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CAS No. : | 73-22-3 | MDL No. : | MFCD00064340 |
Formula : | C11H12N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QIVBCDIJIAJPQS-VIFPVBQESA-N |
M.W : | 204.23 | Pubchem ID : | 6305 |
Synonyms : |
Tryptophan;Tryptophane;L-Tryptophane;Ardeytropin;(–)-Tryptophan;NSC 13119
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 57.36 |
TPSA : | 79.11 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.3 cm/s |
Log Po/w (iLOGP) : | 0.99 |
Log Po/w (XLOGP3) : | -1.06 |
Log Po/w (WLOGP) : | 1.12 |
Log Po/w (MLOGP) : | -1.66 |
Log Po/w (SILICOS-IT) : | 1.53 |
Consensus Log Po/w : | 0.18 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.68 |
Solubility : | 42.2 mg/ml ; 0.207 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.11 |
Solubility : | 158.0 mg/ml ; 0.772 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.76 |
Solubility : | 0.357 mg/ml ; 0.00175 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.09 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: With sodium hydroxide In water at 20℃; for 5 h; Reflux Stage #2: With hydrogenchloride In water |
A mixture of l-tryprophan (4) (817 mg, 4 mmol) and 2.5 M NaOH (1.6 ml) was stirred until the mixture became clear at room temperature, and then 37percent formalin (4.87 ml) was added. The mixture was stirred for 2 h at this temperature, refluxed for 3 h and then neutralized (pH 5) with 2 M HCl. The precipitate was filtered, washed with H2O, MeOH and dried in vacuo to give the title compound [22]. Yield 99percent; colorless solid, mp 302.2-304.6 °C. MS (FAB) m/z 217 (M + 1, 100percent). |
85% | at 60℃; for 2 h; | L-tryptophan (10.2 g, 50 mmol) was dissolved in 20 ml of 2.5N H2SO4 solution,A solution of 13.8 ml of formaldehyde (115 mmol)Stirring at 60 ° C for 2 h.Reaction is completed,The reaction solution was adjusted to pH = 5 with 2N HCl,Precipitated a large amount of white solid,Washed with water,And dried in vacuo to give 9.8 g of a white solid in 85percent yield. |
78% | at 20℃; for 4 h; | 1) 1,2,3,4-Tetrahydro-pyrido[3,4-b]indole-3-carboxylic acid To a mixture of 0.1 NH2SO4 (150 mL) and 37percent formaldehyde (80 mL) was added portionwise L-tryptophane (50 g, 245 mmol) with stirring. After being stirred for 4 h at room temperature, the white solid separated out was collected by filtration. The solid cake was washed with water and dried to give 1,2,3,4-tetrahydro-pyrido[3,4-b]indole-3-carboxylic acid, 41 g, (78percent); mp 275-276° C. (lit. mp 280-282° C.). 1H NMR (DMSO-d6) δ 2.84 (1H, m, CH2), 3.16 (1H, m, CH2), 3.66 (1H, m, CH2), 4.23 (1H, m, CH2), 4.38 (1H, m, CH), 6.98-7.02 (1H, m, ArH), 7.13-7.16 (1H, m, ArH), 7.32-7.34 (1H, m, ArH), 7.45-7.48 (1H, m, ArH), 11.03 (1H, brs, exchangeable, NH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hydroxide In acetone at 20℃; | 4.1.8.4 Syntheses of N-acetamido-l-tryptophan (10b) l-Tryptophan (1.00 g, 4.95 mmol) was added to a solution of acetone (20 mL) and 2 N NaOH (15 mL). Acetyl chloride (0.821 mL, 9.90 mmol) and 2 N NaOH were added simultaneously slowly at room temperature. The solution was maintained at a pH greater than 10 and stirred for 1 h. The acetone was evaporated in vacuo and the remaining solution was made acidic with 3 N HCl. The aqueous layer was extracted with EtOAc (3 * 50 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The