CAS 2018-61-3 N-Acetyl-L-phenylalanine (HCID 74839)

Overview

N-acetyl-L-phenylalanine is the N-acetyl derivative of L-phenylalanine. It has a role as a metabolite. It is a N-acetyl-L-amino acid, a N-acetylphenylalanine and a N-acyl-L-phenylalanine. It is a conjugate acid of a N-acetyl-L-phenylalaninate. It is an enantiomer of a N-acetyl-D-phenylalanine.

Names & identifiers

Preferred name: N-Acetyl-L-phenylalanine
IUPAC: (2S)-2-acetamido-3-phenylpropanoic acid
English name: N-Acetyl-L-phenylalanine
Molecular formula: C11H13NO3
Molecular weight: 207.23

Names & synonyms

N-Acetyl-L-phenylalanine2018-61-3Acetyl-L-phenylalanineL-Phenylalanine, N-acetyl-N-AcetylphenylalanineL-N-Acetylphenylalanine(2S)-2-acetamido-3-phenylpropanoic acidacetylphenylalanineAlanine, N-acetyl-3-phenyl-, L-NP5BT39467CHEBI:16259DTXSID20883539

Show more names

Ac-L-Phe-OHN-Ac-L-Phe-OHAc-L-PheNSC 45699H-Ac-Phe-OH

NSC-45699CHEBI:21626RefChem:927006DTXCID901023062217-959-8(2S)-2-acetamido-3-phenylpropanoateAc-Phe-OH(S)-2-Acetamido-3-phenylpropanoic acid

Database identifiers

CAS: 2018-61-3、2901-75-9
PubChem CID: 74839
DTXSID: DTXSID20883539
ChEBI: CHEBI:16259
UNII: NP5BT39467
EC Number: 217-959-8
Nikkaji: J27.562J

Properties

Computed structural properties

XLogP: 0.6
Topological polar surface area: 66.4 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 15
Formal charge: 0
Complexity: 234

Experimental & physicochemical properties

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy

LogP · 2 items

0.93

0.4

Melting Point171 - 173 °C

Physical DescriptionSolid

Collision Cross Section · 3 items

149.8 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

142.22 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

149.6 Å² [M+Na]+

Physicochemical properties

Melting point: 171 · 171-173 °C(lit.)
alpha: 40 · 40 º (c=1,methanol)
Boiling point: 346.25 °C · 346.25°C (rough estimate)
Density: 1.1878 · 1.1878 (rough estimate)
refractive index: 40 ° · 40 ° (C=5, MeOH)
storage temp.: Sealed in dry,Room Temperature
solubility: Solubility in methanol (almost transparency). Soluble in acetone and ethanol (20 mg/ ml).
form: Fine Crystalline Powder or Needles
pka: 3.56 · 3.56±0.10(Predicted)
color: White to off-white
optical activity: 22 · [α]22/D +40.0°, c = 1 in methanol
Major Application: peptide synthesis
InChI: 1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1
InChIKey: CBQJSKKFNMDLON-JTQLQIEISA-N
SMILES: CC(=O)N[C@@H](Cc1ccccc1)C(O)=O
CAS DataBase Reference: 2018 · 2018-61-3(CAS DataBase Reference)
FDA UNII: 5 BT39467 · NP5BT39467
NIST Chemistry Reference: L-phenylalanine, n-acetyl-(2018-61-3)
EPA Substance Registry System: L-Phenylalanine, N-acetyl- (2018-61-3)
UNSPSC Code: 12352209 · 12352209
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
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29242990 · 29242990
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) 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 2 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
tsca: TSCA listed
hs_code: 29242990
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

General Manufacturing InformationL-Phenylalanine, N-acetyl-: INACTIVE

Applications · 3 items

UsesIt is an essential amino acid produced for medical, feed, and nutritional applications such as in the preparation of aspartame. It is applied as an antidepressant.

UsesN-Acetyl-L-phenylalanine is an protected analogue of L-Phenylalanine (P319415), an essential amino acid produced for medical, feed, and nutritional applications such as in the preparation of Aspartame.

General DescriptionN-Acetyl-L-phenylalanine is an acetyl analog of L-phenylalanine. It is widely used as a reactant to synthesize methyl or ethyl esters of N-acetyl-L-phenylalanine, which are employed as versatile building blocks in peptide synthesis.

Preparation methods · 1 item

PreparationThe catalytic hydrogenation activity of N-acetyl-(S)-phenyl methyl esters was measured under controlled pressure and temperature conditions in a conventional low-pressure hydrogenator (Parr Inst. Co., Mod. 3911). Hydrogenation was carried out in methanol as a solvent with 20 mL of 0.80 M substrate solution and 0.034 g of cis-Δ-(R)-(S)-2.5H₂O (Scheme 1), yielding [subs]/[cat] = 0.016/0.000029 = 547 under all conditions, with an initial hydrogen pressure of 6.8 atm and a temperature of 50–70°C. Methanol (99%, Scharlau) and hydrogen (99.999% SEO) were added to the reaction mixture. Methyl acetoacetate and 1-hexene were added. The mixture was distilled under reduced pressure and at low temperature. Dimethyl itaconic acid and methyl 2-acetamidoacrylate, supplied by Aldrich, were added. The reaction mixture was refluxed with a boron trifluoride-methanol complex (Merck). The hydrogenation product was purified by a Konik-3000 gas chromatograph equipped with a Supelco (BETA DEX 120) β-cyclodextrin chiral column to give the product N-acetyl-L-phenylalanine.