Product Name

  • Name

    N-Acetyl-L-tryptophan

  • EINECS 214-935-9
  • CAS No. 1218-34-4
  • Article Data79
  • CAS DataBase
  • Density 1.33g/cm3
  • Solubility
  • Melting Point 186 °C
  • Formula C13H14N2O3
  • Boiling Point 586.6 °C at 760 mmHg
  • Molecular Weight 246.266
  • Flash Point 308.6 °C
  • Transport Information
  • Appearance solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 1218-34-4 (N-Acetyl-L-tryptophan)
  • Hazard Symbols
  • Synonyms Ac-Trp-OH;Ac-L-Trp-OH;Tryptophan,N-acetyl-, L- (8CI);(S)-N-Acetyltryptophan;Acetyl-L-tryptophan;Acetyltryptophan;L-N-Acetyltryptophan;N-Acetyltryptophan;NSC 90726;
  • PSA 82.19000
  • LogP 1.69060

Synthetic route

N-acetyltryptophan methyl ester
2824-57-9, 16108-06-8, 36060-94-3

N-acetyltryptophan methyl ester

A

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4 In tetrahydrofuran Ambient temperature;A 99%
B 99%
With methanol; water; α-chymotrypsin bei pH 7.8;
acetyl chloride
75-36-5

acetyl chloride

L-Tryptophan
73-22-3

L-Tryptophan

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With sodium hydroxide In acetone at 20℃; pH=> 10;80%
thioacetic acid
507-09-5

thioacetic acid

L-Tryptophan
73-22-3

L-Tryptophan

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
Stage #1: tiolacetic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: L-Tryptophan With 2,4-Dinitrofluorobenzene In N,N-dimethyl-formamide at 20℃; for 3h;
76%
acetic anhydride
108-24-7

acetic anhydride

L-Tryptophan
73-22-3

L-Tryptophan

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With sodium In water for 2h;73%
Stage #1: L-Tryptophan With sodium hydroxide In water for 0.5h;
Stage #2: acetic anhydride In water at 20℃;
71.8%
With sodium hydroxide; water
N-acetyl-L-tryptophane ethyl ester
2382-80-1

N-acetyl-L-tryptophane ethyl ester

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With ammonium bicarbonate; water In dichloromethane for 21h; α-chymotrypsin;45%
With α-chymotrypsin In phosphate buffer at 25℃; pH=7.8; Kinetics; Further Variations:; Reaction partners; Catalysts; Hydrolysis; Enzymatic reaction;
acetyltryptophan ethylester
42717-06-6

acetyltryptophan ethylester

A

N-AcTrp
1218-34-4

N-AcTrp

B

N-acetyl-D-tryptophan
2280-01-5

N-acetyl-D-tryptophan

C

N-acetyl-D-tryptophan ethyl ester
92520-19-9

N-acetyl-D-tryptophan ethyl ester

Conditions
ConditionsYield
With water In ethanol at 25℃; for 24h; Microbiological reaction; optical yield given as %ee; enantioselective reaction;A n/a
B n/a
C 40%
tetrachloromethane
56-23-5

tetrachloromethane

acetic anhydride
108-24-7

acetic anhydride

L-Tryptophan
73-22-3

L-Tryptophan

N-AcTrp
1218-34-4

N-AcTrp

N-acetyl-DL-tryptophan
1218-34-4, 87-32-1

N-acetyl-DL-tryptophan

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With (S)-1-phenyl-ethylamine
With (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
With (1S,2S)-(+)-thiomicamine
N-acetyl-DL-tryptophan
1218-34-4, 87-32-1

N-acetyl-DL-tryptophan

A

N-AcTrp
1218-34-4

N-AcTrp

B

N-acetyl-D-tryptophan
2280-01-5

N-acetyl-D-tryptophan

Conditions
ConditionsYield
With water bei der Einwirkung einer Amidase;
mit Hilfe von Amidase aus Penicillium vinaceum oder Aspergillus orizae;
mit Hilfe von Pseudomonas;
With water bei der Einwirkung einer Amidase;
(Z)-2-acetamido-3-(3-indolyl)-2-propenoic acid
70082-70-1

