CN104710307A - Hexahydrocolupulone di-aliphatic ester and utilization thereof as animal feed additive - Google Patents
Hexahydrocolupulone di-aliphatic ester and utilization thereof as animal feed additive Download PDFInfo
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- CN104710307A CN104710307A CN201510085473.0A CN201510085473A CN104710307A CN 104710307 A CN104710307 A CN 104710307A CN 201510085473 A CN201510085473 A CN 201510085473A CN 104710307 A CN104710307 A CN 104710307A
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- hydrogen
- sour
- acid ester
- acid
- hexahydrocolupulone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/16—Acetic acid esters of dihydroxylic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
Abstract
The invention discloses hexahydrocolupulone di-aliphatic ester and utilization thereof as an animal feed additive. The hexahydrocolupulone di-aliphatic ester has the structural formula 1 shown in the description, wherein R1 is isopropyl, isobutyl or 2-butyl and R2 is any alkyl of methyl-heptadecyl. The Hexahydrocolupulone di-aliphatic ester is low-toxic or nontoxic to livestock, is suitable for serving as a growth promoter for feeds and has a very good application prospect in the breeding industry.
Description
Technical field:
The invention belongs to animal and fowl fodder field, be specifically related to six hydrogen β-sour double acid ester and the application as animal feedstuff additive thereof.
Background technology:
Although a series of US Patent No. 8197863B2, US8012516B2, US20080213342A1, US20060269588, US20040219240, US7090873, US20060134248, US8012516, US20110311663, US7553504, US20130018106, US6251461 etc. and a series of European patent EP 2606742A1, EP1542543A1, EP2429311A2, EP1722635A2 etc. all describe the application of hop acid (Hops acids) and hydrogenated beta-acid compounds feeding antibiotic quasi-growth promoter as an alternative.
But, first described by these patents is all that the extract (alpha-acid and β-acid mixture etc.) applying hops plant or hop acid is applied as fodder additives, and these hop extraction things (mixture) are in fact in Chinese fodder additives kind catalogue, just as food fragrance applications; Secondly, these patent institute foundations be in vitro tests result and In vitro digestion trial etc. substantially, Animal experiment result is little; Again, the security of these natural products and their ester etc. and stability, do not have data support meeting to apply in required requirement as animal feedstuff additive.
Summary of the invention:
First object of the present invention be to provide have high stability, growth of animals or poultry can be promoted, be more suitable for the six hydrogen β-sour double acid ester as fodder additives application.
Six hydrogen β-sour double acid ester of the present invention, its structural formula as shown in Equation 1:
R
1=sec.-propyl, isobutyl-or 2-butyl; R
2any one alkyl in=methyl-heptadecyl.
Preferably, described R
2=nonyl, undecyl or heptadecyl.
Above-mentioned six hydrogen β-sour double acid ester is preparing the application in animal feed additive for promoting growth.
Described animal is the pig of each growth phase, chicken, duck, goose, beef cattle, milk cow, sheep, fish, shrimp, fox, the animal such as ermine or racoon dog.
Described promoting animal growth feed is perfect compound feed, and the six hydrogen β-sour double acid ester added as shown in Equation 1 is 0.1 ~ 200ppm of perfect compound feed quality as consumption during animal feed additive for promoting growth.
Six hydrogen β-acid, containing hexahydrolupulon, six hydrogen adlupulones, Hexahydrocolupulone 3 main ingredients, belong to material of the prior art.
Six hydrogen β-sour double acid ester comprises the two stearates of the two ethyl ester of six hydrogen β-acid to 18 carbon.
Six hydrogen β-sour double acid ester as shown in Equation 1 of the present invention, to livestock and poultry low toxicity or nontoxic, possess feeding growth stimulant effect, and stability is high, has extraordinary application prospect in cultivation industry.
Embodiment:
Following examples further illustrate of the present invention, instead of limitation of the present invention.
