CAS 3978-80-1 L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl- (HCID 117439)

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Basic information

CAS: 3978-80-1
Standard SMILES: CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O
InChIKey: CNBUSIJNWNXLQQ-NSHDSACASA-N
Molecular formula: C14H19NO5
Average molar mass: 281.3 g/mol
Monoisotopic mass: 281.12632271

Overview

N-Boc-L-tyrosine is a L-tyrosine derivative that is L-tyrosine in which the amino group is replaced by a (tert-butoxycarbonyl)amino group. It is a tert-butyl ester and a L-tyrosine derivative.

Names & identifiers

Preferred name: L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-
IUPAC: (2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
English name: BOC-L-Tyrosine
Molecular formula: C14H19NO5
Molecular weight: 281.3

Names & synonyms

L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-L-Tyrosine, N-((1,1-dimethylethoxy)carbonyl)-RefChem:798165L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-Boc-Tyr-OH3978-80-1Boc-L-tyrosineN-Boc-L-tyrosineN-(tert-Butoxycarbonyl)-L-tyrosineN-(tert-Butyloxycarbonyl)-L-tyrosinMFCD00037179N-(TERT-BUTOXYCARBONYL)TYROSINE

Show more names

Boc-TyrBOC-L-TYR-OHBOC-TYROSINE(2S)-3-(4-Hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoateTYRO-006

N-tert-butoxycarbonyl-L-tyrosine(S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoic acidCHEMBL65386(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acidN-[(1,1-DIMETHYLETHOXY)CARBONYL]-L-TYROSINE(TERT-BUTOXYCARBONYL)-L-TYROSINEM03338N-Boc-tyrosine

Database identifiers

CAS: 3978-80-1
PubChem CID

Properties

Computed structural properties

XLogP: 1.5
Topological polar surface area: 95.9 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 6
Heavy atoms: 20
Formal charge: 0
Complexity: 342

Physicochemical properties

Melting point: 133 · 133-135 °C(lit.)
alpha: 2.5 · 2.5 º (c=2, acetic acid)
Boiling point: 423.97 °C · 423.97°C (rough estimate)
Density: 1.1755 · 1.1755 (rough estimate)
refractive index: 1.523 · 1.5230 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Methanol (Sparingly)
pka: 2.98 · 2.98±0.10(Predicted)
form: Powder
color: White to off-white
optical activity: 20 · [α]20/D +3.0°, c = 2 in acetic acid
BRN: 2816406 · 2816406
Major Application: peptide synthesis
InChI: InChI=1S/C14H19NO5/c1-14(2,3)20-13(19)15-11(12(17)18)8-9-4-6-10(16)7-5-9/h4-7,11,16H,8H2,1-3H3,(H,15,19)(H,17,18)/t11-/m0/s1
InChIKey: CNBUSIJNWNXLQQ-NSHDSACASA-N

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 37.5% (3 of 8) of reports.

Warning

H315 (62.5%): 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 8 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationL-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (62.5%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29242990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 22-24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 1 item

UsesN-Boc-L-tyrosine is an N-Boc-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.