Method for synthesizing and purifying fat-soluble rosmarinic acid

A technology of rosmarinic acid ester and rosmarinic acid, which is applied in the field of organic acid ester production in the organic chemical industry, can solve problems such as limited application range, and achieve expanded application range, strong oxidation resistance, and good fat solubility Effect

Active Publication Date: 2011-06-01
JINAN JIUZHOU FUDE FLAVOR
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, because the solubility of rosmarinic acid is limited to polar solvents such as water, slightly soluble in absolute ethanol, and almost insoluble in oils and fats, the scope of application is limited.

Method used

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  • Method for synthesizing and purifying fat-soluble rosmarinic acid
  • Method for synthesizing and purifying fat-soluble rosmarinic acid
  • Method for synthesizing and purifying fat-soluble rosmarinic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Such as figure 1 As shown, in the present embodiment, 1Kg rosmarinic acid is added to a 200L reactor (equipped with a reflux device), and 100L of 1,4-dioxane, 0.5Kg of p-toluenesulfonic acid, 766g of dodecanol are added ,500 g Molecular sieves are heated to the boiling point of 1,4-dioxane, and the 1,4-dioxane is slowly refluxed, and the reaction time is 30 hours.

[0020] After the reaction, remove the molecular sieve through a filter, collect the filtrate in a 200L concentration tank 1, concentrate in vacuo at 53°C and recover the solvent 1,4-dioxane until no liquid flows out; then slowly add 100L of acetic acid to the concentration tank Dissolve the ethyl ester, and wash the organic phase with 30L of deionized water, and separate the water phase and the ethyl acetate phase with a disc separator; the water phase is decontaminated, and the ethyl acetate phase is transferred to the 200L mixing tank 1, and 30L is added to the mixing tank 1 Wash with deionized water; s...

Embodiment 2

[0023] Such as figure 1 As shown, in the present embodiment, 1Kg rosmarinic acid is added to a 200L reactor (equipped with a reflux device), and 100L of 1,4-dioxane, 0.5Kg of p-toluenesulfonic acid, and 883g of tetradecyl alcohol are added ,500 g Molecular sieves are heated to the boiling point of 1,4-dioxane, and the 1,4-dioxane is slowly refluxed, and the reaction time is 36 hours.

[0024] After the reaction, remove the molecular sieve through a filter, collect the filtrate in a 200L concentration tank 1, concentrate in vacuo at 53°C and recover the solvent 1,4-dioxane until no liquid flows out; then slowly add 100L of acetic acid to the concentration tank Dissolve the ethyl ester, and wash the organic phase with 30L of deionized water, and separate the water phase and the ethyl acetate phase with a disc separator; the water phase is decontaminated, and the ethyl acetate phase is transferred to the 200L mixing tank 1, and 30L is added to the mixing tank 1 Wash with deion...

Embodiment 3

[0027] Add 1Kg rosmarinic acid to a 200L reactor (equipped with a reflux device), and add 100L of 1,4-dioxane, 0.6Kg of p-toluenesulfonic acid, 906g of cetyl alcohol, 600g Molecular sieves are heated to the boiling point of 1,4-dioxane, and the 1,4-dioxane is slowly refluxed, and the reaction time is 38 hours.

[0028] After the reaction is over, remove the molecular sieves through a filter, collect the filtrate in a 200L concentration tank 1, concentrate in vacuo at 55°C and recycle the solvent 1,4-dioxane until no liquid flows out; then slowly add 120L of tris Methyl chloride was dissolved, and the organic phase was washed with 35L of deionized water, and the water phase and the chloroform phase were separated with a disc separator; the water phase was decontaminated, and the chloroform phase was transferred to the 200L mixing tank 1, and 35L was added to the mixing tank 1 Wash with deionized water; separate the water phase and the chloroform phase with a disc separator aga...

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Abstract

The invention discloses a method for synthesizing and purifying a fat-soluble rosmarinic acid, which comprises the following steps of: performing esterification reaction on a rosmarinic acid and high-grade monohydric alcohol for 30 to 40 hours by taking 1,4-dioxane as a solvent, taking a p-toluenesulfonic acid as a catalyst and taking a molecular sieve as a water absorbent; and after the reactionis finished, performing purification to prepare the fat-soluble rosmarinic acid product with the purity of over 95 percent. The rosmarinic acid and the high-grade monohydric alcohol undergo the esterification reaction and hydrophobic structural groups are introduced onto the rosmarinic acid structure, so the method keeps high oxidation resistance, endows the fat-soluble rosmarinic acid with high fat solubility, greatly expands the application range of the product, and can be widely applied to the industries of medicine, food fat, meat product processing, cosmetics, other fatty food and the like.

Description

technical field [0001] The invention relates to a method for synthesizing and purifying fat-soluble rosmarinic acid ester through esterification reaction between rosmarinic acid and higher monohydric alcohol, and belongs to the technical field of organic acid ester production in the organic chemical industry. Background technique [0002] Rosmarinic acid (RosA) is a natural multifunctional phenolic acid compound with certain physiological activities. It was first discovered by Ellis from the plant rosemary (Rosmarnus officinalis L), hence the name. Rosmarinic acid is a dimeric derivative of caffeic acid, the molecular formula is: C 18 h 16 o 8 , molecular weight: 360.33, its chemical name is [R(t)]2-[[3-(3,4-dihydroxyphenylpropionic acid)-1-oxo-2-propenyl]oxy]-3,4 -Dihydroxyphenylpropionic acid. Rosmarinic acid has obvious anti-inflammatory, anti-oxidative, anti-thrombotic and fibrinolytic activities, and is an ideal raw material for the development of functional foods s...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/08
Inventor 郑小嘎兰文忠赵昌政李继峰王迎新王峰韦绪伦王爱春渊辛华
Owner JINAN JIUZHOU FUDE FLAVOR
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