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Magnolol derivatives and their preparation methods and applications

A technology of phenol derivatives and derivatives, applied in the field of magnolol and its preparation, can solve the problems of decreased antibacterial ability and achieve good water solubility

Active Publication Date: 2021-11-19
GUANGDONG HEJI BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a magnolol derivative and its preparation method and application

Method used

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  • Magnolol derivatives and their preparation methods and applications
  • Magnolol derivatives and their preparation methods and applications
  • Magnolol derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
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Embodiment approach

[0036] According to a preferred implementation method of the present invention, the compound of the structure shown in formula (1) is selected from at least one of the following compounds:

[0037] Compound 1: Compound 2:

[0038] Compound 3: Compound 4:

[0039] Compound 5:

[0040] The inventors of the present invention found that the magnolol derivatives involved in this specific embodiment have better water solubility and antibacterial ability.

[0041] In a second aspect, the present invention provides a method for preparing magnolol derivatives, the method comprising the following steps: in the presence of a phase transfer catalyst, the compound with the structure of formula (2) and bisulfite and / or Sulfites undergo a contact reaction,

[0042]

[0043] Among them, in formula (2), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently selected from hydrogen, halogen, substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 1 -...

Embodiment 1

[0059] Weigh 10g of magnolol (content is 90%) of plant origin, ultrasonically dissolve in 40ml of methanol, be methanol phase; weigh 3.9g of sodium bisulfite and dissolve it in 14ml of deionized water, add 0.01g of dodecane in addition Trimethylammonium chloride, as the aqueous phase. Slowly put the water phase and the methanol phase into a 250ml three-necked flask and mix, control the addition rate to 4ml / min, and magnetically stir at a speed of 450rmp / min. The reaction temperature is about 60°C, and the reaction time is 8h. Use a rotary evaporator to remove excess methanol, recrystallize in isopropanol at low temperature, filter and freeze-dry to obtain magnolol derivatives, with a yield of 40% based on magnolol in the reaction raw materials. It is characterized by a flight mass spectrometer and a nuclear magnetic resonance instrument, and it is confirmed that it is a magnolol derivative of the structure shown in formula (1) of the present invention. The mechanism of the r...

Embodiment 2

[0062]Take magnolol (content is 90%) 10g of plant source, ultrasonically dissolve in 40ml methanol, be methanol phase; Take 5.1g ammonium sulfite monohydrate and dissolve into 8ml deionized water, add 0.02g benzyl Triethylammonium chloride is the aqueous phase. Slowly put the water phase and the methanol phase into a 250ml three-necked flask and mix, control the addition rate to 4ml / min, and magnetically stir at a speed of 450rmp / min. The reaction temperature is about 80°C, and the reaction time is 5h. Use a rotary evaporator to remove excess methanol, recrystallize in isopropanol at low temperature, filter, and freeze-dry to obtain a magnolol derivative. The yield is 28% based on magnolol in the reaction raw materials. It is characterized by a flight mass spectrometer and a nuclear magnetic resonance instrument, and it is confirmed that it is a magnolol derivative of the structure shown in formula (1) of the present invention. The mechanism of the reaction is as follows:

...

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Abstract

The invention relates to the field of magnolol derivatives, in particular to magnolol and its preparation method and application. A magnolol derivative is disclosed, and the magnolol derivative has a structure represented by formula (1). The magnolol derivatives provided by the invention have good water solubility, are colorless and transparent after dissolving, have significant inhibitory effects on common Escherichia coli, staphylococcus aureus, etc., and can be used as green and natural preservatives in food, Medicines and cosmetics and other fields.

Description

technical field [0001] The invention relates to the field of magnolol derivatives, in particular to magnolol and its preparation method and application. Background technique [0002] Food, medicine and cosmetics are rich in a large amount of water and various nutrients, which provide a good growth environment for microorganisms, and it is inevitable that microorganisms will invade during the production and use of cosmetics, which makes them easily spoiled and deteriorates the quality of products. fall, posing a threat to the health of users. Adding preservatives to cosmetics is an important means to protect products from microbial contamination, extend product shelf life, and ensure product safety. [0003] At present, there are many kinds of preservatives used in food, medicine and cosmetics. Most of them are chemical preservatives. There are dozens of commonly used ones, including acid preservatives (benzoic acid) and ester preservatives (parabens). Wait. However, with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/24C07C303/32A61K31/095A61P31/04A61P31/10A61P31/02
CPCA61P31/02A61P31/04A61P31/10C07C309/24Y02A50/30
Inventor 张兵张炽坚张文云何廷刚胡丽云艾勇张文环伍宇飞屈恋克里斯特勒热夫雷弗兰克吉隆
Owner GUANGDONG HEJI BIOTECH CO LTD