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| 5g |
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| Other Sizes |
| Targets |
Leukotriene A4 hydrolase (LTA4H), an enzyme in the arachidonic acid metabolism pathway that converts leukotriene A4 (LTA4) to leukotriene B4 (LTB4), a potent chemoattractant and pro-inflammatory mediator. Methyl arachidate acts as an inhibitor of LTA4H, blocking the production of LTB4 and thereby reducing inflammation. By inhibiting LTA4H, the compound may modulate inflammatory responses, making it of interest for research into inflammatory diseases such as asthma, arthritis, and inflammatory bowel disease. Methyl arachidate also has antifungal, antioxidant, and anti-inflammatory properties that may be mediated through additional mechanisms beyond LTA4H inhibition.
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| ln Vitro |
Methyl arachidate (Methyl eicosanoate) is a natural compound that functions as an inhibitor of leukotriene A4 hydrolase (LTA4H). The compound has been shown to inhibit LTA4H activity in cell-free enzyme assays, although the exact IC₅0 value has not been widely reported in publicly available literature. Beyond its LTA4H inhibitory activity, Methyl arachidate exhibits antifungal, antioxidant, and anti-inflammatory properties based on relevant research findings. As a fatty acid methyl ester, it is a saturated long-chain fatty acid ester that may also affect membrane fluidity and lipid signaling pathways. The compound has been studied in the context of lipidomics and metabolic research for its effects on lipid metabolism. It may also have potential as a standard for GC-MS analysis of fatty acid methyl esters in biological samples. The compound's ability to modulate immune system function and lipid metabolism makes it a promising tool for further research.
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| ln Vivo |
In vivo studies have shown that Methyl arachidate and related compounds may have anti-inflammatory effects in animal models. For example, a related compound (aramchol, arachidyl amido cholanoic acid) prevents the formation of cholesterol gallstones in inbred mice, suggesting that fatty acid derivatives can affect lipid metabolism and cholesterol homeostasis in vivo. However, specific in vivo studies on Methyl arachidate itself are limited. Based on its LTA4H inhibitory activity, Methyl arachidate would be expected to reduce LTB4 production and inflammation in vivo, potentially in models of acute inflammation (e.g., carrageenan-induced paw edema) or chronic inflammation (e.g., collagen-induced arthritis). The compound's natural occurrence in food sources (potatoes) suggests that it may have low toxicity in vivo at dietary levels. Further animal studies are needed to fully characterize its in vivo efficacy, pharmacokinetics, and anti-inflammatory effects.
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| Enzyme Assay |
In vitro LTA4H enzyme inhibition assay: Human recombinant LTA4H is incubated with varying concentrations of Methyl arachidate (0.1-100 microM) in assay buffer (e.g., 50 mM Tris-HCl, pH 7.8, 100 mM NaCl) for 10-30 minutes at 37degC. The substrate leukotriene A4 (LTA4, typically prepared from methyl ester or generated enzymatically) is added. The reaction is carried out for 1-5 minutes at room temperature or 37degC. The product LTB4 is extracted and quantified by reverse-phase HPLC with UV detection (270 nm) or by LC-MS/MS. Alternatively, a fluorogenic substrate (e.g., alanine-AMC or other LTA4H substrates) can be used to measure enzyme activity, with inhibition calculated based on reduction in fluorescence. IC₅0 values are calculated from concentration-response curves. Methyl arachidate is a natural LTA4H inhibitor, and its activity has been confirmed in this type of assay. Positive controls (e.g., bestatin, a known LTA4H inhibitor) should be included. The compound should be dissolved in DMSO or ethanol, and final solvent concentration should be kept low to avoid interference with enzyme activity.
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| Cell Assay |
For cell-based studies, appropriate cell lines (e.g., neutrophils, macrophages, or LTA4H-expressing cell lines) are seeded in culture plates. Cells are treated with Methyl arachidate (0.1-100 microM) for 1-24 hours. For LTB4 production assays, cells are stimulated with calcium ionophore A23187 or other LTA4H activators. LTB4 levels in cell culture supernatants are quantified by ELISA or LC-MS/MS. Cell viability is assessed by MTT or CCK-8 assay to ensure that any reduction in LTB4 is not due to cytotoxicity. Inflammation-related gene expression (e.g., IL-6, TNF-alpha, COX-2) can be assessed by qPCR. The compound‘s effects on lipid metabolism can be studied by lipidomic analysis of cellular lipid profiles (fatty acid composition, lipid classes) using GC-MS or LC-MS after lipid extraction. All experiments should be performed in triplicate with appropriate controls (vehicle-treated cells). The compound is often used as a standard for GC-MS and LC-MS analysis of fatty acid methyl esters; therefore, careful attention should be paid to potential contamination from endogenous fatty acids in the cell culture medium. The use of lipid-depleted serum or defined media may be necessary for some experiments.
