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Lignoceric acid

Lignoceric acid, also known as tetracosanoic acid, is a saturated very long-chain fatty acid characterized by a 24-carbon backbone and the molecular formula C₂₄H₄₈O₂, with a molecular weight of 368.64 g/mol.^[1] It features a linear structure represented as CH₃(CH₂)₂₂COOH, and exhibits physical properties including a melting point of 80–82 °C, a boiling point of approximately 406 °C, and a density of about 0.9 g/cm³.^[2] Naturally occurring in sources such as wood tar, plant lipids, and small amounts in dietary fats like those from peanuts and olives, lignoceric acid is synthesized in mammals during brain development and serves as a key component of cerebrosides, which are essential lipids in the myelin sheath of nerve tissues.^[1]^[3] In biological systems, lignoceric acid plays a critical role in myelination, where it is incorporated into cerebrosides and can undergo alpha-hydroxylation to form cerebronic acid, contributing to the structural integrity and function of myelin lipids in both central and peripheral nervous systems.^[4] Its activation via acyl-CoA synthetases is implicated in cerebroside synthesis, supporting nerve conduction and maintenance.^[5] As a human metabolite and plant-derived compound, lignoceric acid is present in trace amounts in various foods and has been studied for its involvement in metabolic pathways, though it is not considered an essential fatty acid.^[1]

Chemical identity

Nomenclature and structure

Lignoceric acid is the common name for tetracosanoic acid, a straight-chain saturated fatty acid consisting of a 24-carbon hydrocarbon chain attached to a carboxylic acid group.^[6] The name "lignoceric" derives from the Latin lignum (meaning "wood") and Greek kēros (meaning "wax"), reflecting its initial isolation from wood tar, although it is not directly related to lignin. This fatty acid was first identified in the late 19th century through the distillation of beechwood or rotten oak wood tar.^[7] The molecular formula of lignoceric acid is C_{24}H_{48}O_2, and its structural formula is CH_3(CH_2)_{22}COOH, highlighting the unbranched alkyl chain with no double bonds.^[6] Under the International Union of Pure and Applied Chemistry (IUPAC) nomenclature for carboxylic acids, it is systematically named tetracosanoic acid, where "tetracos" refers to the 24-carbon chain derived from the parent alkane tetracosane (C_{24}H_{50}), with the suffix "-oic acid" indicating the carboxyl group at carbon 1. This naming convention standardizes fatty acids as alkanoic acids based on chain length and saturation. Lignoceric acid is classified as a very long-chain fatty acid (VLCFA) due to its 24 carbon atoms, surpassing the typical boundary of 22 carbons that distinguishes VLCFAs from long-chain fatty acids (12–22 carbons).^[8] This categorization is important in lipid biochemistry, as VLCFAs like lignoceric acid play specialized roles in cellular membranes, though such functions are beyond the scope of its chemical structure.

Physical properties

Lignoceric acid appears as a white to off-white crystalline solid at room temperature.^[9]^[10] Its melting point is approximately 84–86 °C.^[11]^[10] The boiling point is reported as 272 °C at 10 mm Hg pressure.^[12] Lignoceric acid is insoluble in water, with a solubility of approximately 5.93 × 10^{-6} mg/L at 25 °C, but it is soluble in organic solvents such as chloroform, ethanol, ethyl acetate (slightly when heated), and diethyl ether.^[11]^[13]^[14] The density of lignoceric acid is about 0.879 g/cm³.^[12] Its molecular weight is 368.64 g/mol.^[12] In infrared spectroscopy, lignoceric acid exhibits a characteristic carbonyl absorption band at approximately 1710 cm⁻¹, typical of saturated carboxylic acids.^[15] For nuclear magnetic resonance, the ^1H NMR spectrum shows signals for the long alkyl chain, including a terminal methyl group at around 0.9 ppm, methylene protons at 1.2–1.3 ppm, and the alpha-methylene to the carboxyl at about 2.3 ppm.

