Octadecanedioic acid
[CAS# 871-70-5]

Identification

• Classification: Biochemical >> Common amino acids and protein drugs
• Name: Octadecanedioic acid
• Molecular Formula: C₁₈H₃₄O₄
• Molecular Weight: 314.46
• CAS Registry Number: 871-70-5
• EC Number: 617-978-5
• SMILES: C(CCCCCCCCC(=O)O)CCCCCCCC(=O)O

Properties

• Melting point: 125 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Octadecanedioic acid, also known as C18-dicarboxylic acid, is a significant organic compound with a structure featuring two carboxyl groups separated by an eighteen-carbon chain. It is a member of the dicarboxylic acid family and is used in various industrial and research applications due to its unique chemical properties.

The discovery of octadecanedioic acid dates back to the early 20th century when it was first isolated from natural sources, such as castor oil and other vegetable oils. The synthesis of this compound was later achieved through the oxidation of oleic acid, a common fatty acid found in many natural fats and oils. Its production has since been refined to meet the demands of industrial applications.

In the industrial sector, octadecanedioic acid is primarily used as a monomer in the production of high-performance polymers. It serves as a key building block for polyamide and polyester materials. The presence of the long carbon chain in its structure imparts unique properties to the resulting polymers, including enhanced flexibility, thermal stability, and chemical resistance. These characteristics make octadecanedioic acid-derived polymers suitable for use in various applications, such as coatings, adhesives, and engineering plastics.

Additionally, octadecanedioic acid is utilized in the synthesis of surfactants and plasticizers. Its ability to form esters with alcohols allows it to be used in the production of surfactants that are employed in detergents and cleaning products. The compound's role as a plasticizer helps to modify the physical properties of polymers, such as improving their flexibility and processing characteristics.

In the pharmaceutical industry, octadecanedioic acid is used as a starting material for the synthesis of various bioactive compounds. Its chemical structure allows for the creation of derivatives that can be employed in the development of new drugs and therapeutic agents. The compound's versatility in chemical reactions makes it a valuable intermediate in pharmaceutical synthesis.

Overall, octadecanedioic acid is a versatile compound with a broad range of applications across different industries. Its role as a monomer in polymer production, surfactant synthesis, and pharmaceutical research underscores its importance in both industrial and research contexts.

References

2019. Antitumor Activity of 1,18-Octadecanedioic Acid-Paclitaxel Complexed with Human Serum Albumin. Journal of the American Chemical Society, 141(28).
DOI: 10.1021/jacs.9b04272

2016. Candida guilliermondii as a potential biocatalyst for the production of long-chain α,ω-dicarboxylic acids. Biotechnology Letters, 38(11).
DOI: 10.1007/s10529-016-2264-3

2010. Selectively Functionalized Glycerol/Diacid Dendrimers via Click Chemistry of Azido Fatty Acids. Journal of the American Oil Chemists' Society, 87(12).
DOI: 10.1007/s11746-010-1675-x