6-Aminocaproic acid
[CAS# 60-32-2]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluoropropane series
• Name: 6-Aminocaproic acid
• Synonyms: 6-Aminohexanoic acid
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17
• CAS Registry Number: 60-32-2
• EC Number: 200-469-3
• SMILES: C(CCC(=O)O)CCN

Properties

• Solubility: soluble 25 mg/mL, 6 mg/mL (DMSO) (Expl.)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 207-209 °C (Expl.)
• Index of Refraction: 1.467, Calc.^*
• Boiling Point: 255.6±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 108.4±22.6 °C, Calc.^*

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
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

6-Aminocaproic acid is an organic compound with the chemical formula C6H13NO2. It is a six-carbon chain amino acid derivative, commonly referred to as ε-aminocaproic acid. The compound features an amino group (-NH2) and a carboxyl group (-COOH) attached to a caproic acid chain, making it a lysine precursor. The discovery of 6-aminocaproic acid dates back to the early 20th century when researchers were investigating amino acid derivatives and their roles in biological systems. It was initially noted for its potential to act as a building block in the synthesis of various bioactive molecules.

The chemical structure of 6-aminocaproic acid has a linear chain of six carbon atoms with functional groups at each end. This simple structure allows it to be a versatile compound in chemical synthesis. In particular, the amino group is reactive and can participate in a variety of reactions, making the substance useful in both industrial and pharmaceutical applications. The compound is produced through the catalytic hydrogenation of a precursor such as 6-cyanohexanoic acid or by other synthetic routes involving amino acid chemistry. The development of efficient and cost-effective synthesis methods has contributed to its widespread use in different industries.

6-Aminocaproic acid is primarily known for its role in medicine as an antifibrinolytic agent. It is commonly used in the treatment of bleeding disorders such as excessive bleeding following surgery or trauma. The compound works by inhibiting the activation of plasminogen to plasmin, thereby preventing the breakdown of fibrin in blood clots. This action helps stabilize clot formation and is particularly important in surgeries where excessive bleeding is a concern. The drug is marketed under various brand names for these purposes and is often used in cardiac surgery, dental procedures, and liver transplantations.

Beyond its medical use, 6-aminocaproic acid has applications in the production of synthetic polymers. It is employed in the manufacture of nylon-6, a widely used polymer in textiles and industrial products. Nylon-6 is synthesized by polymerizing 6-aminocaproic acid through a ring-opening polymerization process, forming long chains of the polymer that exhibit excellent strength and durability. This polymer is found in various everyday products, including clothing, automotive parts, and packaging materials. Additionally, the compound is used as a stabilizer and dispersant in the production of certain emulsions and coatings.

In conclusion, 6-aminocaproic acid is an important chemical with significant applications in medicine and industry. Its ability to inhibit fibrinolysis makes it a valuable agent for controlling bleeding, while its role in polymer production contributes to the manufacture of versatile and durable materials. Ongoing research continues to explore additional uses for this compound in various fields, including biotechnology and materials science.

References

1990. Zinc Acexamate Inhibits Gastric Acid and Pepsinogen Secretion in the Rat. The Journal of pharmacy and pharmacology, 42(4).
DOI: 10.1111/j.2042-7158.1990.tb05402.x

1984. Microassay of epsilon-aminocaproic acid by liquid chromatography. Annales de biologie clinique, 42(5).
URL: https://pubmed.ncbi.nlm.nih.gov/6507958

1979. Effects of tranexamic acid, CIS-AMCHA, and 6-aminohexanoic acid on the activation rate of plasminogen by urokinase in the presence of clot. Thrombosis Research, 15(3-4).
DOI: 10.1016/0049-3848(79)90009-4