Compound monograph
Matrixyl
Palmitoyl pentapeptide-4 is the pentapeptide KTTKS with an N-terminal palmitoyl group, corresponding to a fragment sequence of type I procollagen.
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Identity & nomenclature
Palmitoyl pentapeptide-4 is the pentapeptide KTTKS with an N-terminal palmitoyl group, corresponding to a fragment sequence of type I procollagen.
Matrixyl is a trade name for palmitoyl pentapeptide-4, the pentapeptide Lys-Thr-Thr-Lys-Ser (KTTKS) carrying an N-terminal palmitoyl group. The source review notes that KTTKS has become erroneously associated with the term pentapeptide in cosmetic marketing, and that the material has also been designated palmitoyl pentapeptide-3 under earlier INCI naming. Identity should be established against CAS 214047-00-4.
Declared aliases and development codes: Pal-KTTKS, Palmitoyl-KTTKS, Palmitoyl pentapeptide-3.
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Molecular properties
| Molecular formula | C39H75N7O10 |
|---|---|
| Molecular mass | 802.1 Da |
| CAS Registry Number | 214047-00-4 |
| PubChem CID | 9897237 |
| UNII | KK181SM5JG |
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Structural characteristics
The palmitoyl group is a sixteen-carbon acyl chain attached at the N-terminus, and accounts for a substantial share of the molecular mass relative to the five-residue peptide core. The source review reports an in vitro basis for action on fibroblasts through stimulation of extracellular matrix synthesis, describing the reported stimulatory effect as specific to collagen types I and III and to fibronectin expression.
Terminal features: N-terminal palmitoyl.
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Molecular targets & mechanisms
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Analytical considerations
The palmitoyl modification dominates the lipophilicity of the molecule and is part of its declared identity; an unmodified KTTKS preparation is a different substance with a different mass. The sequence contains no aromatic residues, so UV detection at 280 nm gives no useful chromophore response. The source review notes a surprising absence of in vitro skin penetration data in the published literature.
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Verified bibliography
- Topically applied KTTKS: a review.current
Abu Samah NH, Heard CM
International journal of cosmetic science · 2011-05-03 · Review
- A pentapeptide from type I procollagen promotes extracellular matrix production.current
Katayama K, Armendariz-Borunda J, Raghow R, Kang AH, Seyer JM
The Journal of biological chemistry · 1993-05-15 · Journal Article
- Dermal Stability and In Vitro Skin Permeation of Collagen Pentapeptides (KTTKS and palmitoyl-KTTKS).current
Choi YL, Park EJ, Kim E, Na DH, Shin YH
Biomolecules & therapeutics · 2014-07 · Journal Article
- Development of a LC-MS/MS method to monitor palmitoyl peptides content in anti-wrinkle cosmetics.current
Chirita RI, Chaimbault P, Archambault JC, Robert I, Elfakir C
Analytica chimica acta · 2009-03-20 · Journal Article
- Self-assembly of palmitoyl lipopeptides used in skin care products.current
Castelletto V, Hamley IW, Whitehouse C, Matts PJ, Osborne R, Baker ES
Langmuir : the ACS journal of surfaces and colloids · 2013-07-12 · Journal Article
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Methodology & citation verification
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