(Z)-2-acetamido-3-(3-indolyl)-2-propenoic acid

A

N-AcTrp
1218-34-4

N-AcTrp

B

N-acetyl-D-tryptophan
2280-01-5

N-acetyl-D-tryptophan

Conditions
ConditionsYield
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (-)-Diop In ethanol at 50℃; for 1.75h; Title compound not separated from byproducts;
With hydrogen; triethylamine; ClO4; (2S,4S)-MOD-BPPM In ethanol at 50℃; under 15200 Torr; for 20h; Title compound not separated from byproducts;
N-acetyl-L-triptophanyl-L-leucine amide
65356-77-6

N-acetyl-L-triptophanyl-L-leucine amide

B

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With pH=7; α-chymotrypsin In water; ethyl acetate Equilibrium constant;
(S)-2-Acetylamino-5-(phenyl-hydrazono)-pentanoic acid methyl ester
85148-76-1

(S)-2-Acetylamino-5-(phenyl-hydrazono)-pentanoic acid methyl ester

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide 1.) reflux, 1 h;; Yield given. Multistep reaction;
4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

L-Tryptophan
73-22-3

L-Tryptophan

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
β‐cyclodextrin In water; dimethyl sulfoxide at 25℃; Rate constant; Mechanism; various conditions;
Nα-acetyl-L-tryptophan-amide
2382-79-8

Nα-acetyl-L-tryptophan-amide

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With Peptidamidase aus dem Flavedo von Orangen; water at 30℃; diff. Peptidamiden; diff. solvents; diff. pH;
With potassium phosphate buffer at 30℃; for 1h; amidase from Erwina carotovora; determination of relative rate of deamination;
With water at 30℃; Peptidamidase aus dem Flavedo von Orangen; Yield given;
With subtilisin-CLEC at 40℃; pH 7.5, phosphate buffer; Yield given;
N-acetyl-L-tryptophan methyl ester
2824-57-9, 16108-06-8, 36060-94-3

N-acetyl-L-tryptophan methyl ester

A

methanol
67-56-1

methanol

B

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With water In dimethyl sulfoxide at 35℃; Rate constant; Equilibrium constant; pH 5.0, pH 7.1; influence of enzyme chymotrypsin; influence of BzPheal=Ala;
(S)-2-Acetylamino-4-cyano-butyric acid methyl ester
75161-70-5

(S)-2-Acetylamino-4-cyano-butyric acid methyl ester

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 88 percent / hydrogen / Raney-Ni deactivated with 3percent Pb / H2O; acetic acid
3: 1.) 0.1 N HCl; 2.) 1 N NaOH / 1.) reflux, 1 h;
View Scheme
methyl 2-acetamido-5-amino-5-oxopentanoate
56159-64-9

methyl 2-acetamido-5-amino-5-oxopentanoate

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 61 percent / p-TsCl / pyridine
2: 88 percent / hydrogen / Raney-Ni deactivated with 3percent Pb / H2O; acetic acid
4: 1.) 0.1 N HCl; 2.) 1 N NaOH / 1.) reflux, 1 h;
View Scheme
(2S,5R)-1-Acetyl-5-hydroxy-pyrrolidine-2-carboxylic acid methyl ester
85148-75-0

(2S,5R)-1-Acetyl-5-hydroxy-pyrrolidine-2-carboxylic acid methyl ester

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 1.) 0.1 N HCl; 2.) 1 N NaOH / 1.) reflux, 1 h;
View Scheme
DL-tryptophan ethyl ester hydrochloride
6519-67-1

DL-tryptophan ethyl ester hydrochloride

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous K2CO3
2: α-chymotrypsin; methanol; water / bei pH 7.8
View Scheme
N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With acetic anhydride In water
Fmoc-Trp-OH
35737-15-6

