N-benzyloxycarbonyl-l-tyrosine

HCID 712438

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Basic information

CAS: 1164-16-5
Standard SMILES: O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)O)OCc1ccccc1
InChIKey: MCRMUCXATQAAMN-HNNXBMFYSA-N
Molecular formula: C17H17NO5
Average molar mass: 315.32 g/mol
Monoisotopic mass: 315.11067264

Overview

structure in first source

Names & identifiers

Preferred name: N-benzyloxycarbonyl-l-tyrosine
IUPAC: (2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoic acid
English name: Z-Tyr-OH
Molecular formula: C17H17NO5
Molecular weight: 315.32

Names & synonyms

N-Benzyloxycarbonyl-L-tyrosineRefChem:5741761164-16-5Z-Tyr-OHN-Cbz-L-tyrosineN-Carbobenzoxy-L-tyrosineL-Tyrosine, N-[(phenylmethoxy)carbonyl]-Cbz-L-TyrosineCbz-Tyr-OHMFCD00037180N-Carbobenzyloxy-L-tyrosineZ-Tyr

Show more names

CBZ-L-TYR-OHBENZYLOXYCARBONYL-L-TYROSINEN-Benzyloxycarbonyl-L-tyrosine, 99%, may contain up to ca 10% waterZ-L-TyrZ-TYROSINEZ-TYR-OH.H2O

Z-L-Tyrosine(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoic acid(2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoic acid(S)-2-(((Benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoic acidSCHEMBL221300CHEMBL291833((Benzyloxy)carbonyl)-L-tyrosineBDBM50043803

Database identifiers

CAS: 1164-16-5
PubChem CID: 712438
DTXSID: DTXSID301313627
ChEMBL: CHEMBL291833
Nikkaji: J80.060K

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 95.9 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 7
Heavy atoms: 23
Formal charge: 0
Complexity: 386

Physicochemical properties

Melting point: 57 · 57-60 °C(lit.)
Boiling point: 454.88 °C · 454.88°C (rough estimate)
Density: 1.1781 · 1.1781 (rough estimate)
refractive index: 10 ° · 10.0 ° (C=1, AcOH)
storage temp.: Sealed in dry,Room Temperature
solubility: Acetic Acid (Sparingly), DMSO (Slightly), Methanol (Sparingly)
pka: 2.97 · 2.97±0.10(Predicted)
form: Solid
color: Off-White
optical activity: 22 · [α]22/D +11°, c = 1 in acetic acid
Water Solubility: 1.53 g/L · 1.53g/L(25 ºC)
BRN: 2169918 · 2169918
Major Application: peptide synthesis
InChI: 1S/C17H17NO5.H2O/c19-14-8-6-12(7-9-14)10-15(16(20)21)18-17(22)23-11-13-4-2-1-3-5-13;/h1-9,15,19H,10-11H2,(H,18,22)(H,20,21);1H2/t15-;/m0./s1
InChIKey: BBPCQKGWAVVMSL-RSAXXLAASA-N
SMILES: O=C(N[C@H](C(O)=O)CC1=CC=C(O)C=C1)OCC2=CC=CC=C2
CAS DataBase Reference: 1164 · 1164-16-5(CAS DataBase Reference)
UNSPSC Code: 12352209 · 12352209
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi,Xn
Risk Statements: 20 · 20/21/22-36/37/38
Safety Statements: 22 · 22-24/25-36-26-45-36/37/39
WGK Germany: 3 · 3
Hazard Note: Irritant
HS Code: 29242990 · 29242990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29242990
risk_code: 20/21/22-36/37/38
hazard_code: Xi,Xn
hazard_note: Irritant
safety_code: 22-24/25-36-26-45-36/37/39
Storage Class: 11 - Combustible Solids

Chemistry & industry

Applications · 1 item

UsesN-Cbz-L-tyrosine is an N-Cbz-protected form of L-Tyrosine (T899975). L-Tyrosine is an essential amino acid that exhibits in vitro antioxidant and antiradical activities. L-Tyrosine is used as a precursor to synthesize catecholamines (e.g. Norepinephrine HCl [N674500]) in human keratinocytes, and also for the synthesis of proteins and thyroid hormones.