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| Animal Protocol |
For in vivo studies to assess anti-inflammatory effects, male rats or mice can be used in a carrageenan-induced paw edema model. Methyl arachidate (10-100 mg/kg) is administered orally or intraperitoneally 1-2 hours prior to subplantar injection of 1% carrageenan (50-100 microL) into the hind paw. Paw volume is measured using a plethysmometer at 0, 1, 2, 3, 4, and 6 hours after carrageenan injection. Percentage inhibition of edema is calculated compared to vehicle control. LTB4 levels in paw tissue homogenates can be measured by ELISA to confirm target engagement. Alternatively, in an LPS-induced inflammation model, animals are treated with Methyl arachidate (10-100 mg/kg, oral or ip) 1-2 hours prior to LPS injection (1-5 mg/kg, ip). Blood and tissue samples are collected 2-6 hours after LPS for measurement of inflammatory cytokines (TNF-alpha, IL-6, IL-1beta by ELISA) and LTB4 levels. Endpoints include reduction in cytokine levels, body temperature, and inflammatory markers. For studies on lipid metabolism, animals may be fed a high-fat diet with or without Methyl arachidate supplementation. Serum lipid profiles (triglycerides, cholesterol, free fatty acids) are measured. Animal studies should be conducted in accordance with institutional animal care and use guidelines.
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| ADME/Pharmacokinetics |
Methyl arachidate (Methyl eicosanoate) has a molecular weight of 326.56, molecular formula C21H42O2, and purity typically ≥95-98%. The compound appears as a white to off-white solid powder with a melting point of 45-48degC. Solubility: DMSO (2 mg/mL, 6.12 mM) and likely soluble in organic solvents such as ethanol, methanol, chloroform, and hexane. For in vivo studies, formulations may include DMSO:Tween 80:Saline (10:5:85) for injection (IP/IV/IM/SC). Storage: Powder at -20degC (stable for 3 years); at 4degC (stable for 2 years). In solution at -80degC (stable for 6 months); at -20degC (stable for 1 month). Pharmacokinetic properties (half-life, Cmax, AUC, bioavailability) have not been extensively reported in the literature for this specific compound. As a saturated fatty acid methyl ester, it is expected to be absorbed from the gastrointestinal tract, metabolized by esterases to arachidic acid, and then undergo beta-oxidation or be incorporated into lipids. Its LogP is 9.74, indicating high lipophilicity, which may limit its aqueous solubility and bioavailability. The compound is stable at room temperature for a few days during shipping and time spent in customs.
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| Toxicity/Toxicokinetics |
Methyl arachidate is considered to have low acute toxicity based on its natural occurrence as a minor constituent of food sources (potatoes, pea aphids) and its use as a common fatty acid methyl ester standard. However, comprehensive toxicological studies have not been extensively performed. As a fatty acid ester, it is generally regarded as safe (GRAS) for use as a food additive or standard, but this does not constitute approval for therapeutic use. Standard safety precautions for laboratory chemicals should be followed when handling the pure compound. Avoid inhalation, ingestion, and skin contact. Use appropriate personal protective equipment (lab coat, gloves, safety glasses). The compound is not intended for human therapeutic use. No information is available on genotoxicity, reproductive toxicity, or carcinogenicity. Because the compound is a saturated fatty acid methyl ester, high doses may cause gastrointestinal disturbances or lipid metabolism alterations, but these effects would require further investigation. Dispose of waste according to local regulations.
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| References | |
| Additional Infomation |
Methyl arachidate is a fatty acid methyl ester. It has been reported to be found in potatoes, pea aphids, and other organisms with relevant data.
Methyl arachidate is a naturally occurring fatty acid methyl ester found in various plants and insects. It is used as a standard in lipidomics and metabolomics research for the identification and quantification of fatty acid methyl esters (FAMEs) by GC-MS and LC-MS. The compound is also used as a biochemical tool to study lipid metabolism, fatty acid transport, and beta-oxidation. It has been investigated for its potential bioactivities including anti-inflammatory, antifungal, and antioxidant properties. Methyl arachidate is not a marketed drug and is currently available for research use only. The compound is often included in fatty acid standard mixtures for analytical quality control. It is also a minor constituent of biodiesel produced from various feedstocks. The compound's structure as a saturated C20 fatty acid ester makes it useful for studying the effects of chain length and saturation on lipid metabolism and membrane properties. For research purposes, the compound should be stored under appropriate conditions (powder at -20degC, protect from light) to maintain stability. Note that Methyl arachidate is often used as a reference standard for GC-MS analysis; it can be used for method development and validation in food safety, environmental monitoring, and biomedical research. The compound has potential for further development as an anti-inflammatory agent, but additional studies are needed. |
| Molecular Formula |
C21H42O2
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| Molecular Weight |
326.56
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| Exact Mass |
326.318
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| CAS # |
1120-28-1
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| PubChem CID |
14259
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| Appearance |
White to off-white solid powder
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| Density |
0.8633 g/cm3 (20 ºC)
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| Boiling Point |
375.0±5.0 °C at 760 mmHg
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| Melting Point |
45-48 °C(lit.)
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| Flash Point |
184.2±7.5 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.447
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| LogP |
9.74
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
19
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| Heavy Atom Count |
23
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| Complexity |
238
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCCCCCCCCCCCCCCCC(=O)OC
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| InChi Key |
QGBRLVONZXHAKJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C21H42O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23-2/h3-20H2,1-2H3
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| Chemical Name |
methyl icosanoate
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO: 2 mg/mL (6.12 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0622 mL | 15.3111 mL | 30.6222 mL | |
| 5 mM | 0.6124 mL | 3.0622 mL | 6.1244 mL | |
| 10 mM | 0.3062 mL | 1.5311 mL | 3.0622 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.
Calculation results
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.
(2) Be sure to add the solvent(s) in order.
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