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Novel ferulic acid derivative, its application and synthetic method

A synthetic method, the technology of ethyl ferulate, applied in the direction of chemical instruments and methods, drug combinations, medical preparations containing active ingredients, etc., can solve the problem of inability to solve stability, affect the therapeutic effect of the product, and attenuate the antioxidant capacity and other problems, to achieve the effect of strong expansion of blood vessels, strong antioxidant capacity, and strong anticoagulant effect

Active Publication Date: 2012-06-27
李志强
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  • Abstract
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Problems solved by technology

This not only seriously affects the therapeutic effect of the product, but also produces new impurities, which may cause new adverse reactions
[0007] At present, ferulic acid derivatives, including sodium ferulate, piperazine ferulate, and ethyl ferulate, cannot solve their stability problems. In actual production, transportation, storage, especially in high temperature environments, their antioxidant capacity Decay faster

Method used

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  • Novel ferulic acid derivative, its application and synthetic method
  • Novel ferulic acid derivative, its application and synthetic method
  • Novel ferulic acid derivative, its application and synthetic method

Examples

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Embodiment Construction

[0028] Implementation example one:

[0029] Synthetic method of ethyl acetyl ferulate

[0030] Put 10~20g of ethyl ferulate and 30~100ml of tetrahydrofuran in a reaction vessel, stir, add 8~20g of anhydrous sodium carbonate after completely dissolving, and weigh 5~15g of acetic anhydride in a funnel, add slowly in a normal temperature water bath Acetic anhydride, stirred, heated up to 30~55°C and reacted for 0.5~2 hours, added 30~100ml of purified water, stirred, collected the organic layer, filtered the solid with suction and dried to obtain ethyl acetyl ferulate. Its synthetic reaction formula is as follows:

[0031] C 12 h 15 o 4 (Ethyl ferulate) + C 4 h 6 o 3 (Acetic anhydride) → C 2 h 4 o 2 (Acetic acid) +C 14 h 17 o 5 (Ethyl Acetyl Ferulate)

[0032] CH 3 COOH (acetic acid) + Na 2 CO 3 (sodium carbonate) → NaHCO 3 (sodium bicarbonate) + CH 3 COONa (sodium acetate)

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Abstract

The invention discloses a synthetic method of a ferulic acid derivative, which comprises the steps of adding 10-20 g of ferulic acid ethyl ester and 30-100 ml of tetrahydrofuran into a reaction vessel; stirring to completely dissolve the ferulic acid ethyl ester in the tetrahydrofuran; adding 8-20 g of anhydrous sodium carbonate in the above mixture; adding 5-15 g of acetic anhydride in a hopper; slowly adding acetic anhydride in a normal-temperature water bath; stirring and heating the mixture at 30-55 DEG for 5 to 2 hours; adding 30-100 ml of purified water; stirring the mixture and collecting the organic horizon; leaching and drying the solid compound to obtain acetyl ferulic acid ethyl ester as shown in the formula (I), wherein R1 and R2 are respectively C1-10 alkyl. According to the compound as shown in the formula (I), ferulic acid molecule is used as the base. By modification or reconstruction of the side-chain structure of the ferulic acid molecule, stability of ferulic acid is raised, and its pharmacological effects are substantially enhanced.

Description

technical field [0001] The invention belongs to the technical field of medicines, and relates to a new ferulic acid derivative having the same skeleton structure as ferulic acid, its use and a synthesis method. Background technique [0002] The chemical name of Ferulic Acid is 4-hydroxy 3-methoxycinnamic acid (see Figure 1), which is one of the derivatives of cinnamic acid (also known as cinnamic acid, 3-phenyl 2-acrylic acid). Ferulic acid is a non-peptide endothelin receptor antagonist that relaxes vascular smooth muscle, resists platelet aggregation, inhibits platelet 5-hydroxytryptamine release, and inhibits platelet thromboxane A 2 (TXA 2 ), enhance the activity of prostaglandins, analgesia, and relieve vasospasm. It is the basic raw material for the production of medicines for the treatment of cardiovascular and cerebrovascular diseases, kidney diseases and leukopenia. Such as Xinxuekang, Limai Capsules, Taitai Oral Liquid, etc., it can also play a role in bodybuild...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/734C07C67/08A61K31/222A61P9/10A61P3/10A61P13/12
Inventor 唐楷熊传捷
Owner 李志强
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