NZ614841B2 - Enhanced bioavailable iodine molecules - Google Patents
Enhanced bioavailable iodine molecules Download PDFInfo
- Publication number
- NZ614841B2 NZ614841B2 NZ614841A NZ61484112A NZ614841B2 NZ 614841 B2 NZ614841 B2 NZ 614841B2 NZ 614841 A NZ614841 A NZ 614841A NZ 61484112 A NZ61484112 A NZ 61484112A NZ 614841 B2 NZ614841 B2 NZ 614841B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- iodine
- amino acid
- zinc
- lysine
- group
- Prior art date
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- 239000011630 iodine Substances 0.000 title claims abstract description 76
- 229910052740 iodine Inorganic materials 0.000 title claims abstract description 76
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 229910052751 metal Inorganic materials 0.000 claims abstract description 32
- 239000002184 metal Substances 0.000 claims abstract description 32
- 241001465754 Metazoa Species 0.000 claims abstract description 13
- 230000036912 Bioavailability Effects 0.000 claims abstract description 8
- 230000035514 bioavailability Effects 0.000 claims abstract description 8
- 235000005911 diet Nutrition 0.000 claims abstract description 7
- 230000037213 diet Effects 0.000 claims abstract description 6
- 150000001413 amino acids Chemical class 0.000 claims description 32
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 28
- 239000004472 Lysine Substances 0.000 claims description 24
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052725 zinc Inorganic materials 0.000 claims description 21
- 230000001502 supplementation Effects 0.000 claims description 20
- 239000011701 zinc Substances 0.000 claims description 20
- 239000000969 carrier Substances 0.000 claims description 15
- 239000003797 essential amino acid Substances 0.000 claims description 14
- 235000020776 essential amino acid Nutrition 0.000 claims description 14
- 229910052742 iron Inorganic materials 0.000 claims description 14
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 12
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052748 manganese Inorganic materials 0.000 claims description 11
- 239000011572 manganese Substances 0.000 claims description 11
- 150000002500 ions Chemical class 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 244000144972 livestock Species 0.000 claims description 9
- 244000144977 poultry Species 0.000 claims description 9
- 235000016709 nutrition Nutrition 0.000 claims description 7
- 235000015097 nutrients Nutrition 0.000 claims description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 5
- 235000005822 corn Nutrition 0.000 claims description 5
- 235000005824 corn Nutrition 0.000 claims description 5
- 230000002708 enhancing Effects 0.000 claims description 5
- 238000000855 fermentation Methods 0.000 claims description 5
- 230000004151 fermentation Effects 0.000 claims description 5
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 4
- 241000209149 Zea Species 0.000 claims description 4
- 235000013339 cereals Nutrition 0.000 claims description 4
- 235000000346 sugar Nutrition 0.000 claims description 4
- 235000007466 Corylus avellana Nutrition 0.000 claims description 3
- 240000007582 Corylus avellana Species 0.000 claims description 3
- 229960000310 ISOLEUCINE Drugs 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 3
- 229960005190 Phenylalanine Drugs 0.000 claims description 3
- 239000004473 Threonine Substances 0.000 claims description 3
- 239000005862 Whey Substances 0.000 claims description 3
- 235000013312 flour Nutrition 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 3
- 239000004474 valine Substances 0.000 claims description 3
- 230000003000 nontoxic Effects 0.000 claims 4
- 231100000252 nontoxic Toxicity 0.000 claims 4
- 150000008163 sugars Chemical class 0.000 claims 2
- 235000020639 clam Nutrition 0.000 claims 1
- -1 amino acid iodide compounds Chemical class 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 5
- DDKJKQVNNATMAD-JEDNCBNOSA-N (2S)-2,6-diaminohexanoic acid;zinc Chemical compound [Zn].NCCCC[C@H](N)C(O)=O DDKJKQVNNATMAD-JEDNCBNOSA-N 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 235000001014 amino acid Nutrition 0.000 description 31
- 239000000203 mixture Substances 0.000 description 21
- 210000002966 Serum Anatomy 0.000 description 13
- 235000018102 proteins Nutrition 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- 241001286462 Caio Species 0.000 description 8
- 238000002390 rotary evaporation Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 230000002194 synthesizing Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 210000004767 Rumen Anatomy 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 5
- UHWJJLGTKIWIJO-UHFFFAOYSA-L Calcium iodate Chemical compound [Ca+2].[O-]I(=O)=O.[O-]I(=O)=O UHWJJLGTKIWIJO-UHFFFAOYSA-L 0.000 description 4
- 239000004151 Calcium iodate Substances 0.000 description 4
- 210000004080 Milk Anatomy 0.000 description 4
- 235000019390 calcium iodate Nutrition 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
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- 239000008267 milk Substances 0.000 description 4
- 235000021239 milk protein Nutrition 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000011573 trace mineral Substances 0.000 description 4
- 235000013619 trace mineral Nutrition 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 102000014171 Milk Proteins Human genes 0.000 description 3
