Naringenin

Naringenin is the predominant flavanone in grapefruit; displays strong anti-inflammatory and antioxidant activities.

Solid

(S)-naringenin is the (S)-enantiomer of naringenin. It has a role as an expectorant and a plant metabolite. It is a naringenin and a (2S)-flavan-4-one. It is a conjugate acid of a (S)-naringenin(1-). It is an enantiomer of a (R)-naringenin.

A mixture of 52 g of naringin and 5 w / vpercent of hydrochloric acid was mixed at a solid-to-liquid ratio of 1: 100 g / mL and hydrolyzed at 100 ° C for 1 hour. And then quickly cooled to room temperature, and then put it aside for 12 hours, precipitation of solid, after filtration with purified water to wash the solid to neutral, and then filtered to 25percent moisture content of naringenin wet crude 24. 5 grams; The crude naringenin obtained in the step (1) was added to a 30W / Vpercent acetic acid solution at a solid-to-liquid ratio of 1: 7g / mL, stirred at room temperature for 30 minutes, and then the solid was added to the same concentration Of acetic acid solution for 15 minutes, and then filtered, the solid washed with water to neutral, and then solid-liquid ratio of 1: 10g / mL volume concentration of 95percent ethanol dissolved, and then neutral alumina chromatography column, 100mL volume concentration of 95percent ethanol column chromatography column combined solution after the column, and then added to the solution volume of 10percent activated carbon at room temperature for 30 minutes, after filtration, the filtrate and then add the solution volume 10 The activated carbon was stirred at room temperature for 30 minutes. After filtration, the filtrate was concentrated to 1/3 volume by volume, distilled water was added into the same volume of distilled water, cooled to room temperature and placed in the refrigerator at 5 ° C for 24 hours. And then the white nacre crystals are precipitated and filtered to obtain naringenin wet fine product. The naringenin wet boutique is heated and boiled with 95percent ethanol by solid-liquid ratio of l: 6g / mL, and dissolved in ethanol An equal volume of distilled water was recrystallized once, and the precipitated white needle-like crystals were collected by filtration and then dried to obtain naringenin 14 g. In this case, the content of naringenin was 99.92percent and the yield was 26.9percent.Taking 98percent naringin 10g, macroporous resin D101 type 100g (about 200 ml), is placed in the 500 ml triangle flask, add 6percent sulfuric acid (6 ml _AOE 28692X0AO _ 100 ml) 150 ml, is connected to the 30 cm - 40 cm air condensing tube, water bath 90 °C closed hydrolysis 48h (macroporous resin by the white-light yellow, colorless solution), remove and cool, filtered, macroporous resin to a little water to wash, macroporous resin end to burn in the cup, add 300 ml water liquid, adding sodium bicarbonate, to neutral, filtered, 200 ml water washing, drying, using ethanol as solvent, reflux extraction 3 times (macroporous resin recovery white), each 20min, combined ethanol solution, decompression recovering ethanol, to obtain white of the naringenin 4.62g, determine its purity by HPLC is 94.5percent.Take a dry 50 mL round bottom flask and weigh it.5, 7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one (naringenin, 0.2723 g, 1 mmol) was placed therein.N, N'-dimethylformamide (DMF, 3 mL) was added dropwise to the bottle at room temperature.After stirring for 5 min, sodium hydride (0.0480 g, 2 mmol) was weighed and added to the reaction solution, and stirring was continued until no more gas was formed.Then, chloroacetonitrile (503 muL, 4 mmol) was added dropwise thereto at room temperature, and after reacting for 30 min, chloroacetonitrile (76 muL, 1 mmol) was added.The reaction flask was placed in an oil bath at 61 C and stirring was continued, followed by a reaction for 13 hours, and TLC was monitored until the starting material was completely reacted. willThe reaction solution was transferred to a 500 mL beaker, 300 mL of distilled water was added and stirred with a glass rod, followed by extraction with ethyl acetate.The organic layer was separated, and the organic layer was separated by liquid separation funnel, and washed with water and brine several times until the brine was clarified, and then anhydrous.The Mg2SO4 is dried, and then steamed under reduced pressure to obtain a crude product. The crude product is separated and purified by silica gel column chromatography (200 mesh silicon).The gum was eluted with (petroleum ether/ethyl acetate) to give the desired product (0.0880 g, 32.60%).To a solution containing 5.00 g (18.4 mmol) of 4', 5, 7-trihydroxyflavanone in 150 niL of acetone was added 10.0 g (7.00 mL, 57.0 mmol) of BnBr followed by 15.4 g (110 mmol) OfK2CO3. The reaction mixture was heated at reflux overnight under N2. The cooled reaction mixture was then concentrated under diminished pressure. The residue was redissolved in 300 mL of ethyl acetate, washed with three 100-mL portions OfH2O, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (28 x 4 cm).Elution with 3:1 hexanes-ethyl acetate gave 2 as a bright yellow solid: yield 8.07 g (81%); mp 127-129 0C; silica gel TLC Rf 0.53 (3:1 hexanes-ethyl acetate); 1H NMR (CDCl3) delta 5.02 (s, 2H), 5.07 (s, 4H), 6.17 (dd, 2H, J= 17.4, 2.1 Hz), 6.76 (d, 2H, J= 8.4 Hz), 6.97 (d, 2H, J= 8.7 Hz), 7.32 (m, 15H), 7.74 (dd, 2H, J= 15.3, 14.7 Hz) and 14.81 (br s, IH); 13C NMR (CDCl3) delta 70.3, 70.5, 71.6, 92.7, 95.3, 106.5, 115.2, 125.4, 127.5, 127.7, 127.9, 128.3, 128.4, 128.6, 128.8, 128.9, 129.1, 129.2, 130.4, 135.7, 136.1, 136.8, 143.0, 160.5, 161.9, 165.3, 169.1 and 192.8; mass spectrum (FAB), m/z 543.2177 (M + H)+ (C36H31O5 requires 543.2171).

antiulcer, antioxidant, immunomodulator, cholesterol lowering

Molecular Weight:272.25
XLogP3:2.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:272.06847348
Monoisotopic Mass:272.06847348
Topological Polar Surface Area:87
Heavy Atom Count:20
Complexity:363
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes