Ceramides
[CAS# 100403-19-8]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: Ceramides
• Synonyms: N-(1,3,4-trihydroxyoctadecan-2-yl)octadec-9-enamide
• Molecular Formula: C₃₆H₇₁NO₄
• Molecular Weight: 581.95
• CAS Registry Number: 100403-19-8
• EC Number: 309-560-3
• SMILES: CCCCCCCCCCCCCCC(C(C(CO)NC(=O)CCCCCCCC=CCCCCCCCC)O)O

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.486, Calc.^*
• Boiling Point: 721.3±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 390.0±32.9 °C, Calc.^*

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

Discovery and Applications

Ceramides are a class of lipid molecules composed of sphingosine and a fatty acid. They were first identified in the early 1880s by Johann Ludwig Wilhelm Thudichum, a pioneer in brain chemistry who studied the composition of brain tissues. Thudichum’s work laid the foundation for understanding the role of complex lipids in biological systems. Ceramides derive their name from "cera," meaning wax, due to their wax-like properties. These molecules are fundamental components of cell membranes, particularly in the outermost layer of the skin.

In biological systems, ceramides play critical roles in maintaining the skin’s barrier function and regulating water permeability. They are present in high concentrations in the stratum corneum, the skin’s outer layer, where they help prevent transepidermal water loss. Ceramides also participate in cellular signaling, influencing processes such as cell growth, differentiation, apoptosis, and inflammation. Disruption in ceramide levels has been linked to various skin disorders, including atopic dermatitis, psoriasis, and ichthyosis.

The synthesis of ceramides occurs through several metabolic pathways. One of the most widely studied methods is the de novo synthesis pathway, which begins with the condensation of serine and palmitoyl-CoA to produce 3-ketodihydrosphingosine. This intermediate is then reduced to dihydrosphingosine, which subsequently undergoes N-acylation and desaturation to form ceramides. This pathway has been extensively explored due to its significance in both physiological processes and therapeutic applications. Researchers have also developed synthetic analogs of ceramides to study their biological functions and potential medical applications.

Ceramides are widely used in skincare and dermatology. Because of their essential role in maintaining skin hydration and integrity, they are key ingredients in moisturizers, cleansers, and barrier repair creams. Products containing ceramides help improve the skin’s moisture content, enhance its protective barrier, and alleviate symptoms of dry and damaged skin. In addition to skincare, ceramides have garnered interest in cancer research due to their involvement in apoptosis regulation. Elevated ceramide levels can induce cell death in cancerous tissues, making them potential targets for therapeutic intervention.

The significance of ceramides extends beyond dermatology. Recent studies have highlighted their involvement in metabolic disorders, including insulin resistance and cardiovascular diseases. As signaling molecules, ceramides influence pathways that impact lipid metabolism, energy homeostasis, and inflammatory responses. This multifaceted role positions ceramides as crucial targets for ongoing research in both health and disease contexts.

References

2002. Deficiency of epidermal protein-bound omega-hydroxyceramides in atopic dermatitis. The Journal of Investigative Dermatology, 119(1).
DOI: 10.1046/j.1523-1747.2002.01833.x

2008. Ceramide 1 and ceramide 3 act synergistically on skin hydration and the transepidermal water loss of sodium lauryl sulfate‐irritated skin. International Journal of Dermatology, 47(8).
DOI: 10.1111/j.1365-4632.2008.03687.x

2015. Safety and risk assessment of ceramide 3 in cosmetic products. Food and Chemical Toxicology, 84.
DOI: 10.1016/j.fct.2015.07.012