NO20160468A1 - Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors - Google Patents
Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors Download PDFInfo
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- NO20160468A1 NO20160468A1 NO20160468A NO20160468A NO20160468A1 NO 20160468 A1 NO20160468 A1 NO 20160468A1 NO 20160468 A NO20160468 A NO 20160468A NO 20160468 A NO20160468 A NO 20160468A NO 20160468 A1 NO20160468 A1 NO 20160468A1
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- Prior art keywords
- feed
- birds
- compounds
- phenylcapsaicin
- growth
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical class COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 title abstract description 33
- 241000287828 Gallus gallus Species 0.000 claims description 31
- 241000271566 Aves Species 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 8
- -1 C3-C12cycloalkyl Chemical group 0.000 claims description 6
- 244000144977 poultry Species 0.000 claims description 5
- 235000013594 poultry meat Nutrition 0.000 claims description 5
- 241000272517 Anseriformes Species 0.000 claims description 4
- 241000286209 Phasianidae Species 0.000 claims description 4
- 235000013330 chicken meat Nutrition 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 244000105624 Arachis hypogaea Species 0.000 claims description 2
- 235000007319 Avena orientalis Nutrition 0.000 claims description 2
- 241000209763 Avena sativa Species 0.000 claims description 2
- 235000007558 Avena sp Nutrition 0.000 claims description 2
- 244000062793 Sorghum vulgare Species 0.000 claims description 2
- 241000272534 Struthio camelus Species 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 230000037396 body weight Effects 0.000 claims description 2
- 238000009395 breeding Methods 0.000 claims description 2
- 230000001488 breeding effect Effects 0.000 claims description 2
- 235000005822 corn Nutrition 0.000 claims description 2
- 239000003651 drinking water Substances 0.000 claims description 2
- 235000020188 drinking water Nutrition 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 235000012041 food component Nutrition 0.000 claims description 2
- 239000005417 food ingredient Substances 0.000 claims description 2
- 235000019713 millet Nutrition 0.000 claims description 2
- 235000020232 peanut Nutrition 0.000 claims description 2
- 239000008188 pellet Substances 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- 229960002504 capsaicin Drugs 0.000 description 15
- 235000017663 capsaicin Nutrition 0.000 description 13
- 238000011282 treatment Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000005313 fatty acid group Chemical group 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 231100000159 OECD 404 Acute Dermal Irritation/Corrosion Toxicity 0.000 description 2
- 231100000490 OECD 405 Acute Eye Irritation/Corrosion Toxicity 0.000 description 2
- 206010070835 Skin sensitisation Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 231100000460 acute oral toxicity Toxicity 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 231100000150 mutagenicity / genotoxicity testing Toxicity 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 231100000370 skin sensitisation Toxicity 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 235000002566 Capsicum Nutrition 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 235000002568 Capsicum frutescens Nutrition 0.000 description 1
- 206010064571 Gene mutation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 231100000251 OECD 403 Acute Inhalation Toxicity Toxicity 0.000 description 1
- 231100000442 OECD 406 Skin Sensitisation Toxicity 0.000 description 1
- 231100000322 OECD 423 Acute Oral toxicity - Acute Toxic Class Method Toxicity 0.000 description 1
- 231100000107 OECD 471 Bacterial Reverse Mutation Test Toxicity 0.000 description 1
- 241000288049 Perdix perdix Species 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241001247145 Sebastes goodei Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940100228 acetyl coenzyme a Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000036757 core body temperature Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000037433 frameshift Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- 230000003868 tissue accumulation Effects 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
Abstract
The invention relates to synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors.
Description
Title of Invention
Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors.
Field of the invention and related prior art
The invention relates to synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors in animals and in particular in birds/chickens.
The growth rate of poultry and chickens is of great economic importance and for feeding of the world population. Even a small increase in the growth rate will have a significant influence for farmers and producers.
aXichem is a global supplier of natural-analogue industrial compounds and its mission is to develop, patent and market natural-analogue substances. aXichem is focusing on phenylcapsaicin, an analogue of natural capsaicin and derivatives thereof. Since phenylcapsaicin is synthetically produced, the substance offers a wide range of benefits compared with natural capsaicin, which is extracted from chili peppers and therefore has a varying quality. Synthetic capsaicinoids can be prepared with high purity and in good yields and quantity and at a reasonable cost. Additionally, the available amounts of naturally occurring capsaicin is limited. The standardized natural capsaicin extract contains at least 3 isomers, which all have different chemical properties but which are difficult to differentiate between. It may therefore be difficult to obtain capsaicin extracts which have sufficiently uniform purity and composition for the intended use.
