Organic Chemistry

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Pentadecanoic Acid

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Organic Chemistry

Definition

Pentadecanoic acid is a saturated fatty acid with 15 carbon atoms. It is a naturally occurring compound found in various food sources and is an important intermediate in the catabolism of triacylglycerols through the process of β-oxidation.

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5 Must Know Facts For Your Next Test

  1. Pentadecanoic acid is a saturated fatty acid with an odd number of carbon atoms, which is less common in nature compared to even-numbered fatty acids.
  2. It is found in small amounts in dairy products, such as milk and cheese, as well as in some plant oils and animal fats.
  3. During the β-oxidation of pentadecanoic acid, the odd-numbered carbon chain results in the formation of propionyl-CoA as the final product, which can then be converted to succinyl-CoA and enter the citric acid cycle.
  4. The presence of pentadecanoic acid in the body can be used as a biomarker for the consumption of dairy products and can provide information about dietary intake and metabolism.
  5. Pentadecanoic acid is an important intermediate in the catabolism of triacylglycerols, as it is produced during the breakdown of odd-chain fatty acids.

Review Questions

  • Explain the role of pentadecanoic acid in the catabolism of triacylglycerols through β-oxidation.
    • Pentadecanoic acid is an important intermediate in the catabolism of triacylglycerols through the process of β-oxidation. During β-oxidation, the long-chain fatty acid, pentadecanoic acid, is progressively broken down into acetyl-CoA units, which can then enter the citric acid cycle to generate ATP. The odd-numbered carbon chain of pentadecanoic acid results in the formation of propionyl-CoA as the final product, which can be converted to succinyl-CoA and enter the citric acid cycle. This process allows the body to efficiently utilize the energy stored in triacylglycerols, making pentadecanoic acid a key player in the overall metabolism of fats.
  • Describe the sources and potential significance of pentadecanoic acid in the human body.
    • Pentadecanoic acid is a naturally occurring saturated fatty acid that is found in small amounts in various food sources, such as dairy products and some plant oils and animal fats. The presence of pentadecanoic acid in the body can be used as a biomarker to provide information about dietary intake and metabolism. For example, the level of pentadecanoic acid in the body can indicate the consumption of dairy products, as it is a relatively unique fatty acid found in these foods. Additionally, the odd-numbered carbon chain of pentadecanoic acid makes it an important intermediate in the catabolism of triacylglycerols through the β-oxidation pathway, as it can be converted to propionyl-CoA and then enter the citric acid cycle to generate energy.
  • Analyze the significance of the odd-numbered carbon chain of pentadecanoic acid in the context of its metabolism and potential implications for human health.
    • The odd-numbered carbon chain of pentadecanoic acid is a unique feature that sets it apart from the more common even-numbered fatty acids. This structural difference has important implications for its metabolism and potential health effects. During β-oxidation, the odd-numbered carbon chain of pentadecanoic acid results in the formation of propionyl-CoA as the final product, rather than the typical acetyl-CoA. Propionyl-CoA can then be converted to succinyl-CoA, which can enter the citric acid cycle, providing an alternative pathway for energy production. This unique metabolic pathway may have implications for the overall energy metabolism and potentially influence factors such as insulin sensitivity, glucose homeostasis, and even the gut microbiome. Additionally, the presence of pentadecanoic acid in the body may serve as a biomarker for dietary intake and provide insights into an individual's overall metabolic profile, which could have implications for the prevention and management of various health conditions.

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