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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Cinnamaldehyde is a major and a bioactive compound isolated from the leaves of Cinnamomum osmophloeum kaneh. Cinnamaldehyde is a cytokine production inhibitor. Cinnamaldehyde has anti-bacteria, anti-oxidation, and anti-inflammatory properties .
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CAS No. : | 104-55-2 |
Formula : | C9H8O |
M.W : | 132.16 |
SMILES Code : | O=CC=CC1=CC=CC=C1 |
MDL No. : | MFCD00007000 |
InChI Key : | KJPRLNWUNMBNBZ-QPJJXVBHSA-N |
Pubchem ID : | 637511 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H317-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* 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 |
---|---|---|
75.0% | In ethanol;Reflux; | General procedure: solutionof acid hydrazide (0.01 mol) and appropriate benzaldehyde/acetophenone (0.01 mol) in ethanol was refluxed for 5-6 h. The precipitated title compounds were then filtered off, washed with water and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In isopropyl alcohol; for 3h;Heating / reflux; | Example 2 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 20 mg Huperzine A, and 77 mg cinnamaldehyde were refluxed in 2 mL isopropanol for 3 hours. Solvent was removed under vacuum. The crude reaction mixture was dissolved in 3 mL anhydrous THF and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H). | |
In isopropyl alcohol; for 3h;Heating / reflux; | Example 2 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 20 mg of Huperzine A, 77 mg of cinnamaldehyde were refluxed in 2 mL of isopropanol for 3 hours, and then solvent was removed under vacuum, 3 mL of anhydrous THF added and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With Ag(I) exchanged montmorillonite K10; In neat (no solvent); at 120℃; for 3h;Green chemistry; | General procedure: Amine (1.50 mmol) and aldehyde (1.00 mmol) were dissolved in 1.5 mL of Et2O in a reaction vial equipped with a magnetic stirrer bar, followed by the addition of Ag(I)-exchanged Montmorillonite K10 (0.50 g). After 5 min stirring, the solvent was removed in vacuo to obtain a dry powder. The reaction mixture was heated at a temperature of 120 oC for 3 h. After cooling to room temperature, the reaction mixture was filtered through a short silica plug and the solid residues washed well with CH2Cl2. The solvent was removed in vacuo and the crude product purified by column chromatography over silica gel eluting with a mixture of Hexane EtOAc to produce the title compounds (3a-3k). NOTE. For the recycle/reuse study, the crude product was gravity filtered and the clay material washed several times with CH2Cl2, air dried and weighed. This process was repeated for consecutive recycle/reuse reactions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In methanol; water; at 20℃; for 6h; | General procedure: An aqueous solution of NaOH (5%, 4 ml) was added slowly to the stirring solution of appropriate aryl aldehyde (1mmol) and <strong>[5234-26-4]N-(2-acetylphenyl)acetamide</strong> (1 mmol) in methanol (20 ml) in a 100 ml conical flask. The stirring was continued at room temperature for 6 hours and the completion of reaction was monitored by TLC. The reaction on completion was poured onto ice cold water, yellow solid was obtained after filteration which was recrystallized from ethanol. The physical data for the characterstic compound is shown below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In ethanol; at 20℃; | To a clear solution of 3a (1mmol) in EtOH containing 2, 4, 6-trimethoxy benzaldehyde (1mmol), 40% KOH was added and the resulting reaction mixture was stirred for complition of the reaction at r.t. (TLC control). The separated solid was filtered, washed with excess of water, neutralized with dil HCl, dried over anhydrous Na2SO4, recrystallised from ethanol to obtain product 13. The product was pure enough for further reactions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With oxygen; potassium hydroxide; In dimethyl sulfoxide; at 120℃; under 760.051 Torr; for 12h;Green chemistry; | General procedure: A mixture of benzamidine hydrochloride 1a (0.25mmol), cinnamaldehyde 2a (0.30mol) and KOH (0.50mmol, 2equiv.) was stirred in DMSO (1.0mL) under 1atm O2 atmosphere at 120°C for 12h. After completion of the reaction (monitored by TLC), water (10mL) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The combined organic layers were then dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the desired product 3aa as a white solid (using the mixture of petroleum ether and ethyl acetate as eluents). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With oxygen; potassium hydroxide; In dimethyl sulfoxide; at 120℃; under 760.051 Torr; for 12h;Green chemistry; | General procedure: A mixture of benzamidine hydrochloride 1a (0.25mmol), cinnamaldehyde 2a (0.30mol) and KOH (0.50mmol, 2equiv.) was stirred in DMSO (1.0mL) under 1atm O2 atmosphere at 120°C for 12h. After completion of the reaction (monitored by TLC), water (10mL) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The combined organic layers were then dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the desired product 3aa as a white solid (using the mixture of petroleum ether and ethyl acetate as eluents). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 70 - 80℃; for 3h; | General procedure: The mixture of <strong>[78364-55-3]6-fluoro-2-hydrazinylbenzo[d]thiazole</strong> (2) (0.01 mol) and benzalde-hyde/substituted benzaldehyde (0.01 mol) was reuxed in ethanol (15 ml) at 70?80 °C for 3 h. The separated product obtained was ltered off, washed withdistilled water and recrystallized from methanol to give the correspondinghydrazone. The product obtained was further dissolved in acetic acid (20 ml) atroom temperature followed by the addition of sodium acetate (0.5 g). Bromine(2 mmol) in acetic acid (10 ml) was added dropwise to the reuxing reactionmixture. After 1 h, the mixture was poured onto crushed ice (100 g). The precipitateobtained was ltered off and crystallized from ethanol-dimethylformamide (1:1) togive crystals of (3a?3t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: In the presence of sodium sulfate, 2-furaldehyde (1 equivalent) and (S) -<strong>[2936-62-1]2-methylbenzhydrylamine</strong> (1 equivalent) were stirred overnight at room temperature in dichloromethane. Thereafter, sodium sulfate was removed by filtration, and the solvent was distilled off. The residue was recrystallized to obtain an imine compound in a yield of 89%.(Addition of hydrogen cyanide to imine compound)(S) -imine compound (enantiomer excess ratio 98% ee, 1.81 mmol, 500 mg) was suspended in methanol (2.0 mL), reacted with HCN (1.98 mmol, 53 mg), and after 4 minutes the desired Crystals of the amino nitrile compound precipitated spontaneously. After 140 hours from the start of the reaction, crystals were separated by filtration and the crystals were washed with isopropyl alcohol (IPA) (2 mL)To give an (αS, NS) -aminonitrile compound (1.57 mmol, 476 mg) having a diastereomeric ratio dr = 30: 1 or more in a yield of 87%. The relationship between the reaction time and the diastereomer ratio dr at this time is shown in FIG. The enantiomeric excess was confirmed by HPLC after dissolving the crystals in a solvent. The diastereomeric ratio dr was measured by NMR nuclear magnetic resonance spectrometer and HPLC.Further, the filtrate was concentrated, the residue was subjected to column chromatography and eluted with hexane / chloroform= 1/1 (v / v) elution part, (αR, NS) -aminini having a diastereomer ratio dr = 1: 0.84Tril (0.1 mmol, 30 mg) was obtained in 5% yield.The obtained (αS, NS) -aminonitrile compound crystal was dissolved in concentrated hydrochloric acid trifluoroacetic acid (1: 1, v / v) and hydrolyzed to obtain optically active amino acid (S isomer). It was dissolved in concentrated hydrochloric acid-trifluoroacetic acid (1: 1, v / v) as a mixed solvent so that the concentration of amino nitrile was 0.5 mol / L, and hydrolysis reaction was carried out. The above reaction equation is shown below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In toluene; at 120℃; for 12h;Inert atmosphere; | Under nitrogen atmosphere, <strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (150 mg, 1 mmol), [Cp*IrCl2]2 (8 mg, 0.01 mmol, 1 molpercent), toluene (1.0 mL), cinnamaldehyde (132 mg, 1 mmol)Add to a 25 mL Schlenk reaction flask.The mixture was reacted at 120°C for 12 hours and then cooled to room temperature.The solvent was removed in vacuo under reduced pressure and then purified by column chromatography (developer: ethyl acetate/petroleum ether) to give the pure target compound, yield: 80percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In toluene; at 120℃; for 12h;Inert atmosphere; | Under nitrogen protection, <strong>[5900-59-4]2-amino-4-chlorobenzamide</strong> (171 mg, 1 mmol), [Cp*IrCl2]2 (8 mg, 0.01 mmol, 1 molpercent), toluene (1.0 mL), cinnamaldehyde (132 mg, 1 mmol)Add 25mL Schlenk reaction flasks one by one.The mixture was reacted at 120°C for 12 hours and then cooled to room temperature.The solvent was removed in vacuo under reduced pressure and then purified by column chromatography (developer: ethyl acetate/petroleum ether) to give the pure target compound in a yield of 86 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20℃; for 0.5h;Molecular sieve; | 9H-fluoren-9-amine (English name: 9H-fluoren-9-amine, 1 mmol), cinnamaldehyde (1 mmol), stirred with molecular sieve (0.3 g) in dichloromethane (5 ml) at room temperature for half time Hours and then filtered to remove the solvent to give Substrate-1.1-5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | for 0.166667h;Microwave irradiation; | General procedure: Second step consists of condensation of <strong>[6761-52-0]3-aminopyrazine-2-carbohydrazide</strong> (0.5 gm, 0.003 mol) with aromatic aldehydes (0.5 gm, 0.008 mol) using microwaveirradiation (8 - 10 min, 350 W). After cooling and filtration,the product was recrystallized using ethanol [6, 9] (Fig. 1). |