Palmitoyl tripeptide-8
[CAS# 936544-53-5]

Identification

• Classification: API >> Antibiotics >> Peptide drug
• Name: Palmitoyl tripeptide-8
• Synonyms: N-[(2S)-1-[[(2R)-1-[[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]hexadecanamide
• Molecular Formula: C₃₇H₆₁N₉O₄
• Molecular Weight: 695.94
• CAS Registry Number: 936544-53-5
• SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Index of refraction: 1.593 (Calc.)^*, 1.593 (Expl.)

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

Discovory and Applicatios

Palmitoyl tripeptide-8 is a synthetic peptide derivative that was developed for use in cosmetic and dermatological applications. Its discovery is linked to research into bioactive peptides that can modulate skin physiology, particularly in the context of aging and inflammation. The peptide consists of a short amino acid sequence, typically lysine–threonine–lysine, conjugated at the N-terminus with palmitic acid, a 16-carbon saturated fatty acid. The palmitoylation enhances the lipophilicity of the peptide, facilitating its penetration through the stratum corneum, the outermost layer of the skin, and improving stability in topical formulations.

The peptide backbone of palmitoyl tripeptide-8 was designed to mimic naturally occurring signaling peptides known as cytokines or matrikines, which regulate inflammatory processes and extracellular matrix production in the skin. By synthesizing a short peptide sequence that retains biological activity, researchers were able to create a molecule that could interact with skin cells to modulate signaling pathways. The conjugation with palmitic acid ensures that the peptide can be incorporated effectively into lipid-based creams, serums, and other topical products.

Applications of palmitoyl tripeptide-8 are primarily in anti-aging and skin-soothing formulations. Studies have demonstrated that the peptide can reduce the expression of pro-inflammatory mediators in skin cells, thereby mitigating chronic inflammation associated with skin aging. It has also been reported to stimulate the production of extracellular matrix components such as collagen and glycosaminoglycans, which are important for maintaining skin elasticity and firmness. These properties have made palmitoyl tripeptide-8 a common ingredient in serums, creams, and other cosmetic products aimed at reducing the appearance of wrinkles and promoting skin health.

Beyond cosmetic applications, palmitoyl tripeptide-8 is of interest in research on peptide delivery and bioactivity. Its design exemplifies the strategy of conjugating short peptide sequences with lipophilic moieties to enhance skin permeability and stability, a principle that is applied to other bioactive peptides in dermatological science. The molecule serves as a model for studying peptide–cell interactions, signaling modulation, and the development of topical agents that can influence biological processes in the skin.

The development of palmitoyl tripeptide-8 reflects broader trends in peptide chemistry and cosmetic science, where synthetic peptides are tailored to achieve specific functional outcomes. Its combination of a biologically active tripeptide sequence with a fatty acid conjugate demonstrates the utility of chemical modification in enhancing peptide performance in topical applications. Today, palmitoyl tripeptide-8 continues to be used in a variety of skincare products, illustrating the intersection of synthetic chemistry, peptide biology, and applied dermatology.

References

2023. Novel combination products combining cannabis derivatives and at least one peptide and uses thereof. Publication Number: CN-116615171-A.