Synthesis process of gingerol derivative

A technology of derivatives and gingerol, which is applied in the field of synthetic technology of gingerol derivatives, can solve the problems that synthesis research and process development are still in their infancy, and achieve the advantages of convenient industrial production, high yield, and inhibition of by-products generated effect

Inactive Publication Date: 2013-06-19
朱志成
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The medical value of shogaol and its hydrogenated reduction products has been concerned for a long time, but unfortunately, its synthesis research and process development are still in its infancy or blank

Method used

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  • Synthesis process of gingerol derivative

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Experimental program
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Effect test

Embodiment 1

[0024] Embodiment 1, ( E )-1-(4-hydroxy-3-methoxyphenyl)pent-1-en-3-one ( gingerol-a-1 )Synthesis:

[0025] Into a 5 liter glass reactor was charged 120 grams of glacial acetic acid and 140 grams of tetrahydropyrrole. The flask is equipped with an electric stirring rod, a thermometer and a dropping funnel. Soak the flask in ice water, and when the temperature of the solution in the bottle drops to gingerol-a-1 Crude. oily crude gingerol-a-1 Dissolve in 10 liters of warmed petroleum ether (30°C) containing 100 g of activated carbon. The mixture was stirred for 1 hour, filtered while hot, and the filtrate was cooled to 5°C to obtain pale yellow needle-like crystals. Yield: 350 g. Melting point: 93 degrees.

Embodiment 2

[0026] Embodiment 2, 1-(4-hydroxy-3-methoxyphenyl)pentan-3-one ( Gingerol-b-1 )Synthesis:

[0027] In a 5 liter flask add 100 g gingerol-a-1 , 2 liters of methanol and 2 grams of palladium on carbon catalyst (containing 10% palladium). The reaction mixture was replaced with hydrogen 3 times, then stirred under hydrogen atmosphere for 3 hours. The mixture was filtered and the filtrate was concentrated to give the crude product Gingerol-b-1 . Pure Gingerol-b-1 Obtained by silica gel column chromatography. per 100g crude product Gingerol-b-1 The oil was dispersed with 200g of silica gel (100mesh), and then eluted with ethyl acetate / petroleum ether (2%~10%) to obtain a pure oil Gingerol-b-1. Gingerol-b-1 It can be recrystallized into needle crystals by petroleum ether. Yield: 79 grams. Melting point: 37~38 degrees.

Embodiment 3

[0028] Embodiment 3, ( E )-1-(4-hydroxy-3-methoxyphenyl)hex-1-en-3-one ( gingerol-a-2 ) and 1-(4-hydroxy-3-methoxyphenyl)hexan-3-one ( Gingerol-b-2) Synthesis:

[0029] gingerol-a-2 and gingerol-b-2 It is synthesized by a method similar to that of Examples 1 and 2. gingerol-a-2 Melting point: 89 degrees; gingerol-b-2 Melting point: 44 degrees.

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Abstract

The invention relates to a synthesis process of a gingerol derivative. A shogaol derivative is obtained by condensation of vanillin, aliphatic aldehyde and ketone in acid and base solvents in an appropriate ratio. The novel gingerol derivative is obtained by catalytic hydrogenation reduction of shogaol. The synthesis process disclosed by the invention is simple, and the gingerol derivative can be obtained through the reaction with one step-two steps and through a simple and convenient purification method.

Description

technical field [0001] The invention relates to a synthesis process of a pharmaceutical candidate compound and a food additive, which is a new synthesis process of a natural product with anti-cancer, anti-inflammation, anti-oxidation and antihypertensive effects, and belongs to the technical field of innovative drug preparation and process. Background technique [0002] Ginger is a kind of rhizome spice seasoning widely planted in the world. In China and even the whole of Asia, it is also a traditional medicinal and edible plant. , The effect of drying dampness and eliminating phlegm. Modern medical research shows: Ginger has anticoagulant, anti-oxidation, anti-tumor, boosting blood pressure, strengthening the heart, lowering blood fat, anti-atherosclerosis, protecting gastric mucosa, protecting liver and gallbladder, anti-inflammatory, antitussive, anti-dizzy and anti-emetic, Central nervous system inhibition and other effects. [0003] 6-gingerol (6-gingerol) is the mai...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/62C07C49/255
Inventor 朱志成
Owner 朱志成
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