Fmoc-Trp-OH

acetic acid
64-19-7

acetic acid

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
Stage #1: Fmoc-Trp-OH With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Wang resin; Inert atmosphere;
Stage #2: acetic acid With ammonium bicarbonate In methanol at 20℃; for 3h;
Stage #3: With piperidine; trifluoroacetic acid In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
N-Acetyl-N(1)-nitroso-L-tryptophan
53602-74-7

N-Acetyl-N(1)-nitroso-L-tryptophan

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With L-Cysteine In aq. phosphate buffer at 37℃; for 1h; pH=7.4; Kinetics;
4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

L-Tryptophan
73-22-3

L-Tryptophan

N-AcTrp
1218-34-4

N-AcTrp

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 24.84℃; pH=8.5 - 9; Kinetics;
benzyl bromide
100-39-0

benzyl bromide

N-AcTrp
1218-34-4

N-AcTrp

Nα-acetyl-(L)-tryptophan benzyl ester

Nα-acetyl-(L)-tryptophan benzyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 23h; Inert atmosphere;99%
N-AcTrp
1218-34-4

N-AcTrp

L-Tryptophan
73-22-3

L-Tryptophan

Conditions
ConditionsYield
With pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle In acetonitrile at 20℃; for 48h; pH=2;98%
With hydrogenchloride; water
With sulfuric acid; water
With Aspergillus oryzae acylase relative rates;
sodium thiocyanide
540-72-7

sodium thiocyanide

acetic anhydride
108-24-7

acetic anhydride

N-AcTrp
1218-34-4

N-AcTrp

(S)-5-((1H-indol-3-yl)methyl)-1-acetyl-2-thioxoimidazolidin-4-one
182002-62-6

(S)-5-((1H-indol-3-yl)methyl)-1-acetyl-2-thioxoimidazolidin-4-one

Conditions
ConditionsYield
In acetic acid at 80 - 85℃; for 0.5h;95%
benzylamine
100-46-9

benzylamine

N-AcTrp
1218-34-4

N-AcTrp

Nα-acetyl-(L)-tryptophan benzyl ester

Nα-acetyl-(L)-tryptophan benzyl ester

Conditions
ConditionsYield
Stage #1: N-AcTrp With N-chlorobenzotriazole; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.25h;
Stage #2: benzylamine With triethylamine at 20℃; for 1.83333h;
95%
trans-dihydroxo (2,3,6,7,12,13,16,17-octaethylporphyrinato)-tin(IV)
29008-64-8

trans-dihydroxo (2,3,6,7,12,13,16,17-octaethylporphyrinato)-tin(IV)

N-AcTrp
1218-34-4

N-AcTrp

trans-di(N-acetyl-L–tryptophanato)[2,3,6,7,12,13,16,17-octa-ethylporphyrinato]-tin(IV)

trans-di(N-acetyl-L–tryptophanato)[2,3,6,7,12,13,16,17-octa-ethylporphyrinato]-tin(IV)

Conditions
ConditionsYield
In chloroform for 12h; Reflux;92%
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

N-AcTrp
1218-34-4

N-AcTrp

(S)-methyl 2-((S)-2-acetamido-3-(1H-indol-3-yl)propanmido)-3-phenyl propanoate

(S)-methyl 2-((S)-2-acetamido-3-(1H-indol-3-yl)propanmido)-3-phenyl propanoate

Conditions
ConditionsYield
Stage #1: methyl (2S)-2-amino-3-phenylpropanoate hydrochloride With potassium carbonate In water at 25℃; for 0.166667h;
Stage #2: N-AcTrp With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 12h;
91%
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique;
Stage #2: methyl (2S)-2-amino-3-phenylpropanoate hydrochloride In dichloromethane Schlenk technique;
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique;
Stage #2: methyl (2S)-2-amino-3-phenylpropanoate hydrochloride In dichloromethane Schlenk technique;
trans-dihydroxo(meso-tetraphenylporphyrinato)tin(IV)
26334-89-4

trans-dihydroxo(meso-tetraphenylporphyrinato)tin(IV)