Sources and biosynthesis

Natural occurrence

Lignoceric acid occurs naturally in small amounts across various biological materials, primarily as a saturated very long-chain fatty acid (VLCFA) component of lipids. In plants, it is present in waxes such as beeswax, where it contributes to the free fatty acid fraction alongside cerotic and montanic acids.^[16] Similarly, carnauba wax from the leaves of Copernicia prunifera contains lignoceric acid at concentrations up to approximately 30% of its fatty acid content.^[17] It is also found in wood extractives and tall oil fractions derived from coniferous trees, often as a byproduct associated with lignin processing.^[18] In animal tissues, lignoceric acid is notably enriched in nervous system lipids, particularly within sphingomyelins of brain tissue, where it typically comprises 1–5% of the fatty acids, though VLCFAs as a group can reach up to 40% in certain myelin-related fractions.^[19] The overall concentration in human brain tissue averages 6–7 μmol/g, with higher levels in the cerebral cortex compared to the medulla.^[19] Traces are reported in other animal fats and in microbial lipids, including those from microalgae, seaweeds, and certain fungi, though often at low or undetectable levels in thermophilic species.^[18] In peanut oil, concentrations range from 1.1% to 2.2% of total fatty acids.^[11] As a minor VLCFA, lignoceric acid is evolutionarily conserved across eukaryotes, reflecting its incorporation into sphingolipids that are ubiquitous in eukaryotic membranes.^[20] Its identification in natural samples commonly relies on gas chromatography-mass spectrometry (GC-MS), which enables precise quantification after derivatization to fatty acid methyl esters.^[21]

Biosynthetic pathways

Lignoceric acid, a saturated very long-chain fatty acid (VLCFA) with 24 carbon atoms (C24:0), is biosynthesized through iterative elongation of shorter-chain fatty acids, primarily starting from palmitic acid (C16:0) in both animals and plants.^[22] In mammals, this process occurs in the endoplasmic reticulum (ER) and involves a multi-enzymatic cycle that adds two-carbon units to the acyl chain.^[20] The key rate-limiting enzyme is the elongase ELOVL1, which preferentially elongates saturated and monounsaturated acyl-CoAs from C20 to C26, including the production of C24:0-CoA essential for sphingolipid synthesis. ELOVL3 also contributes by elongating C16–C22 acyl-CoAs, supporting the stepwise extension toward C24:0.^[22] The elongation cycle consists of four sequential steps: (1) condensation of acyl-CoA with malonyl-CoA to form β-ketoacyl-CoA, catalyzed by ELOVL enzymes; (2) reduction of the β-keto group to β-hydroxyacyl-CoA using NADPH, mediated by β-ketoacyl-CoA reductase (KAR); (3) dehydration to form trans-2-enoyl-CoA by 3-hydroxyacyl-CoA dehydratase (HACD); and (4) a second NADPH-dependent reduction to yield the elongated acyl-CoA, catalyzed by trans-2-enoyl-CoA reductase (TER).^[20] The net reaction for one cycle of elongation can be outlined as:

\text{R-CH}_2\text{-CH}_2\text{-CO-SCoA} + \text{malonyl-CoA} + 2\text{ NADPH} \rightarrow \text{R-(CH}_2\text{)}_4\text{-CO-SCoA} + \text{CO}_2 + 2\text{ NADP}^+

This cycle repeats multiple times (typically four iterations from C16:0 to reach C24:0), with malonyl-CoA serving as the two-carbon donor derived from acetyl-CoA carboxylation. Regulation of lignoceric acid biosynthesis is influenced by the ER localization of the elongase complex, where enzyme activity is coordinated with downstream ceramide synthases (e.g., CERS2 for C24 sphingolipids) to match cellular demand, particularly in tissues like the brain where VLCFAs are enriched.^[23] In plants, the pathway shares similarities but utilizes a distinct set of ER-bound enzymes from the 3-ketoacyl-CoA synthase (KCS) family, such as KCS2 and KCS20, which elongate C16:0 or C18:0 precursors to C24:0 for incorporation into cuticular waxes, suberins, and sphingolipids; Arabidopsis possesses 21 KCS isoforms enabling greater chain-length diversity (up to C38) compared to the seven ELOVLs in mammals, reflecting adaptations for extracellular barrier functions rather than primarily membrane sphingolipids.^[24]

Biochemical roles

In sphingolipids

Lignoceric acid functions as a primary fatty acid component in sphingolipids, where it is attached via an amide linkage to the sphingosine backbone of ceramides, forming structures such as sphingomyelins and cerebrosides.^[25] This integration is particularly evident in kerasin, a type of cerebroside that incorporates lignoceric acid as its defining acyl chain.^[26] By esterifying to the ceramide core, lignoceric acid enhances the stability of the myelin sheath in nervous tissue, supporting the insulation of nerve fibers essential for efficient signal transmission. The extended 24-carbon chain of lignoceric acid imparts significant structural effects on sphingolipid-containing membranes, increasing their rigidity and elevating the gel-to-liquid crystalline phase transition temperature.^[27]^[28] These properties arise from stronger van der Waals interactions among the saturated, very long-chain fatty acyl groups, which promote tighter packing in lipid bilayers and contribute to the compact, multilayered architecture of myelin.^[29] In human brain sphingolipids, lignoceric acid is a major constituent of very long-chain fatty acids, with prominent occurrence in galactocerebrosides of nervous tissue.^[19] This composition underscores its role in maintaining myelin integrity; deficiencies or dysregulation in pathways involving lignoceric acid incorporation, such as those affected by mutations in peroxisomal transport genes, are linked to leukodystrophies that impair nerve insulation.^[30] Recent studies as of 2024 have also linked circulating levels of very long-chain saturated fatty acids, including lignoceric acid, to cognitive function and potential roles in neurodegenerative diseases.^[31]