Embodiment 1: β-acid-extraction
Take hop extract β-acid medicinal extract 1KG in 5L container, add 1L dehydrated alcohol, 90gKOH (being dissolved in 100mL water), stirring at room temperature is even subsequently, adds 3L tap water, stir after 1 hour under stirring, leave standstill 30min, suction filtration, except degrease and insolubles.Collect filtrate, separatory, collect lower floor's aqueous phase.In aqueous phase, CO is passed under stirring
2, separate out a large amount of solid, add the 1.2L 10%KOH aqueous solution.Stirring at room temperature is even, adds 200mL normal hexane, separatory, and removing organic phase and middle oil reservoir, collect aqueous phase.Filtrate regulates with 20% phosphate aqueous solution, and normal hexane (1L) extracts.After organic phase vacuum concentration, obtain the thick product of β-acid and be about 400g (content about 90%).
Embodiment 2 six hydrogen β-sour hydrogenation synthesis technique
Add the thick product of about 360g β-acid in hydriding reactor, add 95% ethanol subsequently to 2.5L, add 36g 10% palladium carbon, open and stir, system displacement nitrogen three times, hydrogen three times, room temperature reaction 12 ~ 15h under 0.6 ~ 0.7MPa pressure, sampling detects.React complete to be extracted out by reaction solution, cross and filter palladium carbon, after filter vacuum concentrates 3/4 solvent, be added dropwise to 3.5L tap water under stirring, stir about 1 ~ 2h, suction filtration, collect solid and obtain six hydrogen β-acid, 50 ° of dried overnight, weigh about 340g.
The synthesis of embodiment 3 six hydrogen β-acid diesters
R
1=sec.-propyl, isobutyl-or 2-butyl; R
2=methyl---any one alkyl in heptadecyl.
The synthesis of embodiment 3.1 6 hydrogen β-sour capric diesters
The six hydrogen β-acid (HPLC 98%) of getting 100g drying drop in the reactor of 2L drying, nitrogen protection.Add 500ml normal heptane, 1gDMAP.Add 137g decanoyl chloride fast, be cooled to 0 degree.Drip 72g triethylamine.Add rear continuation and stir 2h.Point plate, raw material point disappears.Cross and filter triethylamine hydrochloride, decompression desolventizing obtains yellow oil.Column chromatography for separation obtains 88g six hydrogen β-sour capric diesters, yield about 50%.
The synthesis of embodiment 3.2 6 hydrogen β-sour lauric acid diester
The six hydrogen β-acid (HPLC 98%) of getting 100g drying drop in the reactor of 2L drying, nitrogen protection.Add 500ml normal heptane, 1gDMAP.Add 157g lauroyl chloride fast, be cooled to 0 degree.Drip 72g triethylamine.Add rear continuation and stir 2h.Point plate, raw material point disappears.Cross and filter triethylamine hydrochloride, decompression desolventizing obtains yellow oil.Column chromatography for separation obtains 95g six hydrogen β-sour lauric acid diester, yield about 50%.
The synthesis of embodiment 3.3 6 hydrogen β-sour stearic acid diester
The six hydrogen β-acid (HPLC 98%) of getting 100g drying drop in the reactor of 2L drying, nitrogen protection.Add 500ml normal heptane, 1gDMAP.Add 218g stearic fast, be cooled to 0 degree.Drip 72g triethylamine.Add rear continuation and stir 2h.Point plate, raw material point disappears.Cross and filter triethylamine hydrochloride, decompression desolventizing obtains yellow oil.Column chromatography for separation obtains 116g six hydrogen β-sour stearic acid diester, yield about 50%.
Embodiment 4: the different sorts six hydrogen β-effect of sour double acid ester in broiler chicken material
The fast large yellow-feathered broiler of 800 plumage 1 ages in days is divided into 8 treatment group at random by table 1, often organizes 100 plumages, and adds six hydrogen β-sour double acid ester, six hydrogen β-sour mono fatty acid ester or the β-acid of six hydrogen respectively in each group.Trial period, raises in cages, free choice feeding and freely drinking water.Totally 30 days trial period, test-results shows, different types of six hydrogen β-sour double acid ester is all significantly improved to the weightening finish of test chicken and feedstuff-meat ratio aspect, and the effect of six hydrogen β-sour double acid ester is better than the effect (table 1) of the β-acid of same dose six hydrogen or monoesters.
The table 1 different sorts six hydrogen β-effect of sour double acid ester in broiler chicken material
*: dosage is in six hydrogen β-acid.