N-AcTrp
1218-34-4

N-AcTrp

trans-di(N-acetyl-L–tryptophanato)[5,10,15,20-tetraphenyl-porphyrinato]-tin(IV)

trans-di(N-acetyl-L–tryptophanato)[5,10,15,20-tetraphenyl-porphyrinato]-tin(IV)

Conditions
ConditionsYield
In chloroform for 12h; Reflux;91%
ethanol
64-17-5

ethanol

N-AcTrp
1218-34-4

N-AcTrp

N-acetyl-L-tryptophane ethyl ester
2382-80-1

N-acetyl-L-tryptophane ethyl ester

Conditions
ConditionsYield
lipoglycosylated α-chymotrypsin In chloroform at 30℃; or other solvents;90%
α-chymotrypsin In chloroform; water at 30℃; for 24h; phosphate buffer, pH 6.8;86%
α-chymotrypsin at 30℃; for 24h; Equilibrium constant; effect of water concentration, solvent, pH;78%
N-AcTrp
1218-34-4

N-AcTrp

butan-1-ol
71-36-3

butan-1-ol

acetyl-L-tryptophan n-butyl ester
2743-54-6

acetyl-L-tryptophan n-butyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid a) 50 deg C, 0.5 h, b) RT, 4 h;90%
L-valine methylester hydrochloride
6306-52-1

L-valine methylester hydrochloride

N-AcTrp
1218-34-4

N-AcTrp

Ac-Trp-Val-OMe
248589-70-0

Ac-Trp-Val-OMe

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;89%
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique;
Stage #2: L-valine methylester hydrochloride In dichloromethane Schlenk technique;
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique;
Stage #2: L-valine methylester hydrochloride In dichloromethane Schlenk technique;
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
2491-18-1

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride

N-AcTrp
1218-34-4

N-AcTrp

Ac-Trp-Met-OMe

Ac-Trp-Met-OMe

Conditions
ConditionsYield
Stage #1: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride With potassium carbonate In water at 25℃; for 0.166667h;
Stage #2: N-AcTrp With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 12h;
89%
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique;
Stage #2: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride In dichloromethane Schlenk technique;
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique;
Stage #2: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride In dichloromethane Schlenk technique;
O-Methyl (S)-prop-2-ynyl dithiocarbonate
123972-87-2

O-Methyl (S)-prop-2-ynyl dithiocarbonate

N-AcTrp
1218-34-4

N-AcTrp

N-acetyl-L-tryptophan methyl ester
2824-57-9, 16108-06-8, 36060-94-3

N-acetyl-L-tryptophan methyl ester

Conditions
ConditionsYield
In toluene Heating;87%
(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

N-AcTrp
1218-34-4

N-AcTrp

(S)-2-Acetylamino-3-(1H-indol-3-yl)-N-((R)-1-phenyl-ethyl)-propionamide

(S)-2-Acetylamino-3-(1H-indol-3-yl)-N-((R)-1-phenyl-ethyl)-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight;87%
(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

N-AcTrp
1218-34-4

N-AcTrp

(S)-2-Acetylamino-3-(1H-indol-3-yl)-N-((S)-1-phenyl-ethyl)-propionamide

(S)-2-Acetylamino-3-(1H-indol-3-yl)-N-((S)-1-phenyl-ethyl)-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight;85%
[(η6-phenylbutyric acid)tris(acetone)ruthenium(II)] triflate

[(η6-phenylbutyric acid)tris(acetone)ruthenium(II)] triflate

N-AcTrp
1218-34-4

N-AcTrp

[(η6-phenylbutyric acid)(η6-N-acetyltriptophane)ruthenium(II)] triflate

[(η6-phenylbutyric acid)(η6-N-acetyltriptophane)ruthenium(II)] triflate

Conditions
ConditionsYield
In trifluoroacetic acid Ar, stirred at 50°C for 3 h; concd., pptd. (diethyl ether), washed (methanol/diethyl ether), dried (vac.); elem. anal.;84%
S-(1-butyn-3-yl)-O-methyl xanthate