solution was concentrated in vacuo to give N-acetamido-l-tryptophan 10b (0.96 g, 80percent) 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium hydroxide In water at 0 - 20℃; | L-Tryptophan (10.24 g, 50 mmol) was dissolved in 1M NaOH (50 mL) and stirred at 0°C. Benzyl chloroformate (7.15 mL, 50.1 mmol) and 1M NaOH (50 mL) where then simultaneously added in drop-wise fashion. The mixture was stirred for 1 hour at room temperature. The solution was acidified with 6M HCl to pH 1 after which the product was extracted with EtOAc (3x 200 mL). The organic layers were combined, dried by Na2SO4 and evaporated. The product was obtained a yellow solid and used directly in the following step (16.72 g, 99percent). Analytical data: Rf 0.43 (95:4:1 CH2Cl2/MeOH/AcOH); Mp: 132-134 ºC; 1H NMR (DMSO-d6): δ 7.57-7.53 (m, 2H), 7.35-7.22 (m, 6H), 7.16-7.15 (m, 1H), 7.09-7.04 (m, 1H) 7.00-6.95 (m, 1H), 5.02-4.92 (m, 2H), 4.28-4.21 (m, 1H), 3.22-3.16 (m, 1H), 3. 04-2.96 (m, 1H); 13C NMR (DMSO-d6): δ 174.2, 156.5, 137.4, 136.6, 128.8, 128.2, 128.0, 127.6, 124.2, 121.4, 118.8, 118.6, 111.9, 110.5, 65.8, 55.5, 27.4; LRMS (ESI): calcd for C19H19N2O4 [M+H]+ 339.13, found 339.35. |
64% | With sodium hydroxide In water at 20℃; Cooling with ice | 4.1.2 Synthesis of (S)-2-(benzyloxycarbonylamino)-3-(1H-indol-3-yl)propanoic acid 19 To a stirred mixture of l-tryptophan (20.07 g, 98.04 mmol) and NaOH (9.41 g, 235.25 mmol) in water (250 mL) was added dropwise benzyl chloroformate (20.18 g, 117.65 mmol) in an ice bath. The mixture was allowed to stir overnight at room temperature, then acidified to pH = 1 with hydrochloric acid, and filtered. The cake was washed with cold water and dried to give the product as a white solid (21.02 g) in 64percent yield: 1H NMR (300 MHz, DMSO-d6): δ 10.85 (s, 1H,COOH), 7.54 (d, 3JHH = 7.8 Hz, 1H, Ar-H), 7.40-7.20 (m, 6H, Ar-H), 7.14 (s, 1H, Ar-H), 7.06 (t, 3JHH = 7.5 Hz, 1H, Ar-H), 6.96 (t, 3JHH = 7.5 Hz, 1H, Ar-H), 4.97 (s, 2H, CH2), 4.25-4.10 (m, 1H, CH), 3.21 (dd, 3JHH = 4.2 Hz, 2JHH = 14.4 Hz, 1H, CH2), 2.99 (dd, 3JHH = 9.0 Hz, 2JHH = 14.4 Hz, 1H, CH2). 13C NMR (100 MHz, DMSO-d6): δ 174.0, 173.9, 155.8, 137.1, 136.0, 128.3, 127.6, 127.5, 123.6, 120.7, 118.2, 111.3, 110.5, 65.1, 55.4, 27.1. |
64% | With sodium hydroxide In water at 20℃; | A 500 mL single-necked round bottom flask was charged with 20. 07 g (98.04 mmol) of L-tryptophan, 250 mL of water, 9.41 g (235.5 mmol) of sodium hydroxide, 20 liters of (117.65 mmol) of Cbz- Stir overnight at room temperature. TLC monitoring reaction is complete, add ether extraction, the water phase pH = 1, a white solid precipitation, filtration, filter cake with the mother liquor washing, drying, white solid 2L02g, melting point 123-125 ° C yield 64percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.5% | With hydrogenchloride In ethanol | EXAMPLE 110 Preparation of L-Tryptophan ethyl ester hydrochloride A mixture of L-tryptophan (14.3 g, 0.07 mol) in 200 ml of ethanol containing ~7 g of anhydrous HCl was refluxed for 5 hours. The mixture was cooled and the solid which separated was recrystallized from ethanol/ether. Yield 17.4 g (92.5percent), m.p. 226°-228° C. The product has the formula: STR1575 The product may also be named ethyl L-2-amino-3-indolepropionate. |
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