid (C18:1, cis-9-octadecenoic acid), an 18-carbon chain common in olive oil, while polyunsaturated fatty acids contain multiple double bonds. Chain length further categorizes fatty acids, influencing their physical properties and biological roles: short-chain fatty acids have fewer than 6 carbon atoms (e.g., butyric acid, C4:0), medium-chain have 6 to 12 carbons (e.g., lauric acid, C12:0), long-chain have 13 to 21 carbons (e.g., stearic acid, C18:0), and very long-chain exceed 22 carbons (e.g., lignoceric acid, C24:0).^[9]^[10] Nomenclature for fatty acids employs both systematic IUPAC names, which specify chain length, double bond positions, and configuration (e.g., (9Z)-octadec-9-enoic acid for oleic acid), and common or trivial names derived from their discovery sources, such as palmitic acid from palm oil or oleic acid from olea (Latin for olive).^[11] The shorthand notation Cn:m indicates total carbons (n) and double bonds (m), with delta (Δ) or omega (ω) specifying positions.^[11] Naturally occurring fatty acids are primarily sourced from plant oils, animal fats, and microbial lipids, with saturated types predominant in animal tissues and coconut oil, while unsaturated types abound in seed oils like soybean and fish oils.^[12]^[13]

Alcohols

In simple lipids, particularly triacylglycerols, the primary alcohol component is glycerol, systematically named propane-1,2,3-triol, which serves as the backbone due to its three hydroxyl groups that enable esterification with fatty acids.^[3] Glycerol's structure is represented as HO-CH₂-CH(OH)-CH₂-OH, featuring a three-carbon chain with hydroxyl groups attached to each carbon, making it a polyhydric alcohol essential for forming the glycerol-based esters characteristic of these lipids.^[14] In contrast, waxes as simple lipids incorporate long-chain monohydric alcohols, such as cetyl alcohol (hexadecan-1-ol, C₁₆H₃₃OH) or higher homologs typically ranging from C₁₆ to C₃₆, which possess a single hydroxyl group at the end of an unbranched hydrocarbon chain.^[15] These alcohols differ markedly from glycerol in their monohydric nature, contributing to the hydrophobic and solid properties of waxes through ester linkages with fatty acids, unlike the more versatile polyhydric structure of glycerol that supports multiple ester bonds in triacylglycerols.^[16] This variety in alcohol types—polyhydric in glycerol versus monohydric in wax alcohols—highlights the structural diversity among simple lipids, where alcohols provide the variable partner to the relatively consistent fatty acid components.^[5]

Types

Triacylglycerols

Triacylglycerols, also known as triglycerides, are the most abundant simple lipids and serve as the primary form of fat storage in animals and plants. They consist of a glycerol molecule esterified with three fatty acid chains through ester linkages, forming a neutral, hydrophobic compound. The glycerol backbone has three hydroxyl groups that are replaced by acyl groups from the fatty acids, resulting in a structure where the fatty acids are attached at specific stereospecific positions: sn-1 (the top carbon), sn-2 (the middle carbon), and sn-3 (the bottom carbon) when the glycerol is oriented in the Fischer projection with the secondary hydroxyl group to the left. This stereospecific numbering (sn) system distinguishes the positions and is crucial for enzymatic specificity in biological processes.^[17] Triacylglycerols exhibit structural variations based on the nature and combination of their constituent fatty acids. Simple triacylglycerols feature three identical fatty acid chains, such as tristearin, which is composed of three stearic acid (C18:0, saturated) molecules and appears as a solid at room temperature. In contrast, mixed triacylglycerols contain two or three different fatty acids, allowing for greater diversity in composition, as seen in most natural fats and oils. Additionally, the degree of saturation influences the molecule: saturated triacylglycerols, with no double bonds in their fatty acid chains, tend to pack tightly due to straight hydrocarbon chains, while unsaturated ones, including those with polyunsaturated fatty acids (multiple double bonds), introduce kinks that reduce packing efficiency.^[3]^[8] The physical state of triacylglycerols at room temperature differentiates fats from oils, primarily determined by the unsaturation level of the fatty acids. Fats, such as lard derived from animal sources, are solid due to a higher proportion of saturated fatty acids that enable strong van der Waals interactions. Oils, like olive oil from plant sources, remain liquid because their unsaturated fatty acids, often monounsaturated or polyunsaturated, create bends in the chains that prevent close packing. For instance, triolein, a simple triacylglycerol with three oleic acid (C18:1, monounsaturated) chains, exemplifies an oil-like substance with a low melting point. These variations underscore the adaptability of triacylglycerols in biological energy storage and industrial applications.^[3]^[18]

