Fluorene Myristate

Sinónimos: Fluorene-9-yl tetradecanoate, 9-Fluorenyl myristate, Myristic acid fluoren-9-yl ester, Fluorene myristate ester

Fluorene Myristate is a synthetic ester formed by the esterification of fluorene-9-ol with myristic acid (tetradecanoic acid). The molecule features a rigid, planar fluorene moiety linked via an ester bond to a long, saturated C14 alkyl chain. This structural combination imparts unique physicochemical properties, including a high degree of lipophilicity and a strong tendency to form crystalline solids. The fluorene core is known for its fluorescence, which can be exploited in analytical and imaging applications, while the myristate chain enhances membrane affinity and interaction with lipid bilayers.

While not a naturally occurring compound, Fluorene Myristate is synthesized for specialized applications in pharmaceutical and biochemical research. It serves as a model compound for studying ester hydrolysis, lipid metabolism, and drug delivery systems. Its ability to intercalate into lipid membranes makes it a valuable tool for investigating membrane dynamics and protein-lipid interactions. Additionally, the fluorene moiety allows for easy detection via UV-Vis or fluorescence spectroscopy, facilitating quantitative analysis in complex biological matrices.

In the pharmaceutical industry, Fluorene Myristate is primarily used as an intermediate or reference standard in the development of lipophilic prodrugs and drug delivery vehicles. Its ester linkage is susceptible to hydrolysis by esterases, making it a potential candidate for sustained-release formulations. Researchers also employ it as a fluorescent probe to track the distribution and metabolism of fatty acid derivatives in cells and tissues. The compound’s high purity and well-defined structure ensure reliable performance in these demanding applications.

Estructura química y propiedades

Fluorene Myristate consists of a fluorene ring system (a tricyclic aromatic hydrocarbon) substituted at the 9-position with a myristoyloxy group. The ester carbonyl and the adjacent methylene groups create a polar region, while the long alkyl chain provides a nonpolar tail, resulting in an amphiphilic character. The compound typically appears as a white to off-white crystalline powder with a melting point range of 60-65°C. It is stable under normal storage conditions but should be protected from excessive heat and moisture to prevent hydrolysis. Its logP value is estimated to be around 9, indicating very high lipophilicity.

Mecanismo de acción

• Esterase-mediated hydrolysis: The ester bond is cleaved by cellular esterases, releasing fluorene-9-ol and myristic acid, which can then participate in cellular processes.
• Membrane intercalation: The myristate chain inserts into lipid bilayers, altering membrane fluidity and permeability.
• Fluorescent probing: The fluorene moiety exhibits fluorescence, enabling visualization and quantification in biological samples.
• Lipid raft modulation: Due to its saturated chain, it may preferentially partition into ordered lipid domains, affecting signaling platforms.

Especificaciones de calidad

Suministro y documentación

• Capacidad: 500 kg per month
• Plazo de entrega: 3-5 días laborables (artículos en stock)
• Documentación: Certificado de análisis (COA), ficha de datos de seguridad (MSDS) y ficha técnica del producto (TDS) disponibles previa solicitud
• Embalaje: 25 kg fiber drum with double polyethylene liner, or customized packaging

Solicitud de presupuesto

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