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Lignoceric acid (wood tar acid; Tetracosanoic acid)

Cat No.:V81997 Purity: ≥98%
Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid synthesized in the developing brain.
Lignoceric acid (wood tar acid; Tetracosanoic acid)
Lignoceric acid (wood tar acid; Tetracosanoic acid) Chemical Structure CAS No.: 557-59-5
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes

Other Forms of Lignoceric acid (wood tar acid; Tetracosanoic acid):

  • Lignoceric acid-d47 (Tetracosanoic acid-d47)
  • Lignoceric acid-d4-1 (lignoceric acid d4-1)
  • Lignoceric acid-d4-2
  • Lignoceric acid-d9
  • Lignoceric acid-d3 (lignoceric acid-d3; Tetracosanoic acid-d3)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid may be utilized in the study of Zellweger's cerebral-hepatic-renal syndrome and adrenoleukodystrophy.
Lignoceric acid (wood tar acid; Tetracosanoic acid) is a saturated very long-chain fatty acid (VLCFA) with a 24-carbon chain; it is found naturally in wood tar, peanut oil, and various plant and animal lipids and is a component of sphingolipids in the brain and nervous system.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
Lignoceric acid targets fatty acid metabolic pathways; it is a substrate for enzymes involved in fatty acid oxidation, elongation, and incorporation into complex lipids; it does not have a specific pharmacological receptor but is a metabolic intermediate and structural lipid component.
ln Vitro
Normal peroxisomal metabolism is shown by the exothermic heat flux in HepG2 peroxisomes produced by lignoceric acid [1].
In vitro, Lignoceric acid is used in cell culture studies to investigate fatty acid metabolism, lipid synthesis, and the effects of VLCFAs on cellular function; it is incorporated into cellular lipids and can modulate membrane properties and signaling pathways.
ln Vivo
In vivo, Lignoceric acid is a normal constituent of mammalian tissues, particularly in the brain where it is a component of cerebrosides and sulfatides; its levels are elevated in X-linked adrenoleukodystrophy (X-ALD) due to impaired peroxisomal β-oxidation; it is used as a biomarker for VLCFA accumulation.
Enzyme Assay
Non-cellular assay: Lignoceric acid is analyzed by gas chromatography (GC) or LC-MS following derivatization to fatty acid methyl esters (FAMEs); it is used as a standard for the quantification of VLCFAs in biological samples; its concentration is determined by comparison to internal standards in analytical methods.
Cell Assay
Cellular assays: Cells (e.g., fibroblasts from X-ALD patients or control subjects) are cultured with Lignoceric acid or in medium containing the compound; cellular lipid extracts are analyzed by GC or LC-MS to measure VLCFA levels; effects on cell viability, oxidative stress, and gene expression are assessed.
Animal Protocol
In vivo animal experiments: Lignoceric acid is administered to animal models or used as a dietary supplement to study VLCFA metabolism; its levels in plasma and tissues are measured to assess peroxisomal function; in X-ALD model mice, Lignoceric acid levels are monitored as a biomarker of disease progression and therapeutic efficacy.
ADME/Pharmacokinetics
Pharmacokinetic properties: Lignoceric acid is a lipophilic fatty acid that is absorbed from the diet, incorporated into lipoproteins, and distributed to tissues; it is metabolized by peroxisomal β-oxidation; its levels are regulated by synthesis, dietary intake, and degradation.
Toxicity/Toxicokinetics
Toxicological profile: Lignoceric acid is a naturally occurring fatty acid with low toxicity at physiological levels; elevated levels are associated with X-ALD and other peroxisomal disorders; it is not considered toxic per se but its accumulation is pathogenic in the context of metabolic disease.
References

[1]. Thermogenic flux induced by lignoceric acid in peroxisomes isolated from HepG2 cells and from X-adrenoleukodystrophy and control fibroblasts. J Cell Physiol. 2019 Aug;234(10):18344-18348.

[2]. Lignoceric acid biosynthesis in the developing brain. Activities of mitochondrial acetyl-CoA-dependent synthesis and microsomal malonyl-CoA chain-elongating system in relation to myelination. Comparison between normal mouse and dysmyelinating mutants (quaking and jimpy). Eur J Biochem. 1977 Jan 3;72(1):41-7.

Additional Infomation
Tetracosanoic acid (TCA) is a C24 straight-chain saturated fatty acid. It is a volatile oil component, a plant metabolite, a human metabolite, and a metabolite of the dark-colored water flea (Daphnia tenebrosa). It is a long-chain fatty acid and also a straight-chain saturated fatty acid. It is the conjugate acid of TCA. TCA has been reported to exist in hybrid amaranth (Amaranthus hybridus), shield-leaved amaranth (Tornabea scutellifera), and other organisms with relevant data. Cinnamic acid is a saturated fatty acid with a 24-carbon skeleton. Cinnamic acid is naturally found in wood tar, various cerebrosides, and in small amounts in most natural fats. Cinnamic acid is a metabolite found in or produced by the yeast Saccharomyces cerevisiae.
Other information: Lignoceric acid has a molecular formula of C₂₄H₄₈O₂ and a molecular weight of 368.64; it is used as a biomarker for the diagnosis and monitoring of X-linked adrenoleukodystrophy; it is also studied in the context of sphingolipid metabolism and neurodegenerative diseases.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C24H48O2
Molecular Weight
368.64
Exact Mass
368.365
CAS #
557-59-5
Related CAS #
Lignoceric acid-d47;68060-00-4;Lignoceric acid-d4-1;1219794-59-8;Lignoceric acid-d4-2;1219794-61-2;Lignoceric acid-d9;2415226-90-1;Lignoceric acid-d3;851073-55-7
PubChem CID
11197
Appearance
White to off-white solid powder
Density
0.9±0.1 g/cm3
Boiling Point
405.9±8.0 °C at 760 mmHg
Melting Point
84.2 °C
Flash Point
182.2±13.3 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.460
LogP
11.4
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
22
Heavy Atom Count
26
Complexity
275
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(=O)O
InChi Key
QZZGJDVWLFXDLK-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)
Chemical Name
tetracosanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
Ethanol :~8.33 mg/mL (~22.60 mM )
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 0.83 mg/mL (2.25 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear EtOH + stock solution to 900 μL of corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7127 mL 13.5634 mL 27.1267 mL
5 mM 0.5425 mL 2.7127 mL 5.4253 mL
10 mM 0.2713 mL 1.3563 mL 2.7127 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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