N-((Benzyloxy)carbonyl)-L-threonine

HCID 88217

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Basic information

CAS: 19728-63-3
Standard SMILES: C[C@@H](O)[C@H](NC(=O)OCc1ccccc1)C(=O)O
InChIKey: IPJUIRDNBFZGQN-SCZZXKLOSA-N
Molecular formula: C12H15NO5
Average molar mass: 253.25 g/mol
Monoisotopic mass: 253.09502258

Names & identifiers

Preferred name: N-((Benzyloxy)carbonyl)-L-threonine
IUPAC: (2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoic acid
English name: N-Cbz-L-Threonine
Molecular formula: C12H15NO5
Molecular weight: 253.25

Names & synonyms

19728-63-3Z-Thr-OHN-((Benzyloxy)carbonyl)-L-threonineEINECS 243-258-1N-[(benzyloxy)carbonyl]-L-threonineDTXSID50173394NSC 333749RefChem:823165DTXCID0095885243-258-1N-Cbz-L-threonineZ-L-Threonine

Show more names

Z-ThrZ-L-ThrCbz-ThrZ-THREONINECBZ-L-THR-OH

Z-L-Thr-OHL-Threonine, N-[(phenylmethoxy)carbonyl]-N-Carbobenzoxy-L-threonineMFCD00065948(2S,3R)-2-(((Benzyloxy)carbonyl)amino)-3-hydroxybutanoic acidN-Benzyloxycarbonyl-L-threonineN-Carbobenzyloxy-l-threonineCBZ-THR-OH

Database identifiers

CAS: 19728-63-3
PubChem CID: 88217
DTXSID: DTXSID50173394
EC Number: 243-258-1
Nikkaji: J82.894G

Properties

Computed structural properties

XLogP: 0.8
Topological polar surface area: 95.9 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 6
Heavy atoms: 18
Formal charge: 0
Complexity: 288

Physicochemical properties

Melting point: 101 · 101-103 °C(lit.)
alpha: -4.7 · -4.7 º (c=4, acetic acid)
Boiling point: 396.45 °C · 396.45°C (rough estimate)
Density: 1.2499 · 1.2499 (rough estimate)
refractive index: -4.9 ° · -4.9 ° (C=2, AcOH)
storage temp.: -20 °C · Sealed in dry,Store in freezer, under -20°C
solubility: almost transparency in Methanol
form: powder to crystal
pka: 3.58 · 3.58±0.10(Predicted)
color: White to Almost white
optical activity: -7.733 ° · -7.733° (C=1.00 g/100ml, ACOH)
BRN: 2335409 · 2335409
Major Application: peptide synthesis
InChI: 1S/C12H15NO5/c1-8(14)10(11(15)16)13-12(17)18-7-9-5-3-2-4-6-9/h2-6,8,10,14H,7H2,1H3,(H,13,17)(H,15,16)/t8-,10+/m1/s1
InChIKey: IPJUIRDNBFZGQN-SCZZXKLOSA-N
SMILES: C[C@@H](O)[C@H](NC(=O)OCc1ccccc1)C(O)=O
CAS DataBase Reference: 19728 · 19728-63-3(CAS DataBase Reference)
UNSPSC Code: 12352200 · 12352200
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
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: 29242990 · 29242990
Storage Class: 13 · 13 - Non Combustible Solids

Safety & regulation

GHS classification

GHS ClassificationNot Classified

Hazard information

Hazard Classes and CategoriesNot Classified

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29242990
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 22-24/25-36-26
Storage Class: 13 - Non Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 1 item

UsesN-Cbz-L-threonine is an N-Cbz-protected form of L-Threonine (T405500). L-Threonine is an essential amino acid that is commonly used as a feed and food additive. L-Threonine is produced in mass quantities by mutant Escherichia coli strains for research and food nutrition purposes. L-Threonine can be naturally found in fish and poultry, and is incorporated in some important proteins in the human body (such as hemoglobin and insulin).