| Identification | Back Directory | [Name]
Palmitoyl Tripeptide-8 | [CAS]
936544-53-5 | [Synonyms]
Neutrazen
Palmitoyl Tripeptide-8
Palmiltoyl Tripeptide-8
Factory Supplier Palmitoyl Tripeptide-8
L-Argininamide, N-(1-oxohexadecyl)-L-histidyl-D-phenylalanyl- | [EINECS(EC#)]
-0 | [Molecular Formula]
C37H61N9O4 | [MDL Number]
MFCD33404564 | [MOL File]
936544-53-5.mol | [Molecular Weight]
695.94 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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
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