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936544-53-5

936544-53-5 Structure

936544-53-5 Structure
IdentificationBack 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 PropertiesBack Directory
[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
Hazard InformationBack 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
Questions And AnswerBack Directory
[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.
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