Synthesis methods of sunset yellow hapten and artificial antigen

A synthesis method, technology of sunset yellow, applied in chemical instruments and methods, preparation of azo dyes, animal/human proteins, etc.

Inactive Publication Date: 2012-06-20
江苏南通维立科化工有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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Method used

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  • Synthesis methods of sunset yellow hapten and artificial antigen
  • Synthesis methods of sunset yellow hapten and artificial antigen
  • Synthesis methods of sunset yellow hapten and artificial antigen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 2.0g (4.4mmol) of sunset yellow and 25ml of anhydrous toluene into a 100ml round bottom flask, slowly add 2.0ml (28.1mmol) of thionyl chloride under electromagnetic stirring, then drop a few drops of anhydrous DMF, and stop after reflux for 2h reaction. Remove the remaining thionyl chloride and toluene by rotary evaporation, add petroleum ether, filter with suction, and dry to obtain compound I as a dark red solid.

Embodiment 2

[0025] Add 0.17g (1.35mmol) glycine methyl ester hydrochloride, 20ml anhydrous acetone, 0.27g triethylamine to a 50ml round bottom flask, stir to dissolve, add 0.2g (0.45mmol) sunset yellow sulfonyl chloride I, and stir at room temperature for 1h. Acetone was distilled off and separated by silica gel column chromatography to obtain product IIA (R=H).

[0026] 1 H NMR (CDCl 3 , 400M) δ8.67 (d, 1H, J=8.8Hz, Ar-H 5 ), 8.24(s, 1H, Ar-H 3 ), 8.14 (d, 1H, J=9.6Hz, Ar-H 2 ), 8.05(d, 2H, J=8.4Hz, Ar-H 6，6’ ), 7.95(s, 1H, Ar-H 4 ), 7.91 (d, 2H, J=8.4Hz, Ar-H 7，7’ ), 6.96 (d, 1H, J=9.6Hz, Ar-H 1 ), 3.77 (d, 4H, J=7.2Hz, CH 2 ×2), 3.54(s, 3H, -OCH 3 ), 3.51(s, 3H, -OCH 3 ),.

[0027] HRMS (ESR): m / z=573.0726 (caled.for573.0720[M+Na] + )

Embodiment 3

[0029] Add 0.29g (1.35mmol) L-phenylalanine methyl ester hydrochloride, 20ml anhydrous acetone, 0.27g triethylamine into a 50ml single-necked round bottom flask, stir until dissolved, add 0.2g (0.45mmol) sunset yellow Acid chloride I, stirred at room temperature for 1h. Acetone was distilled off and separated by column chromatography to obtain the product IIA (R=CH 2 Ph).

[0030] 1 H NMR (CDCl 3 , 400M) δ16.13 (s, 1H, OH), 8.41 (d, 1H, J=8.4Hz, Ar-H 5 ), 7.91(s, 1H, Ar-H 3 ), 7.78 (d, 3H, J=8.4Hz, Ar-H 6，6’，2 ), 7.63 (d, 3H, J=8.4Hz, Ar-H 7，7’，4 ), 7.18(d, 3H, J=6.8Hz, Ar-H), 7.13(d, 3H, J=7.2Hz, Ar-H), 7.05(d, 1H, J=7.2Hz, Ar-H), 6.90(d, 1H, J=8.4Hz, Ar-H 1 ), 5.82-5.88(m, 2H, 2×NH), 4.23-4.26(m, 2H, 2×CH), 3.51(s, 3H, -OCH 3 ), 3.46(s, 3H, -OCH 3 ), 2.96-3.08 (m, 2H, 2×CH 2 ).

[0031] HRMS (ESR): m / z = 753.1654 (caled. for 753.1659 [M+Na] + )

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Abstract

The invention relates to synthesis methods of a sunset yellow hapten and an artificial antigen, and particularly discloses synthesis methods of the sunset yellow hapten and an antigen thereof, belonging to the technical fields of organic chemistry and immunochemistry. A disodium salt of sunset yellow is converted to sulfonyl chloride, then sulfonyl chloride reacts with different amino-substituted carboxylic ester hydrochlorides, and hydrolysis is carried out to get rid of methyl ester protection so as to obtain the sunset yellow hapten. Then the carbodiimide method is adopted to couple the sunset yellow hapten with carrier protein bovine serum albumin (BSA) to obtain the complete antigen of sunset yellow, which can be used to prepare the corresponding antibody and can provide a technical foundation for the establishment of the relevant enzyme immunoassay method.

Description

【Technical field】 [0001] The invention relates to azo pigment derivatives, in particular to a preparation method of sunset yellow pigment hapten and artificial antigen thereof, belonging to the field of organic synthesis. 【Background technique】 [0002] As a commonly used food additive, food coloring is favored by consumers because it can make the color of food itself brighter, and it has also become an additive that is vigorously used in the food industry. The most used food coloring is food synthetic coloring, and most of them are azo coloring. my country also has strict restrictions on the addition of synthetic pigments to food: all meat and its processed products, fish and its processed products, vinegar, soy sauce, fermented bean curd and other condiments, fruits and their products, milk and dairy products, baby food Food, biscuits, and pastries cannot use artificial pigments. Only soft drinks, cold drinks, candies, mixed wine and fruit juice can be used in small amoun...

Claims

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Application Information

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IPC IPC(8): C09B43/00C07K14/765
Inventor 王文虎徐凤波刘亭亭任新霞周秀秀赵秀杰宋英俊李可庆章奉良
Owner 江苏南通维立科化工有限公司
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