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β-hinokitiol ester or salt and its application in the preparation of animal feed additives

A technology for hinokitiol ester and animal feed, which is applied in the directions of animal feed, animal feed, application, etc., can solve the problems of undisclosed salt structure, light instability, unexplained complexes, etc., and achieves good application prospects and strong growth. The effect of promoting performance and high safety

Active Publication Date: 2015-12-09
GUANGZHOU INSIGHER BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Chinese patent CN101396021A (publication number) describes the activity of hinokitiol and its metal salts against plant pathogenic microorganisms, but does not specifically disclose the structure of the salt, whether it includes complexes is not specified
[0006] However, β-hinokitiol has thermal instability and light instability

Method used

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  • β-hinokitiol ester or salt and its application in the preparation of animal feed additives
  • β-hinokitiol ester or salt and its application in the preparation of animal feed additives
  • β-hinokitiol ester or salt and its application in the preparation of animal feed additives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Structural formula:

[0024]

[0025] Preparation of 3-isopropyl-1,3,5-cycloheptatrien-7-one-ethyl ester

[0026] making process:

[0027] 2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one (1.64g, 10mmol, 1eq) and triethylamine (1~10eq) were dissolved in 100ml of dichloromethane,- 10℃~25℃, take acetyl chloride (0.8~5eq) and dissolve it in about 10ml of dichloromethane, slowly add it dropwise to the mixed solution, then keep stirring for 3~8 hours, TLC (developing agent petroleum ether: ethyl acetate Esters=5:1) shows that the basic reaction of the raw materials is complete, and new spots are generated. About 100ml of water was added to extract the layers, and the organic phase was washed with water once more. The solvent was removed by rotary evaporation of the organic phase to obtain a brown-red oil, which was confirmed to be the target product (3-isopropyl-1,3,5-cycloheptatrien-7-one-ethyl ester) by HNMR, with a yield of about 86%. Unstable, ester hydrolysis oc...

Embodiment 2

[0031] Structural formula:

[0032]

[0033] Preparation of 3-isopropyl-1,3,5-cycloheptatrien-7-one-n-decyl ester

[0034] making process:

[0035] 2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one (3.28g, 20mmol, 1eq) and triethylamine (1~10eq) were dissolved in 100ml of dichloromethane,- 10°C~25°C, take n-decanoyl chloride (0.8~5eq) and dissolve it in about 10ml of dichloromethane, slowly add it dropwise to the mixed solution, then keep stirring for 3~8 hours, TLC (developer petroleum ether: acetic acid Ethyl ester=5:1) shows that a small amount of raw materials are not completely reacted, and new spots are generated. Add 100 ml of water to wash, then wash with saturated saline, TLC shows that there is still fluorescence at the origin. Washing with dilute potassium hydroxide aqueous solution, the raw material point is still not fully washed. Add about 8 grams of silica gel, dry-load the sample, and separate on a silica gel column. The eluent is petroleum ether: ethyl ...

Embodiment 3

[0037] Structural formula:

[0038]

[0039] Preparation of 3-isopropyl-1,3,5-cycloheptatrien-7-one-n-octadecyl ester

[0040] making process:

[0041] 2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one (3.28g, 20mmol, 1eq) and triethylamine (1~10eq) were dissolved in 100ml of dichloromethane,- 10℃~25℃, take n-octadecanoyl chloride (0.8~5eq) and dissolve it in about 30ml of dichloromethane, slowly add it dropwise into the mixed solution, then keep stirring for 3~8 hours, TLC (developing agent petroleum ether : Ethyl acetate = 5: 1) shows that a small amount of raw materials are not completely reacted, and new spots are generated. Add 100 ml of water to wash, then wash with saturated saline, TLC shows that there is still fluorescence at the origin. Washing with dilute potassium hydroxide aqueous solution, the raw material point is still not fully washed. Add about 8 grams of silica gel, dry-load the sample, and separate on a silica gel column. The eluent is petroleum ethe...

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PUM

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Abstract

Disclosed are a β-hinokitiol ester or salt and an application thereof in preparing an animal feed additive. The structural formula of the β-hinokitiol ester or salt compound is shown in formula 1 or formula 2. R1 in formula 1 is n-nonyl or n-heptadecyl, and L in formula 2 is sodium, potassium, calcium, magnesium, zinc, copper or manganese. The β-hinokitiol ester and salt compounds shown in formula 1 and formula 2 are less toxic or non-toxic to livestock, have higher safety, higher stability and better growth promotion performance than those of relevant compounds covered in the current patents, and thus are more suitable for use as a growth promoter for feed and have a great application prospect in the farming industry.

Description

Technical field: [0001] The invention belongs to the field of animal feed growth promoters, in particular to beta-hinokitiol ester or salt and its application in the preparation of animal feed additives. Background technique: [0002] β-hinokitiol (β-hinokitiol), also known as hinokitiol, hinoki alcohol, hinoki alcohol (phenol), chemical name: 2-hydroxy-4-isopropyl-1-cycloheptatrienone, is a natural Edible essential oil components have been used as food additives in Japan for many years. [0003] US6387417B1 discloses the activity of β-hinokitiol and its complex (2:1 or 3:1) against vancomycin-resistant enterococcus and its application in treatment. [0004] Chinese patent CN101396021A (publication number) describes the activity of hinokitiol and its metal salts against plant pathogenic microorganisms, but does not specifically disclose the structure of the salt, and it is not specified whether it includes complexes. In addition hinokitiol includes α-, β-, γ-3 isomers, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/24C07C49/717C07C67/14C07C45/61A23K1/16
CPCC07C49/717A23K1/1612C07C69/24C07C2101/18A23K20/111C07C2601/18
Inventor 彭险峰覃宗华李方黄计军叶晓岚李早龙
Owner GUANGZHOU INSIGHER BIOTECHNOLOGY CO LTD
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