Waxes

Waxes are simple lipids composed of esters formed between long-chain fatty acids and long-chain monohydric alcohols, distinguishing them from other lipid types through their single ester linkage.^[19] These monohydric alcohols, typically containing 16 to 30 carbon atoms, react with fatty acids of similar chain lengths to produce high-molecular-weight compounds that are nonpolar and insoluble in water.^[20] The general structure involves a fatty acid chain esterified to a single hydroxyl group on the alcohol, resulting in a molecule with hydrophobic properties suited for protective functions.^[21] Representative natural examples illustrate the diversity of wax compositions. Spermaceti, derived from the sperm whale, consists principally of cetyl palmitate, the ester of palmitic acid (a 16-carbon saturated fatty acid) and cetyl alcohol (a 16-carbon monohydric alcohol).^[22] Beeswax, produced by honeybees, is primarily myricyl palmitate—an ester of palmitic acid and myricyl alcohol (a 30-carbon alcohol)—along with cerotic acid esters and high-carbon paraffins, forming a complex mixture that contributes to its firmness.^[23] Carnauba wax, extracted from the leaves of the Copernicia prunifera palm, contains approximately 80-85% aliphatic esters, including those of hydroxy fatty acids, along with 10-16% fatty alcohols and minor hydrocarbons, giving it a harder texture compared to animal-derived waxes.^[24] Upon hydrolysis, waxes break down into one equivalent of a long-chain fatty acid and one equivalent of a long-chain monohydric alcohol, a reaction catalyzed by acids, bases, or enzymes, which differs from the multi-component glycerol release in other ester lipids.^[20] This de-esterification process is utilized industrially to recover valuable fatty acids and alcohols from natural waxes.^[25] Natural waxes, as defined in lipid biochemistry, are predominantly ester-based and derived from biological sources, whereas synthetic waxes are typically long-chain hydrocarbons without ester functional groups, such as paraffin wax produced from petroleum.^[21] Synthetic variants mimic the physical properties of natural waxes but lack the biochemical origins and ester structures characteristic of simple lipids.^[26]

Physical Properties

Solubility and Appearance

Simple lipids, such as fats, oils, and waxes, are characterized by their insolubility in water, a property arising from the predominance of nonpolar hydrocarbon chains in their molecular structure.^[3] This hydrophobicity prevents effective interaction with polar water molecules, leading to phase separation in aqueous environments.^[27] In contrast, simple lipids exhibit good solubility in nonpolar organic solvents, including hexane, chloroform, ether, and ethanol, which facilitate their extraction and analysis in laboratory settings.^[28]^[29] In terms of appearance, pure simple lipids are generally colorless and odorless, though natural sources often impart a pale yellow to yellowish hue due to the presence of pigments like carotenoids./17%3A_Lipids/17.2%3A_Fats_and_Oils)^[30] Fats typically present as opaque, solid materials with a greasy texture at room temperature, while oils appear transparent and possess a fluid, oily consistency.^[31] Waxes, another class of simple lipids, often display a waxy, solid texture that is harder and more brittle than fats.^[32] The density of simple lipids generally ranges from 0.8 to 0.95 g/cm³, which is lower than that of water (1.0 g/cm³), causing them to float on aqueous surfaces.^[33]^[34] The degree of unsaturation in the fatty acid components significantly influences the fluidity of simple lipids; unsaturated chains with cis double bonds introduce kinks that hinder tight packing, thereby increasing fluidity and lowering melting points compared to saturated counterparts.^[32]/02%3A_Biological_Membranes/2.02%3A_Maintaining_Fluidity_in_the_Membrane)

Melting and Boiling Points

Simple lipids, particularly triacylglycerols, exhibit melting points that vary significantly based on their composition, distinguishing fats from oils at room temperature. Fats, composed primarily of saturated fatty acids, typically melt between 20°C and 40°C due to the tight packing of their straight hydrocarbon chains, which allows for strong van der Waals interactions in the solid state.^[35] In contrast, oils, rich in unsaturated fatty acids, have melting points below 20°C because the kinks introduced by carbon-carbon double bonds disrupt chain packing and weaken intermolecular forces.^[8] For example, butter, a saturated fat, melts around 32–35°C, while olive oil, an unsaturated oil, melts near -6°C.^[36]^[8] Several factors influence these melting points. Longer fatty acid chain lengths increase the melting point by enhancing van der Waals attractions between molecules, as seen in saturated fatty acids where each additional methylene group raises the transition temperature.^[37] Conversely, a higher degree of unsaturation lowers the melting point, with each double bond reducing chain alignment and thus the energy required for phase transition.^[38] As noted in the fatty acids section, saturated chains pack more efficiently than unsaturated ones, directly impacting the thermal behavior of simple lipids.^[35] Boiling points of simple lipids are notably high, often exceeding 300°C, owing to their large molecular weights and extensive nonpolar surfaces that promote strong intermolecular forces. For instance, triolein and tripalmitin, common triacylglycerols, have normal boiling points around 416–419°C.^[39] However, these compounds frequently decompose thermally before reaching their boiling points, breaking down into glycerol and fatty acids at temperatures typically above 200–250°C.^[40] Fats also display polymorphism, where triacylglycerols can form multiple crystal structures with distinct melting behaviors. Common polymorphs include the alpha (α) form, which is least stable and melts at the lowest temperature; the beta-prime (β') form, offering better stability; and the beta (β) form, the most stable with the highest melting point.^[41] These variations arise from different packing arrangements of the hydrocarbon chains, influencing texture and functionality in applications like food processing.^[42]

Chemical Properties

Hydrolysis Reactions

Hydrolysis reactions of simple lipids involve the cleavage of ester bonds in triacylglycerols and waxes, typically yielding glycerol and fatty acids from triacylglycerols or a fatty acid and an alcohol from waxes.^[43]^[25] In acid-catalyzed hydrolysis, triacylglycerols react with water in the presence of a strong acid such as hydrochloric acid, producing glycerol and three molecules of fatty acids; this process follows a mechanism where the protonated carbonyl facilitates nucleophilic attack by water.^[43] The general equation for the acid hydrolysis of a triacylglycerol (triglyceride) is:

\text{(RCOO)}_3\text{C}_3\text{H}_5 + 3\text{H}_2\text{O} \xrightarrow{\text{H}^+} \text{C}_3\text{H}_5(\text{OH})_3 + 3\text{RCOOH}

where \text{R} represents the alkyl chains of the fatty acids.^[43] For waxes, which are esters of long-chain fatty acids and alcohols, acid hydrolysis similarly breaks the ester linkage to yield one equivalent each of a fatty acid and a fatty alcohol, such as palmitic acid and hexadecanol from a simple wax ester.^[25] Base-catalyzed hydrolysis, or saponification, specifically targets triacylglycerols by reacting them with a strong alkali like sodium hydroxide, resulting in glycerol and the sodium salts of fatty acids (soaps).^[44] This irreversible process proceeds via nucleophilic attack by the hydroxide ion on the carbonyl carbon of the ester, forming a tetrahedral intermediate that collapses to release the carboxylate anion.^[44] Enzymatic hydrolysis of triacylglycerols occurs primarily during digestion through the action of lipases, which catalyze the breakdown into glycerol, free fatty acids, and mono- or diacylglycerols.^[45] These enzymes exhibit regioselectivity, with pancreatic lipase preferentially hydrolyzing the ester bonds at the sn-1 and sn-3 positions of the glycerol backbone, leaving 2-monoacylglycerols, while gastric lipase targets the sn-3 position.^[46] This specificity ensures efficient release of fatty acids for absorption in the intestine.^[47] The rate of hydrolysis for simple lipids is influenced by environmental conditions, including pH and temperature. Acid and base hydrolysis rates increase with temperature due to enhanced molecular kinetic energy, with optimal rates often observed above 100°C under hydrothermal conditions for triacylglycerols.^[48] Enzymatic hydrolysis by lipases is pH-dependent, with maximal activity typically at neutral to slightly alkaline pH (around 7-8), where the enzyme's active site serine is optimally protonated for catalysis; deviations, such as acidic conditions in the stomach, slow the rate but allow initial gastric lipolysis.^[49] Temperature optima for lipases align with physiological conditions at approximately 37°C, beyond which denaturation reduces activity.^[50]