S-(1-butyn-3-yl)-O-methyl xanthate

N-AcTrp
1218-34-4

N-AcTrp

N-acetyl-L-tryptophan methyl ester
2824-57-9, 16108-06-8, 36060-94-3

N-acetyl-L-tryptophan methyl ester

Conditions
ConditionsYield
In toluene Heating;81%
(R)-(+)-N,α-dimethylbenzylamine
5933-40-4

(R)-(+)-N,α-dimethylbenzylamine

N-AcTrp
1218-34-4

N-AcTrp

(S)-2-Acetylamino-3-(1H-indol-3-yl)-N-methyl-N-((R)-1-phenyl-ethyl)-propionamide

(S)-2-Acetylamino-3-(1H-indol-3-yl)-N-methyl-N-((R)-1-phenyl-ethyl)-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight;80%
[Ru(η(6)-cymene)(acetone)3](CF3SO3)2

[Ru(η(6)-cymene)(acetone)3](CF3SO3)2

N-AcTrp
1218-34-4

N-AcTrp

Ru(CH3C6H4C3H7)(CH3CONHCH(CH2C8H6N)CO2H)(2+)*2CF3SO3(1-)=[Ru(CH3C6H4C3H7)(CH3CONHCH(CH2C8H6N)CO2H)](CF3SO3)2

Ru(CH3C6H4C3H7)(CH3CONHCH(CH2C8H6N)CO2H)(2+)*2CF3SO3(1-)=[Ru(CH3C6H4C3H7)(CH3CONHCH(CH2C8H6N)CO2H)](CF3SO3)2

Conditions
ConditionsYield
In trifluoroacetic acid (argon); stirring (room temp., 4 h); pptn. with Et2O, washing, drying (vac.); elem. anal.;80%
N-AcTrp
1218-34-4

N-AcTrp

N-acetyl-L-tryptophan methyl ester
2824-57-9, 16108-06-8, 36060-94-3

N-acetyl-L-tryptophan methyl ester

Conditions
ConditionsYield
In methanol; diethyl ether at 0℃;79%
Dithiocarbonic acid O-(3-methyl-oxetan-3-ylmethyl) ester S-prop-2-ynyl ester

Dithiocarbonic acid O-(3-methyl-oxetan-3-ylmethyl) ester S-prop-2-ynyl ester

N-AcTrp
1218-34-4

N-AcTrp

(S)-2-Acetylamino-3-(1H-indol-3-yl)-propionic acid 3-methyl-oxetan-3-ylmethyl ester

(S)-2-Acetylamino-3-(1H-indol-3-yl)-propionic acid 3-methyl-oxetan-3-ylmethyl ester

Conditions
ConditionsYield
In toluene Heating;79%
methyl (L)-leucinate hydrochloride
7517-19-3

methyl (L)-leucinate hydrochloride

N-AcTrp
1218-34-4

N-AcTrp

(S)-methyl 2-((S)-2-acetamido-3-(1H-indol-3-yl)propanamido)-4-methyl pentanoate

(S)-methyl 2-((S)-2-acetamido-3-(1H-indol-3-yl)propanamido)-4-methyl pentanoate

Conditions
ConditionsYield
Stage #1: methyl (L)-leucinate hydrochloride With potassium carbonate In water at 25℃; for 0.166667h;
Stage #2: N-AcTrp With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 12h;
79%
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique;
Stage #2: methyl (L)-leucinate hydrochloride In dichloromethane Schlenk technique;
Stage #1: N-AcTrp With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Schlenk technique;
Stage #2: methyl (L)-leucinate hydrochloride In dichloromethane Schlenk technique;
(5-(3-(trifluoromethyl)-3H-diazirin-3-yl)pyridin-2-yl)methanol

(5-(3-(trifluoromethyl)-3H-diazirin-3-yl)pyridin-2-yl)methanol

N-AcTrp
1218-34-4

N-AcTrp

(S)-(5-(3-(trifluoromethyl)-3H-diazirin-3-yl)pyridin-2-yl)methyl 2-acetamido-3-(1H-indol-3-yl)propanoate