- 108010011756 Milk Proteins Proteins 0.000 description 3
- 241000282849 Ruminantia Species 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- SOGMDUPYAJRSJA-UHFFFAOYSA-N 2-hydroxy-2-methylbutanethioic S-acid Chemical compound CCC(C)(O)C(S)=O SOGMDUPYAJRSJA-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N Calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 230000036740 Metabolism Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M Perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- 210000001685 Thyroid Gland Anatomy 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L Zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000019728 animal nutrition Nutrition 0.000 description 2
- 244000052616 bacterial pathogens Species 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000006047 digesta Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002183 duodenal Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 150000002496 iodine Chemical class 0.000 description 2
- 150000002497 iodine compounds Chemical class 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000035786 metabolism Effects 0.000 description 2
- 229910001511 metal iodide Inorganic materials 0.000 description 2
- 235000021243 milk fat Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000003044 randomized block design Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- XXLAQBKBVQBYFN-JEDNCBNOSA-N (2S)-2,6-diaminohexanoic acid;iron Chemical compound [Fe].NCCCC[C@H](N)C(O)=O XXLAQBKBVQBYFN-JEDNCBNOSA-N 0.000 description 1
- FWYCEJKPOQMTCU-JEDNCBNOSA-N (2S)-2,6-diaminohexanoic acid;manganese Chemical compound [Mn].NCCCC[C@H](N)C(O)=O FWYCEJKPOQMTCU-JEDNCBNOSA-N 0.000 description 1
- GIIANEWSGYHSDI-UHFFFAOYSA-N 2-aminoacetyl iodide Chemical compound NCC(I)=O GIIANEWSGYHSDI-UHFFFAOYSA-N 0.000 description 1
- 210000003165 Abomasum Anatomy 0.000 description 1
- 206010000210 Abortion Diseases 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
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- 210000000988 Bone and Bones Anatomy 0.000 description 1
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- 210000001198 Duodenum Anatomy 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- IWNWLPUNKAYUAW-UHFFFAOYSA-N Ethylenediamine dihydroiodide Chemical compound I.I.NCCN IWNWLPUNKAYUAW-UHFFFAOYSA-N 0.000 description 1
- 229940088597 Hormone Drugs 0.000 description 1
- 210000000936 Intestines Anatomy 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 229940029985 MINERAL SUPPLEMENTS Drugs 0.000 description 1
- 208000004396 Mastitis Diseases 0.000 description 1
- SXWWKEDVWQNOCG-XRIGFGBMSA-L N[C@@H](CCCCN)C(=O)O.[I-].[I-] Chemical class N[C@@H](CCCCN)C(=O)O.[I-].[I-] SXWWKEDVWQNOCG-XRIGFGBMSA-L 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 210000002435 Tendons Anatomy 0.000 description 1
- 229940045997 Vitamin A Drugs 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000006053 animal diet Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 230000001580 bacterial Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 230000004641 brain development Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052803 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000000378 dietary Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000004383 glucosinolate group Chemical group 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N iodine atom Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M isothiocyanate Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002503 metabolic Effects 0.000 description 1
- 230000035511 metabolization Effects 0.000 description 1
- 235000020786 mineral supplement Nutrition 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000006180 nutrition needs Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001850 reproductive Effects 0.000 description 1
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- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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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
-
- 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
- A23K20/142—Amino acids; Derivatives thereof
-
- 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
- A23K20/20—Inorganic substances, e.g. oligoelements
-
- 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
- A23K20/20—Inorganic substances, e.g. oligoelements
- A23K20/30—Oligoelements
-
- 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
-
- 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
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/07—Acyclic saturated compounds containing halogen atoms containing iodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/76—Metal complexes of amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic System
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/06—Zinc compounds
Abstract
Provided are metal amino acid iodide compounds, of Structure III, and hydroxyl metal acid complexes with iodine, of Structure IV, which supplement the diets of domesticated animals with iodine that has greater bioavailability. The variables of Structure III and IV are as defined in the specification. A preferred metal amino acid iodide compound is zinc lysine diiodide as depicted in Structure I. . A preferred metal amino acid iodide compound is zinc lysine diiodide as depicted in Structure I.
