Dehydrocholic Acid

Sinónimos: 3,7,12-Trioxo-5β-cholan-24-oic acid; Dehydrocholate; DHCA; 5β-Cholan-24-oic acid, 3,7,12-trioxo-; Triketocholanic acid

Dehydrocholic acid is a synthetic bile acid derivative characterized by three ketone groups at positions 3, 7, and 12 on the steroid nucleus. This oxidation pattern distinguishes it from natural bile acids like cholic acid, which carry hydroxyl groups at these positions. The resulting flat, rigid structure enhances its interaction with hepatic transporters and enzymes, making it a valuable tool in pharmaceutical research and a key intermediate in the synthesis of other bile acid analogs.

Commercially, dehydrocholic acid is produced through the oxidation of cholic acid, typically using chromic acid or other oxidizing agents. It is available in high purity grades, often exceeding 98% as determined by HPLC. The compound is a white to off-white crystalline powder, sparingly soluble in water but freely soluble in organic solvents such as ethanol and acetone. Its stability under normal storage conditions makes it suitable for various applications.

In the pharmaceutical industry, dehydrocholic acid serves as a choleretic agent, stimulating bile production and flow. It is also used as an intermediate in the manufacture of ursodeoxycholic acid and other therapeutic bile acids. Research applications include studies on bile acid metabolism, liver function, and drug delivery systems. Its unique chemical properties continue to drive interest in both medicinal chemistry and process development.

Estructura química y propiedades

Dehydrocholic acid belongs to the family of C24 bile acids, featuring a steroid nucleus with a carboxyl side chain. The three ketone groups at C3, C7, and C12 create a more planar and hydrophobic molecule compared to its hydroxylated counterparts. This structural feature influences its physicochemical behavior, including its solubility profile and chromatographic retention. The compound exhibits strong UV absorption due to the conjugated ketone system, which facilitates its detection and quantification.

Mecanismo de acción

• Choleretic effect: Dehydrocholic acid stimulates bile secretion by hepatocytes, increasing bile flow and volume. This effect is mediated through activation of nuclear receptors such as FXR and PXR, which regulate bile acid synthesis and transport.
• Enzyme inhibition: It inhibits 7α-hydroxylase (CYP7A1), the rate-limiting enzyme in bile acid biosynthesis, thereby modulating cholesterol metabolism.
• Transport modulation: The compound interacts with bile salt export pump (BSEP) and multidrug resistance-associated protein 2 (MRP2), affecting biliary excretion of endogenous and exogenous substances.
• Metabolic regulation: Through activation of farnesoid X receptor (FXR), it influences lipid and glucose homeostasis, making it a subject of research in metabolic disorders.

Especificaciones de calidad

Suministro y documentación

• Capacidad: 10 metric tons per year
• 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 inner polyethylene bag

Solicitud de presupuesto

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