(S)-(5-(3-(trifluoromethyl)-3H-diazirin-3-yl)pyridin-2-yl)methyl 2-acetamido-3-(1H-indol-3-yl)propanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 21℃; for 16h; Inert atmosphere;77%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 21℃; for 16h; Inert atmosphere;77%
N-methyl-N-[(S)-1-phenylethyl]amine
19131-99-8

N-methyl-N-[(S)-1-phenylethyl]amine

N-AcTrp
1218-34-4

N-AcTrp

(S)-2-Acetylamino-3-(1H-indol-3-yl)-N-methyl-N-((S)-1-phenyl-ethyl)-propionamide

(S)-2-Acetylamino-3-(1H-indol-3-yl)-N-methyl-N-((S)-1-phenyl-ethyl)-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight;76%
2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

N-AcTrp
1218-34-4

N-AcTrp

(S)-2-Acetylamino-N-(2,6-dimethyl-phenyl)-3-(1H-indol-3-yl)-propionamide

(S)-2-Acetylamino-N-(2,6-dimethyl-phenyl)-3-(1H-indol-3-yl)-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight;75%
hexakis-(6-bromo-6-deoxy)-α-cyclodextrin
53784-82-0

hexakis-(6-bromo-6-deoxy)-α-cyclodextrin

N-AcTrp
1218-34-4

N-AcTrp

hexakis-[6-O-(N-acetyl-L-tryptophanyl)]-α-cyclodextrin
1320346-76-6

hexakis-[6-O-(N-acetyl-L-tryptophanyl)]-α-cyclodextrin

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 70 - 80℃; for 12h;72%
2,6-diethylaniline
579-66-8

2,6-diethylaniline

N-AcTrp
1218-34-4

N-AcTrp

(S)-2-Acetylamino-N-(2,6-diethyl-phenyl)-3-(1H-indol-3-yl)-propionamide

(S)-2-Acetylamino-N-(2,6-diethyl-phenyl)-3-(1H-indol-3-yl)-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) r.t., overnight;70%

N-Acetyl-L-tryptophan Consensus Reports

Reported in EPA TSCA Inventory.

N-Acetyl-L-tryptophan Specification

1. Introduction of N-Acetyl-L-tryptophan

N-Acetyl-L-tryptophan, with the IUPAC Name of 2-Acetamido-3-(1H-indol-3-yl)propanoic acid, is one kind of white crystalline powder, odorless, little bitter taste. And it belongs to the Classification Code which include Drug / Therapeutic Agent; Enzyme Inhibitors; Protease Inhibitors; Reproductive Effect.

2. Properties of N-Acetyl-L-tryptophan

N-Acetyl-L-tryptophan has the following property datas: (1)Melting point: 186°C; (2)Index of Refraction: 1.645; (3)Molar Refractivity: 67.12 cm3; (4)Molar Volume: 185.1 cm3; (5)Surface Tension: 61.6 dyne/cm; (6)Density: 1.33 g/cm3; (7)Flash Point: 308.6 °C; (8)Enthalpy of Vaporization: 92.14 kJ/mol; (9)Boiling Point: 586.6 °C at 760 mmHg; (10)Vapour Pressure: 1.32E-14 mmHg at 25°C.

3. Structure Descriptors of N-Acetyl-L-tryptophan

You could convert the following datas into the molecular structure:
(1)InChI: InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m0/s1
(2)InChIKey: InChIKey=DZTHIGRZJZPRDV-LBPRGKRZSA-N
(3)Smiles: c12c(C[C@@H](NC(C)=O)C(O)=O)c[nH]c1cccc2

4. Toxicity of N-Acetyl-L-tryptophan

The toxicity datas of N-Acetyl-L-tryptophan are as below:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3580mg/kg (3580mg/kg) LIVER: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980.
mouse LD50 oral 10800mg/kg (10800mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980.
rat LD50 intraperitoneal 3900mg/kg (3900mg/kg) LIVER: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980.
rat LD50 oral 15000mg/kg (15000mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980.

5. Safety Information of N-Acetyl-L-tryptophan

WGK Germany: 2
RTECS: YN6160000
Moderately toxic by some routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

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