Fmoc-phenylalanine (HCID 978331)

Overview

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Names & identifiers

Preferred name: Fmoc-phenylalanine
IUPAC: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoic acid
English name: Fmoc-Phe-OH
Molecular formula: C24H21NO4
Molecular weight: 387.43

Names & synonyms

FMOC-PHEFMOC-PHENYLALANINERefChem:599550fluorenylmethoxycarbonyl-conjugated phenylalanineFmoc-Phe-OHFmoc-L-phenylalanine35661-40-6Fmoc-L-Phe-OHN-Fmoc-L-phenylalanine286460-71-7MFCD00037128N-(9-Fluorenylmethoxycarbonyl)-L-phenylalanine

Show more names

Fmoc-Phenylalanine-OH(S)-2-((((9H-fluoren-9-yl)Methoxy)carbonyl)aMino)-3-phenylpropanoic acid

(((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalanineFMOC-L-PHEN-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-phenylalanineCHEMBL357583(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoic acid(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propanoic acidM03370L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-

Database identifiers

CAS: 35661-40-6
PubChem CID: 978331
ChEMBL: CHEMBL357583
UNII: UTY9NU6ZEU
Nikkaji: J256.551J

Properties

Computed structural properties

XLogP: 4.6
Topological polar surface area: 75.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 7
Heavy atoms: 29
Formal charge: 0
Complexity: 551

Physicochemical properties

Melting point: 180 · 180-187 °C(lit.)
alpha: -38 · -38 º (c=1,DMF)
Boiling point: 513.39 °C · 513.39°C (rough estimate)
Density: 1.2379 · 1.2379 (rough estimate)
refractive index: -39.5 ° · -39.5 ° (C=1, DMF)
storage temp.: 2 · 2-8°C
solubility: Chloroform (Slightly), DMF (Sparingly, Sonicated), DMSO (Slightly)
pka: 3.77 · 3.77±0.10(Predicted)
form: Powder
color: White
optical activity: 20 · [α]20/D 37°, c = 1 in DMF
BRN: 3597808 · 3597808
Major Application: peptide synthesis
InChI: InChI=1S/C24H21NO4/c26-23(27)22(14-16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,25,28)(H,26,27)/t22-/m0/s1
InChIKey: SJVFAHZPLIXNDH-QFIPXVFZSA-N
SMILES: C(O)(=O)[C@H](CC1=CC=CC=C1)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O
CAS DataBase Reference: 35661 · 35661-40-6(CAS DataBase Reference)
UNSPSC Code: 12352209 · 12352209
NACRES: 26 · NA.26
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335-H413
Precautionary statements: 261 · P261-P273-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25-26
WGK Germany: 3 · 3
HS Code: 2924 · 2924 29 70
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 2924 29 70
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 22-24/25-26
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335-H413
REACH Registrations: Active
Precautionary statements: P261-P273-P305+P351+P338

Chemistry & industry

Applications

Uses(Fmoc-Phe-OH) L-Phenylalanine (P319415) derivative, used in the preparation of peptides and deltorphin derivatives. A potential inhibitor of IGF-I and IGF-Binding Protein-5 complex.

General DescriptionFmoc-Phe-OH is highly hydrophobic and dissolves easily in DMF and NMP. A photoresponsive hydrogel can be easily created by co-assembling Fmoc-Phe-OH and Azp without the need for chemical synthesis.