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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.
Synonyms: 4-Dimethylaminobenzaldehyde
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Usman Sabir ; Hafiz Muhammad Irfan ; Alamgeer ; Aman Ullah ; Yusuf S. Althobaiti ; Fahad S. Alshehri , et al.
Abstract: Western diet style (fast food), which includes fatty frozen junk food, lard, processed meats, whole-fat dairy foods, cream, mayonnaise, butter, snacks, and fructose, is a primary etiological determinant for developing nonalcoholic steatohepatitis (NASH) worldwide. Here the primary focus is to see the impact of naturally identified essential oil on disease mechanisms developed in an animal model using the same ingredients. Currently, symptomatic therapies are recommended for the management of NASH due to non-availability of specific treatments. Therefore, the present study was designed to evaluate the potential anti-NASH effect of nerolidol in a rat model fed with a purpose-built diet. The diet substantially induced insulin resistance, hepatic steatosis, dyslipidemia, and elevation of liver enzymes in the experimental animals. The levels of liver oxidative stress markers, nitrites (NO2–), serum pro-inflammatory cytokine (TNF-α) and hepatic collagen were increased in disease control rats. Nerolidol oral treatment in ascending dose order of 250 and 500 mg/kg substantially reduced the steatosis (macrovesicular and microvesicular), degeneration of hepatocytes, and inflammatory cells infiltration. The amounts of circulatory TNF-α and tissue collagen were also reduced at 500 mg/kg dose of nerolidol, expressing its anti-fibrotic effect. The current study described the multiple-hit pathophysiology of NASH as enhanced steatosis, pro-inflammatory markers, and oxidative stress in rats, which resulted in the development of vicious insulin resistance. Nerolidol treatment significantly reduced hepatic lipid accumulation and halted disease progression induced by a hypercaloric diet.
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Keywords: Western diet ; Non-alcoholic steatohepatitis ; Insulin resistance ; Inflammation ; Nerolidol
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| CAS No. : | 100-10-7 |
| Formula : | C9H11NO |
| M.W : | 149.19 |
| SMILES Code : | C1=C(N(C)C)C=CC(=C1)C=O |
| Synonyms : |
4-Dimethylaminobenzaldehyde
|
| MDL No. : | MFCD00003381 |
| InChI Key : | BGNGWHSBYQYVRX-UHFFFAOYSA-N |
| Pubchem ID : | 7479 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319 |
| Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 |
* 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.

[ 64-17-5 ]

[ 100-10-7 ]
[ 67-64-1 ]
[ 5432-53-1 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 67.73% | With sodium hydroxide; In water; at 0 - 20℃; | General procedure: A solution of substituted benzaldehydes (50 mmol) in acetone (50 ml) was cooled to 0C in an ice bath. To this a 10% aqueous NaOH solution was added dropwise and the reaction mixture was allowed to attain RT. It was then stirred at room temperature till the completion of the reaction. Acetone was removed under reduced pressure and the reaction was dissolved in ethyl acetate and washed with dilute HCl. The organic layer was separated wash twice with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel, 100-200 mesh, 9:1 hexane/ethyl acetate) to give the pure product. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In chloroform; water; acetone; | EXAMPLE 1 Into a reaction vessel of 1 l in inside volume were placed 290.5 g (5 moles) of acetone, 300 ml of water and 3.6 g (0.05 moles) of pyrrolidine, to which 149.2 g (1 mole) of p-(N,N-dimethylamino) benzaldehyde was dropped over an hour while keeping at 30 C. Then the resulting solution was stirred under reflux for 9 hours. The solution was neutralized with concentrated hydrochloric acid up to pH 4.5, and heated to distill up to the distillation temperature of 100 C. Then 300 ml of chloroform was added, and the solution was neutralized with 28% NaOH aqueous solution to pH 12 and separated. Furthermore, the aqueous layer was extracted with 200 ml of chloroform twice. The obtained chloroform layers were combined to the previous chloroform layer to concentrate. The obtained crystal was recrystallized from a mixture solvent of benzene and hexane to give 113.6 g (crude yield: 60.0%) of yellow crystal with melting point of 137.5 to 140.5 C. The crystal was analyzed by gas chromatography to find that the intended product, 4- [p-(N,N-dimethylamino) phenyl]-3-butene-2-one, was 97.8% in purity. (Yield: 58.7% to p-(N,N-dimethylamino) benzaldehyde) |
[ 120-35-4 ]
[ 100-10-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Example 268 3-(4-Dimethylamino-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-dimethylaminobenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 195-197 C. |
[ 3199-50-6 ]