Phenylcapsaicin is not environmentally harmful and is thus a viable alternative with a wide range of applications in a variety of areas. aXichem holds European (EP1670310) and US patents (US7446226) on their synthetic products their synthesis and use as antifouling agent (WO2005025314). These synthetic low toxicity analogs of capsaicin can by synthezised with high purity with a reasonable cost and in high yield. Phenylcapsaicin has proved to be less toxic and far less irritating than natural capsaicin.
Summary of the invention
The invention relates to at least one compounds with the general formula (1)
wherein R is a substituent selected from the group of C1-C18alkyl, trifluoromethyl, C3-C12cycloalkyl, phenyl, phenoxy, phenylthio, halogen; or tautomers or salts thereof, for use as a growth promotor.
The invention also relates to compositions and feed comprising compounds of formula (1) according to claim 1.
Types of feed and birds are found in the claims 7 and 8.
Detailed description of the invention
The invention relates to at least one compounds with the general formula (1)
wherein R is a substituent selected from the group of C1-C18alkyl, trifluoromethyl, C3-C12cycloalkyl, phenyl, phenoxy, phenylthio, halogen; or tautomers or salts thereof, for use as a growth promotor.
A preferred compound according to claim 1, is phenylcapsaicin.
The invention also relates to a composition comprising a compound according to claim 1 or 2 for use as a food ingredient.
The invention also relates to a feed, comprising 2-500 mg/kg of a compound of formula 1 according to claim 1, preferably 2 to 100 mg/kg, more preferably 2-20 mg/kg.
The invention also relates to a compound according to claim 1 for uses as a growth promotor at a dose of 5 to 200 mg/kg body weight.
The invention also relates to a compound, composition or feed according to any of the previous claims for use in bird feed as a growth promotor.
The invention also relates to bird feed comprising compounds or compositions according to any of the previous claim, wherein the feed is selected from one or more of the group consisting of seeds, corn, worms, millet, oat, peanuts and in the form of pellets, slurry, drinking water and emulsions.
The invention also relates to bird feed according to claim 7 , wherein the bird feed is used for birds selected from the group consisting of poultry, in particular broiler chicken; egg producing birds, in particular chickens; turkey; ostrich; quail; grouse; ducks; geese; wild birds; tame birds and breeding birds.
Synthetic capsaicinoids are well-suited to a variety of applications, including marine antifouling paint, pest control in forestry and agriculture and certain pharmaceutical applications. Phenylcapsaicin has also demonstrated potential properties as an anti-microbial agent in feed for commercial poultry production.
Another use of capsaicin related compounds is as rodent (mammal) repelling agents in outdoor feeding of birds and other animals. Synthetic derivatives produced in high purity and high quantity and to a reasonable cost will be superior to extracts from peppers in this use.
Figures
Figure 1. The predicted growth curves describing broiler mass increase, show that broilers on a diet containing 10 ppm phenylcapsaicin (dot) differs significantly from broilers fed control feed without phenylcapsaicin (square). No differences were found between the 10 and 20 ppm (triangular) treatment groups nor between the 20 ppm and the control group (squares). The mean broiler masses of the 10 ppm treatment group (orange dots) were always higher than the mean of the control group (square) from day 10 and onwards. In general, the 20 ppm means (triangular) are also lower than for the 10 ppm group but this is not statistically significant. The grey vertical dots show individual broiler mass samples for the control (light grey), 10 ppm (grey) and 20 ppm (dark grey) treatment groups, respectively. Figure 2. Broilers fed a diet containing 10 ppm phenylcapsaicin increase in mass faster than broilers in the control group and the difference in mean body mass of broilers between these two treatment groups increase over time. The open circles show the difference in mean broiler mass (10 ppm - control) at any given sampling day, and the solid line shows the linear rate of increase for these data. The broken line at y = 0 shows the expected line giving no difference between treatments. The slopes of these two lines are significantly different (F=34.8, df=7, p<0.001), demonstrating an increase in growth in broilers fed the diet added 10 ppm phenylcapsaicin.