Description
TITLE: ENHANCED BIOAVAILABLE IODINE MOLECULES
BACKGROUND OF THE INVENTION
This invention relates to supplementation of the diets of domesticated animals
(livestock and poultry) with iodine in an enhanced bioavailable manner, that is to say the
iodine is more available to the animal than when using conventional sources of iodine,
such as calcium iodate. The supplementary compound are alpha amino acid metal iodide
complexes.
It is well known that domesticated animals (livestock and poultry) are in need of
bioavailable metal or mineral supplements, essential amino acids, and also are in need of
iodine for healthy animal nutrition.
Iodine is a key component of hormones produced by the thyroid gland. The thyroid
is responsible for growth, brain development and the rate at which animals burn energy.
Two of the most common sources of iodine used in animal nutrition and therefore used in
supplementing animal diets are calcium iodate (CaIO and ethylenediamine dihydoiodide
(EDDI). One test of the efficiency of effective metabolization of the iodine source by an
animal is measuring blood serum levels of iodine after ingesting of the nutrient material.
In the animal feed industry it is known that insufficient availability of iodine to the
animal can result in conditions such as goiters, reproductive failure, weak offspring,
reduced milk yield, mastitis, abnormal respiration, reduced growth rate and even hairless
offspring. The traditional toxicity symptoms of iodine in animals are anorexia, excess
salivation, nasal or ocular discharge, abortion, pneumonia, and bone/tendon deformities.
Furthermore, excessive feeding of ethylenediamine dihydoiodide (EDDI) is known to
interfere with Vitamin A metabolism. High dietary calcium nitrate, thiocyanate,
glucosinolate, perchlorate, rubidium and cobalt interfere with iodine metabolism and can
increase iodine requirements. Metal iron for nutrient use does reduce iodine toxicity, but
can also increase the need for iodine requirements.
It can be seen therefore that the conventional now used iodine sources in animal
feed, such as inorganic iodine salts or amine salts all have their unique problems. There is
therefore a continuing need for the development of unique iodine sources that provide
better availability to the animal, that is, higher blood serum levels without simply adding
more iodine. The primary objective of the present invention is to meet this need by
providing organic trace mineral metal complexes of iodine, particularly with amino acid
metal complexes, and most particularly with naturally occurring amino acids and/or
essential amino acid metal complexes.
Lysine is an essential amino acid in the diet of mammals. That is, lysine cannot be
synthesized by mammals at a rate adequate to meet the metabolic requirements, and so it
must be supplied in the diet. Corn is notoriously low in lysine, and if used for animals in a
single grain ration requires lysine supplementation both to maintain animal health and to
achieve economic animal growth. Protected lysine molecules are a subject of commonly
owned U.S. Patent Nos. 7,704,521 and 7,846,471. As explained below, preferred
compounds of the present invention providing enhanced bioavailability of iodine by
providing two iodine ions per molecule and are those made from lysine reacted with a
compound such as zinc to make lysine zinc diiodide (structure I, below).
