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Thioether type compound as well as synthesis method and application thereof

A synthesis method and compound technology, applied in the preparation, application, food science and other directions of thioether, can solve the problems of adverse effects of antioxidant capacity, limited application scope, low antioxidant efficiency, etc., and achieve excellent antioxidant capacity, non-toxicity, etc. Side effects, mild process conditions

Active Publication Date: 2018-08-24
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

TBHQ has not been approved for use in food by the EU because of its mutagenicity
In addition, most of the existing antioxidants also have some disadvantages in application: such as low antioxidant efficiency and poor antibacterial effect; especially, BHA, BHT, PG and TBHQ have poor thermal stability, and they are The above hot oils are extremely volatile and invalid, which limits the scope of application
For example, the melting point of BHA is 63°C, and the melting point of BHA is 70°C. It is easy to sublime when heated, and easy to volatilize when baked. Therefore, their antioxidant capacity will be seriously adversely affected during food processing.
[0004] In addition, it is worth noting that, according to literature reports, the natural compound (I-0) has a certain inhibitory effect on tyrosinase, is safe and non-toxic, however, its antioxidant activity is weak:

Method used

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  • Thioether type compound as well as synthesis method and application thereof
  • Thioether type compound as well as synthesis method and application thereof
  • Thioether type compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of compound (I-1):

[0046]

[0047] In a three-necked flask with a thermometer, a magnetic stirrer and a reflux condensing device, add 12 g of acetic acid, 8.2 g of sodium acetate, and 200 mL of deionized water, and stir to dissolve; then add 3-methoxy-4-hydroxybenzyl alcohol (II -1) 12.4g, 7.90g of sodium thiosulfate, continue to stir, and heat to 95°C for 15h. After cooling down, add 200mL dichloromethane to extract twice, dry with anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain a bright yellow oil; then add 200mL of 50% ethanol solution for recrystallization to obtain pure product: bis(3- Methoxy-4-hydroxybenzyl)sulfide 8.13g product, yield 66.0%. The melting point of the product is 79.5-82.2°C,1 H-NMR (400MHz, CDCl 3 )δ: 6.847 (2H, s, H-3, 3'), 6.813 (2H, d, J=1.2MHz, H-5, 5'), 6.751 (2H, d, J=1.2MHz, H-6 ,6'), 3.877 (6H, s, CH3), 5.558 (2H, s, OH), 3.557 (4H, s, CH2), 7.26 (CDCl 3 solvent peak).

Embodiment 2

[0049] Synthesis of compound (I-1):

[0050]

[0051] In a three-necked flask with a thermometer, a magnetic stirrer and a reflux condensing device, add 12 g of acetic acid, 8.2 g of sodium acetate, and 200 mL of deionized water, and stir to dissolve; then add 3-methoxy-4-hydroxybenzyl alcohol (II -1) 12.4g, potassium thiosulfate 9.52g, continue to stir, and heat to 100°C for 12h. After cooling down, add 200mL dichloromethane to extract twice, dry with anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain a bright yellow oil; then add 200mL of 50% ethanol solution for recrystallization to obtain pure product: bis(3- Methoxy-4-hydroxybenzyl)sulfide 8.82g product, yield 71.6%. The melting point of the product is 79.5-82.2°C, 1 H-NMR (400MHz, CDCl 3 )δ: 6.847 (2H, s, H-3, 3'), 6.813 (2H, d, J=1.2MHz, H-5, 5'), 6.751 (2H, d, J=1.2MHz, H-6 ,6'), 3.877 (6H, s, CH3), 5.558 (2H, s, OH), 3.557 (4H, s, CH2), 7.26 (CDCl 3 solvent peak).

Embodiment 3

[0053] Synthesis of compound (I-1):

[0054]

[0055] In a three-necked flask with a thermometer, a magnetic stirrer and a reflux condensing device, add 12 g of acetic acid, 8.2 g of sodium acetate, and 200 mL of deionized water, and stir to dissolve; then add 3-methoxy-4-hydroxybenzyl alcohol (II -1) 12.4g, 5.93g of ammonium thiosulfate, continue to stir, and heat to 88°C for 20h. After cooling down, add 200mL dichloromethane to extract twice, dry with anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain a bright yellow oil; then add 200mL of 50% ethanol solution for recrystallization to obtain pure product: bis(3- Methoxy-4-hydroxybenzyl) sulfide 7.36g product, yield 59.7%. The melting point of the product is 79.5-82.2°C, 1 H-NMR (400MHz, CDCl 3 )δ: 6.847 (2H, s, H-3, 3'), 6.813 (2H, d, J=1.2MHz, H-5, 5'), 6.751 (2H, d, J=1.2MHz, H-6 ,6'), 3.877 (6H, s, CH3), 5.558 (2H, s, OH), 3.557 (4H, s, CH2), 7.26 (CDCl 3 solvent peak).

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Abstract

The invention provides a thioether type compound and also relates to a synthesis method of the thioether type compound and application of the thioether type compound. A chemical structure of the thioether type compound enables the thioether type compound to have a relatively high melting point and be not easily sublimated, so that the thioether type compound has relatively good thermal stability;the thioether type compound has an excellent anti-oxidization capability and has no toxic and side effects, so that the thioether type compound has relatively high utilization safety; secondly, a target compound is synthesized by the synthesis method of the thioether type compound, provided by the invention, by adopting one-step reaction; visibly, the synthesis method is simple to operate, moderate in technological conditions, green and environmentally friendly, and is very suitable for large-scale industrial production. A series of experiments prove that the thioether type compound has an obvious inhibition effect on oxidization of various foods and an anti-oxidization effect of the compound has a certain dose-effect relationship with the concentration of the compound; therefore, the thioether type compound provided by the invention has a wide application prospect and a good market potential.

Description

technical field [0001] The present invention relates to an antioxidant, in particular to a thioether compound, a synthesis method of the thioether compound, and an application of the thioether compound. Background technique [0002] Antioxidants are a class of substances that help trap and remove free radicals, preventing the harmful effects of oxygen. It is well known that oxidative rancidity is one of the important causes of food spoilage. In order to prevent food from oxidative rancidity, antioxidants need to be added during food processing, storage and preservation. Currently commonly used food antioxidants include: 2,6-di-tert-butyl-4-methylphenol (BHT), dibutyl hydroxyanisole (BHA), propyl gallate (PG), tert-butyl terephthalate phenol (TBHQ) and tocopherol (VE), etc. For example, tocopherol is vitamin E, and the natural tocopherol is d-tocopherol (dextrorotary), which has 7 isomers such as α, β, γ, and δ, among which α-tocopherol is Most active; tocopherol mixed co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/16C07C319/14A23L29/00A23L3/3535
CPCA23L3/3535A23L29/055A23V2002/00C07C323/16A23V2200/02Y02A40/90
Inventor 金春华曹昊
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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