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Chemical Structure| 1204-06-4 Chemical Structure| 1204-06-4
Chemical Structure| 1204-06-4

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3-Indoleacrylic acid is a potent antialgal agent that increases reactive oxygen species (ROS) production in shrimp from the East China Sea, inhibits nutrient assimilation genes, and downregulates genes for ribulose-1,5-bisphosphate carboxylase/oxygenase II and cytochrome f.

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Product Details of 3-Indoleacrylic acid

CAS No. :1204-06-4
Formula : C11H9NO2
M.W : 187.19
SMILES Code : O=C(O)C=CC1=CNC2=C1C=CC=C2
MDL No. :MFCD00005633
InChI Key :PLVPPLCLBIEYEA-AATRIKPKSA-N
Pubchem ID :5375048

Safety of 3-Indoleacrylic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-Indoleacrylic acid

* 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.

  • Downstream synthetic route of [ 1204-06-4 ]

[ 1204-06-4 ] Synthesis Path-Downstream   1~41

  • 2
  • [ 22948-94-3 ]
  • [ 141-82-2 ]
  • [ 1204-06-4 ]
  • 3
  • [ 22948-94-3 ]
  • [ 141-82-2 ]
  • [ 75629-64-0 ]
  • [ 1204-06-4 ]
  • 4
  • [ 1204-06-4 ]
  • [ 459-73-4 ]
  • [ 61994-18-1 ]
  • 6
  • [ 1204-06-4 ]
  • [ 120681-20-1 ]
  • 11
  • [ 773-64-8 ]
  • [ 1204-06-4 ]
  • [ 156721-17-4 ]
  • 12
  • [ 6066-82-6 ]
  • [ 1204-06-4 ]
  • (E)-3-(1H-Indol-3-yl)-acrylic acid 2,5-dioxo-pyrrolidin-1-yl ester [ No CAS ]
  • 13
  • [ 101620-10-4 ]
  • [ 1204-06-4 ]
  • [ 123530-77-8 ]
  • 17
  • [ 1204-06-4 ]
  • [ 215790-43-5 ]
  • trans-(E)-N-[4-[2-(7-cyano-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]cyclohexyl]-3-(3-1H-indole)-2-propenamide [ No CAS ]
  • 18
  • [ 24424-99-5 ]
  • [ 1204-06-4 ]
  • [ 359700-09-7 ]
YieldReaction ConditionsOperation in experiment
36% With dmap; triethylamine; In tetrahydrofuran; at 15℃; for 12h; To a solution of (E)-3-(1 H-indol-3-yl)prop-2-enoic acid (21 g), Boc2O (48.97 g) and triethylamine (28.38 g) in THE (560 mL) was added 4-dimethylaminopyridine (0.685 g), and the mixturewas stirred at 15 C for 12 h. The mixture reaction was concentrated and the residue was purified by column chromatography (5i02, petroleum ether / ethyl acetate gradient) to give (E)-3-(1 -tertbutoxycarbonylindol-3-yl)prop-2-enoic acid (13 g, 36% yield) as a yellow solid.
With dmap; triethylamine; In tetrahydrofuran; for 16h; Step 1 (E)-3-(1H-indol-3-yl)acrylic acid (4.2 g, 22.44 mmol), (Boc)2O (10.42 ml, 44.9 mmol), and Et3N (7.82 ml, 56.1 mmol) were stirred in THF (112 ml) followed by the addition of DMAP (0.137 g, 1.122 mmol). The reaction was stirred for 16 h. The reaction was quenched with saturated sodium bicarbonate and stirred vigorously for 10 min. The mixture was diluted with EtOAc and acidified with 1 N HCl. The organic layer was collected, dried over sodium sulfate, filtered and concentrated under vacuum to give (E)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acrylic acid which was carried directly to step 2.
  • 19
  • [ 7524-52-9 ]
  • [ 1204-06-4 ]
  • 3-indole-acryltryptophan methyl ester [ No CAS ]
  • 20
  • [ 5680-79-5 ]
  • [ 1204-06-4 ]
  • (E)-N-[3-(1H-indol-3-yl)acryloyl]glycine methyl ester [ No CAS ]
  • 21
  • [ 1204-06-4 ]
  • [ 198821-79-3 ]