The method of achieving the above primary objective as well as others will become
apparent from the detailed description of the invention. It is understood that the invention
is not limited by its primary objective and that other advantages of the invention such as
efficiency of synthesis, lower cost of iodine, blood serum level iodine enhancement, i.e.,
bioavailability, and cost effectiveness of nutritional supplementation are all also achieved.
SUMMARY OF THE INVENTION
Metal amino acid iodide molecules, preferably metal lysine diiodides having one
iodine moiety associated with the metal atom and the second associated with the amine salt
are prepared and used to provide enhanced bioavailable iodine supplementation of animals
(livestock and poultry) with increased blood serum levels of iodine resulting.
The invention particularly relates to a method of enhancing livestock and poultry
iodine bioavailability from iodine nutrient sources, comprising:
feeding animals a nutritional supplementation effective amount of a metal essential amino
acid iodide of the formula:
wherein M is a metal ion selected from the group consisting of zinc, manganese, and iron,
R is a moiety selected to provide the backbone of a naturally occurring amino acid, to an
animal in need of iodine supplementation.
In another embodiment the invention relates to a method of enhancing livestock
and poultry iodine bioavailability from iodine nutrient sources, comprising:
feeding animals a nutritional supplementation effective amount of a metal lysine diiodide
of the formula:
wherein M is a metal ion selected from the group consisting of zinc, manganese, and iron.
In a still further embodiment the invention relates to the lysine diiodide compound
of the formula:
wherein M is a metal ion selected from the group consisting of zinc, manganese
and iron.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
In the ruminant animal, ingested feed first passes into the rumen where it is
partially broken down by bacterial fermentation. During rumen fermentation, rumen
microbes utilize nitrogen from nitrogen compounds that they have degraded to form
microbial protein. Nitrogen sources for rumen microbes include rumen degradable protein
and peptides, free amino acids and urea. Microbial protein and undegraded feed protein
pass to the abomasum and small intestine where hydrochloric acid and mammalian
enzymes degrade microbial protein and undegraded feed protein to free amino acids and
short peptides. The amino acids and short peptides are absorbed in the intestine, and the
ruminant animals utilize the amino acids for synthesis of protein to sustain life, grow,
reproduce and produce milk.
Of the twenty or more amino acids utilized by the animal to synthesize proteins,
nine are considered to be essential. Examples of the essential amino acids include leucine,
isoleucine, valine, methionine, threonine, lysine, histidine, phenylalanine and trytophan.
Essential amino acids are those amino acids which are required in quantities exceeding
amounts produced by the animal, and must be supplied by microbial protein or rumen
undegraded protein. Amino acids supplied in excess are degraded by the animal and
excreted in the form of urea. The process of synthesizing urea from ammonia is a process
requiring energy input from the animal. If certain essential amino acids are not provided in
adequate amounts, the animal will be limited on the amount and types of protein it can
produce, thus limiting animal performance. Supplying the proper amounts of essential
amino acids therefore maximizes animal performance while enhancing efficiency of
energy utilization by the animal.
Lysine and methionine are two of the most limiting essential amino acids when
corn-based rations are fed. Results from studies also indicate that milk protein content is
the most sensitive of the production variables (yield of milk, fat-corrected milk, milk
protein, milk fat, and content of milk fat and protein) to alterations in amino acid content of
duodenal digesta. Researchers have determined, by infusing incremental amounts of the
limiting amino acids into the duodenum of lactating dairy cows, that the required
contribution of lysine and methionine to total essential amino acids in duodenal digesta for
maximum milk protein content approximated 15% and 5.2%, respectively.
The present invention relates to certain iodine complexes which provide to the
animal (livestock or poultry) supplementation that provides both the opportunity for
essential amino acid supplementation, iodine supplementation, and also provides a trace
mineral. To the Applicant's present knowledge, there have been no compounds which
have in the past provided all of these supplementations in the same compound. This is
important because often times space in an animal feed mixture is an issue; and this
invention fulfills three nutritional requirements with one molecule, with a net result of
enhanced bioavailability of the iodine in the blood serum in comparison with normal
sources of iodine, such as EDDI and calcium iodate.