Metabolism and degradation

Lignoceric acid, a very long-chain saturated fatty acid (VLCFA), undergoes activation to lignoceroyl-CoA prior to beta-oxidation, primarily catalyzed by lignoceroyl-CoA ligase enzymes located in peroxisomes and the endoplasmic reticulum, with lower activity in mitochondria.^[32] This activation step is essential for subsequent oxidative processing. In peroxisomal disorders like X-linked adrenoleukodystrophy (X-ALD), transport of lignoceroyl-CoA into peroxisomes is defective due to mutations in the ABCD1 gene, leading to impaired oxidation despite preserved ligase activity.^[33]^[34] Degradation of lignoceroyl-CoA occurs predominantly in peroxisomes, where initial rounds of beta-oxidation shorten the chain length through successive removal of two-carbon units, producing hydrogen peroxide as a byproduct via the action of acyl-CoA oxidase. Once shortened to medium- or long-chain lengths (typically C16-C18), the resulting acyl-CoAs are transferred to mitochondria for complete beta-oxidation to generate energy via the electron transport chain.^[32] This compartmentalized process ensures efficient handling of VLCFAs, which cannot be fully oxidized in mitochondria alone due to their length. Defects in peroxisomal beta-oxidation of lignoceric acid are central to disorders like X-linked adrenoleukodystrophy (X-ALD), caused by mutations in the ABCD1 gene encoding the ALDP protein, which transports VLCFA-CoAs into peroxisomes for oxidation.^[33] In X-ALD, oxidation rates for lignoceric acid are reduced to 38% of normal, leading to VLCFA accumulation in tissues and bodily fluids.^[33] Similarly, peroxisomal oxidation is severely impaired in Zellweger syndrome due to the absence of functional peroxisomes, with rates as low as 1.8% of controls, highlighting the organelle's exclusive role in initial VLCFA degradation.^[32] In normal physiology, lignoceric acid is largely fully oxidized for energy, with minor urinary excretion as shortened metabolites or conjugates, though specific profiles are limited and elevated in peroxisomal disorders. Its metabolism is regulated by dietary fat intake, which can induce peroxisomal enzyme expression via peroxisome proliferator-activated receptor alpha (PPARα), and hormonal signals such as those from liver X receptor alpha (LXRα), which modulates hepatic peroxisomal beta-oxidation activity.^[35]

Applications and research

Industrial uses

Lignoceric acid is primarily extracted from natural sources such as beechwood tar or through distillation of rotten oak wood, where it occurs as a minor component in lignocellulosic materials.^[7] Industrial purification involves isolating it from these mixtures via solvent extraction or distillation processes to achieve high purity for commercial use. Alternatively, it can be obtained as a byproduct from the processing of tall oil or plant waxes like sugar cane wax, which contain lignoceric alcohol as a precursor.^[17] A key industrial synthesis method involves the oxidation of lignoceric alcohol-rich mixtures derived from synthetic fatty alcohols (produced via paraffin oxidation) or natural waxes, using a quaternary ammonium peroxotungstophosphate catalyst and hydrogen peroxide at 90-120°C, followed by saponification, distillation, and acidification to yield the acid.^[17] This process enables bulk production from abundant raw materials, though it is not yet widely commercialized on a large scale. No established industrial hydrogenation routes from unsaturated C24 precursors have been documented for lignoceric acid production. In cosmetics, lignoceric acid serves as an emollient and softener in creams, dermal oils, and hair conditioners, leveraging its long-chain structure to provide moisturizing and conditioning properties that enhance skin barrier function and reduce water loss.^[17] It also functions as a surfactant and material processing agent in formulations for detergents and coatings, contributing to emulsification and stability due to its hydrophobic nature. Additionally, it finds use as a component in adhesives and indirect food additives, where its fatty acid profile aids in binding and protective layering.^[11] Lignoceric acid plays a minor role in the fatty acid mixtures used for soaps and high-performance lubricants, where its chain length imparts viscosity control and wear reduction, though it constitutes a small fraction of overall production volumes in these sectors. Its low natural abundance limits widespread adoption, with applications confined to niche, high-value products rather than bulk commodities.

