| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Targets |
Endogenous Metabolite
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|---|---|
| ln Vitro |
Hexacosanoic acid (C26:0) (1), a very long-chain fatty acid, is related to various diseases such as adrenoleukodystrophy (ALD), adrenomyeloneuropathy (AMN) and atherosclerosis. As the level of 1 higher than the normal is related to diseases above, hexacosanoic acid (1) and the ceramide 2, which contains 1, are thought to play an important role in various tissues. Hexacosanoic acid (1) is known to be a waxy solid and to be hard to dissolve in water as well as organic solvents. Due to this physical property, it is not easy to handle hexacosanoic acid (1) in a laboratory. Therefore, efficient chemical synthesis of the compounds 1 and 2 has not been reported. Here, we report a versatile synthetic method for hexacosanoic acid (1) and the ceramide 2 containing the fatty acid 1. Synthesis of hexacosanoic acid (1) was achieved by applying the coupling of two alkyl units as a key step. Ceramide 2 was efficiently synthesized by applying the reported procedure together with hexacosanoic acid (1) synthesized here. This synthetic strategy has an advantage of getting various carbon chain length fatty acids and their ceramides by using a variety of carbon chain units. This method is also applicable for large-scale synthesis. In addition, these compounds 1 and 2 are useful for investigation of details of these compounds related to diseases such as ALD and AMN. [1]
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| Toxicity/Toxicokinetics |
Toxicity Summary
Adrenoleukodystrophy (ALD) is caused by mutations in the ABCD1 gene, located on the X chromosome, which encodes the peroxisome membrane transporter ALD. The exact pathogenesis of various types of ALD is unclear. Biochemical analysis shows extremely high levels of unbranched saturated long-chain fatty acids, particularly cetyl acid (26:0), in patients with ALD. Plasma cetyl acid levels are not associated with clinical presentation. Health Effects Hexacosanoic acid (or teicosanoic acid) is associated with adrenoleukodystrophy (also known as X-linked adrenoleukodystrophy, ALD, X-ALD, adrenocortical neuropathy, AMN, Simmelin-Kreutzfeldt disease, or Bronze Syld disease). Adrenoleukodystrophy is a peroxisome fatty acid β-oxidation disorder that leads to the accumulation of very long-chain fatty acids in tissues throughout the body. The most severely affected tissues are the myelin sheath of the central nervous system, the adrenal cortex, and the interstitial cells in the testes. Symptoms Clinically, adrenoleukodystrophy (ALD) is a heterogeneous disease, exhibiting several different phenotypes with no clear genotype-phenotype correlation. ALD is an X-linked genetic disorder, most commonly affecting males, but approximately 50% of heterozygous females also develop some symptoms in adulthood. About two-thirds of ALD patients present with the childhood encephalopathy, the most severe type. It is characterized by normal development in early childhood followed by rapid regression to a vegetative state. Other types of ALD vary in onset and clinical severity, ranging from adrenal insufficiency to progressive paraplegia in early adulthood (this type of disease is often referred to as adrenospinal neuropathy). Treatment Treatment options for adrenoleukodystrophy (ALD) are limited. Dietary therapy includes taking lorenzo oil. For pediatric encephalopathy, stem cell transplantation and gene therapy are feasible treatment options if the disease can be detected early in the clinical setting. Adrenal insufficiency in patients with ALD can be successfully treated. |
| References | |
| Additional Infomation |
Hexacosanoic acid is a 26-carbon straight-chain saturated fatty acid. It is a long-chain fatty acid, a straight-chain saturated fatty acid, and also a fatty acid with a 26:0 ratio. It is the conjugate acid of ceric acid. Hexacosanoic acid has been reported to exist in Trichosanthes tricuspidata, Mandragora autumnalis, and other organisms with relevant data. Hexacosanoic acid, also known as ceric acid, is a 26-carbon long-chain saturated fatty acid with the chemical formula CH3(CH2)24COOH. It is most commonly found in beeswax and carnauba wax, and is a white crystalline solid. (Wikipedia) X-linked adrenoleukodystrophy (X-ALD) is a peroxisome disorder characterized by the accumulation of very long-chain fatty acids (VLCFAs) in tissues and body fluids, particularly hexacosanoic acid (C26:0) and tetracosanoic acid (C24:0). (A3378) Ceramic acid is a metabolite found or produced in Saccharomyces cerevisiae.
- hexacosanoic acid (C26:0) is a very long-chain fatty acid (VLCFA). Reference [1] focuses on its chemical synthesis and the synthesis of ceramides containing this fatty acid [1] - The chemical synthesis of hexacosanoic acid reported in Reference [1] uses commercially available short-chain fatty acid derivatives as starting materials. The synthesis process includes key steps such as carboxyl protection, carbon chain extension (to 26 carbon atoms) through iterative reactions and final deprotection to obtain pure hexacosanoic acid with a structure confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry [1]. In addition, [1] also describes the synthesis of ceramides containing hexacosanoic acid: firstly, hexacosanoic acid is activated to form an acyl chloride derivative, then the derivative reacts with a sphingosine derivative (both amino and hydroxyl groups are protected) to form an amide bond, and finally deprotection is performed to obtain the target ceramide [1]. Hexacosanoic acid is naturally present in some biological tissues (such as the brain and skin of mammals) in small amounts and is a component of some sphingolipids (such as ceramides) [1]. |
| Molecular Formula |
C26H52O2
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|---|---|
| Molecular Weight |
396.6899
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| Exact Mass |
396.396
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| CAS # |
506-46-7
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| PubChem CID |
10469
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| Appearance |
White to off-white solid powder
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
418.7±8.0 °C at 760 mmHg
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| Melting Point |
86-87 °C
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| Flash Point |
187.6±13.3 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.461
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| LogP |
12.47
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
24
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| Heavy Atom Count |
28
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| Complexity |
301
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
XMHIUKTWLZUKEX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C26H52O2/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(27)28/h2-25H2,1H3,(H,27,28)
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| Chemical Name |
hexacosanoic acid
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| Synonyms |
HEXACOSANOIC ACID; 506-46-7; Cerotic acid; Ceratinic acid; Ceric acid; Cerinic acid; Hexacosanic acid; Cerylic acid;
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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) |
THF : 5.56 mg/mL (~14.02 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 | 2.5209 mL | 12.6043 mL | 25.2086 mL | |
| 5 mM | 0.5042 mL | 2.5209 mL | 5.0417 mL | |
| 10 mM | 0.2521 mL | 1.2604 mL | 2.5209 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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