13-Methoxy-13-oxotridecanoate
[CAS# 3927-59-1]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 13-Methoxy-13-oxotridecanoate
• Molecular Formula: C₁₄H₂₅O_4-
• Molecular Weight: 257.35
• CAS Registry Number: 3927-59-1
• SMILES: COC(=O)CCCCCCCCCCCC(=O)[O-]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

13-Methoxy-13-oxotridecanoate is a chemical compound that belongs to the family of alkyl esters derived from long-chain dicarboxylic acids, specifically tridecanedioic acid. It is a monoesterified derivative in which one carboxyl group of tridecanedioic acid is converted to a methyl ester, and the other carboxyl group is modified into a methoxy ketone at the terminal position. The molecular structure features a thirteen-carbon linear aliphatic chain with a terminal methyl ester and a terminal methoxy ketone group, resulting in the molecular formula C₁₅H₂₈O₄.

The compound has been synthesized and identified in the context of studies on ω-functionalized fatty acid derivatives. Tridecanedioic acid, the parent molecule, is a saturated, linear dicarboxylic acid that can be obtained through the oxidation of long-chain alkenes or by microbial fermentation using specific strains of Candida or Candida tropicalis. The introduction of both ester and ketone functionalities at opposite ends of the molecule requires a sequence of selective functional group transformations. Typically, the synthesis of 13-methoxy-13-oxotridecanoate begins with the partial esterification of tridecanedioic acid to yield the monomethyl ester. Subsequent conversion of the free carboxylic acid to a ketone via reduction to the aldehyde, followed by methylation, leads to the formation of the methoxy ketone group.

The presence of both a ketone and an ester functional group makes this compound of interest in the field of organic synthesis, particularly in reactions that exploit such bifunctional molecules for chain extension or derivatization. It serves as a model substrate in studies of chemoselective transformations and carbon–carbon bond-forming reactions. The methoxy ketone end can participate in nucleophilic additions, condensations, or be further functionalized into hydroxyl or amine groups, while the ester group remains intact under many reaction conditions. This selectivity is advantageous in the synthesis of complex molecular architectures, especially for surfactants, polymers, or functionalized materials.

In materials chemistry, derivatives like 13-methoxy-13-oxotridecanoate have been explored for their potential as intermediates in the preparation of polyesters and polyurethanes. The dual reactivity of the ester and ketone groups enables step-growth polymerization with a range of diols, diamines, or polyols. The long aliphatic chain contributes to the flexibility and hydrophobicity of the resulting polymeric materials, which can influence their mechanical strength, melting point, and biodegradability. Such compounds are of interest in the design of bio-based or renewable polymers, particularly when starting materials are derived from natural fatty acids or fermentation-based feedstocks.

Although specific biological studies on 13-methoxy-13-oxotridecanoate are limited, structurally related molecules, such as ω-functionalized esters and ketones, have been included in metabolic profiling and lipid oxidation research. These compounds can be relevant in the context of lipid metabolism, peroxisomal β-oxidation, or as potential bioactive molecules with surfactant or antimicrobial properties. In such contexts, the combination of a lipophilic alkyl chain with a polar functional group may influence membrane interactions or enzyme binding affinity.

The physical properties of 13-methoxy-13-oxotridecanoate, such as low water solubility, moderate volatility, and high thermal stability, make it suitable for formulation in non-polar systems, including lubricants, coatings, and plasticizer matrices. Its ketone and ester functionalities also offer UV absorption characteristics that can be tuned for specific applications in industrial formulations.

The study and application of compounds like 13-methoxy-13-oxotridecanoate contribute to the expanding catalog of functionalized aliphatic molecules that are important in both fine chemical synthesis and material science. Their tailored reactivity and derivation from long-chain diacid precursors highlight their relevance in the development of advanced synthetic methodologies and environmentally conscious chemical production.