10,12-Pentacosadiynoic acid
[CAS# 66990-32-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: 10,12-Pentacosadiynoic acid
• Synonyms: 10,12-Pentacosadiynioic acid; DA 3261; Pentacosa-10,12-diynoic acid
• Molecular Formula: C₂₅H₄₂O₂
• Molecular Weight: 374.60
• CAS Registry Number: 66990-32-7
• EC Number: 614-006-1
• SMILES: CCCCCCCCCCCCC#CC#CCCCCCCCCC(=O)O

Properties

• Solubility: Insoluble (7.1E^-6 g/L) (25 °C), Calc.^*
• Density: 0.930±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 62-65 °C (Expl.)
• Index of Refraction: 1.486, Calc.^*
• Boiling Point: 522.5±33.0 °C (760 mmHg), Calc.^*
• Flash Point: 246.9±20.1 °C, Calc.^*

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

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

Discovery and Applications

10,12-Pentacosadiynoic acid is an organic compound known for its distinct structure, which contains a long hydrocarbon chain and conjugated triple bonds. This compound, part of a class of polyynic acids, has garnered attention for its unique chemical properties and potential applications in various scientific fields, including materials science, chemistry, and biotechnology.

The discovery of 10,12-pentacosadiynoic acid can be traced back to the exploration of aliphatic diynes and polyynes, compounds characterized by alternating single and triple bonds. These compounds were studied due to their interesting electronic and structural properties. 10,12-Pentacosadiynoic acid was first synthesized in the context of efforts to develop novel materials with unique properties. Its conjugated system, featuring alternating single and triple bonds, imparts significant electronic characteristics that make it valuable in different areas of chemistry.

One of the most notable applications of 10,12-pentacosadiynoic acid is in the development of functionalized materials for electronic and optical applications. The compound's conjugated system allows it to absorb light efficiently, which makes it useful in optoelectronics. Specifically, 10,12-pentacosadiynoic acid has been investigated for use in the creation of thin films and coatings that exhibit specific optical properties. These films can be utilized in applications such as sensors, displays, and solar cells, where the interaction of light with materials is crucial for performance.

In addition to its optical applications, 10,12-pentacosadiynoic acid has been studied for its role in the creation of self-assembled monolayers (SAMs). SAMs are molecular assemblies that form spontaneously on surfaces, and they have a wide range of applications in nanotechnology, biosensing, and surface modification. The functional groups of 10,12-pentacosadiynoic acid enable it to form robust, ordered structures on metal surfaces, which can be used to modify the surface properties of materials. This makes it useful in areas such as sensor technology and catalysis, where surface characteristics are critical.

10,12-Pentacosadiynoic acid is also of interest in the field of polymer science. Due to its polyynic structure, it can be used as a precursor for the synthesis of new polymeric materials. The compound can undergo polymerization reactions, leading to the formation of polyconjugated systems with enhanced electronic and optical properties. Such polymers have potential applications in organic electronics, including organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs), where conjugated polymers are integral to the function of the device.

In biotechnology, 10,12-pentacosadiynoic acid has shown promise in the creation of bioactive surfaces. Its ability to self-assemble into structured monolayers makes it a useful component for designing surfaces that can interact with biological molecules. Such surfaces can be employed in medical devices, biosensors, and tissue engineering, where interaction with biomolecules is required for functionality.

Overall, 10,12-pentacosadiynoic acid is a compound with significant potential in several fields, including materials science, optoelectronics, polymer chemistry, and biotechnology. Its unique chemical structure, which combines conjugated triple bonds with a long hydrocarbon chain, imparts valuable properties that make it a key material for the development of advanced technologies.

References

Archan Dey, Gijbertus de With and Nico A. J. M. Sommerdijk. In situ techniques in biomimetic mineralization studies of calcium carbonate, Chem. Soc. Rev., 2010, 39, 397.