Health and medical implications

Lignoceric acid, a very long-chain saturated fatty acid (VLCFA), accumulates in patients with X-linked adrenoleukodystrophy (X-ALD) due to mutations in the ABCD1 gene, which impair peroxisomal beta-oxidation of VLCFAs with chain lengths of 22 carbons or more. This accumulation, including elevated levels of lignoceric acid (C24:0), disrupts mitochondrial function, elevates reactive oxygen species (ROS), and deregulates calcium homeostasis, contributing to neurotoxicity particularly in oligodendrocytes and leading to progressive demyelination of the central nervous system.^[36]^[37]^[38] In infantile Refsum disease, a peroxisomal disorder primarily characterized by phytanic acid accumulation, defective beta-oxidation pathways also result in elevated VLCFAs such as lignoceric acid, exacerbating brain lipotoxicity through similar mechanisms of oxidative stress and mitochondrial impairment, which promote neuronal damage and peripheral neuropathy.^[38] Dietary intake of lignoceric acid is generally low, as it occurs in trace amounts in foods such as peanut oil and olive oil, contributing minimally to overall fatty acid consumption compared to shorter-chain fats. In the context of neurological support, particularly for demyelinating conditions like X-ALD, therapeutic diets incorporating related unsaturated VLCFAs (e.g., erucic acid) have been explored to modulate VLCFA levels and potentially mitigate disease progression, though direct supplementation with lignoceric acid remains uncommon.^[39]^[40] Research on lignoceric acid's role in myelin repair has focused on its incorporation into myelin lipids, with studies indicating that VLCFAs like lignoceric acid and its monounsaturated analog nervonic acid (C24:1) are essential for oligodendrocyte maturation and myelin sheath synthesis. In vitro investigations from the 2010s have shown that nervonic acid esters enhance myelin production in human oligodendrocytes by promoting lipid synthesis pathways, suggesting potential for analogs in repairing demyelination, though clinical trials specifically targeting lignoceric acid derivatives are limited. Antioxidant effects of lignoceric acid have not been extensively documented in vitro, but related long-chain fatty acids demonstrate capacity to reduce oxidative stress in cellular models, warranting further exploration for neuroprotective applications.^[41]^[42] Elevated levels of lignoceric acid have been observed in patients with psoriatic arthritis, associating with metabolic syndrome and systemic inflammation.^[43] Lignoceric acid exhibits low acute toxicity at physiological levels, with animal studies on similar saturated fatty acids reporting oral LD50 values exceeding 5 g/kg body weight, indicating general safety in dietary contexts. However, pathological accumulation of lignoceric acid, as seen in peroxisomal disorders, induces neurotoxicity through mitochondrial dysfunction and ROS-mediated cell death, highlighting the importance of metabolic balance for neurological health.^[44]^[45]^[38]

References

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Tetracosanoic Acid
Insufficient relevant content. The provided text only includes a PubChem page header with a logo and a JavaScript requirement notice, lacking specific details about Lignoceric acid (Tetracosanoic Acid | CID 11197). No synonyms, chemical formula, molecular weight, structure, properties, biological occurrence, natural sources, or medical significance are present.
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Lignoceric acid | CAS#:557-59-5 | Chemsrc
Aug 22, 2025 · Molecular Weight, 368.637 ; Density, 0.9±0.1 g/cm3 ; Boiling Point, 405.9±8.0 °C at 760 mmHg ; Molecular Formula, C24H48O ; Melting Point, 80-82 °C.
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Lignoceric acid is a 24-carbon saturated (24:0) fatty acid. In mammals, it is synthesized during brain development and is found in cerebrosides.
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Lignoceric acid is a long-chain fatty acid with more than 12 carbon atoms, found in dietary triglycerides, and involved in metabolic processes.
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Tetracosanoic Acid
**Summary of Tetracosanoic Acid (CID 11197) from PubChem**
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Lignoceric acid is defined as a very long-chain saturated fatty acid characterized by a 24-carbon chain length (C24:0) and can be sourced from various foods, ...
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Rating 5.0 (9) Lignoceric acid is a 24-carbon saturated (24:0) fatty acid. In mammals, it is synthesized during brain development and is found in cerebrosides.<|control11|><|separator|>
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