  • 3-(1<i>H</i>-indol-3-yl)-<i>N</i>-(3-methoxy-4-oxazol-5-yl-phenyl)-acrylamide [ No CAS ]
  • 22
  • [ 1204-06-4 ]
  • [ 637767-83-0 ]
  • (E)-3-(1H-Indol-3-yl)-N-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-piperidin-2-ylmethyl)-acrylamide [ No CAS ]
  • 23
  • [ 1204-06-4 ]
  • [ 252002-18-9 ]
  • C27H31N3O [ No CAS ]
  • 24
  • [ 918663-86-2 ]
  • [ 1204-06-4 ]
  • [ 100-46-9 ]
  • 2-(3-1<i>H</i>-indol-3-yl-acryloylamino)-octanedioic acid 1-benzylamide 8-hydroxyamide [ No CAS ]
  • 25
  • [ 3544-24-9 ]
  • [ 1204-06-4 ]
  • (E)-3-[3-(1H-indol-3-yl)acrylamido]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; EXAMPLE 2: Preparation of 3- (3-lNo.-indol-3-yl-acryloylamino) - benzamide; In 5.0 mL of dimethylformamide were dissolved 3-(1H- indol-3-yl) -acrylic acid (187 mg, 1.0 mmol) and 3-amino- benzamide (68.1 mg, 0.5 mmol), followed by the addition of benzotriazol-1-yl-oxitripyrrolidino phosphonium hexafluorophosphate (520.3 g, 1.0 mmol) and N, N- diisopropylethyl amine (0.17 ml, 1.0 mmol). The resulting solution was stirred at room temperature and mixed with ethyl acetate and an aqueous sodium salt solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and purified using silica gel column chromatography (/i-hexane : ethyl acetate : methanol = 5:3:1) to produce the subject <n="25"/>compound (2) as a yellow solid (34.3 mg, 23%).1H-NMR (CD3OD, 300Hz): 8.17 (IH, s, Aromatic), 7.83-7.97 (3H, m, Aromatic), 7.58 (2H, m, Aromatic), 7.41 (2H, m, Aromatic), 7.19 (2H, m, Aromatic), 6.77 (IH, d, J = 15.9 Hz, Aromatic) .
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; 1-2. Method for synthesis of low-molecular-weight compound RSC-133 (8b) [0135] Among the above-described low-molecular-weight compounds, RSC-133 (3-[3-(1H-indol-3-yl)-acrylamido]-benzamide (8b)) was synthesized in the following manner. [0136] First, trans-3-indoleacrylic acid (7a) and 3-amino-benzamide (6b) were dissolved in DMF, and benzotriazol-1-yl-N-oxy-tris(pyrrolidino)-phosphonium hexafluorophosphate (PyBOP) and N,N-diisopropylethylamine (DIPEA) were added to the solution to perform a coupling reaction. The reaction solution was stirred overnight at room temperature. The resulting material was separated and purified to obtain 3-[3-(1H-indol-3-yl)-acrylamido]-benzamido (RSC-133) as a yellow solid. The chemical characteristics and purity of RSC-133 were analyzed by 1H NMR (FIG. 6) and HPLC (FIG. 7). 1H NMR (CDCl3, 300 MHz) d = 8.90 (s, 1H), 8.21 (s, 1H), 7.86-8.03 (m, 4H), 7.76 (d, J = 8.1 Hz, 1H), 7.36-7.41 (m, 3H), 7.20 (m, 2H), 6.60 (d, J = 15.3 Hz, 2H), 3.88 (s, 3H).
  • 26
  • [ 4518-10-9 ]
  • [ 1204-06-4 ]
  • (E)-3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; EXAMPLE 4: Preparation of 3- (3-liY-indol-3-yl-acryloylamino) - benzoic acid methyl ester; In 5.0 mL of dimethylformamide were dissolved 3-(lif- indol-3-yl) -acrylic acid (150 mg, 0.8 mmol) and 3-amino benzoic acid methyl ester (218 mg, 1.44 mmol), followed by the addition of ethylenedichloride (230 mg, 1.2 mmol), N- hydroxybenzotriazole (163 mg, 1.2 mmol), and N, N- diisopropylethylamine (0.21 ml, 1.2 mmol). The resulting solution was stirred at room temperature and mixed with ethyl acetate and an aqueous sodium salt solution. The organic layer was dried over anhydrous magnesium sulfate. After the <n="27"/>filtration and concentration of the residue, the concentrate was purified using silica gel column chromatography (n-hexane : ethyl acetate : methanol = 9:3:1) to produce the subject compound (4) as a yellow solid (102 mg, 38%) . 1H-NMR (CDCl3, 300Hz): 8.90 (IH, s, NH), 8.21 (IH, s, NH), 7.86-8.03 (4H, m, aromatic), 7.76 (IH, d, J = 8.1 Hz aromatic), 7.36-7.41 (3H, m, aromatic), 7.20 (2H, m, aromatic), 6.60 (2H, d, J = 15.3 Hz, aromatic), 3.88 (3H, s, OCH3).
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; 1-3. Synthesis of low-molecular-weight compound ID-52 (8a) Among the above-described low-molecular-weight compounds, ID-52 (3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester (8a)) was prepared in the following manner. Trans-3-indoleacrylic acid (7a, 150 mg, 0.8 mmol) and 3-amino-benzoic acid methyl ester (6a, 218 mg, 1.44 mmol) were dissolved in DMF, and 1-[3-(dimethyamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 230 mg, 1.2 mmol), hydroxy-7-azabenotriazole (HOAT, 163 mg, 1.2 mmol) and N,N-diisopropylethylamine (DIPEA, 0.21 mL, 1.2 mmol) were added to the solution to cause a coupling reaction. The reaction solution was stirred overnight at room temperature. Then, the resulting material was separated and purified to obtain 3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester (ID-52) as a yellow solid. 1H NMR (CDCl3, 300 MHz) d = 8.90 (s, 1H), 8.21 (s, 1H), 7.86-8.03 (m, 4H), 7.76 (d, J = 8.1 Hz, 1H), 7.36-7.41 (m, 3H), 7.20 (m, 2H), 6.60 (d, J = 15.3 Hz, 2H), 3.88 (s, 3H).
  • 27
  • [ 952285-87-9 ]
  • [ 1204-06-4 ]
  • C29H32FN5O4 [ No CAS ]
  • 29
  • [ 1204-06-4 ]
  • 3-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-<i>N</i>-{2-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-vinyl}-acrylamide [ No CAS ]
  • 30
  • [ 1204-06-4 ]
  • 3-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-<i>N</i>-{2-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-vinyl}-acrylamide [ No CAS ]
  • 31
  • [ 1204-06-4 ]
  • 3-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-2-{3-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-acryloylamino}-propionic acid methyl ester [ No CAS ]
  • 32
  • [ 1204-06-4 ]
  • [ 1026447-98-2 ]
  • 33
  • [ 1204-06-4 ]
  • 3-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-2-{3-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-acryloylamino}-propionic acid [ No CAS ]
  • 34
  • [ 1204-06-4 ]
  • (2S,3S)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid [ No CAS ]
  • 35
  • [ 1204-06-4 ]
  • (2S,3S)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid [ No CAS ]
  • 37
  • [ 1204-06-4 ]
  • 3-[(R)-1-Methyl-3-oxo-3-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propyl]-indole-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 38
  • [ 1204-06-4 ]
  • tert-butyl 3-((2S,3R)-3-bromo-4-oxo-4-((R)-2-oxo-4-phenyloxazolidin-3-yl)butan-2-yl)-1H-indole-1-carboxylate [ No CAS ]
  • 39
  • [ 1204-06-4 ]
  • tert-butyl 3-((2S,3S)-3-azido-4-oxo-4-((R)-2-oxo-4-phenyloxazolidin-3-yl)butan-2-yl)-1H-indole-1-carboxylate [ No CAS ]
  • 40
  • [ 1204-06-4 ]
  • (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid [ No CAS ]
 

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