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SML0395

Sigma-Aldrich

Ac-EEMQRR-NH2 trifluoroacetate salt

≥95% (HPLC)

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Synonym(s):
Acetyl Hexapeptide-3, Acetyl Hexapeptide-8, Acetyl hexapeptide, Hexapeptide 3
Empirical Formula (Hill Notation):
C34H60N14O12S · xC2HF3O2
CAS Number:
616204-22-9
Molecular Weight:
888.99 (free base basis)
MDL number:
MFCD22666393
UNSPSC Code:
12352200
PubChem Substance ID:
329825391
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

lyophilized solid

color

white

shipped in

wet ice

storage temp.

−20°C

SMILES string

OC(=O)C(F)(F)F.CSCC[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(C)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O

InChI

1S/C34H60N14O12S.C2HF3O2/c1-17(49)43-20(8-11-25(51)52)29(57)47-22(9-12-26(53)54)31(59)48-23(13-16-61-2)32(60)46-21(7-10-24(35)50)30(58)45-19(6-4-15-42-34(39)40)28(56)44-18(27(36)55)5-3-14-41-33(37)38;3-2(4,5)1(6)7/h18-23H,3-16H2,1-2H3,(H2,35,50)(H2,36,55)(H,43,49)(H,44,56)(H,45,58)(H,46,60)(H,47,57)(H,48,59)(H,51,52)(H,53,54)(H4,37,38,41)(H4,39,40,42);(H,6,7)/t18-,19-,20-,21-,22-,23-;/m0./s1

InChI key

RSZPECDVLFYJCF-PXILYFGCSA-N

Amino Acid Sequence

Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2

Biochem/physiol Actions

Ac-EEMQRR-NH2 is a SNAP25 N-terminal-derived peptide that inhibits the SNARE complex and possibly blocks neuronal exocytosis. Ac-EEMQRR-NH2 exhibits anti-inflammatory and anti-wrinkle activity. It is used as anti-wrinkle cosmetics ingredient.
Ac-EEMQRR-NH2 trifluoroacetate salt is considered 4000 times less toxic than botulin toxin. It has restricted transdermal penetration and hence has limited application for topical usage.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Wooseon Hwang et al.
Scientific reports, 10(1), 21514-21514 (2020-12-11)
Facial wrinkles are the predominant phenotypes of skin aging. To date, one of the most effective ways to improve wrinkles is botulinum toxin type A (BoNT/A) injection, which inhibits muscle contractions by reducing acetylcholine release from neurons. However, since BoNT/A
Enhanced delivery of hydrophilic peptides in vitro by transdermal microneedle pretreatment
Zhang S, et al.
Acta Pharmaceutica Sinica. B, 4(1), 100-104 (2014)

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