N'-Laruoyl-L-lysine
[CAS# 52315-75-0]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Lysine derivative
• Name: N'-Laruoyl-L-lysine
• Synonyms: N6-(1-Oxododecyl)-L-lysine
• Molecular Formula: C₁₈H₃₆N₂O₃
• Molecular Weight: 328.49
• Protein Sequence: X
• CAS Registry Number: 52315-75-0
• EC Number: 257-843-4
• SMILES: CCCCCCCCCCCC(=O)NCCCC[C@@H](C(=O)O)N

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 229-231 °C
• Index of Refraction: 1.482, Calc.^*
• Boiling Point: 528.0±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 273.1±28.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

N'-Lauroyl-L-Lysine is an innovative compound that has carved out a niche in the cosmetics and personal care industry due to its unique properties and benefits. The compound is formed by reacting lauric acid, a fatty acid commonly found in coconut and palm kernel oils, with L-lysine, an essential amino acid. The resulting compound, which has the molecular formula C18H36N2O3, combines the beneficial properties of both ingredients to provide enhanced functionality for a variety of applications.

The discovery of N'-Lauroyl-L-Lysine stemmed from a quest for new, effective, and safe ingredients in skin care and personal care products. The researchers aimed to develop a compound that could provide skin conditioning, moisturizing, and texture-enhancing benefits while also being biocompatible and environmentally friendly. By utilizing lauric acid and L-lysine, they were able to create a compound that met these criteria.

One of the primary applications for N'-Lauroyl-L-Lysine is in cosmetics, where it is valued for its excellent skin feel and sensory properties. The compound is often used as a thickener to provide a silky, smooth feel to lotions, creams, and powders. Its ability to enhance product spread and absorption makes it a popular ingredient in high-end skincare formulations.

In addition to its sensory benefits, N'-lauroyl-L-lysine can also be used as a conditioning agent. It helps to improve the texture and hydration of the skin by forming a protective barrier to reduce water loss. This property is particularly beneficial in moisturizing products designed for dry or sensitive skin. The compound's biocompatibility ensures that it is gentle on the skin, reducing the risk of irritation, making it suitable for products intended for sensitive or damaged skin.

In addition, N'-lauroyl-L-lysine can be used in hair care products. Its conditioning properties also extend to the hair, helping to improve manageability, reduce static and enhance shine. It is often included in shampoos, conditioners and styling products to provide a smooth and soft texture to the hair.

The uses of N'-lauroyl-L-lysine are not limited to skin and hair care. It is also used in color cosmetics such as foundation, blush and eye shadow. In these products, it acts as a binder and texturizing agent, helping to improve the application and wear of the product. Its ability to provide a silky, non-greasy finish makes it a go-to ingredient in formulations designed to achieve a natural, flawless look.

Safety and environmental considerations are paramount in the development and application of any cosmetic ingredient. N'-Lauroyl-L-Lysine excels on both counts. It is derived from natural sources, ensuring it is biodegradable and environmentally friendly. Additionally, extensive safety testing has shown that N'-Lauroyl-L-Lysine is non-toxic, non-irritating, and suitable for use in a wide range of personal care products.

References

2005. A Novel Acylase from Streptomyces mobaraensis that Efficiently Catalyzes Hydrolysis/Synthesis of Capsaicins as Well as N-Acyl-l-amino Acids and N-Acyl-peptides. Journal of Agricultural and Food Chemistry, 53(26).
DOI: 10.1021/jf052102k

2009. Efficient Nepsilon-lauroyl-L-lysine production by recombinant epsilon-lysine acylase from Streptomyces mobaraensis. Journal of Biotechnology, 141(3-4).
DOI: 10.1016/j.jbiotec.2009.03.008