benzyloxycarbonyl-L-tryptophan

HCID 101176CAS 7432-21-5

Substructure search Find similar structures

Basic information

Standard SMILES: O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O)OCc1ccccc1
InChIKey: AHYFYYVVAXRMKB-KRWDZBQOSA-N
Molecular formula: C19H18N2O4
Average molar mass: 338.4 g/mol
Monoisotopic mass: 338.12665706

Overview

receptor antagonist for peptides from gastrin family; RN given refers to (L)-isomer

Names & identifiers

Preferred name: benzyloxycarbonyl-L-tryptophan
IUPAC: (2S)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid
English name: N-Cbz-L-Tryptophan
Molecular formula: C19H18N2O4
Molecular weight: 338.36

Names & synonyms

7432-21-5BenzyloxycarbonyltryptophanDTXSID00225332z-tryptophanRefChem:829274DTXCID00147823BENZYLOXYCARBONYL-L-TRYPTOPHAN231-074-4Z-Trp-OHN-Cbz-L-tryptophanNalpha-Cbz-L-tryptophanCbz-L-Trp-OH

Show more names

Z-TrpCbz-L-Try-OHN-CARBOBENZOXY-L-TRYPTOPHANCbz-TrpZ-L-TRP-OHNSC 521831

L-Tryptophan, N-[(phenylmethoxy)carbonyl]-Na-Cbz-L-tryptophanMFCD00065700N-CBZ-tryptophaneN-Benzyloxycarbonyl-L-tryptophan(S)-2-(((Benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoic acidCBZ-TRP-OHNalpha-benzyloxycarbonyl-L-tryptophan

Database identifiers

CAS: 7432-21-5
PubChem CID: 101176
DTXSID: DTXSID00225332
ChEMBL: CHEMBL291603
EC Number: 231-074-4
Nikkaji: J81.395H

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 91.4 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 7
Heavy atoms: 25
Formal charge: 0
Complexity: 464

Physicochemical properties

Melting point: 124 · 124-127 °C(lit.)
alpha: 2.5 · 2.5 º (c=3, EtOH)
Boiling point: 474.51 °C · 474.51°C (rough estimate)
Density: 1.2855 · 1.2855 (rough estimate)
refractive index: 1.614 · 1.6140 (estimate)
storage temp.: 2 · Inert atmosphere,2-8°C
solubility: 0.1 g/mL, · methanol: 0.1 g/mL, clear
pka: 3.98 · 3.98±0.10(Predicted)
form: Solid
color: White
optical activity: 20 · [α]20/D +2.9±0.3°, c = 3% in acetic acid
BRN: 96743 · 96743
CAS DataBase Reference: 7432 · 7432-21-5(CAS DataBase Reference)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-36/37/38
Safety Statements: 22 · 22-24/25-36-26
WGK Germany: 3 · 3
HS Code: 29339900 · 29339900

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 4 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (50%)

Safety data

wgk: 3
hs_code: 29339900
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 22-24/25-36-26
Hazard statements: H315-H319-H335
Precautionary statements: P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362

Chemistry & industry

Applications · 1 item

UsesNα-Cbz-L-tryptophan is an N-Cbz-protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.