Oxidation and Rancidity

Oxidation of simple lipids, particularly those containing unsaturated fatty acids, leads to rancidity through auto-oxidation, a free radical chain reaction primarily targeting double bonds in the lipid chains.^[51] This process is especially relevant for triacylglycerols and waxes with polyunsaturated components, where the allylic hydrogens at double bonds are abstracted, initiating degradation.^[52] The mechanism proceeds in three phases: initiation, propagation, and termination. In initiation, external factors generate the first lipid radical (L•) from a lipid molecule (LH). Propagation involves the lipid radical reacting with oxygen to form a peroxy radical (LOO•), which then abstracts a hydrogen from another lipid, yielding a lipid hydroperoxide (LOOH) and regenerating L•. This cycle is depicted in the following simplified equations for the propagation steps:

\text{L}^\bullet + \text{O}_2 \rightarrow \text{LOO}^\bullet

\text{LOO}^\bullet + \text{LH} \rightarrow \text{LOOH} + \text{L}^\bullet

Termination occurs when radicals combine, halting the chain.^[53] Hydroperoxides decompose further into secondary products like aldehydes, contributing to off-flavors and odors.^[54] Rancidity in simple lipids manifests in two main types: oxidative rancidity, driven by exposure to oxygen and leading to peroxide formation and volatile compounds, and hydrolytic rancidity, resulting from moisture-induced breakdown into free fatty acids, though the former predominates in unsaturated lipids.^[55] Oxidative rancidity shortens shelf life by producing rancid tastes and smells, such as those from hexanal or malondialdehyde, which render food unpalatable and nutritionally degraded. Several factors accelerate oxidative rancidity, including light, which generates singlet oxygen to initiate radicals; heat, which lowers activation energy for bond breaking; and pro-oxidant metals like iron or copper, which catalyze peroxide decomposition. Prevention strategies employ antioxidants, such as butylated hydroxytoluene (BHT), which donate hydrogens to scavenge radicals and interrupt the chain reaction, thereby extending shelf life in stored lipids.^[56]

Biological Roles

Energy Storage and Metabolism

Simple lipids, particularly triacylglycerols, serve as the primary form of energy storage in animals, providing approximately 9 kcal per gram upon oxidation, compared to 4 kcal per gram for carbohydrates.^[57] This high energy density makes them efficient for long-term energy reserves, as they are stored in specialized adipose tissue without the osmotic drawbacks associated with carbohydrate storage.^[58] In times of energy demand, such as fasting or exercise, triacylglycerols are hydrolyzed to release free fatty acids, which are then transported to tissues for utilization.^[59] The catabolism of fatty acids occurs primarily through the β-oxidation pathway in the mitochondrial matrix, where fatty acyl-CoA molecules are sequentially shortened by two-carbon units to produce acetyl-CoA.^[58] Each cycle of β-oxidation involves four enzymatic steps: dehydrogenation by acyl-CoA dehydrogenase (yielding FADH₂), hydration by enoyl-CoA hydratase, a second dehydrogenation by 3-hydroxyacyl-CoA dehydrogenase (yielding NADH), and thiolysis by β-ketothiolase to release acetyl-CoA./09%3A_Food_to_energy_metabolic_pathways/9.06%3A_Oxidation_of_fatty_acids) The overall equation for one cycle is:

