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L-ascorbic acid-6-(E-2-caproleic acid)ester or derivatives thereof and application thereof

A technology of ascorbic acid and decenoic acid, which is applied in the field of heterocyclic compounds, can solve the problems of undocumented neurotrophic factor-like effects and undisclosed decenoic acid derivatives, etc., achieve excellent activity in promoting adenoblast proliferation and increase bioavailability , the effect of increasing stability

Active Publication Date: 2015-01-07
SHIJIAZHUANG KANGNUO BIOTECH
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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-(E-2-caproleic acid)ester or derivatives thereof and application thereof
  • L-ascorbic acid-6-(E-2-caproleic acid)ester or derivatives thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1: Synthesis of L-ascorbic acid-6-(E-2-decenoic acid) ester.

[0075] Add E-2-decenoic acid (17.25g, 0.10mol) and L-ascorbic acid (22.91g, 0.13mol) into a four-necked flask, add 300ml of dichloromethane as a solvent, add 13.2g of triethylamine under stirring, and add chlorine Sulfoxide 15.4g. After the reaction was completed, the reaction solution was poured into 250ml of water, stirred and left to stand, the oil layer was separated, washed with 100ml×3 water, the solvent was removed, and recrystallized with ethanol to obtain white crystals.

[0076] The physical and chemical parameters of the product are:

[0077] MW328.36;

[0078] MS (m / z+) 328;

[0079] IR (v / cm) 2450~3600 (-OH), 1657 (-CH=CH-conjugated double bond), 1700 (C=O), 1675 (C=O, in the ring).

[0080] 1H NMR (CDCl3, ppm): 1.01(CH3, 3H), 1.20~1.75(br, 10H, -CH2-×5), 2.21(q, 2H, -CH2-), 3.73(O-C-H, 1H), 5.79( d, 1H, =CH-), 7.04 (dt, 1H, -CH=), 8.31 (=C-OH, 1H).

Embodiment 2

[0081] Example 2: Synthesis of 2,3,5-triacetyl L-ascorbic acid-6-(E-2-decenoic acid) ester.

[0082] Add 3.28g (0.01mol) of L-ascorbic acid (2-decenoic acid) ester into a four-necked flask, add 100ml of dichloromethane as a solvent, add 3.8g (0.036mol) of acetic anhydride dropwise under nitrogen protection under stirring, and the reaction is completed. The reaction solution was poured into 250ml of water, stirred and left to stand, the oil layer was separated, washed three times with 300ml of water, 100ml each time, the solvent was removed, and recrystallized with ethyl acetate to obtain 3.75g of the product, HPLC (high performance liquid chromatography) The measured content is 98.5%, and the yield is 81.2%w.

[0083] 2. The pure product of 3, 5-triacetyl L-ascorbic acid-6-(E-2-decenoic acid) ester is a white crystal, and its physical and chemical parameters are as follows:

[0084] MW454.47;

[0085] MS (m / z+) 454;

[0086] IR (v / cm) 1656 (-CH=CH-conjugated double bond), 1...

Embodiment 3

[0088] Example 3: Synthesis of L-ascorbic acid-6-(E-2-decenoic acid) ester derivatives.

[0089] As in Example 2, the synthesis of derivatives can all use known methods in the art, such as when the substituent is propionyl, propionylation can use propionic anhydride, propionyl halide + tertiary amine, etc. and L-ascorbic acid-6-( E-2-decenoic acid) ester is obtained by reaction, and the purification of the product can be realized by known methods such as chromatography and recrystallization, and the confirmation of the compound can also be determined by known methods.

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Abstract

The invention discloses new compounds and application thereof. The compounds are L-ascorbic acid-6-(E-2-caproleic acid)ester or derivatives thereof, or acceptable salts or solvates thereof in food, pharmacy, veterinary medicine, animal feed, daily chemicals, relating to the technical field of heterocyclic compounds. The chemical general formula of the L-ascorbic acid-6-(E-2-caproleic acid)ester or derivatives thereof is disclosed in the specification, wherein R1-3 are H or C2-20 aliphatic acyl groups. The compounds are applicable to the fields of pharmacy, food, health food, daily chemicals, veterinary medicine, animal feed and the like. The compounds have the advantages of simple preparation method, low cost, stable structure and obvious effect, and have favorable 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 [0004] [0005] I, [0006] L-ascorbic acid can promote collagen synthesis, promote neurotransmitter (5-hydroxytryptamine and norepinephrine) synthesis, promote steroid hydroxylation, promote organic matter or poison hydroxylation detoxification, promote antibody formation, promote iron absorption, and promote tetrahydrofolate Forming and maintaining the activity of sulfhydryl enzymes, etc. In addition, it also has the functions of detoxification, cancer prevention and free radical scavenging. [0007] E-2-decenoic acid is an organic acid isolated from royal jelly, its molecular formula ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/62A61K31/365A61P25/28A61P25/16A61P21/00A61P25/14A61P25/00A61P27/06A61P25/24A61P25/22A61P25/18A61P1/16A61P19/08A61K8/49A61Q19/10A61Q5/02A61Q5/12A61Q19/00A23L1/29A23L33/00
CPCA23V2002/00A61K8/4973A61Q5/02A61Q5/12A61Q19/00A61Q19/10C07D307/62A23V2250/616A23V2250/708A23V2200/30A23V2200/334A23V2250/02A23V2200/31
Inventor 赵瑞林赵玮璇王占喜周晓雅李彦芬朱智甲武红卫赵银龙张良才
Owner SHIJIAZHUANG KANGNUO BIOTECH
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