Palmitoyl Tripeptide-8 CAS 936544-53-5

Introduction：Basic information about Palmitoyl Tripeptide-8 CAS 936544-53-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Palmitoyl Tripeptide-8 Basic information

• Product Name: Palmitoyl Tripeptide-8
• Synonyms: Neutrazen;Palmitoyl Tripeptide-8;Palmiltoyl Tripeptide-8;L-Argininamide, N-(1-oxohexadecyl)-L-histidyl-D-phenylalanyl-;Factory Supplier Palmitoyl Tripeptide-8;Cosmetic Peptide Palmitoyl Tripeptide-8 Neutrazen Powder CAS 936544-53-5 for Anti-Allergic and Repair;Pal-His-D-Phe-Arg-NH2;PALMITOYL TETRAPEPTIDE-8
• CAS: 936544-53-5
• MF: C37H61N9O4
• MW: 695.94
• EINECS: 000-000-0
• Mol File: 936544-53-5.mol

Palmitoyl Tripeptide-8 Chemical Properties

• density: 1.20±0.1 g/cm3(Predicted)
• pka: 13.34±0.46(Predicted)
• Sequence: {palmitoyl-His}-{d-Phe}-Arg-NH2
• Cosmetics Ingredients Functions: SKIN CONDITIONING
• 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

Application

Palmitoyl tripeptide-5 can inhibit melanin production in melanocytes by suppressing tyrosinase activity and downregulating the mRNA levels of microphthalmia-associated transcription factor (MITF) and tyrosinase. Its application as a whitening additive in cosmetics could be considered. Clinical trials have shown that, compared to placebo and reference substances, skincare products containing palmitoyl tripeptide-8 significantly reduced skin laxity and reduced and altered age lines. It also exhibited significantly higher activity compared to 10 ppm palmitoyl pentapeptide-4. This ingredient is listed in China's 2015 Catalogue of Used Cosmetic Ingredients and can be legally added.

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