Experimental
A study with a total of 9000 broilers of the breed Partridge K90 (both males and females) where used in a broiler feed study for verification of the increasing growth rate.
There were 3000 individuals in the control group (t=2.84590, df=653, p=0.0046, figure 1) and 3000 individuals in each of the groups feed with a diet of 10 ppm phenylcapsaicin and 20 ppm phenylcapsaicin respectively.
Mean broiler masses at day 59 were 1551,1521 and 1470 g for the 10 ppm, 20 ppm and control groups, respectively.
The growth of the broilers in the 20 ppm treatment group was not significantly different from neither the 10 ppm nor the control group.
The mean difference in broiler mass between the 10 ppm and control group at day 59 was 81 g, i.e. the increase in mean broiler mass of the 10 ppm group compared to the control group was 5.5 %. However, this difference is not statistically different when considering only the final broiler masses between these feed groups.
At sampling days 10-59 the mean broiler masses of the 10 ppm treatment group was consistently higher than the mean masses of the control group, and this difference in mean broiler mass between the 10 ppm and control groups increased over time (figure 2). This increase in mean difference between the two treatment groups is significantly different from the null-hypothesis expected if there was no effect of adding 10 ppm phenylcapsaicin to the feed on broiler growth (F=34.8, df=7, pO.001).
The described differences in broiler growth between the 10 ppm and control groups are believed to be smaller than expected (conservative estimates) in the current study due to the following reasons: The mean body mass of broilers in the control group were c. 5 % larger (not significant)
than for the broilers in the 10 ppm treatment group at the beginning of the feed study (day
3). In most biological systems such a 'head start' is expected to increase during a growth
study. This was not found in this study.
• The cold spell is expected to result in reduced growth, as resources otherwise used for growth must be used in thermoregulation to maintain core body temperature. • The treatment of broilers with antibiotics removes the cost of bacterial growth otherwise expected to differ between the phenylcapsaicin and control groups, thus reducing the
expected differences between treatment groups.
• The population of broiler in the present study consists of both males and females. Males have been shown to have increased growth rates compared to females and this results in a sample with higher variance. Increased variance makes it more difficult to get statistically different results between treatments.
These results demonstrate, in a full size feeding experiment, that 10 ppm phenylcapsaicin has the potential to be added as a growth factor in poultry feed and suggest that this effect should be higher than the observed 5.5 % increase.
Toxicity studies
Comparative toxicity data between capsaicin and phenylcapsaicin:
Capsaicin and Phenylcapsaicin are rapidly absorbed from the gastro-intestinal tract and almost completely metabolized. The major route of excretion was biliary excretion and therefore, in the mass balance study, the majority of metabolites were detected in feces. Although the low recovery lowers the reliability of the study, derivation of reference values is still possible when considering a correction factor for systemic exposure. The metabolic pathways identified for Capsaicin and Phenylcapsaicin are identical, although the major metabolite is glucuronidated and oxidated for Phenylcapsaicin while the major metabolite of capsaicin is just glucuronidated. Tissue accumulation is unlikely to occur for both substances. In conclusion, the data support the read-across from capsaicin to close data gaps of phenylcapsaicin.
The 14C located on the carbonyl group could easily be lost from the farty acid chain and transferred to 14C-acetyl coenzyme A upon hydrolysis of the amide linkage, which means the radioactivity generated from 14C could be transferred to numerous endogenous substances. The author of the study concluded that therefore un-assigned radioactive peaks on the radiochromatograms are most likely endogenous substances which acquired their radioactivity from the biochemical metabolism of HClabeled fatty acid chain. Such metabolism of 14C-labeled fatty acid chain could also explain the low recovery in the mass balance studies, as the biochemical product of fatty acid chain could either be numerous 14C-endogenous substances which are finally exhaled as 14C02. Low radioactivity in carcasses at the end of the study support thatl4C -phenyl-capsaicin and 14C-capsaicin was biotransformed to other HClabeled volatile organic compounds in multiple steps and these metabolites were gradually released as expired air via the lung. If needed correction of the internal reference values (AEL) using the total recovery (50%) seems to be valid as the majority of metabolites are excreted in bile. Only 2-3% parent were detected in bile. Thus systemic availablity of the a.s.
is likely. A complete absorption of Capsaicin was also postulated by
Donnerer et al. 1990. Naunyn- Schmiedeberg' s Arch. Pharmacol., 342, 357-361)
Acute Oral Tox - OECD 423:
2000 mg/Kg is applied by oral without produce mortality. Based on the test results, the test substance is unclassified according to the GHS. The acute oral toxicity LD50 value: LD50 > 5000 mg/Kg.
Acute Dermal Irritation/ Corrosion - OECD 404:
The test item 0,5 mL was applied to the a gauze patch, then cover the gauze patch on a small area (approximately 6 cm<2>) of skin, which is held in place with non-irritating tape. The test item is non-irritationg to the rabbits skin within an observation period of up to 14 days starting after an exposure time of 4 hours.
Acute Eye Irritation/ Corrosion - OECD 405:
0,1 ml of the test item was placed in the conjunctival sac of one eye of rabbit. The test substance is slightly irritant to the rabbit eye within an observation period of up to 7 days without washout after the test substance was placed in the conjunctival sac of one eye.
Acute Inhalation Tox - OECD 403. 2009:
Under the condtions of this study the single exposure acute inhalation LC50 of phenylcapsaicin is not greater than 5.65 mg/L in male and female rats based on active substance.
Skin Sensitisation - OECD 406. 1992:
All animals survived throughout the test period without showing any clinical signs of toxicity. Under the conditions of the present study it can be stated that the test item Phenylcapsaicin caused no reactions identified as sensitisation at the tested concentration. According to Commission Regulation (EU) No. 286/2011 as well as GHS (Globally Harmonized Classification System) the test item Phenylcapsaicin has no obligatory labelling requirement for skin sensitisation and is unclassified.
Reverse Mutation Assav - OECD 471. 1997:
In conclusion, it can be stated that during the described mutagenicity test and under the experimental conditions reported, Phenylcapsaicin did not cause gene mutations by base pair changes or frameshifts in the genome of the tester strains used. Therefore, Phenylcapsaicin is considered to be non-muytagenic in this bacterial reverse mutation assay.
Claims (8)
1. At least one compounds with the general formula (1)
wherein R is a substituent selected from the group of C1-C18alkyl, trifluoromethyl, C3-C12cycloalkyl, phenyl, phenoxy, phenylthio, halogen; or tautomers or salts thereof, for use as a growth promotor.
2. A compound according to claim 1, which is phenylcapsaicin.
3. A composition comprising a compound according to claim 1 or 2 for use as a food ingredient.
4. A feed, comprising 2-500 mg/kg of a compound of formula 1 according to claim 1, preferably 2 to 100 mg/kg, more preferably 2-20 mg/kg.
5. A compound according to claim 1 for uses as a growth promotor at a dose of 5 to 200 mg/kg body weight.
6. A compound, composition or feed according to any of the previous claims for use in bird feed as a growth promotor.
7. Bird feed comprising compounds or compositions according to any of the previous claim, wherein the feed is selected from one or more of the group consisting of seeds, corn, worms, millet, oat, peanuts and in the form of pellets, slurry, drinking water and emulsions.
