**Introduction to 10,11,14,15-¹³C₄-Retinol** 10,11,14,15-¹³C₄-Retinol is a stable isotope-labeled form of retinol (vitamin A), where four carbon atoms (positions 10, 11, 14, and 15) are replaced with the non-radioactive ¹³C isotope. This labeled compound is widely used as an internal standard in mass spectrometry-based assays, enabling precise quantification of retinol and its metabolites in biological samples. Its high isotopic purity and structural authenticity ensure accurate tracking in pharmacokinetic, metabolic, and nutritional studies. Researchers leverage 10,11,14,15-¹³C₄-retinol to investigate vitamin A absorption, distribution, and turnover, making it a valuable tool in clinical, pharmaceutical, and nutritional research.
Preparation Process: To prepare **10,11,14,15-<sup>13</sup>C<sub>4</sub>-retinol**, follow these steps: 1. **Synthesis of <sup>13</sup>C-labeled β-ionone**: React <sup>13</sup>C-labeled acetone with acetylene to form methylbutynol, then condense with citral to yield labeled β-ionone. 2. **C<sub>15</sub> phosphonium salt formation**: Convert β-ionone to the C<sub>15</sub> phosphonium salt using triphenylphosphine and HBr. 3. **Wittig reaction**: React the labeled phosphonium salt with a C<sub>5</sub> aldehyde (e.g., 3-methyl-2-butenal) to form labeled retinol. 4. **Purification**: Isolate the product via column chromatography and recrystallization. 5. **Characterization**: Confirm structure using NMR and mass spectrometry. (100 words)
Usage Scenarios: 10,11,14,15-13C4-retinol is a stable isotope-labeled form of retinol (vitamin A) used as an internal standard in mass spectrometry-based assays to quantify endogenous retinol levels with high precision. Its four carbon-13 (13C) labels minimize interference with unlabeled retinol, ensuring accurate detection in biological samples like plasma, tissues, or fortified foods. This compound aids in studying retinol absorption, metabolism, and pharmacokinetics in nutrition and medical research. It is also employed in tracer studies to track vitamin A turnover, storage, and transport dynamics in vivo, providing insights into deficiencies or metabolic disorders. The labeled retinol ensures reproducibility in analytical workflows.