16-(Benzyloxy)-16-oxohexadecanoic acid
[CAS# 146004-98-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 16-(Benzyloxy)-16-oxohexadecanoic acid
• Synonyms: 16-oxo-16-phenylmethoxyhexadecanoic acid
• Molecular Formula: C₂₃H₃₆O₄
• Molecular Weight: 376.53
• CAS Registry Number: 146004-98-0
• SMILES: C1=CC=C(C=C1)COC(=O)CCCCCCCCCCCCCCC(=O)O

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.502, Calc.^*
• Boiling Point: 505.8±23.0 ºC (760 mmHg), Calc.^*
• Flash Point: 164.0±16.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

16-(Benzyloxy)-16-oxohexadecanoic acid is a synthetic compound that falls within the category of long-chain fatty acid derivatives. Its structure comprises a 16-carbon aliphatic chain with a benzyloxy functional group attached to the terminal carbon, which is also oxidized to form a ketone group. The benzyloxy and oxo functional groups are significant in the synthetic chemistry of fatty acid derivatives, giving the molecule unique chemical reactivity and making it useful for a variety of applications in both organic chemistry and materials science.

The discovery of 16-(Benzyloxy)-16-oxohexadecanoic acid and similar compounds has its roots in the exploration of fatty acids and their synthetic modifications. Long-chain fatty acids have long been studied due to their roles in biological systems, particularly in lipid metabolism, membrane structure, and energy storage. The ability to introduce specific functional groups such as benzyloxy or ketones into fatty acid chains expands the versatility of these molecules, enabling researchers to create new materials, study biochemical pathways, or design molecules with pharmaceutical potential.

The synthesis of 16-(Benzyloxy)-16-oxohexadecanoic acid typically involves multi-step organic reactions, starting from simpler fatty acids or aldehyde derivatives. The introduction of the benzyloxy group, which is often derived from benzyl alcohol, and the oxidation of the terminal carbon to form the ketone group are key steps in its preparation. Protecting groups, solvents, and catalysts are used to achieve the desired specificity in these reactions, as the functional groups need to be selectively introduced without altering the core structure of the fatty acid chain.

One of the primary applications of 16-(Benzyloxy)-16-oxohexadecanoic acid is in the field of organic synthesis, where it serves as an intermediate for the preparation of more complex molecules. Its functional groups allow it to participate in a range of reactions, including nucleophilic substitutions, reductions, and condensations. As such, it is valuable in constructing molecules for pharmaceutical research, particularly for designing drugs that target lipid pathways or interact with membranes.

Additionally, the compound has potential uses in materials science, especially in the design of surface-active agents and surfactants. Long-chain fatty acid derivatives, especially those with polar functional groups, can be engineered to influence the properties of surfaces or interfaces, making them useful in coatings, emulsions, or delivery systems. The benzyloxy group offers a hydrophobic region, while the carboxyl and ketone functionalities provide polar characteristics, allowing the molecule to interact with both hydrophilic and hydrophobic environments.

In biochemical research, 16-(Benzyloxy)-16-oxohexadecanoic acid and its analogs may also serve as probes to study fatty acid metabolism or lipid signaling pathways. By modifying the structure of natural fatty acids, researchers can investigate how changes in the chain length or functional groups affect biological activity. This approach is critical in understanding diseases related to lipid metabolism, such as obesity, diabetes, or cardiovascular disorders.

Overall, 16-(Benzyloxy)-16-oxohexadecanoic acid is a versatile compound whose synthetic development has broadened the scope of applications for fatty acid derivatives in organic chemistry, materials science, and biomedical research.