11-Methoxy-11-oxoundecanoic acid
[CAS# 3927-60-4]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives
• Name: 11-Methoxy-11-oxoundecanoic acid
• Molecular Formula: C₁₂H₂₂O₄
• Molecular Weight: 230.30
• CAS Registry Number: 3927-60-4
• SMILES: COC(=O)CCCCCCCCCC(=O)O

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 340.2±15.0 ºC 760 mmHg (Calc.)^*
• Flash point: 121.0±13.9 ºC (Calc.)^*
• Index of refraction: 1.455 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

11-Methoxy-11-oxoundecanoic acid is a synthetic organic compound that belongs to the class of ω-functionalized aliphatic acids. Structurally, it is derived from undecanoic acid, a saturated straight-chain fatty acid with eleven carbon atoms. The terminal methyl group of undecanoic acid is modified into a methoxy-substituted ketone (methoxy ketone), resulting in a molecule containing both a terminal carboxylic acid group and a terminal methoxy ketone group. The molecular formula of 11-methoxy-11-oxoundecanoic acid is C₁₂H₂₂O₄, and it combines the chemical characteristics of a carboxylic acid and a masked aldehyde or ketone.

This compound has been reported in the scientific literature as an intermediate in the synthesis of ω-methoxyketones, which are of interest in the study of long-chain functionalized acids and their behavior under oxidative, reductive, or substitution conditions. The synthesis of 11-methoxy-11-oxoundecanoic acid generally begins with undecanoic acid or its methyl ester. The terminal carboxyl group is protected or converted to an ester, and the opposite end of the chain is oxidized to an aldehyde. This intermediate is then reacted with methanol under acid catalysis to produce the corresponding methoxy ketone. Finally, hydrolysis of the ester yields the free acid form of 11-methoxy-11-oxoundecanoic acid.

Compounds with both polar and non-polar functionalities at opposite ends of a linear aliphatic chain are useful as synthetic intermediates in the preparation of surfactants, polymers, and amphiphilic molecules. The methoxy ketone moiety in 11-methoxy-11-oxoundecanoic acid serves as a versatile functional group that can undergo further transformations, including nucleophilic addition, reduction, or substitution reactions. These transformations are important for modifying chain-end functionality in step-growth polymerizations or in preparing advanced materials with tailored surface properties.

The presence of a carboxylic acid group also makes this compound reactive toward alcohols and amines, enabling its incorporation into polyesters, polyamides, or urethane derivatives. In experimental polymer formulations, such bifunctional compounds are valued for their ability to introduce asymmetric and selectively reactive sites into the polymer backbone. The long hydrocarbon chain provides flexibility and hydrophobicity, contributing to the mechanical strength and chemical resistance of the resulting polymers.

Although not known for any specific pharmacological activity, 11-methoxy-11-oxoundecanoic acid is structurally related to a range of medium-chain fatty acid derivatives that have been investigated for bioactivity, including antimicrobial or surface-active properties. Studies on similar ω-functionalized fatty acids have explored their interactions with lipid bilayers and their degradation pathways under enzymatic or oxidative conditions.

The compound has also been used as a model substrate in mechanistic studies of ester hydrolysis and carbonyl reactivity. The methoxy-substituted ketone group provides insight into the influence of alkoxy substituents on the electrophilicity of carbonyl compounds. These types of studies have relevance for understanding biochemical oxidation mechanisms and for designing protective groups in complex molecule synthesis.

11-Methoxy-11-oxoundecanoic acid is typically characterized using spectroscopic techniques such as nuclear magnetic resonance and mass spectrometry, along with infrared spectroscopy to identify the carbonyl and carboxylic acid functional groups. Its physical properties, including low water solubility and high thermal stability, make it suitable for applications in non-aqueous formulations, including experimental coatings, lubricants, and controlled-release systems.

This compound continues to be referenced in the context of synthetic organic chemistry and industrial intermediate development, especially where chain-end functionalization and selective reactivity are essential. It illustrates the utility of modified fatty acid derivatives in both small-molecule synthesis and material design.

References

2007. Base-Catalyzed Hydrolysis. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-020-00049

2004. Partial Hydrolysis of Diesters. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-007-00727

1977. Preparation of specifically dideuterated octadecanoates and oxooctadecanoates. Lipids, 12(1).
DOI: 10.1007/bf02532978