Embodiment 5: the various dose six hydrogen β-effect of sour lauric acid diester in broiler chicken material
The fast large yellow-feathered broiler of 500 plumage 1 ages in days is divided into 8 treatment group at random by table 2, often organizes 100 plumages, and is often organizing in feed the six hydrogen β-sour lauric acid diester adding various dose respectively.Trial period, raises in cages, free choice feeding and freely drinking water.Totally 30 days trial period, test-results shows, and the six hydrogen β-sour lauric acid diester of various dose is all significantly improved to the weightening finish of test chicken and feedstuff-meat ratio, and in dosage effect (table 2).
The table 2 various dose six hydrogen β-effect of sour lauric acid diester in broiler chicken material
*: dosage is in six hydrogen β-acid.
The embodiment 5 six hydrogen β-effect of sour capric diesters in pig feed
70 ages in days Du that 150 body weight are close greatly enhance ternary lean meat species piggy of mixing and are divided into 5 groups at random, often organize 3 repetitions, each repetition 10 pigs.The six hydrogen β-sour capric diesters adding various dose is often organized in feed by table 3.Trial period free choice feeding and drinking-water.Totally 28 days trial period, result shows that six hydrogen β-sour capric diesters group is all significantly improved (table 3) in the weightening finish and feedstuff-meat ratio of test pig.
The table 3 six hydrogen β-effect of sour capric diesters in pig feed
*: dosage is in six hydrogen β-acid.
The effect of embodiment 6 six hydrogen β-sour capric diesters in meat duck material
900 plumage 1 age in days Cherry Village Duckss are divided into 3 test group at random by table 4, often organize 4 repetitions, each repetition 50 plumage, and add six hydrogen β-sour capric diesters or the β-acid of six hydrogen often organizing in feed respectively.Trial period, raises in cages, free choice feeding and freely drinking water.Totally 28 days trial period.Test-results shows, and six hydrogen β-sour capric diesters group is all significantly increased in the weightening finish and feedstuff-meat ratio of test duck, and effect is better than six hydrogen β-acid (table 4) of same dose.
The effect of table 4 six hydrogen β-sour capric diesters in meat duck material
*: dosage is in six hydrogen β-acid.
Claims (5)
1. six hydrogen β-sour double acid ester, its structural formula as shown in Equation 1:
R
1=sec.-propyl, isobutyl-or 2-butyl; R
2any one alkyl in=methyl-heptadecyl.
2. six hydrogen β-sour double acid ester according to claim 1, is characterized in that, described R
2=nonyl, undecyl or heptadecyl.
3. six hydrogen β-sour double acid ester according to claim 1 is preparing the application in animal feed additive for promoting growth.
4. application according to claim 3, is characterized in that, described animal is the pig of each growth phase, chicken, duck, goose, beef cattle, milk cow, sheep, fish, shrimp, fox, ermine or racoon dog.
