Buy N-octanoylsphingosine (BT-262371)

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N-octanoylsphingosine

Catalog Number: BT-262371

CAS Number: 74713-59-0

Molecular Formula: C26H51NO3

Molecular Weight: 425.7 g/mol

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Product Introduction

Description

N-octanoylsphingosine, also known as C8-ceramide, is a bioactive sphingolipid that plays a crucial role in various cellular processes. It is a member of the ceramide family, which is composed of sphingosine and a fatty acid. C8-ceramide has gained significant attention in recent years due to its potential therapeutic applications in various diseases, including cancer, diabetes, and neurodegenerative disorders. This paper aims to provide a comprehensive review of the synthesis, chemical structure, biological activity, effects, applications, and future perspectives of N-octanoylsphingosine.

Properties

CAS Number

74713-59-0

Product Name

N-octanoylsphingosine

IUPAC Name

N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide

Molecular Formula

C26H51NO3

Molecular Weight

425.7 g/mol

InChI

InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24-,25+/m0/s1

InChI Key

APDLCSPGWPLYEQ-WRBRXSDHSA-N

SMILES

CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCCCC)O

Solubility

Soluble in DMSO

Synonyms

2,3-N-octanoyl-D-erythro-trans-sphingosine
2,3-N-octanoylsphingosine
C8-ceramide

Canonical SMILES

CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCCCC)O

Isomeric SMILES

CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCC)O

Method of Synthesis or Extraction

N-octanoylsphingosine can be synthesized using various methods, including chemical synthesis, enzymatic synthesis, and extraction from natural sources. Chemical synthesis involves the reaction of sphingosine with octanoyl chloride in the presence of a base catalyst. Enzymatic synthesis involves the use of ceramide synthase enzymes to catalyze the reaction between sphingosine and a fatty acyl-CoA. Extraction from natural sources involves the isolation of N-octanoylsphingosine from biological tissues, such as animal or plant tissues. The efficiency and yield of each method vary depending on the specific conditions used. Chemical synthesis is the most commonly used method, with a yield of up to 80%. However, it requires the use of toxic chemicals and poses environmental and safety considerations. Enzymatic synthesis is a more environmentally friendly method, but it has a lower yield. Extraction from natural sources is a time-consuming and expensive process, but it provides a natural source of N-octanoylsphingosine.

Chemical Structure and Biological Activity

N-octanoylsphingosine has a chemical structure consisting of a sphingosine backbone and an octanoyl fatty acid chain. It is a bioactive molecule that plays a crucial role in various cellular processes, including apoptosis, cell proliferation, and inflammation. N-octanoylsphingosine exerts its biological activity by binding to and activating various intracellular targets, including protein kinase C, caspases, and ceramide-activated protein phosphatases. It has been shown to induce apoptosis in cancer cells, inhibit insulin resistance in diabetes, and improve cognitive function in neurodegenerative disorders. N-octanoylsphingosine has also been shown to have anti-inflammatory and anti-oxidant properties.

Biological Effects

N-octanoylsphingosine has various effects on cell function and signal transduction. It induces apoptosis in cancer cells by activating the caspase cascade and inhibiting the anti-apoptotic protein Bcl-2. It also inhibits cell proliferation by inducing cell cycle arrest and suppressing the expression of cyclin-dependent kinases. In diabetes, N-octanoylsphingosine improves insulin sensitivity by activating the protein kinase C pathway and increasing glucose uptake. In neurodegenerative disorders, N-octanoylsphingosine improves cognitive function by enhancing synaptic plasticity and reducing oxidative stress. However, N-octanoylsphingosine also has potential toxic effects, including inducing apoptosis in healthy cells and promoting inflammation.

Applications

N-octanoylsphingosine has various applications in medical, environmental, and industrial research. In medical research, N-octanoylsphingosine has been studied for its potential role in drug development, with promising results in preclinical studies. Clinical trials are currently underway to evaluate its safety and efficacy in various diseases, including cancer, diabetes, and neurodegenerative disorders. In environmental research, N-octanoylsphingosine has been studied for its effects on ecosystems and its potential role in pollution management. It has been shown to have toxic effects on aquatic organisms and may have implications for sustainability and environmental impact. In industrial research, N-octanoylsphingosine has been studied for its use in manufacturing processes, improving product quality and efficiency, and health and safety considerations.

Future Perspectives and Challenges

Despite the promising results of N-octanoylsphingosine in preclinical studies, there are still limitations in its use and study. One of the main challenges is the lack of understanding of its pharmacokinetics and pharmacodynamics in humans. Another challenge is the potential toxic effects of N-octanoylsphingosine on healthy cells and its implications for clinical use. Future research should focus on addressing these challenges and developing more efficient and safe methods for synthesizing and using N-octanoylsphingosine. The future trends and prospects in the application of N-octanoylsphingosine in scientific research are promising, with potential applications in various diseases and industries.

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