The most preferred amino acid for use in the present invention is lysine to provide
compounds such as zinc lysine diiodide of the formula:
(Structure I)
As can be seen from Structure I, the iodine is provided in this compound at two
sources; first, in association with the zinc atom and secondly in the iodine amine salt form.
There is thus an opportunity of "double enhancement" with this compound. To say it
another way, the structure has both amine salt iodine and a metal salt with iodine. The
Structure I for the lysine diiodides can be generalized replacing the zinc atom with M
representing the metal ion. For the present invention, suitable metal ions can be
manganese and iron in case the generalized formula would be:
(Generalized formula for metal diiodide lysine salts - Structure II)
As heretofore mentioned, lysine is the preferred amino acid but not the only one
which may be employed in the present invention. M can be zinc, manganese or iron. In
fact, the invention may be generalized to other naturally occurring amino acids as follows:
(Structure III)
In Structure III in the formula above, M represents the metal ion and can be zinc
manganese or iron. R represents any remaining portion of a naturally occurring amino acid
and can be selected from the group derived from essential amino acids including leucine,
isoleucine, valine, methionine, threonine, lysine, histidine, phenylalanine and trytophan.
The amino acid can also be one of the other 20 or more amino acids utilized by animals to
synthesize proteins and also be a mixture of a variety of amino acids leading to a mixture
of amino acid iodine metal salts (see Example II below).
It should be noted that in Structure (III) the amino group may be replaced with a
hydroxy to form hydroxyl acid metal complexes with iodine. Put another way to
generalize, the amino group of Structure (III) can be replaced with “X”, and “X” can be
either amino or hydroxyl. Other possibilities include R is CH , R is H, R is C H , and R is
3 2 5
C H SCH , in which case the acid is respectively lactic acid, glycolic acid, hydroxybutyric
2 4 3
acid and hydroxy-methylthio-butyric acid (see Example III).
The process of preparation of the amino acid metal iodide salts is straight forward,
simply mixing equimolar amounts in an aqueous medium of the amino acid and the source
of the metal ion, for example if its zinc, zinc iodide. It is stirred and heated for a time
sufficient to allow the reaction to occur, preferably around 100º C for 30-40 minutes. This
is followed by cooling to room temperature, drying to leave a solid which if not powdered
is ground to produce a powder material. It can be dried by spraying or rotary evaporation
drying, etc. One of the efficiencies providing for cost effectiveness is the simple
methodology for preparation.
The compounds prepared as above, and especially those listed as preferred, are
easily processable. They can be sold pure as a supplementing additive or they can be
mixed with carriers to improve packaging, processability, and taste. Preferred carriers are,
for example, powdered sugar which significantly improves taste for the ruminants that
ingest the same. For example, the Benzaldehyde derivatives have an almond taste which
can be masked with powdered sugar.
The compounds can also be used as a part of the overall trace mineral
supplementation for the animal.
While it is preferred that the compounds of the present invention be added without
additional carriers or filler material, as heretofore mentioned flavorants can be used as or
with the carrier. If carriers are employed, the carrier can be suitable carriers such as
distillers fermentation solubles, feed grains, corn cob flour, whey, or other cellulosic
carrier materials. They can also be added at the same time or with other trace mineral
preparations.
The amount of supplement added to the feed ration will vary, of course, depending
on whether one is using the pure compositions or the composition with a carrier. Basically
the supplement will simply mix with the feed ration, as sold.
Generally the compounds should be added at a level to provide sufficient essential
Iodine for the animals performance levels and daily nutritional needs, i.e., within the range
of about 25mg/head/day to about 50 milligrams per animal per day for performance level
and 5-10mg/day for nutrition level. Thus, the overall range of addition is from 5mg to
50mg per head per day, depending upon objective.
The following examples are offered to further illustrate but not limit of the
invention compounds and how to show their use for effective enhancement of iodine
supplementation in livestock or poultry at the blood serum level.
EXAMPLE I
Synthesis of Zinc Lysine diiodide (Structure I)
Lysine (4.24 gr, 0.029 moles) was dissolved in water (200mL). To this solution
was added ZnI (9.26 gr, 0.29 moes). This mixture was stirred and heated to 100 C for 35
minutes. This solution was allowed to cool to room temperature and the resulting solution
was dried by rotary evaporation resulting in an off white solid. The material was analyzed
for zinc content and iodine content. Zinc percentage 12.8 and Iodine percentage 50.5.
