Preparation method of magnolia bark phenol derivative

A technology of magnolol and its derivatives, which is applied in the field of preparation of magnolol derivatives, can solve the problems such as synthesis research rarely reported, and achieve the effects of enhanced oil solubility, good symmetry, and strong antioxidant activity

Inactive Publication Date: 2007-04-18
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, a series of compounds have been synthesized using honokiol as the precursor, but there are few reports on the synthesis of honokiol as the lead compound
Isomagnanolol is also one of the active ingredients of Magnolia officinalis, and there is no report on its synthesis and antioxidant activity.

Method used

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  • Preparation method of magnolia bark phenol derivative
  • Preparation method of magnolia bark phenol derivative
  • Preparation method of magnolia bark phenol derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0026] 5,5'-dipropenyl biphenol is generated by isomerization reaction with magnolol.

[0027] First, add 0.15 mol of potassium hydroxide and 0.15 mol of glycerin into a 100ml two-necked flask. One of the two-necked flasks is connected to a spherical condenser tube, and the other is connected to a nitrogen tube. The flask is placed on a constant temperature magnetic stirrer, and the heating switch and stirring switch are turned on. Heating and stirring are carried out so that all potassium hydroxide is dissolved in glycerin, and nitrogen protection is introduced at the same time. Continue to heat up to 140°C, add 0.01mol of magnolol ground into powder, then raise the oil bath temperature to 190°C for reaction, the reaction time is 2 to 3 hours; after the reaction, the reaction product is cooled to room temperature, and Adjust the pH to about 2-3 with 20% sulfuric acid, add an appropriate amount of distilled water, and stir to make it uniform; extract the above mixture with eth...

Embodiment 2

[0029] Preparation of 3,3'-diallyl-5,5'-dipropenyl biphenol, the first step of the reaction is the Williamson reaction of 5,5'-dipropenyl biphenol and allyl bromide Synthesis of allyl ether; in the second step, Claisen rearrangement of allyl ether can generate 3,3'-diallyl-5,5;--dipropenyl biphenol.

[0030] Add 30ml of acetone, 0.01mol of magnolol and 0.02mol of anhydrous potassium carbonate into a 100ml single-necked flask, then add 0.026mol of allyl bromide into the flask (ice bath), connect the flask to a spherical condenser, and place the flask under a constant temperature magnetic force On the stirrer, turn on the heating switch and the stirring switch, carry out heating and stirring, and finish the reaction at 65° C. for 6 hours. The product was filtered to remove K 2 CO, concentrated by distillation, and applied to a silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain a pale yellow oil. Transfer it to a 50mo two-necked flask. One of the...

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Abstract

The present invention relates to two magnolol derivatives and their preparation methods. In the concrete, one is compound 5,5'-dipropenyl diphenyl diphenol and its preparation method, said preparation method is characterized by making magnolol undergo the process of isomerization reaction to obtain said compound; and another derivative is compound 3,3'diallyl-5,5'-dipropenyl diphenyl diphenol and its preparation method, said method is characterized by including the following steps: making 5,5-dipropenyl diphenyl diphenol and allyl bromide undergo the process of Williamson reaction to synthesize allyl ether, then making Claisen rearrangement so as to obtain said derivative.

Description

technical field [0001] The present invention relates to the preparation method of two kinds of magnolol derivatives, more specifically, relate to magnolol derivatives 5,5'-dipropenyl diphenol and 3,3'-diallyl-5, The invention discloses 5'-dipropenyl biphenol and a preparation method thereof, which belong to the technical field of chemical manufacturing. Background technique [0002] Antioxidants are widely used in the fields of food, medicine, health care and cosmetics. From the perspective of the overall development trend of antioxidants, the development of low-toxicity, high-efficiency, and cheap food antioxidants with complex molecular structures and large molecular weights is still an important direction for the development of the food industry. Due to the advantages of natural antioxidants, especially plant-derived antioxidants, which have a wide range of sources, high extraction rate, strong antioxidant activity, strong affinity with the body, and high safety, they ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/00C07C37/18A61K31/05A61P39/06
Inventor 翁新楚李加晓李嘉燚王沂
Owner SHANGHAI UNIV
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