8-Aminooctanoic acid
[CAS# 1002-57-9]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: 8-Aminooctanoic acid
• Synonyms: omega-Aminocaprylic acid
• Molecular Formula: C₈H₁₇NO₂
• Molecular Weight: 159.23
• CAS Registry Number: 1002-57-9
• EC Number: 213-687-9
• SMILES: C(CCCC(=O)O)CCCN

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 194 ºC (Expl.)
• Index of Refraction: 1.469, Calc.^*
• Boiling Point: 286.0±23.0 ºC (760 mmHg), Calc.^*
• Flash Point: 126.8±22.6 ºC, 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
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
Flammable solids	Flam. Sol.	2	H228
Self-heating substances or mixtures	Self-heat.	2	H252

Discovory and Applicatios

8-Aminooctanoic acid is an aliphatic amino acid with an eight-carbon backbone and an amino group at one terminal. This compound, also known as 8-aminooctanoate or aminocaprylic acid, is a versatile building block in organic chemistry and biochemistry. Its properties make it valuable in the synthesis of polymers, pharmaceuticals, and materials with specific functional characteristics.

The discovery of 8-aminooctanoic acid dates back to early studies on synthetic amino acids. Researchers initially aimed to explore the reactivity and structural properties of longer-chain amino acids to develop novel materials and biochemical analogs. The synthesis of 8-aminooctanoic acid typically involves the reaction of octanoic acid derivatives with ammonia or other amination reagents, producing the terminal amino-functionalized compound under controlled conditions. Advances in synthetic methodologies have made the process more efficient, enabling scalable production.

One of the notable applications of 8-aminooctanoic acid is in the synthesis of nylon derivatives and other polyamides. As a monomer, it contributes to the development of polymers with tailored mechanical and chemical properties, making it essential in the production of durable fibers and films. Its relatively long aliphatic chain imparts flexibility and hydrophobic characteristics to the resulting materials, making them suitable for diverse industrial applications.

In the pharmaceutical industry, 8-aminooctanoic acid serves as a precursor or intermediate in the synthesis of biologically active compounds. Its structural features allow it to mimic certain naturally occurring amino acids, making it useful in drug design and discovery. The compound's functional groups also make it an attractive candidate for modification, enabling the development of compounds with enhanced bioavailability and targeted therapeutic effects.

8-Aminooctanoic acid is also studied for its potential role in designing surfactants and amphiphilic molecules. These applications leverage its dual hydrophilic and hydrophobic nature, with the amino group providing a site for water solubility and the octanoic chain offering hydrophobic interactions. These properties make it suitable for applications in detergents, emulsifiers, and stabilizers in industrial and biomedical contexts.

Although the compound offers significant advantages, its use requires attention to safe handling practices due to potential irritant properties associated with primary amines. Ensuring proper storage and adherence to safety protocols is essential in industrial and laboratory settings.

Current research continues to explore the potential of 8-aminooctanoic acid in advanced materials and medical applications. Innovations in its functionalization and integration into complex chemical frameworks highlight its growing importance in scientific and industrial fields.

References

2023. Effects of Polyethylene Glycol and 8-Aminooctanoic Acid Linkers on Melanoma Uptake of [99mTc]Tc-Tricarbonyl-NOTA-Conjugated Lactam-Cyclized a-MSH Peptides. Bioconjugate Chemistry, 34(6).
DOI: 10.1021/acs.bioconjchem.3c00164

2020. Enzymatic Synthesis of Aliphatic Primary ?-Amino Alcohols from ?-Amino Fatty Acids by Carboxylic Acid Reductase. Catalysis Letters, 150.
DOI: 10.1007/s10562-020-03233-9

2020. Lipoic acid rejuvenates aged intestinal stem cells by preventing age-associated endosome reduction. EMBO Reports, 21(8).
DOI: 10.15252/embr.201949583