EXAMPLE II
Synthesis of Zinc (Amino Acid) iodide (Structure III with mixed amino acids and M = Z)
A mixture of amino acids was prepared by blending the following amino acids:
Amino
MW Weight
Acid
ARG 174.20 7.22
ASP 133.10 7.32
240.30 1.14
GLU 147.13 11.88
75.07 9.31
HIS 209.63 0.84
131.20 8.52
LYS 182.65 1.97
149.20 2.63
PRO 115.13 7.35
105.09 12.26
TYR 181.19 3.06
VAL 117.15 6.76
Total AA 80.26gr
This amino acid mixture has an average molecular weight of 130.57
.2 gr of this amino acid mixture (0.078 moles) was dispersed in 250 mL of water
and ZnI (24.9 gr, 0.078 moles) was added. This mixture was heated until it was a
solution. This solution was then heated to 100º C for 28 minutes. The mixture was cooled
to room temperature and the water removed by rotary evaporation. The resulting product
had 13.9 percent zinc and 53.2 percent iodine.
EXAMPLE III
(Zinc hydroxy-methylthio-butyric acid iodide) (Structure III, M = Z and R is from
methionine)
Hydroxyl methylthio butanoic acid (88% solution) (35.7 gr, 0.21 moles) was
dissolved in 350 mL of water. To this mixture was added ZnI (67 gr , 0.21 moles). This
mixture was stirred and the pH adjusted to pH = 3 by the addition of 10N NaOH dropwise.
The mixture was heated for 1.5 hours at 100º C. The resulting mixture was cooled and
then dried down to a solid by rotary evaporation. This solid analyzed for 11.9 % zinc and
% iodine.
EXAMPLE IV
(Zinc glycine iodide) (Structure III, M = Zn and R is from glycine)
Glycine (28.6 gr, 0.381 moles) was dissolved in 150 mL of water. To this mixture
was added ZnI ( 121.6 gr, 0.381 moles) and the entire solution stirred and heated to 100º
C for 45 minutes. The mixture is cooled to room temperature and the solvent removed by
rotary evaporation. The solid is analyzed for zinc and iodine. The dried product is
analyzed for 14.3% zinc and 40% iodine.
EXAMPLE V
(Synthesis of Iron Lysine diiodide)
Lysine (4.76 gr, 0.0326 moles) was dissolved in water (100mL). To this solution
was added Fel2 (10.1 gr, 0.0326 moles). This mixture was stirred and heated to 100º C for
minutes. This solution was allowed to cool to room temperature and the resulting
solution was dried by rotary evaporation resulting in a brown solid. The material was
analyzed for iron content and iodine content. Iron percentage 11.7% and Iodine percentage
53.4%.
EXAMPLE VI
(Synthesis of Manganese Lysine diiodide)
Lysine (4.7 gr, 0.0323 moles) was dissolved in water (100mL). To this solution
was added Mnl2 (10.1 gr, 0.0323 moles). This mixture was stirred and heated to 100º C
for 35 minutes. This solution was allowed to cool to room temperature and the resulting
solution was dried by rotary evaporation resulting in an off white solid. The material was
analyzed for zinc content and iodine content. Manganese percentage 11.6% and Iodine
percentage 52.1%.
EXAMPLE VII
This example illustrates the enhanced blood serum levels of iodine, demonstrating
the superiority over conventional sources.
EDDI = ethylenediamine dihydroiodide
CaIO = Calcium Iodate
Angus Simmental, nonlactating, pregnant beef cows, weighing between 1200 and
1700 lbs were assigned to a study with a completely randomized block design to determine
the effect of novel iodine compounds on serum iodine concentration as compared to EDDI
and CaIO . Cows were blocked on body weight at 7 days before the start of the trial.
