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Synthetic method of oat alkaloids

A technology of oat alkaloids and synthesis methods, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., and can solve problems such as harsh reaction conditions and complicated preparation processes

Inactive Publication Date: 2018-08-28
YICHUN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent announcement number is CN 106631865A disclosed "A Preparation Method of Avena Alkaloids and Its Derivatives", which synthesizes avena alkaloids and their derivatives through a three-step method, but this synthesis method needs to be activated by thionyl chloride Carboxyl to prepare acid chloride, and then react with aminobenzoic acid, requiring anhydrous solvent and nitrogen protection, etc., the reaction conditions are harsh, and the preparation process is complicated

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  • Synthetic method of oat alkaloids
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  • Synthetic method of oat alkaloids

Examples

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Effect test

Embodiment 1

[0046] Synthesis of 2-(2-carboxyacetamido)-5-hydroxybenzoic acid

[0047] Weigh 15.3 g (0.1 mol) and 15.1 g (0.105 mol) of 2-amino-5-hydroxybenzoic acid and 15.1 g (0.105 mol) Michaelis acid, add them to a 500 mL round-bottomed flask, fully disperse them evenly with 300 mL of anhydrous toluene, and heat to reflux for reaction After 6-8 hours, cool to room temperature, remove the toluene by suction filtration to obtain an off-white solid, wash twice with toluene, and air-dry the obtained off-white solid in a fume hood, wait for the toluene to volatilize, and recrystallize the product after drying. The synthesized primary product of 2-(2-carboxyacetamido)-5-hydroxybenzoic acid was stirred evenly with ice water, and sodium hydroxide solution was slowly added dropwise until all the products were dissolved and the solution was light purple, and the stirring was continued for 30 min. Then add cold hydrochloric acid solution (6 mol / L), and add ice cubes to the reaction solution to co...

Embodiment 2

[0053] Synthesis of avenous alkaloid B,

[0054] Weigh 2.39 g (10 mmol) of 2-(2-carboxyacetamido)-5-hydroxybenzoic acid and 1.28 g (10.5 mmol) of 3-methoxy-4-hydroxybenzaldehyde and add them to a 100 mL double-necked circular In the bottom flask, fully dissolve with 20 mL of pyridine, then add the catalyst β-alanine (0.2 mmol), and heat to 90 o C, cooled to room temperature after 24 hours of reaction. After the reaction was completed, the reaction solution was poured into a 500 mL beaker, ice cubes were added, and the solution was cooled to 0 o C, then slowly add dilute hydrochloric acid solution, add ice cubes in time to control the temperature at 0 o About C, adjust the pH value to 2~3, precipitate a large amount of light yellow solid, stand still, filter with suction, wash the product with a large amount of deionized water, and recrystallize the product oat alkaloid B with hot acetone and water, and wash the initial product with acetone Heat and stir to dissolve, then ...

Embodiment 3

[0057] Synthesis of avenous alkaloid C,

[0058] Weigh 2.39 g (10 mmol) of 2-(2-carboxyacetamido)-5-hydroxybenzoic acid and 1.28 g (10.5 mmol) of 3,4-dihydroxybenzaldehyde into a 100 mL double-neck round bottom flask , fully dissolved with 20 mL of pyridine, then added catalyst β-alanine (0.2 mmol), heated to 90 o C, cooled to room temperature after 24 hours of reaction. After the reaction was completed, the reaction solution was poured into a 500 mL beaker, ice cubes were added, and the solution was cooled to 0 o C, then slowly add dilute hydrochloric acid solution, add ice cubes in time to control the temperature at 0 o About C, adjust the pH value to 2~3, precipitate a large amount of yellow-green solid, stand still, filter with suction, the product is washed with a large amount of deionized water, the product oat alkaloid C is further recrystallized with hot acetone and water, and the initial product is washed with acetone Heat and stir to dissolve, then slowly add de...

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Abstract

The invention provides a synthetic method of oat alkaloid and studies a chemical synthesis process of oat alkaloids A, B and C. The oat alkaloids A, B and C are synthesized by taking 2-amino-5-hydroxybenzoic acid, meldrum's acid, 4-hydroxybenzaldehyde, 4-hydroxyl-3-methoxybenzaldehyde and 3,4-dihydroxy benzaldehyde as raw materials and using a Knoevenagel condensation reaction. Analysis means suchas infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectroscopy and elemental analysis are applied to perform structural characterization on a compound, so that the feasibility of a process route of synergizing the oat alkaloids is demonstrated, and the synthetic process conditions are optimized; the synthetic method has important research significance for further developmentof application of oat alkaloids with multiple bioactive functions such as oxidation resistance. The development of the chemical synthesis technology has a very broad application prospect.

Description

Technical field: [0001] The invention relates to a method for preparing organic alkaloids used in skin care products, creams for external use on skin and other products, in particular to a method for synthesizing oat alkaloids. Background technique: [0002] Modern medical research shows that the effects of oatmeal on human health are mainly reflected in the following aspects: anti-oxidative radiation, balancing blood sugar, enhancing immunity, laxative, stabilizing blood pressure, weight loss and body shaping, etc. This health function of oats is not only due to the high content of β-glucan, but also due to it contains a variety of antioxidants, one of which is a nitrogen-containing phenolic acid derivative with a unique structure --- - Oat alkaloids. Oat alkaloids not only have a strong antioxidant effect, but also have various biological activities such as anti-itching, anti-proliferation, and anti-inflammation. They also play an important role in the prevention and trea...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C235/38
CPCC07C231/12C07C231/02C07C235/38C07C233/54
Inventor 刘万云霍平周秀明高绍斌
Owner YICHUN UNIVERSITY
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