[ 100-10-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 55.4% | In ethanol; | Synthesis of 1-(5-bromo-2-furanyl)-3-(4-dimethylaminophenyl)-prop-2-en-1-one (32) Compound 29 (500 mg, 2.65 mmol) and 4-dimethylaminobenzaldehyde (394 mg, 2.65 mmol) were dissolved in ethanol (5 mL), followed by addition of 10% aqueous potassium hydroxide (10 mL). The mixture was stirred at room temperature for 1 h, and then the precipitated crystals were collected by filtration and washed with 50% aqueous ethanol to obtain Compound 32. Yield 470 mg (yield rate 55.4%). 1H NMR (300 MHz, CDCl3) delta 3.04 (s, 6H), 5.22 (d, J=3.9 Hz, 1H), 6.80 (d, J=3.6 Hz, 1H), 6.89 (d, J=15.0 Hz, 1H), 7.46 (d, J=14.7 Hz, 1H), 7.70 (d, J=8.1 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H). MS m/z 321 (MH+). |
[ 3199-50-6 ]
[ 100-10-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 55.4% | With potassium hydroxide; In ethanol; water; at 20℃; for 1h; | Synthesis of 1-(5-bromo-2-furanyl)-3-(4-dimethylaminophenyl)-prop-2-en-1-one (32) Compound 29 (500 mg, 2.65 mmol) and 4-dimethylaminobenzaldehyde (394 mg, 2.65 mmol) were dissolved in ethanol (5 mL), followed by addition of 10% aqueous potassium hydroxide (10 mL). The mixture was stirred at room temperature for 1 h, and then the precipitated crystals were collected by filtration and washed with 50% aqueous ethanol to obtain Compound 32. Yield 470 mg (yield rate 55.4%). 1H NMR (300 MHz, CDCl3) delta 3.04 (s, 6H), 5.22 (d, J = 3.9 Hz, 1H), 6.80 (d, J = 3.6 Hz, 1H), 6.89 (d, J = 15.0 Hz, 1H), 7.46 (d, J = 14.7 Hz, 1H), 7.70 (d, J = 8.1 Hz, 2H), 7.81 (d, J = 8.7 Hz, 2H). MS m/z 321 (MH+). |
[ 78364-55-3 ]
[ 100-10-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 68% | With acetic acid; In ethanol; at 80℃; for 0.166667h;Microwave irradiation; | General procedure: 2-(2-Arylidenehydrazino)-6-fluorobenzothiazoles 6a-r. General Procedure D. A mixture of compound 2 (0.0549 g, 0.0003 mol), the appropriate aromatic aldehyde (0.00033 mol) and glacial acetic acid (0.1 mL) in ethanol (5 mL) was heated under microwave (20 W) at 80 °C for 10 min. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized from the appropriate solvent to give the desired compounds 6a-r. |
| 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). |
[ 6761-52-0 ]
[ 100-10-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64% | for 0.116667h;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). |
| In ethanol;Microwave irradiation; | General procedure: Asolution of aromatic/substituted aldehydes (0.008 mole, 0.9gm) in 25ml ethanolwas added to a solution of compound 2(0.003 mol, 0.5gm) in 10 ml ethanol and wasirradiated in a microwave oven for 8-10 min (350 W). The resultanthydrazone was precipitated by addition of water (30 ml). The product wasfiltered and purified using ethanol. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 0.762 mg | With pyrrolidine; acetic acid; In dimethyl sulfoxide; at 70℃; for 24h;Inert atmosphere; | Weigh the content of 95% <strong>[520-26-3]hesperidin</strong> 1.5 g,4-N, N-dimethylbenzene 0.402 g,Add 170 mul of anhydrous DMSO, 170 mul of tetrahydropyrrole, add glacial acetic acid 150 muL, under nitrogen protection, stirring at 70 C for 24 h, adding silica gel, the chloroform-methanol gradient elution, the red powder 0.762 mg, Is 3- (4-N, N-dimethylbenzylidene) -pentanthrene (cpd 6). |
[ 54396-44-0 ]
[ 868-85-9 ]
[ 100-10-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | With chitosan; In neat (no solvent); at 75℃; for 0.0333333h;Microwave irradiation; Green chemistry; | General procedure: An equimolar mixture of <strong>[54396-44-0]2-methyl-3-(trifluoromethyl)aniline</strong> (0.351 g, 0.002 mol), corresponding aldehyde (0.002 mol), dimethyl phosphite (0.18 ml, 0.002 mol) and chitosan catalyst (10 molpercent) were taken in a reaction glass tube, degassed for 10 min and microwave irradiated at 180 W for 2 min at 60 °C. The progress of the reaction was monitored by TLC using petroleum ether and ethyl acetate (3:7) as solvent. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with water (2 x 15 ml) followed by brine (1 x 10 ml), dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silicagel (100-200 mesh) by using a 7:3 mixture of ethyl acetate in hexane to afford the pure alpha-aminophosphonates. |
[ 1986-47-6 ]
[ 100-10-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 18% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |