Dodecanedioic Acid Monomethyl Ester
[CAS# 3903-40-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Dodecanedioic Acid Monomethyl Ester
• Synonyms: 12-methoxy-12-oxododecanoic acid
• Molecular Formula: C₁₃H₂₄O₄
• Molecular Weight: 244.33
• CAS Registry Number: 3903-40-0
• EC Number: 675-951-3
• SMILES: COC(=O)CCCCCCCCCCC(=O)O

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 355.3±15.0 ºC 760 mmHg (Calc.)^*
• Flash point: 124.3±13.9 ºC (Calc.)^*
• Index of refraction: 1.456 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

Dodecanedioic acid monomethyl ester is a monoalkyl ester derived from dodecanedioic acid, a saturated linear aliphatic dicarboxylic acid containing twelve carbon atoms. The structure of this compound features one terminal carboxylic acid group and one esterified methyl group, giving it amphiphilic properties that can be leveraged in various chemical and industrial applications. Its molecular formula is C₁₃H₂₄O₄, and it is categorized as a monoester of a long-chain aliphatic diacid.

The synthesis of dodecanedioic acid monomethyl ester was initially pursued in the context of modifying long-chain dicarboxylic acids to explore their ester derivatives for polymer and surfactant chemistry. The compound is typically prepared by the controlled esterification of dodecanedioic acid using methanol in the presence of an acid catalyst such as sulfuric acid. Careful stoichiometric control and temperature regulation are required to ensure that only one carboxyl group undergoes esterification, leaving the second carboxyl group free for further reaction or functionalization. Purification is commonly achieved through crystallization or distillation under reduced pressure.

The compound has gained attention as an intermediate in the synthesis of specialty polyesters, polyamides, and surface-active agents. In polyester production, the presence of one free acid and one ester group allows for selective chain extension or branching when reacted with multifunctional alcohols or amines. This capability enables the design of materials with tailored thermal, mechanical, or solubility characteristics. In some polymerization schemes, the use of monoesters like dodecanedioic acid monomethyl ester facilitates the incorporation of terminal functionality or alters the degree of polymer crystallinity, affecting processing and final performance.

In the context of surfactant and lubricant chemistry, dodecanedioic acid monomethyl ester has been explored for its amphiphilic nature. The hydrophobic alkyl backbone provides compatibility with nonpolar media, while the polar acid and ester groups contribute to surface activity or dispersibility in polar solvents. These properties make it a candidate for use in formulations requiring controlled hydrophilicity or reactivity, such as emulsifiers or rheology modifiers in cosmetic or industrial applications. Its long chain length contributes to low volatility and oxidative stability, qualities that are desirable in high-performance lubricant systems or in slow-release formulations.

The compound has also been studied as part of broader investigations into the reactivity and degradation behavior of monoesters derived from long-chain dicarboxylic acids. Hydrolysis studies have evaluated the conditions under which dodecanedioic acid monomethyl ester reverts to dodecanedioic acid and methanol, with attention paid to reaction kinetics and pH dependence. These studies have applications in environmental chemistry and in the design of biodegradable materials, as the ester’s cleavage yields non-toxic, naturally occurring components that are subject to microbial degradation.

While its biological activity has not been a major focus, related compounds derived from dicarboxylic acids have been examined for their role in metabolic processes and therapeutic applications. Dodecanedioic acid itself has been researched as an energy substrate in medical nutrition, particularly in metabolic disorders, owing to its capacity to generate energy via β-oxidation without relying on glucose metabolism. Although the methyl monoester has not been similarly evaluated for direct medical use, its inclusion in analytical studies helps establish the metabolic fate and physicochemical behavior of esterified fatty dicarboxylic acids.

Dodecanedioic acid monomethyl ester remains of interest in research and industrial chemistry as a versatile building block. Its asymmetric functionalization supports a wide range of synthetic transformations, and its physicochemical properties offer utility in advanced material applications. Its production from dodecanedioic acid, which can be synthesized by chemical oxidation or microbial fermentation of renewable substrates, also contributes to its relevance in the development of sustainable chemical processes.

References

2017. Hydrolase BioH knockout in E. coli enables efficient fatty acid methyl ester bioprocessing. Journal of Industrial Microbiology and Biotechnology, 44(3).
DOI: 10.1007/s10295-016-1890-z

2005. Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of alpha,omega-alkanedithiols. Applied Microbiology and Biotechnology, 68(2).
DOI: 10.1007/s00253-005-027-5

2002. Light induced controlled release of fragrances by Norrish type II photofragmentation of alkyl phenyl ketones. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 1(10).
DOI: 10.1039/b207918f