1,20-Eicosanedioic acid
[CAS# 2424-92-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Acyclic carboxylic acid
• Name: 1,20-Eicosanedioic acid
• Synonyms: C 20; C 20 fatty acid; Eicosan-1,20-dioic acid; Octadecamethylenedicarboxylic acid; SL 20-90; SL 20-93; SL 20-99
• Molecular Formula: C₂₀H₃₈O₄
• Molecular Weight: 342.51
• CAS Registry Number: 2424-92-2
• EC Number: 679-934-1
• SMILES: C(CCCCCCCCCC(=O)O)CCCCCCCCC(=O)O

Properties

• Solubility: Insoluble (2.4E^-3 g/L) (25 °C), Calc.^*
• Density: 0.984±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 125.5-126.5 °C (acetone )^**
• Index of Refraction: 1.474, Calc.^*
• Boiling Point: 504.1±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 272.8±19.1 °C, Calc.^*

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

^** Hunig, Siegfried

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

1,20-Eicosanedioic acid, also known as eicosanedioic acid, is a long-chain dicarboxylic acid with the molecular formula C20H38O4. This compound was first synthesized and studied as part of a broader effort to explore long-chain fatty acids and their derivatives for use in various industrial and biomedical applications. It is composed of a 20-carbon linear chain with two terminal carboxyl groups, which imparts it with unique chemical properties useful in polymer synthesis, surfactant development, and specialty coatings.

The discovery of eicosanedioic acid arose from research into the modification of natural fatty acids to create novel compounds with enhanced properties. Long-chain dicarboxylic acids like eicosanedioic acid have attracted interest due to their potential as monomers in the production of polyamides and polyesters. The dual functionality of the two carboxyl groups allows them to react with other molecules, forming strong, durable polymers with applications in high-performance materials such as nylon, resins, and adhesives.

In the biomedical field, 1,20-eicosanedioic acid has been studied for its role in metabolic processes. Some research suggests that dicarboxylic acids, including eicosanedioic acid, may play a role in energy metabolism, particularly in fatty acid oxidation. They are being investigated for potential therapeutic applications in treating metabolic disorders, where the regulation of fatty acid metabolism is of interest. Additionally, its biocompatibility and ability to form stable polymers make it an attractive candidate for drug delivery systems and medical implants.

Eicosanedioic acid’s structure also enables it to be used in surfactant chemistry. It can act as a building block for the development of surfactants that are useful in personal care products, detergents, and industrial cleaning agents. The hydrophobic long chain combined with the hydrophilic carboxyl groups provides amphiphilic properties, allowing it to lower surface tension and stabilize emulsions.

The diverse applications of 1,20-eicosanedioic acid, from polymer chemistry to biomedical research, underscore its importance in both industrial and scientific fields. Its ability to integrate into various chemical processes while offering unique functional properties continues to drive interest in its use and further study.

References

2023. Aliphatic polyesters based on 1,4-butanediol and even numbered C4 - C20 dicarboxylic acids - synthesis and properties including after surface treatment by VUV photo-oxidation. *Journal of Polymer Research*, 30(8).
DOI: 10.1007/s10965-023-03693-8

1992. Preparation and thermotropic properties of copoly(4,4'-biphenylene sebacate-co-eicosanedioate)s. *Polymer Bulletin*, 29(1-2).
DOI: 10.1007/bf00296044

2004. Structural study on polymorphism of long-chain dicarboxylic acids using oblique transmission method for micro FT-IR spectrometers. *Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy*, 60(1-2).
DOI: 10.1016/s1386-1425(03)00181-1