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Preparation method of avenanthramide and derivative thereof

A technology for oat alkaloids and derivatives, applied in the field of preparation of oat alkaloids and their derivatives, can solve the problems of high cost, low yield, high reaction temperature, etc.

Inactive Publication Date: 2017-05-10
NANJING HUASHI NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional synthesis method is the direct dehydration reaction of carboxylic acid and amino group. The reaction temperature of this method is high, resulting in dark color of the product, and the yield is low and the cost is high.

Method used

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  • Preparation method of avenanthramide and derivative thereof
  • Preparation method of avenanthramide and derivative thereof
  • Preparation method of avenanthramide and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] ① Weigh 180.0g of p-acetoxyphenylpropionic acid and suspend it in 90mL of toluene, quickly drop 400.0g of thionyl chloride into it at room temperature, and after overnight, react at 80°C for 2h and distill until no obvious fraction distills out to obtain brown Yellow liquid - p-acetoxyphenylpropionyl chloride, yield 94.0%.

[0028]

[0029] ②Weigh 100.0g of anthranilic acid and suspend in 1200mL of dichloromethane, under the protection of nitrogen, control the temperature at 10°C, add dropwise 220.0g of p-acetoxyphenylpropionyl chloride obtained in step ①, and drop it in about 2.0h. Then add 120.0g of triethylamine dropwise, control the temperature at 10°C, drop it for about 1h, keep stirring for 0.5h, add 500.0g of cold hydrochloric acid (2.0%), evaporate dichloromethane, filter with suction, wash with water, and dry to obtain brown Yellow solid, yield 81.1%.

[0030]

[0031] ③ Add 600.0 g of sodium hydroxide (15%) to the reaction product obtained in step ②, co...

Embodiment 2

[0034] ①Weigh 160.0g of p-acetoxyphenylacrylic acid and suspend it in 100mL of chloroform, quickly drop 400.0g of thionyl chloride into it at room temperature, stir overnight, react at 80°C for 3.0h, and distill off excess solvent and thionyl chloride , to obtain brownish yellow liquid - p-acetoxy phenylacryloyl chloride, yield 93.0%.

[0035]

[0036] ②Suspend 100.0g of anthranilic acid in 1200mL of dichloromethane, under the protection of nitrogen, control the temperature at 10°C, add dropwise 222.0g of p-acetoxyphenylacryloyl chloride obtained in step ①, and drop it in about 2.5 hours. Then add 150.0g sodium hydroxide (30%) dropwise, control the temperature at 5-10°C, drop it for about 1h, continue stirring for 1.5h, add 500mL cold hydrochloric acid (2%), distill off dichloromethane, suction filter, wash with water , and dried to give a light brown solid with a yield of 91.2%.

[0037]

[0038] ③Add 600.0g sodium hydroxide (15%) to the reaction product in step ②, con...

Embodiment 3

[0041] ①Weigh 180.0g of 2-methoxy-3-acetoxyphenylacrylic acid and suspend it in 100mL of cyclohexane, quickly drop 400.0g of thionyl chloride into it at room temperature, react overnight at 80°C for 2.5h, and distill off Excessive solvent and thionyl chloride give a brownish-yellow liquid, which is set aside.

[0042]

[0043] ②Suspend 120.0g of 2-amino-5-hydroxybenzoic acid in 1500.0g of chloroform, under the protection of nitrogen, control the temperature at 10°C, add dropwise the 3-methoxy-4-acetoxybenzene obtained in step ① 240.0g of acryloyl chloride, dripped for about 2.5 hours, then added dropwise 110.0g of triethylamine, controlled the temperature at 10°C, dropped for about 1 hour, kept stirring for 0.5 hours, added 100.0g of cold hydrochloric acid (10%), distilled under reduced pressure Chloromethane, suction filtered, washed with water, and suction filtered to obtain a light yellow solid with a yield of 91.8%.

[0044]

[0045] ③Add 310.0g sodium hydroxide (30...

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Abstract

The invention provides a preparation method of avenanthramide and a derivative thereof. The avenanthramide and the derivative thereof are synthesized and obtained by mainly utilizing an organic acid and aminobenzoic acid as major reactants. The method is high in yield, few in by-products and applicable to the industrialized production of the avenanthramide and the derivative thereof. The avenanthramide has multiple bioactivities of anti-oxidation, anti-anaphylaxis, anti-proliferation and itching relief, meanwhile, also has certain effects of treating coronary disease and colonic cancer, and is often used in products of a emulsion skincare article, an after-sun repairing article, a rhinitis spray, a skin itching relieving infantile product, an externally used cream for treating dermatitis and the like.

Description

technical field [0001] The invention relates to a preparation method of oat alkaloids and derivatives thereof, which are mainly used in skin care products, hair shampoo products, baby products, creams for external use on skin and the like. Background technique [0002] Oat alkaloids only exist in oat grains and silkworm eggs. They have various biological activities such as anti-oxidation, anti-allergy, anti-proliferation and anti-itching. At the same time, they also have certain effects on the treatment of coronary heart disease and colon cancer. They are often used in lotion skin care products, sunscreen After repair, rhinitis spray, baby products for skin itching, topical cream for dermatitis and other products. [0003] Avena alkaloids are a class of phenolic compounds consisting of anthranilic acid linked to hydroxyl-substituted cinnamic acid through an amide bond. There are more than 20 types of oat alkaloids, mainly including three structures of Bf, Bp, and Bc. The st...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C235/38
CPCC07C235/38C07C67/287C07C231/02C07C231/12
Inventor 苏桂珍史鲁秋孔惠胡海霞薛虹宇
Owner NANJING HUASHI NEW MATERIAL
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