\text{C}_n\text{-acyl-CoA} + \text{FAD} + \text{NAD}^+ + \text{H}_2\text{O} + \text{CoA} \rightarrow \text{C}_{n-2}\text{-acyl-CoA} + \text{FADH}_2 + \text{NADH} + \text{H}^+ + \text{acetyl-CoA}

This process generates reducing equivalents that enter the electron transport chain to produce ATP, with complete oxidation of a typical fatty acid yielding significantly more energy than glucose.^[58] Conversely, lipogenesis enables the synthesis of fatty acids from excess carbohydrates, primarily in the liver and adipose tissue, when energy intake exceeds immediate needs. Glucose is metabolized to acetyl-CoA via glycolysis and pyruvate dehydrogenase; this acetyl-CoA is then carboxylated to malonyl-CoA by acetyl-CoA carboxylase, the rate-limiting enzyme.^[60] Subsequent elongation occurs through fatty acid synthase, a multifunctional enzyme complex that adds two-carbon units from malonyl-CoA to build palmitate, the precursor for longer-chain fatty acids incorporated into triacylglycerols.^[61] Hormonal signals tightly regulate this balance between storage and mobilization. Insulin, elevated after meals, promotes lipogenesis by activating acetyl-CoA carboxylase and inhibiting hormone-sensitive lipase, favoring fatty acid synthesis and triacylglycerol storage in adipose tissue.^[59] In contrast, glucagon, released during fasting, stimulates lipolysis by activating hormone-sensitive lipase and adenylate cyclase, mobilizing fatty acids for β-oxidation while suppressing lipogenic enzymes.^[62] This reciprocal control ensures metabolic flexibility in response to nutritional status.^[59]

Structural and Protective Functions

Simple lipids, particularly waxes, serve as essential waterproof barriers in both plants and animals, leveraging their hydrophobic nature to prevent water loss and external threats. In plants, cuticular waxes form a protective layer on leaf surfaces, reducing transpiration and desiccation by creating a hydrophobic barrier that minimizes water evaporation.^[63] For instance, these epicuticular waxes on plant cuticles act as the primary interface against environmental stresses, including drought and pathogen entry.^[64] In animals, cerumen (earwax), composed of simple lipid esters, coats the ear canal to provide waterproofing, trap debris, and inhibit microbial invasion, thereby protecting the auditory system.^[65] Triacylglycerols in adipose tissue fulfill critical structural roles in mammals, including thermal insulation through subcutaneous fat layers that reduce heat loss by acting as a poor conductor of thermal energy.^[66] This insulation is vital for maintaining core body temperature in endothermic organisms, with the fat layer surrounding vital organs further providing mechanical cushioning against physical trauma.^[29] Additionally, adipose deposits contribute to buoyancy in aquatic mammals, such as whales, where blubber layers not only insulate but also enhance flotation and protect internal structures from compressive forces during diving.^[67] Simple lipids also facilitate the absorption of fat-soluble vitamins A, D, E, and K in the digestive system, as these vitamins require incorporation into lipid micelles for efficient uptake in the small intestine.^[68] Dietary fats enhance this process by promoting micelle formation, ensuring that these essential micronutrients are solubilized and transported across the intestinal epithelium, which is crucial for functions like vision, bone health, and antioxidant defense.^[69]

Occurrence and Sources

In Animals

In animals, simple lipids, primarily in the form of triglycerides, are predominantly stored in adipose tissue, which serves as the main reservoir for energy and insulation. White adipose tissue (WAT) consists of adipocytes that contain a large single lipid droplet, enabling efficient long-term storage of excess energy derived from dietary intake.^[70] In contrast, brown adipose tissue (BAT) features multiple smaller lipid droplets per cell alongside abundant mitochondria, facilitating thermogenesis through uncoupled respiration to generate heat, particularly in newborns and hibernating species.^[71] These tissues highlight the dual roles of simple lipids in energy conservation and thermal regulation across vertebrate physiology. Specialized adaptations underscore the distribution of simple lipids in animal tissues. In marine mammals like whales, blubber—a thick layer of subcutaneous adipose tissue—comprises up to 93% lipids, primarily triglycerides, providing superior thermal insulation with conductivity about one-tenth that of water, essential for survival in cold oceanic environments.^[72] Similarly, mammalian milk fats, dominated by triacylglycerols, supply 40-50% of the energy needs for neonatal growth and development, with compositions varying by species to optimize nutrient delivery.^[73] These examples illustrate how simple lipids contribute to protection and nutrition in specific physiological contexts. Dietary animal fats, such as tallow from beef and lard from pork, represent concentrated sources of simple lipids for human and animal consumption, typically featuring high saturated fatty acid content for stability. Beef tallow contains approximately 50% saturated fats, while lard has about 40%, influencing their use in energy-dense diets and industrial applications.^[74] Evolutionarily, many mammals have adapted fat reserves for seasonal survival, as seen in hibernators like bears and ground squirrels, where pre-hibernation hyperphagia builds triglyceride stores to fuel prolonged torpor, enabling metabolic suppression and reliance on lipid oxidation without external food intake.^[75] This adaptation reflects convergent evolutionary pressures for enduring nutritional scarcity.^[76]

In Plants and Microorganisms

In plants, simple lipids such as triglycerides are predominantly stored as oils and fats in seeds, fruits, and other reproductive structures, serving as energy reserves for germination and growth. For instance, sunflower seeds can contain up to 70% triglycerides by weight, primarily in the embryo, while soybeans accumulate around 20% in their cotyledons. Other notable examples include peanut seeds (44% lipids), almond kernels (55%), and walnut seeds (65%), where these triglycerides are composed mainly of unsaturated fatty acids like oleic and linoleic acid. Pulp oils from fruits, such as olive (from mesocarp) and avocado, also consist largely of triglycerides, often exceeding 50% oleic acid content.^[77]^[3] Plant waxes, another class of simple lipids, form a hydrophobic coating on leaves, stems, fruits, and flowers, providing protection against water loss, pathogens, and environmental stress. These waxes are esters of long-chain fatty acids (typically C16-C34) and long-chain alcohols, with common examples including cuticular waxes on leafy surfaces that reduce transpiration and deter herbivores. In specialized cases, such as jojoba seeds, waxes replace triglycerides as the primary storage lipid, comprising liquid wax esters rich in eicosenoic acid.^[3]^[19]^[77] In microorganisms, triglycerides (triacylglycerols or TAGs) function as neutral storage lipids in oleaginous species, accumulating in lipid bodies within the cytoplasm to support energy needs during nutrient limitation. Oleaginous yeasts like Yarrowia lipolytica and Rhodotorula glutinis can amass TAGs up to 70% of their dry biomass, synthesized via the Kennedy pathway involving glycerol-3-phosphate acylation. Certain fungi, such as Mucor species, and bacteria like Rhodococcus opacus also store significant TAGs, often exceeding 20-50% of cell weight under carbon-rich conditions, making them promising for biofuel production. These lipids typically feature a mix of saturated and unsaturated fatty acids, with palmitic and oleic acids predominant.^[78]^[79]^[80] Microbial waxes, including wax esters, occur less frequently than TAGs but play roles in cell envelope structure and protection, particularly in bacteria and fungi. In mycobacteria like Mycobacterium tuberculosis, a thick waxy layer comprising mycolic acids (long-chain fatty acid derivatives) forms up to 40% of the cell envelope, conferring resistance to antibiotics, desiccation, and host immune responses. Fungi and engineered yeasts such as Yarrowia lipolytica can produce wax esters through fatty acid reduction and alcohol acylation, often alongside TAGs for applications in cosmetics and lubricants. Some bacteria, including Escherichia coli variants, synthesize wax esters at low levels (up to 25% of total lipids) when metabolically engineered, highlighting their potential as non-food lipid sources.^[81]^[82]^[78]

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The composition of carnauba wax is esterified fatty dialcohols, hydroxylated fatty acids, cinnamic acid, fatty esters, free alcohols, hydrocarbons, and acids ( ...
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May 12, 2023 · In this paper we describe a simple method to 1) isolate the wax esters from the other lipid classes present in the oil, 2) hydrolyze the wax esters, and 3) ...
[25]
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Lipid Classification For purposes of simplicity of study lipids are divided into five categories based on their function: • Energy-storage lipids – A fat, ...
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[35]
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[36]
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[37]
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Based on the number of carbon atoms in the alkyl chain length, fatty acids can be classified into short-chain (2–4 carbon atoms), medium-chain (6–10 carbon ...
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The measure of some triacylglycerols and ethyl esters boiling points at 709.20 mm Hg and normal boiling points was accomplished in this work. Additionally ...
[39]
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This feature gives the fat its plasticity. Heating causes the triglycerides to break down into their component parts and decompose.
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Fat crystal polymorphism is characterized by the capability of triacylglycerol (TAG) molecules to arrange in different crystal lattice structures yet having an ...
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Acid hydrolysis of a triglyceride (triacylglycerol) produces glycerol and 3 fatty acids as shown in the general chemical equation given below.
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May 30, 2020 · The hydrolysis of fats and oils in the presence of a base is used to make soap and is called saponification.
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Jul 17, 2023 · Lipolysis is the metabolic process through which triacylglycerols (TAGs) break down via hydrolysis into their constituent molecules: glycerol and free fatty ...<|separator|>
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Investigating effect of temperature on the activity of lipase
When the pH drops below pH 8.3 phenolphthalein goes colourless. Here, an alkaline solution of milk, lipase and phenolphthalein will change from pink to ...
[50]
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Within the process of lipid peroxidation three partially overlapping phases of radical reactions can be distinguished: initiation, propagation, and termination ...
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[53]
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[55]
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Butylated hydroxytoluene (BHT) is a phenolic antioxidant; Phenolic antioxidants prevent rancidity of fats and oils in food by protecting against lipid oxidation ...
[56]
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The energy content (bomb calorimetry) of MCTs is approximately 8 kcal/g, in comparison with 9 kcal/g for LCTs because a higher fraction of the carbon atoms in ...
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Transportation of long-chain fatty acids into the mitochondrial matrix requires three enzymes in addition to acyl-CoA synthetase. The transport of fatty acyl- ...
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Oct 19, 2022 · Hormones like adrenaline, norepinephrine, and glucagon triggered by fasting, starvation and sympathetic excitement stimulate fat mobilization.
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Barrier properties of cuticles are established by cuticular wax deposited on the outer surface of the cuticle (epicuticular wax) and in the cutin polymer ( ...
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Earwax helps to keep pathogens out of your ear by providing waterproofing and stickiness that catches things before they go deeper. Using cotton swabs in the ...
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In addition, to its energy storing function, WAT serves numerous nonmetabolic functions, including thermal insulation, and support and cushioning of organs 4.
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By itself, blubber is a good insulator because it can be up to 93% lipid, has even less thermal conductance than asbestos, and about 1/10th that of water (Table ...
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Feb 7, 2024 · 50% saturated fat · 42% monounsaturated fat · 4% polyunsaturated fat.
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Lipid metabolism in adaptation to extreme nutritional challenges
May 17, 2021 · These large fat depots, coupled with a dramatic reduction in the whole-body metabolism, allow extended use of fatty acid oxidation throughout ...
[75]
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These physiological shifts allow hibernators to rely solely on fat reserves, simultaneously avoiding the adverse effects of prolonged immobility seen in ...<|control11|><|separator|>
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Plant oils and fats, mainly in seeds, are mostly triglycerides. They are classified as pulp or seed oils, with varying lipid amounts, and are used for ...
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Microbial lipids refer to lipids produced by microorganisms, including a diverse range of compounds such as triacylglycerols, biosurfactants, and polyesters ...
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A comprehensive review on oleaginous bacteria: an alternative ...
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May 29, 2020 · This pathogen's remarkable resilience and infectivity is largely due to its unique waxy cell envelope, 40% of which comprises complex lipids.
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Introduction. Wax esters (WE) are neutral lipid compounds composed of fatty acids esterified to long-chain fatty alcohols.Missing: simple | Show results with:simple<|control11|><|separator|>