Palmitoyl pentapeptide-4

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Palmitoyl pentapeptide-4
File:Palmitoyl pentapeptide-4.svg
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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EC Number
  • 606-757-9
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UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C39H75N7O10/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-23-32(50)42-29(21-17-19-24-40)36(52)45-34(28(3)49)38(54)46-33(27(2)48)37(53)43-30(22-18-20-25-41)35(51)44-31(26-47)39(55)56/h27-31,33-34,47-49H,4-26,40-41H2,1-3H3,(H,42,50)(H,43,53)(H,44,51)(H,45,52)(H,46,54)(H,55,56)/t27-,28-,29+,30+,31+,33+,34+/m1/s1
    Key: WSGCRSMLXFHGRM-DEVHWETNSA-N
  • CCCCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)O
Properties
C39H75N7O10
Molar mass 802.068 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Palmitoyl pentapeptide-4 (palmitoyl pentapeptide-3 before 2006) is a matrikine used in anti-wrinkle cosmetics. It was launched in 2000 as an active ingredient for the personal care industry under the trade name Matrixyl by the Spanish cosmetic active ingredient manufacturer Sederma SAS.

Chemistry

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Palmitoyl pentapeptide-4 (Pal-Lys-Thr-Thr-Lys-Ser = Pal-KTTKS) contains 5 amino acids linked to a 16-carbon aliphatic chain for improving the penetration of the molecule through the lipid structures of the skin. It is a matrikine.[1] A number of similar molecules are known.[2][3][4][5]

Matrikines are messenger peptides capable of regulating cell activities by interacting with their specific receptors. They activate certain genes involved in the process of extracellular matrix renewal and cell proliferation.[6] By activating the neosynthesis of extracellular matrix macromolecules, palmitoyl pentapeptide-4 provides an anti-wrinkle effect.[medical citation needed] Studies (in vitro and in vivo) demonstrating the anti-wrinkle efficacy of this peptide have been conducted and published by Sederma and by independent organisations.[7][8][9]

References

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