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Synthesis method of (-)-chicoric acid

A synthesis method and technology of cichoric acid, applied in the synthesis field of cichoric acid, can solve the problems of heavy metal residues, influence on the quality of medicines, and high prices, and achieve the effect of reducing manufacturing costs

Inactive Publication Date: 2013-01-23
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In this method, dibenzyl caffeic acid needs to be synthesized from caffeic acid through three steps. In the route, heavy metal salt palladium acetate is used. The price of palladium acetate is high, which increases the production cost. The use of palladium catalyst in the last step will cause heavy metal residues in the final product. , affecting the quality of medicines, and the double bond is reduced by-products in the debenzylation reaction

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The specific steps of this embodiment are as follows:

[0030] (1) Preparation of (-)-tetraacetylcichoric acid: first mix (22.0g, 84mmol) diacetylcaffeic acid (the product obtained in the reference example) and (6.0g, 40mmol) (L)-tartaric acid, add 190ml Toluene, stir, add 16ml (0.22mol) SOCl dropwise at 85°C 2 Mix the solution with 50ml of toluene, react at this temperature for 1 hour after dripping, and then reflux for 5 hours; remove the solvent under reduced pressure, dissolve the residue in 200ml of acetone, decolorize the activated carbon, remove the activated carbon by filtration, remove the acetone from the filtrate under reduced pressure, and obtain The solid was washed with 2000ml of water, dried in vacuo to constant weight to obtain the crude product; 0.6g (-)-tartaric acid was recovered from the aqueous solution, and the crude product was recrystallized with acetone / petroleum ether (volume ratio 5:3) to obtain 13.7g of white powder, which was collected Rate...

Embodiment 2

[0033] The specific steps of this embodiment are as follows:

[0034] (1) Preparation of (-)-tetraacetylcichoric acid: first mix (2.20g, 8.4mmol) diacetylcaffeic acid and (0.60g, 4.0mmol) (L)-tartaric acid, add 20ml xylene, stir , add 1.6 ml (22 mmol) SOCl dropwise at 85 °C 2 Mix the solution with 5ml of xylene, react at this temperature for 1 hour after dripping, and then reflux for 5 hours; remove the solvent under reduced pressure, dissolve the residue with 20ml of acetone, decolorize the activated carbon, remove the activated carbon by filtration, and remove the acetone from the filtrate under reduced pressure. The obtained solid was washed with 200ml of water, and vacuum-dried to constant weight to obtain a crude product; the crude product was recrystallized with acetone / petroleum ether (volume ratio 5:3) to obtain 1.0 g of white powder, yield: 38.9%, m.p.189.5-192.5°C; 1 H NMR and (-)-tetraacetylcichoric acid in embodiment 1 1 H NMR agrees.

[0035](2) Preparation of ...

Embodiment 3

[0037] The specific steps of this embodiment are as follows:

[0038] (1) Preparation of (-)-tetraacetylcichoric acid: first mix (2.2g, 8.4mmol) diacetylcaffeic acid and (0.6g, 4.0mmol) (L)-tartaric acid, add 20ml of toluene, stir, Add 2.1ml of oxalyl chloride (about 22mmol) and 5ml of toluene dropwise at 65°C, react at this temperature for 1 hour after dropping, and then reflux for 5 hours; remove the solvent under reduced pressure, dissolve the residue with 20ml of acetone, activate carbon Decolorize, remove activated carbon by filtration, remove acetone from the filtrate under reduced pressure, wash the obtained solid with 200ml of water, and dry it in vacuum to constant weight to obtain the crude product; the crude product is recrystallized with acetone / petroleum ether (volume ratio 5:3) to obtain 1.08g of white powder, Yield: 42.5%, m.p. 189.0-192.5°C. 1 H NMR and (-)-tetraacetylcichoric acid in embodiment 1 1 H NMR agrees.

[0039] (2) Preparation of (-)-cichoric acid...

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Abstract

The invention relates to a synthesis method of (-)-chicoric acid, which comprises the following steps: reacting diacetylcaffeic acid with (L)-tartaric acid in the presence of thionyl chloride or oxalyl chloride to obtain (-)-tetraacetylchicoric acid; or reacting diacetylcaffeic acid with thionyl chloride to obtain diacetyl caffeic acyl chloride, and reacting with (L)-tartaric acid to obtain the (-)-tetraacetylchicoric acid; and finally, removing acetyl group in the (-)-tetraacetylchicoric acid in a mixed solution of an acid solution and a water-soluble organic solvent, thereby obtaining the (-)-chicoric acid. By removing the steps of tartaric acid carboxyl protection and deprotection, the invention has the advantage of simple synthesis technique, and is economical and practical.

Description

technical field [0001] The invention relates to a method for synthesizing (-)-cichoric acid. Background technique [0002] (-)-cichoric acid is a derivative of caffeic acid, chemical name: 2-O,3-O-bis[3-(3,4-dihydroxyphenyl)acryloyl]-tartaric acid , its structural formula is as follows: . [0003] Pharmacological studies have shown that (-)-cichoric acid has immune-enhancing and anti-inflammatory effects, and can inhibit hyaluronidase, protect collagen from free radicals that can lead to degradation, and also inhibit HIV-1 and HIV- 1 The role of integrase, therefore, (-)-cichoric acid has received more and more international attention as an immunostimulator and immunomodulator. At present, the source of (-)-cichoric acid is mainly extracted from plants such as Echinacea purpurea, which is very expensive. In order to break the pattern of high prices of cichoric acid, it is of great significance to develop a low-cost artificial synthesis method. [0004] At present, the s...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/31C07C67/08C07C67/14
CPCY02P20/55
Inventor 徐广宇周希杰陈波
Owner HUNAN NORMAL UNIVERSITY
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