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Salt amino acid of ferulic acid

A technology of amino acid salt and ferulic acid, applied in the field of medicine, can solve problems such as poor stability of sodium ferulate, and achieve the effects of easy large-scale industrial production, storage convenience, and stable quality

Active Publication Date: 2008-06-11
NANJING YOKO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problem of poor stability of sodium ferulic acid, the inventors have worked through a lot of screening and found that amino acid salts of ferulic acid and hydrates thereof can greatly improve its stability

Method used

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  • Salt amino acid of ferulic acid
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  • Salt amino acid of ferulic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] The preparation of embodiment 1 ferulic acid L-arginine salt

[0079] Put 194g (1mol) of ferulic acid into the reaction flask, add 1000ml of 95% ethanol, 2g of sodium bisulfite, slowly heat up and stir until dissolved, then add 500ml of an aqueous solution containing 174g (1mol) of L-arginine at about 70°C , when the pH of the solution is measured with precision test paper 6.0-7.0, stop adding lye, stir for 10 minutes, add 10 g of activated carbon for decolorization, filter, freeze and crystallize the filtrate for 2 hours, filter, wash the filter cake with absolute ethanol, and dry it in vacuum at 60 ° C to obtain The crude product of ferulic acid L-arginine salt was 348.6g, yield: 94.7%.

[0080] Dissolve the crude product of ferulic acid L-arginine salt in 500ml of deionized water, add 1g of activated carbon, stir and decolorize at 70°C for 15 minutes, filter, freeze the filtrate to 5-10°C, slowly add 1500ml of acetone under stirring, and precipitate A large number...

Embodiment 2

[0084] The preparation of embodiment 2 ferulic acid L-lysine salt

[0085] Refer to Example 1 for specific operation and feeding ratio, replace L-arginine with L-lysine, and the total yield is 78.3%.

[0086] Elemental analysis (molecular formula: C 16 h 24 N 2 o 6 )

[0087] Measured value: C: 54.37%; H: 7.15%; N: 8.19%;

[0088] Theoretical values: C: 54.46%; H: 7.11%; N: 8.23%.

Embodiment 3

[0089] The preparation of embodiment 3 ferulic acid DL-ornithine salt or ferulic acid L-ornithine salt

[0090] The specific operation and feeding ratio refer to Example 1, and the L-arginine is replaced by DL-ornithine or L-ornithine, and the total yield is 74.2%.

[0091] Elemental analysis (molecular formula: C 15 h 22 N 2 o 6 )

[0092] Measured value: C: 55.13%; H: 6.95%; N: 8.49%;

[0093] Theoretical value: C: 55.21%; H: 6.79%; N: 8.58%;

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Abstract

The invention belongs to the medicinal technical field and relates to 4-hydroxy-3-methoxy phenylacrylic acid which is amino acid salt and hydrate of ferulaic acid and a method for preparation and application in the drug for treating cardiovascular and cerebrovascular disease. The experiment proves that the stability of amino acid salt of ferulaic acid and hydrate, especially for argininate, lysinate, ornithinate of ferulaic acid is improved obviously in contrast to sodium ferulate, which is more beneficial to store the drug and improves the security of clinical dosage.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to an amino acid salt of 4-hydroxy-3-methoxyphenylacrylic acid, namely ferulic acid, and a hydrate thereof, a preparation method thereof, and an application in preparation of medicines for treating cardiovascular and cerebrovascular diseases. 2. Background technology [0002] Ferulic acid (that is, 4-hydroxy-3-methoxyphenylacrylic acid), is a kind of phenolic acid ubiquitous in the plant kingdom, rarely exists in free form in plants, and mainly interacts with oligosaccharides, polyamines, lipids and Polysaccharides form a bound state. Ferulic acid is one of the active ingredients of many traditional Chinese medicines such as Ferulicum, Chuanxiong, Angelica, Cimicifuga, Equisetum, etc. It has a variety of pharmacological effects: 1) anti-oxidation and scavenging free radicals; 2) antithrombotic effect; 3) hypolipidemic effect; 4) prevention and treatment of coronary h...

Claims

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Application Information

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IPC IPC(8): C07C59/64C07C279/14C07C229/26C07C257/10C07D233/64A61K31/192A61K31/198A61K31/4172A61K9/00A61P9/00
Inventor 黄振华
Owner NANJING YOKO PHARMA
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