Preparation method and application of tyrosol phenolate compound

A technology of tyrosol phenolate and tyrosol phenate, which is applied in the field of preparation of tyrosol phenate compounds, can solve the problems of high reactivity of phenolic acid chloride, low yield of target substance, instability and easy decomposition, etc. Achieve the effects of improving pharmacokinetics, high yield, and reducing production costs

Inactive Publication Date: 2019-01-18
TONGHUA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is that the reactivity of the prepared phenolic acid chloride is too high, unstable and easy to decompose, and the selectivity is poor. It reacts with the phenolic hydroxyl group of tyrosol while reacting with tyrosol, and needs protection and deprotection. (2) take phenolic acid and tyrosol as raw material, utilize dicyclohexylcarbodiimide and 4-dimethylaminopyridine to prepare tyrosol phenolic acid ester, but side reaction is serious, and yield is very low Low

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  • Preparation method and application of tyrosol phenolate compound
  • Preparation method and application of tyrosol phenolate compound
  • Preparation method and application of tyrosol phenolate compound

Examples

Experimental program
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Embodiment 1

[0024] The preparation method of 3,4-dihydroxybenzoic acid-4-hydroxyphenethyl ester is:

[0025] Continuously feed nitrogen into the reactor to protect the reaction, sequentially add 4mmol tyrosol, 4mmol triphenylphosphine and 4mmol 3,4-dihydroxybenzoic acid, then add 10mL tetrahydrofuran, and add 6mmol dihydrofuran dropwise at 0°C. Diisopropyl nitrogen dicarboxylate, remove the ice bath after the dropwise addition, heat up to room temperature and stir for 20 hours to react. After the reaction is completed, seal and evaporate the reaction solution to dryness, dissolve it in 140mL ethyl acetate and wash it with 150mL saturated aqueous sodium bicarbonate solution for 3 times, and then washed 3 times with 150mL saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, desalted by suction filtration, and concentrated to obtain a concentrate; the concentrate was subjected to column chromatography with dichloromethane as a solvent, and 3,4- Dihydroxybenzoic ac...

Embodiment 2

[0027] The preparation method of 3,5-dihydroxybenzoic acid-4-hydroxyphenethyl ester is:

[0028] at N 2 Weigh 4 mmol of tyrosol under protection and put it in a reaction flask, then add 4 mmol of triphenylphosphine, then add 5 mmol of 3,5-dihydroxybenzoic acid, add 10 mL of tetrahydrofuran, add 5 mmol of azodicarboxylate dropwise under stirring at 0°C Isopropyl ester, react at room temperature for 40 hours after the drop, evaporate the reaction solution to dryness after the reaction, add 150mL ethyl acetate to dissolve, wash 3 times with 140mL saturated aqueous sodium bicarbonate solution, wash 3 times with 140mL saturated aqueous sodium chloride solution, anhydrous Dry over sodium sulfate, remove salt by suction filtration, evaporate the solvent under reduced pressure and purify by gel column chromatography to obtain a white solid which is the target compound with a yield of 68%.

Embodiment 3

[0030] The preparation method of 2,3-dihydroxybenzoic acid-4-hydroxyphenethyl ester is:

[0031] Under the protection of nitrogen, add 4mmol tyrosol to the reactor, then add 6mmol triphenylphosphine, 4mmol 2,3-dihydroxybenzoic acid and 12mL tetrahydrofuran in sequence, and add 6mmol diisoazodicarboxylate dropwise at 0°C. Propyl ester, after the dropwise addition, warm up to room temperature, stir and react for 24 hours, evaporate the reaction solution to dryness after the reaction, dissolve the residue with 140mL ethyl acetate, and then use 144mL saturated aqueous sodium bicarbonate solution, 144mL saturated sodium chloride The aqueous solution was washed 4 times respectively, dried with anhydrous sodium sulfate, filtered to remove salt, and concentrated to obtain a concentrate; a mixture prepared with dichloromethane and methanol at a volume ratio of 1:1 was used as a solvent, and the concentrate was subjected to column chromatography , and isolated 2,3-dihydroxybenzoic acid-...

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Abstract

The invention discloses a preparation method and application of a tyrosol phenolate compound, belonging to the technical field of biological medicines. A chemical structure of tyrosol is derived, andphenolic acid is introduced into the structure, so that the structure is greatly different from tyrosol, and a relatively good anti-oxidation effect is achieved. The invention further provides a preparation method of the tyrosol phenolate compound. The preparation method comprises the steps of with tyrosol, triphenyl phosphine and phenolic acid as the raw materials, adding tetrahydrofuran under the protection of nitrogen, dropwise adding diisopropyl azodicarboxylate for reaction under an ice bath condition, and processing by virtue of column chromatography, so as to obtain the tyrosol phenolate compound. The preparation method is simple in operation, phenolic hydroxyl groups of phenolic acid and tyrosol do not need to be protected or deprotected, and a target compound is obtained through one-step reaction, so that the yield is relatively high, and the preparation method is environment-friendly; and tyrosol phenolate disclosed by the invention can be used for resisting oxidation.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a preparation method and application of tyrosol phenate compounds. technical background [0002] Tyrosol, also known as p-hydroxyphenylethanol, is a component widely found in Rhodiola plants, an aglycone of salidroside, and one of the main phenolic compounds contained in olive oil. Because of its antioxidant capacity, it has a variety of pharmacological effects, especially good at scavenging toxic hydroxyl radicals. Tyrosol acts as a neuroprotective agent to antagonize Aβ and inhibit apoptosis of dopaminergic neurons, thereby effectively preventing Alzheimer's disease Meridian disease and Parkinson's disease, tyrosol can effectively prolong life, protect the heart, and prevent the occurrence of tumors. Tyrosol is mild in nature and has almost no toxic and side effects. It has broad application prospects in the fields of medicine and food, and has attracted the attention of r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/84C07C67/08C07C69/92C07C69/732C07C69/734C07D311/66A61P39/06A61P35/00
CPCA61P35/00A61P39/06C07C67/08C07C69/732C07C69/734C07C69/84C07C69/92C07D311/66
Inventor 臧皓沈鹏张露云徐倩郭鑫耿晓宇刘雪坤徐晶夏广清朱俊义
Owner TONGHUA NORMAL UNIV
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