8. Bird feed according to claim 7 , wherein the bird feed is used for birds selected from the group consisting of poultry, in particular broiler chicken; egg producing birds, in particular chickens; turkey; ostrich; quail; grouse; ducks; geese; wild birds; tame birds and breeding birds.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20160468A NO341559B1 (en) | 2016-03-18 | 2016-03-18 | Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors |
| PCT/NO2017/050071 WO2017160165A1 (en) | 2016-03-18 | 2017-03-17 | Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20160468A NO341559B1 (en) | 2016-03-18 | 2016-03-18 | Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20160468A1 true NO20160468A1 (en) | 2017-09-19 |
| NO341559B1 NO341559B1 (en) | 2017-12-04 |
Family
ID=59851599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20160468A NO341559B1 (en) | 2016-03-18 | 2016-03-18 | Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors |
Country Status (2)
| Country | Link |
|---|---|
| NO (1) | NO341559B1 (en) |
| WO (1) | WO2017160165A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11471429B2 (en) | 2017-10-20 | 2022-10-18 | Axichem Ab | Synthetic capsaicin analogues as bioenhancers |
| NO346665B1 (en) * | 2020-11-17 | 2022-11-21 | Axichem Ab | Capsaicyns in the treatment of leaky gut |
| NO20220225A1 (en) * | 2022-02-18 | 2023-08-21 | Axichem Ab | Bioenhancers |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1670310B1 (en) * | 2003-09-12 | 2007-11-14 | Aximed AS | Capsaicin derivates and the production and use thereof |
| EP2070428A1 (en) * | 2007-12-11 | 2009-06-17 | DSMIP Assets B.V. | Use of a composition comprising sesquiterpenes from curcuma essential oil and/or tea tree oil in the manufacture of an animal feed |
| WO2010014038A1 (en) * | 2008-07-31 | 2010-02-04 | The Thailand Research Fund | Feed for poultry and swine |
| CN102613442A (en) * | 2012-04-27 | 2012-08-01 | 天津生机集团股份有限公司 | Composition capable of increasing broiler feed intake |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL60530A (en) * | 1979-08-16 | 1984-10-31 | American Cyanamid Co | Animal feed compositions useful as growth promotors and for reduction of fat in animals,comprising phenylethanolamine derivatives and certain such novel compounds |
| KR20010099502A (en) * | 2001-10-11 | 2001-11-09 | 황찬호 | How to make poultry feed containing poxicin or red pepper and its feed to poultry to produce poultry meat and its eggs containing beneficial ingredients for human body |
| MX348214B (en) * | 2006-03-10 | 2017-06-05 | Archer Daniels Midland Co | Methods and compositions for increased productivity in animals. |
| FR2908600B1 (en) * | 2006-11-21 | 2009-01-02 | Axiss France Sas Soc Par Actio | CAPSICUM MICROENCAPSULE, PROCESS FOR PREPARING THE SAME, AND USE |
| DE102008006430A1 (en) * | 2008-01-28 | 2009-08-06 | Florian Galow | Beverage recipe for a drink with a specific water portion and a flavorful stimulatory essence, which contains a capsaicinoid and has a specific severity level |
| US20110165291A1 (en) * | 2008-11-12 | 2011-07-07 | Andrew Loblaw | Nutritional supplement |
| BE1019713A3 (en) * | 2010-12-24 | 2012-10-02 | Axichem Ab | REPELLENT PAINTING BASED ON CAPSAICIN DERIVATIVES. |
| CN102318754A (en) * | 2011-07-22 | 2012-01-18 | 大连理工大学 | Method for preparing natural feed for reducing salmonellas on surfaces of eggs |
| WO2015160843A1 (en) * | 2014-04-14 | 2015-10-22 | Flex Pharma, Inc. | Ion channel activators and methods of use |
| CN103976145A (en) * | 2014-05-23 | 2014-08-13 | 重庆泰业农业开发有限公司 | Feed for pig and poultry and preparation method thereof |
| ES2759360T3 (en) * | 2015-10-09 | 2020-05-08 | Axichem Ab | Feed for poultry, and in particular feed for poultry, comprising synthetic capsaicinoid derivatives and feed of this type for prophylactic use or treatment of salmonella infection |
-
2016
- 2016-03-18 NO NO20160468A patent/NO341559B1/en unknown
-
2017
- 2017-03-17 WO PCT/NO2017/050071 patent/WO2017160165A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1670310B1 (en) * | 2003-09-12 | 2007-11-14 | Aximed AS | Capsaicin derivates and the production and use thereof |
| EP2070428A1 (en) * | 2007-12-11 | 2009-06-17 | DSMIP Assets B.V. | Use of a composition comprising sesquiterpenes from curcuma essential oil and/or tea tree oil in the manufacture of an animal feed |
| WO2010014038A1 (en) * | 2008-07-31 | 2010-02-04 | The Thailand Research Fund | Feed for poultry and swine |
| CN102613442A (en) * | 2012-04-27 | 2012-08-01 | 天津生机集团股份有限公司 | Composition capable of increasing broiler feed intake |
Also Published As
| Publication number | Publication date |
|---|---|
| NO341559B1 (en) | 2017-12-04 |
| WO2017160165A1 (en) | 2017-09-21 |
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