Benzyloxycarbonyl-L-phenylalanine

HCID 70878

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Basic information

CAS: 1161-13-3
Standard SMILES: O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1
InChIKey: RRONHWAVOYADJL-HNNXBMFYSA-N
Molecular formula: C17H17NO4
Average molar mass: 299.32 g/mol
Monoisotopic mass: 299.11575802

Overview

RN given refers to (L-Phe)-isomer

Names & identifiers

Preferred name: Benzyloxycarbonyl-L-phenylalanine
IUPAC: (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid
English name: N-Cbz-L-Phenylalanine
Molecular formula: C17H17NO4
Molecular weight: 299.32

Names & synonyms

1161-13-3CarbobenzoxyphenylalanineZ-Phebenzyloxycarbonyl-L-phenylalaninebenzyloxycarbonylphenylalanineDTXSID30151276RefChem:829269DTXCID3073767214-599-3Z-Phe-OHN-CBZ-L-PHENYLALANINEZ-L-Phenylalanine

Show more names

Cbz-PheZ-L-PHE-OHCBZ-L-PHECBZ-L-Phe-OHL-PHENYLALANINE, N-[(PHENYLMETHOXY)CARBONYL]-Z-L

N-Carbobenzoxy-L-phenylalanineN-(Carbobenzyloxy)-L-phenylalanineCbz-Phe-OHCBZ-L-PhenylalanineCarbobenzoxy-L-phenylalanineMFCD00020418(Benzyloxycarbonyl)phenylalanine((benzyloxy)carbonyl)-L-phenylalanine

Database identifiers

CAS: 1161-13-3
PubChem CID: 70878
DTXSID: DTXSID30151276
ChEMBL: CHEMBL66143
EC Number: 214-599-3
Nikkaji: J80.209C

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 75.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 7
Heavy atoms: 22
Formal charge: 0
Complexity: 360

Physicochemical properties

Melting point: 85 · 85-87 °C(lit.)
alpha: 5 · 5 º (c=5,acetic acid)
Boiling point: 440.65 °C · 440.65°C (rough estimate)
Density: 1.1441 · 1.1441 (rough estimate)
refractive index: 5.3 ° · 5.3 ° (C=4, AcOH)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: DMF (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka: 3.86 · 3.86±0.10(Predicted)
form: Powder
color: White to off-white
optical activity: 20 · [α]20/D +5°, c = 5 in acetic acid
BRN: 2222826 · 2222826
Major Application: peptide synthesis
InChI: 1S/C17H17NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/t15-/m0/s1
InChIKey: RRONHWAVOYADJL-HNNXBMFYSA-N
SMILES: OC(=O)[C@H](Cc1ccccc1)NC(=O)OCc2ccccc2
CAS DataBase Reference: 1161 · 1161-13-3(CAS DataBase Reference)
UNSPSC Code: 12352209 · 12352209
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P271-P280
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xn
Risk Statements: 62 · 62-36/37/38-20/21/22
Safety Statements: 22 · 22-24/25-36-26
WGK Germany: 3 · 3
RTECS: 4343000 · AY4343000
HS Code: 29242990 · 29242990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Danger

H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P233, P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
rtecs: AY4343000
hs_code: 29242990
risk_code: 62-36/37/38-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 22-24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P271-P280

Chemistry & industry

Applications · 3 items

UsesInhibitor of thermolysin

UsesN-(Carbobenzyloxy)-L-phenylalanine is used in the synthesis of neurokinin antagonists. Furthermore it is used in the preparation of Co(II), Zn(II), and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine that displays antimicrobial activity against common strains of bacteria.

UsesN-Cbz-L-Phenylalanine is used in the synthesis of neurokinin antagonists. Furthermore it is used in the preparation of Co(II), Zn(II), and Cd(II) complexes with N-benzyloxycarbonyl-S-phen ylalanine that displays antimicrobial activity against common strains of bacteria.