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L-ascorbic acid-6-(10-hydroxyl-2-caproleic acid) esters or derivatives thereof and application of esters or derivatives

A technology of ascorbic acid and decenoic acid, applied in applications, medical preparations containing active ingredients, animal feed, etc., can solve the problems of undisclosed decenoic acid derivatives, unrecorded neurotrophic factor-like effects, etc., and achieve good results Physiological activity, improving immunity, and reducing dosage

Active Publication Date: 2014-12-03
SHIJIAZHUANG KANGNUO BIOTECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent Document 11 does not specifically disclose decenoic acid derivatives, and does not describe neurotrophic factor-like effects

Method used

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  • L-ascorbic acid-6-(10-hydroxyl-2-caproleic acid) esters or derivatives thereof and application of esters or derivatives
  • L-ascorbic acid-6-(10-hydroxyl-2-caproleic acid) esters or derivatives thereof and application of esters or derivatives
  • L-ascorbic acid-6-(10-hydroxyl-2-caproleic acid) esters or derivatives thereof and application of esters or derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Example 1: Synthesis of L-ascorbic acid 6-(10-hydroxy-2-decenoic acid) ester.

[0076] Under nitrogen protection, add 18.62g (0.10mol) of royal jelly acid and 22.91g (0.13mol) of L-ascorbic acid into a four-necked flask, add 300ml of dichloromethane as a solvent, add 13.2g of triethylamine under stirring, and dropwise add chlorinated 15.4 g of sulfoxide, after the reaction was completed, the reaction solution was poured into 250 ml of water, stirred, left to stand, the oil layer was separated, washed three times with 300 ml of water, the solvent was removed, and recrystallized with ethanol to obtain the product.

[0077] The product is a white crystal, and its physical and chemical parameters are as follows:

[0078] MW344.4;

[0079] MS (m / z + ) 344;

[0080] IR (v / cm) 2450~3600 (-OH), 1655 (-CH=CH-conjugated double bond), 1702 (C=O), 1673 (C=O, inside the ring);

[0081] 1H NMR (CDCl 3 , ppm) : 1.20~1.75 (br, 10H, -CH 2 -×5), 2.21(q,2H,-CH 2-), 3.45(O-C-H, 2H)...

Embodiment 2

[0082] Example 2: Synthesis of L-ascorbic acid-6-(10-acetoxy-2-decenoic acid) ester.

[0083] Acetylate 10-hydroxy-2-decenoic acid by known methods to obtain 10-acetoxy-2-decenoic acid; 22.83g (0.10mol) of 10-acetoxy-2-decenoic acid, L- Add 22.91g (0.13mol) of ascorbic acid into a four-necked flask, add 300ml of solvent dichloromethane, stir under nitrogen protection, add 13.2g of triethylamine, dropwise add 15.4g of thionyl chloride, after the reaction is complete, pour the reaction solution into In 250ml of water, stir and stand still, separate the oil layer, wash three times with 300ml of water, remove the solvent, and recrystallize with ethanol to obtain the product. The purity of the product measured by HPLC (high performance liquid chromatography) is 98.5%.

[0084] L-Ascorbic acid-6-(10-acetoxy-2-decenoic acid) ester is a white crystal, and its physical and chemical parameters are as follows:

[0085] MW386.39;

[0086] MS (m / z+) 385;

[0087] IR (v / cm) 2450~3600 (-O...

Embodiment 3

[0089] Example 3: Synthesis of other derivatives of L-ascorbic acid 6-(10-hydroxy-2-decenoic acid) ester.

[0090] Derivatives can be synthesized by first adding designated substituents to L-ascorbic acid or / and 10-hydroxy-2-decenoic acid through substitution reaction, and then esterifying the substituted product into a product, or by first synthesizing L-ascorbic acid 6-(10-hydroxy-2-decenoic acid) ester, and then add a designated substituent to it through a substitution reaction, wherein the substitution and esterification can use well-known methods in the art, such as the substituent is acetyl When the base is used, acetylation can be obtained by reacting acetic anhydride, acetyl halide + tertiary amine, etc. with L-ascorbic acid-6-(10-hydroxy-2-decenoic acid) ester, and the product can be purified by chromatography, recrystallization, etc. It can be realized by known methods, and the confirmation of the compound can also be realized by measuring the parameters listed above...

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PUM

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Abstract

The invention discloses novel compounds and application thereof, or acceptable salts or solvates of the compounds in foods, medicines, veterinary drugs, animal feeds and daily chemicals and relates to the technical field of heterocyclic compounds. The compounds refer to L-ascorbic acid-6-(10-hydroxyl-2-caproleic acid) esters or derivatives thereof. The chemical general formula of the L-ascorbic acid-6-(10-hydroxyl-2-caproleic acid) esters or derivatives is as shown in the specification, wherein R refers to H or C2-20 aliphatic acyl, and R1, R2 and R3 respectively refer to H or C2-10 aliphatic acyl. The compounds can be applied to the fields of medicines, foods, health foods, daily chemicals, veterinary drugs or animal feeds, are simple in preparation method, low in cost, stable in structure and obvious in effect and have good application prospects.

Description

technical field [0001] The present invention relates to the technical field of heterocyclic compounds. Background technique [0002] Both L-ascorbic acid and royal jelly acid are substances with strong biological activity. They have good medical and health effects on living organisms, and are often used in medicine or health food. [0003] The structural formula of L-ascorbic acid is shown in I [0004] [0005] I, [0006] It has the functions of promoting collagen synthesis, promoting the synthesis of neurotransmitters (5-hydroxytryptamine and norepinephrine), promoting the hydroxylation of steroids, promoting the hydroxylation and detoxification of organic substances or poisons, promoting the formation of antibodies, promoting the absorption of iron, and promoting the formation of tetrahydrofolate, Maintain the activity of sulfhydrylase and other functions. In addition, it also has the functions of detoxification, cancer prevention and free radical scavenging. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/62A61K31/365A61P25/28A61P25/16A61P25/14A61P25/00A61P3/10A61P1/16A61P19/10A61P37/02A61P17/16A61P27/02A61P25/24A61P25/18A23L1/29A23L2/52A61K8/49A61Q5/02A61Q5/12A61Q19/10A61Q19/00A61Q19/08A61Q11/00A61Q7/00A23K1/16A23L33/00
CPCA23K20/00A23L33/10A23V2002/00C07D307/62A23V2250/616A23V2250/708A23V2200/30A23V2250/636A23V2200/318A23V2250/16A23V2250/161
Inventor 赵玮璇赵瑞林王占喜王海芳赵银龙武红卫张良才
Owner SHIJIAZHUANG KANGNUO BIOTECH
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