5. application according to claim 4, is characterized in that, the six hydrogen β-sour double acid ester described in interpolation is 0.1 ~ 200ppm of feeding quality as consumption during animal feed additive for promoting growth.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510085473.0A CN104710307A (en) | 2015-02-16 | 2015-02-16 | Hexahydrocolupulone di-aliphatic ester and utilization thereof as animal feed additive |
| PCT/CN2015/074464 WO2016131204A1 (en) | 2015-02-16 | 2015-03-18 | Hexahydro beta-acid di-fatty acid ester and application thereof as animal feed additive |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510085473.0A CN104710307A (en) | 2015-02-16 | 2015-02-16 | Hexahydrocolupulone di-aliphatic ester and utilization thereof as animal feed additive |
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| CN104710307A true CN104710307A (en) | 2015-06-17 |
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| CN201510085473.0A Pending CN104710307A (en) | 2015-02-16 | 2015-02-16 | Hexahydrocolupulone di-aliphatic ester and utilization thereof as animal feed additive |
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| WO (1) | WO2016131204A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481893A (en) * | 2015-12-09 | 2016-04-13 | 广州英赛特生物技术有限公司 | Hexahydro beta-acid monophosphate derivative, and applications thereof in preparing animal feed additives |
| WO2020232689A1 (en) * | 2019-05-23 | 2020-11-26 | 广州英赛特生物技术有限公司 | FEED COMPOSITION COMPRISING HEXAHYDRO-β-ACID COMPONENT COMPOUNDS AND APPLICATION THEREOF |
| CN112500289A (en) * | 2020-11-20 | 2021-03-16 | 广州英赛特生物技术有限公司 | Precursor compounds for hexahydro-beta-acid component compounds, feed compositions and uses thereof |
| RU2783761C1 (en) * | 2019-05-23 | 2022-11-17 | Висориг Текнолоджис Пте. Лимитед | FEED COMPOSITION CONTAINING HEXAHYDRO-β-ACID DERIVATIVES AND ITS APPLICATION |
| WO2023280327A1 (en) * | 2021-08-13 | 2023-01-12 | 广州英赛特生物技术有限公司 | Use of cyclohexanetrione derivative in preparation of drug for animals |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102481000A (en) * | 2009-04-21 | 2012-05-30 | J.I.哈斯 | Animal feed compositions and feeding methods |
| CN103739487A (en) * | 2013-12-30 | 2014-04-23 | 广州英赛特生物技术有限公司 | Beta-acid monoester salt and application of Beta-acid monoester serving as animal feed additive |
| CN103980104A (en) * | 2014-02-19 | 2014-08-13 | 广州英赛特生物技术有限公司 | hexahydrocolupulone monoesters, inner complex salts or monoester salts, and application as animal feed additive |
-
2015
- 2015-02-16 CN CN201510085473.0A patent/CN104710307A/en active Pending
- 2015-03-18 WO PCT/CN2015/074464 patent/WO2016131204A1/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102481000A (en) * | 2009-04-21 | 2012-05-30 | J.I.哈斯 | Animal feed compositions and feeding methods |
| CN103739487A (en) * | 2013-12-30 | 2014-04-23 | 广州英赛特生物技术有限公司 | Beta-acid monoester salt and application of Beta-acid monoester serving as animal feed additive |
| CN103980104A (en) * | 2014-02-19 | 2014-08-13 | 广州英赛特生物技术有限公司 | hexahydrocolupulone monoesters, inner complex salts or monoester salts, and application as animal feed additive |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481893A (en) * | 2015-12-09 | 2016-04-13 | 广州英赛特生物技术有限公司 | Hexahydro beta-acid monophosphate derivative, and applications thereof in preparing animal feed additives |
| WO2020232689A1 (en) * | 2019-05-23 | 2020-11-26 | 广州英赛特生物技术有限公司 | FEED COMPOSITION COMPRISING HEXAHYDRO-β-ACID COMPONENT COMPOUNDS AND APPLICATION THEREOF |
| CN112292039A (en) * | 2019-05-23 | 2021-01-29 | 广州英赛特生物技术有限公司 | Feeding composition containing hexahydro-beta-acid component compound and application thereof |
| RU2783761C1 (en) * | 2019-05-23 | 2022-11-17 | Висориг Текнолоджис Пте. Лимитед | FEED COMPOSITION CONTAINING HEXAHYDRO-β-ACID DERIVATIVES AND ITS APPLICATION |
| CN112500289A (en) * | 2020-11-20 | 2021-03-16 | 广州英赛特生物技术有限公司 | Precursor compounds for hexahydro-beta-acid component compounds, feed compositions and uses thereof |
| WO2022022752A1 (en) * | 2020-11-20 | 2022-02-03 | 源至技术有限公司 | Precursor compound of hexahydro-beta-acid component compound, feed composition and use thereof |
| CN112500289B (en) * | 2020-11-20 | 2023-12-26 | 广州英赛特生物技术有限公司 | Precursor compounds for hexahydro-beta-acid component compounds, feed compositions and uses thereof |
| WO2023280327A1 (en) * | 2021-08-13 | 2023-01-12 | 广州英赛特生物技术有限公司 | Use of cyclohexanetrione derivative in preparation of drug for animals |
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| Publication number | Publication date |
|---|---|
| WO2016131204A1 (en) | 2016-08-25 |
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Application publication date: 20150617 |