Cows were fed a bolus containing 60 mg of iodine from the various sources from day 0-
day 10. Blood serum iodine was measured and reported as an average of day 2-14 and as a
peak value at day 10. Compounds 1 and 2 showed higher blood levels of iodine than
CaIO or EDDI.
60 mg Iodine/day for 10 days
Average Serum iodine level Day 10
Treatment (day 2 - day 14) (last treatment day)
No Iodine 35 34
EDDI 141 274
CaIO 148 290
Structure I 184 380
Structure II 173 348
EXAMPLE VIII
In another efficacy trial, Angus Simmental, nonlactating, pregnant beef cows,
weighing between 1200 and 1700 lbs were assigned to a study with a completely
randomized block design to determine the effect of novel iodine compounds as compared
to EDDI and CaIO on serum iodine concentration. Cows were blocked on body weight at
7 days before the start of the trial.
60 mg Iodine/day for 10 days
Average Serum iodine level Day 10
Treatment (day 2 - day 14) (last treatment day)
No Iodine 94 86
EDDI 233 341
CaIO 227 359
Compound of
Example III 386 630
Compound of
Example IV 380 637
As can be seen from the above examples, the metal amino acid bound iodine is
producing a much higher blood serum level of iodine than the standard (EDDI, CaIO )
materials, indicating enhanced bioavailable levels of iodine.
Similar results are achieved if the metal is manganese or iron, and if other naturally
occurring amino acids are employed, singly or in combination.
Claims (16)
1. A method of enhancing livestock and poultry iodine bioavailability from iodine nutrient sources, comprising: feeding animals a nutritional supplementation effective amount of a metal essential amino acid iodide of the formula: wherein M is a metal ion selected from the group consisting of zinc, manganese, and iron, R is a moiety selected to provide the backbone of a naturally occurring amino acid, to an animal in need of iodine supplementation.
2. The method of claim 1 wherein the diet supplementing effective amount is an amount sufficient to provide a level of from about 5 milligrams per head per day to about 50 milligrams of iodine per head per day.
3. The method of claim 1 or 2 wherein the supplement is added in conjunction with non-toxic carriers.
4. The method of claim 3 wherein the non-toxic carriers are selected from the group consisting of sugars, fermentation solubles, feed grains, corn cob flour, whey, and other cellulosic carrier materials.
5. The method of any one of claims 1-4 wherein the amino acid is an essential amino acid selected from the group consisting of leucine, isoleucine, valine, methionine, threonine, lysine, histidine, phenylalanine and trytophan.
6. A method of enhancing livestock and poultry iodine bioavailability from iodine nutrient sources, comprising: feeding animals a nutritional supplementation effective amount of a metal lysine diiodide of the formula: wherein M is a metal ion selected from the group consisting of zinc, manganese, and iron.
7. The method of claim 6 wherein the diet supplementing effective amount is an amount sufficient to provide a level of from about 5 milligrams per head per day to about 50 milligrams of iodine per head per day.
8. The method of claim 6 or 7 wherein the supplement is added in conjunction with non-toxic carriers.
9. The method of claim 8 wherein the non-toxic carriers are selected from the group consisting of sugars, fermentation solubles, feed grains, corn cob flour, whey, and other cellulosic carrier materials.
10. The lysine diiodide compound of the formula: wherein M is a metal ion selected from the group consisting of zinc, manganese and iron.
11. The compound of claim 10 wherein M is zinc.
12. The compound of claim 10 wherein M is manganese.
13. The compound of claim 10 wherein M is iron.
14. A method according to clam 1, substantially as herein described or exemplified.
15. A method according to claim 6, substantially as herein described or exemplified.
16. A lysine diiodide according to claim 10, substantially as herein described or exemplified.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/037,716 US9149057B2 (en) | 2011-03-01 | 2011-03-01 | Enhanced bioavailable iodine molecules |
US13/037,716 | 2011-03-01 | ||
PCT/US2012/026246 WO2012118688A2 (en) | 2011-03-01 | 2012-02-23 | Enhanced bioavailable iodine molecules |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ614841A NZ614841A (en) | 2014-11-28 |
NZ614841B2 true NZ614841B2 (en) | 2015-03-03 |
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