Palmitoyl Tripeptide-8 Chemical Properties

Density 

1.20±0.1 g/cm3(Predicted)

pka

13.34±0.46(Predicted)

InChIKey

WBHUVOTYPRYBNG-QAXCHELISA-N

SMILES

C(N)(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1N=CNC=1)NC(=O)CCCCCCCCCCCCCCC

Palmitoyl Tripeptide-8 Usage And Synthesis

Description

Palmitoyl tripeptide-8 is a synthetic peptide ester based on a α-melanocyte stimulating hormone (α-MSH), originating from POMC, and it is composed by the sequence N-(1-oxohexadecyl)-L-histidyl-D-phenylalanyl-L-argininamide. Palmitoyl Tripeptide-8 is the product obtained by the reaction of palmitic acid and Tripeptide-8, wherein Tripeptide-8 is a three-residue synthetic peptide consisting of arginine, histidine and phenylalanine[1].

benefits

PalmitoylTripeptide-8 has a high affinity with MC1-R, specific anti-inflammatory activity, inhibit effectively lL-8release induced by UVB, maintain and restore anormal skin sensitivity threshold.Its recommended dosage is 0.3~2.5%.

Synthesis

Palmitoyl Tripeptide-8 can be obtained via a solid-phase peptide synthesis using the fluorenylmethyloxycarbonyl (Fmoc) strategy on an ACT496S2 automated synthesizer with PS-Rink amide (RAM) resin. The deprotection and coupling steps are carried out until the desired sequences are synthesized. Final side-chain deprotection and cleavage from the resin with a cleavage cocktail (trifluoroacetic acid/water/triisopropylsilane) afford palmitoyl tripeptide-8.

in vitro

In in vitro models, palmitoyl tripeptide-8 showed the ability to significantly inhibit IL-8 production up to 32% in UVB-irradiated keratinocytes, which was comparable to α-MSH, and also in IL-1 stimulated fibroblasts, reaching 64% inhibition which is greater that the achieved by α-MSH. In skin explants exposed to substance P, palmitoyl tripeptide-8 significantly reduced the number of dilated capillaries and the size of dilated vessels up to 30% and 51%, respectively. Edema was also reduced by 60% due to palmitoyl tripeptide-8. Palmitoyl tripeptide-8 can prevent and soothe an irritative response.

References

[1] Resende, Diana I S P et al. “Usage of Synthetic Peptides in Cosmetics for Sensitive Skin.” Pharmaceuticals (Basel, Switzerland) vol. 14,8 702. 21 Jul. 2021, doi:10.3390/ph14080702

Palmitoyl Tripeptide-8(936544-53-5)Related Product Information

• Copper Peptide
• (2S)-N2-(1-Oxohexadecyl)-L-lysyl-L-valyl-2,4-diaminobutanoic acid bis(trifluoroacetate)
• Palmitoyl Tetrapeptide-10
• Palmitoyl Hexapeptide-12
• Palmitoyl Isoleucine
• Palmitoyl Tripeptide-36
• Palmitoyl Pentapeptide
• Palmitoyl Tetrapeptide-20
• Palmitoyl Dipeptide-7
• Palmitoyl Tripeptide 38
• Palmitoyl tetrapeptide-7
• PalMitoyl Tripeptide-1
• Palmitoyl Tripeptide-5
• PalmitoylTripeptide-28
• PALM OIL
• Acetyl Hexapeptide-39
• HEXAPEPTIDE-2
• Myristoyl Hexapeptide-16