Laurocapram
[CAS# 59227-89-3]

Identification

• Classification: API >> Other chemicals
• Name: Laurocapram
• Synonyms: Azon; Azone; 1-Dodecylazacycloheptan-2-one; N-Dodecylcaprolactam; 1-Dodecylhexahydro-2H-azepin-2-one
• Molecular Formula: C₁₈H₃₅NO
• Molecular Weight: 281.48
• CAS Registry Number: 59227-89-3
• EC Number: 261-668-9
• SMILES: CCCCCCCCCCCCN1CCCCCC1=O

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.466, Calc.^*
• Boiling Point: 404.9±14.0 °C (760 mmHg), Calc.^*
• Flash Point: 165.2±10.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H315-H319-H335-H413
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Laurocapram, also known as A-9 or lauramide diethanolamide, is an organic compound derived from the fatty acid lauric acid, which is a major component of coconut oil and palm kernel oil. It is a synthetic derivative of lauric acid and is classified as an amide. Laurocapram is primarily used in the formulation of personal care products, such as shampoos, conditioners, and skin care products, due to its surfactant and emulsifying properties.

The discovery of laurocapram can be traced to the need for effective surfactants and emulsifiers in various industries, including cosmetics and pharmaceuticals. Surfactants like laurocapram are key ingredients in cleaning products, as they help to lower the surface tension between oils and water, facilitating the removal of dirt, oil, and other substances from surfaces.

In personal care products, laurocapram serves as a mild surfactant and emulsifier, providing skin conditioning and cleansing effects without the harshness associated with other surfactants. It is often used in formulations where a gentle, non-irritating cleaning agent is required, particularly for sensitive skin. Additionally, laurocapram's ability to form stable emulsions makes it useful in products such as lotions, creams, and other formulations that require a stable mixture of oil and water components.

Beyond the cosmetic industry, laurocapram has applications in the pharmaceutical sector. It has been used as an ingredient in topical drug formulations, where its emulsifying properties help deliver active ingredients effectively to the skin. Laurocapram is also being studied for its potential use in drug delivery systems, where its ability to modify the permeability of biological membranes could improve the absorption of therapeutic agents.

In laboratory research, laurocapram has been investigated for its potential to enhance the penetration of certain molecules across the skin. This ability to alter membrane permeability is important for improving the bioavailability of various pharmaceutical compounds. Additionally, laurocapram has been explored as a component in formulations designed to treat conditions like dry skin or eczema due to its moisturizing and skin barrier-enhancing properties.

Overall, laurocapram is valued for its surfactant and emulsifying properties, which make it a versatile ingredient in the cosmetic and pharmaceutical industries. Its applications range from personal care products to potential use in advanced drug delivery systems, showcasing its importance as a functional compound in various fields.

References

2024. Skin Penetration and Permeation Properties of Transcutol® in Complex Formulations. AAPS PharmSciTech.
DOI: 10.1208/s12249-024-02886-8

2024. Drug delivery to and through the skin. Drug Delivery and Translational Research.
DOI: 10.1007/s13346-024-01614-w

2024. Design of Ionic Liquid Formulations with Azone-Mimic Structures for Enhanced Drug Skin Permeation. Journal of Pharmaceutical Sciences.
DOI: 10.1016/j.xphs.2017.12.007