| Identification | More | [Name]
N-Acetyl-L-tryptophan | [CAS]
1218-34-4 | [Synonyms]
ACETYL-L-TRYPTOPHAN
ACETYL-L-TRYPTOPHANE
AC-TRP-OH
AC-TRYPTOPHAN
H-N-ACETYL-TRP-OH
L-ACETYLTRYPTOPHAN
L-N-ACETYL-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID
N-ACETYL-L-TRYPTOPHAN
N-ACETYL-L-TRYTOPHAN
N-ACETYL-TRP-OH
N-ACETYL-TRYPTOPHAN
N-ALPHA-ACETYL-L-TRYPTOPHAN
RARECHEM AH BS 0070
TRYPTOPHAN, N-ACETYL-
(S)-N-Acetyltryptophan
Acetyl-L-trp
Ac-Try
l-tryptopha
L-Tryptophan, N-acetyl-
n-acetyl-l-tryptopha | [EINECS(EC#)]
214-935-9 | [Molecular Formula]
C13H14N2O3 | [MDL Number]
MFCD00065976 | [Molecular Weight]
246.26 | [MOL File]
1218-34-4.mol |
| Chemical Properties | Back Directory | [Appearance]
solid | [Melting point ]
186°C | [alpha ]
+24.0～+30.0°(20℃/D)(c=1,C2H5OH) | [Boiling point ]
389.26°C (rough estimate) | [density ]
1.1855 (rough estimate) | [refractive index ]
1.6450 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
3.65±0.10(Predicted) | [color ]
White to Off-white | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [LogP]
0.702 (est) | [CAS DataBase Reference]
1218-34-4(CAS DataBase Reference) | [NIST Chemistry Reference]
L-tryptophan, n-acetyl-(1218-34-4) | [EPA Substance Registry System]
1218-34-4(EPA Substance) |
| Safety Data | Back Directory | [WGK Germany ]
2
| [RTECS ]
YN6160000
| [TSCA ]
Yes | [HS Code ]
29339900 | [Safety Profile]
Moderately toxic by some routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOX,. |
| Hazard Information | Back Directory | [Chemical Properties]
solid | [Uses]
N-Acetyl-L-Tryptophan, is a derivative of L-Tryptophan (T947210), that can be used as competitive inhibitor to identify and characterize tryptophanases. It can also be used as an NK1 tachykinin receptor antagonist, that may help to develop a novel therapeutic intervention for the treatment of reperfusion injury in acute ischemic stroke. | [Definition]
ChEBI: A N-acetyl-L-amino acid that is the N-acetyl derivative of L-tryptophan. | [Biological Activity]
N-Acetyl-L-tryptophan (NATAc-Trp-OH) is used a substance P NK1 tachykinin receptor antagonist. N-Acetyl-L-tryptophan is also used as a competitive inhibitor to identifydifferentiate and characterized tryptophanase(s). | [Synthesis]
4.1.8.4 Synthesis of N-acetyl-L-tryptophan (10b)
L-tryptophan (1.00 g, 4.95 mmol) was dissolved in a mixed solution of acetone (20 mL) and 2 N NaOH (15 mL). Acetyl chloride (0.821 mL, 9.90 mmol) was added slowly and dropwise at room temperature, while 2 N NaOH was added to maintain the pH of the reaction system greater than 10. The reaction mixture was stirred at room temperature for 1 hr. Upon completion of the reaction, the acetone was removed by vacuum evaporation and the remaining aqueous phase was acidified to acidity with 3 N HCl. The aqueous phase was extracted with ethyl acetate (3 × 50 mL) and the organic phase was combined. The organic phase was washed with saturated saline and dried over anhydrous Na2SO4. The organic phase was concentrated under reduced pressure to give N-acetyl-L-tryptophan 10b (0.96 g, 80% yield) as a colorless solid.ESI/MS m/z: 246.1 [M + H]+; 1H NMR (500 MHz, DMSO) δ 12.55 (s, 1H), 10.84 (s, 1H), 8.14 (d, J = 8.0 Hz, 1H), 7.52 (d, J = 8.0 Hz, 1H), 7.33 (d, J = 8.0 Hz, 1H), 7.13 (d, J = 2.0 Hz, 1H), 7.06 (dd, J = 11.0, 4.0 Hz, 1H), 6.98 (t, J = 7.5 Hz, 1H), 4.46 (td, J = 8.5, 5.0 Hz, 1H), 3.15 (dd, J = 14.5, 5.0 Hz, 1H), 2.98 (dd, J = 14.5, 8.5 Hz, 1H), 1.80 (s, 3H). | [References]
[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 6089 - 6104 |
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