CA2488696A1 - Metal complexes of alpha amino dicarboxylic acids - Google Patents

Metal complexes of alpha amino dicarboxylic acids Download PDF

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Publication number
CA2488696A1
CA2488696A1 CA002488696A CA2488696A CA2488696A1 CA 2488696 A1 CA2488696 A1 CA 2488696A1 CA 002488696 A CA002488696 A CA 002488696A CA 2488696 A CA2488696 A CA 2488696A CA 2488696 A1 CA2488696 A1 CA 2488696A1
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CA
Canada
Prior art keywords
group
acid
neutral complex
dicarboxylic
alpha amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002488696A
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French (fr)
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CA2488696C (en
Inventor
Mahmoud M. Abdel-Monem
Michael D. Anderson
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Zinpro Corp
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Individual
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Filing date
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Publication of CA2488696A1 publication Critical patent/CA2488696A1/en
Application granted granted Critical
Publication of CA2488696C publication Critical patent/CA2488696C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/76Metal complexes of amino carboxylic acids
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/20Inorganic substances, e.g. oligoelements
    • A23K20/30Oligoelements
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K50/00Feeding-stuffs specially adapted for particular animals
    • A23K50/70Feeding-stuffs specially adapted for particular animals for birds
    • A23K50/75Feeding-stuffs specially adapted for particular animals for birds for poultry

Abstract

Neutral alpha amino diacid complexes of trace minerals and their use for animal nutrition.

Claims (14)

1. A neutral complex of an essential trace element and a dicarboxylic alpha amino-acid.
2. A neutral complex of claim 1 wherein the essential trace element is selected from the group consisting of zinc, copper, manganese, iron cobalt, nickel, vanadium and molybdenum.
3. A neutral complex of claim 1 wherein the dicarboxylic alpha amino acid is selected from the group consisting of zinc, copper and manganese.
4. A neutral complex of claim 1 wherein the dicarboxylic alpha amino acid is selected from the group consisting of aspartic, glutamic, 1,6-Dicarboxylic-2-amino hexanoic, 1,7-dicarboxylic-2-amino heptanoic and 1,8-dicarboxylic-2-amino octanoic acid.
5. A neutral complex of claim 1 wherein the diacid is selected from the group consisting of aspartic acid and glutamic acid.
6. A neutral complex of claim 1 combined with a suitable animal feed carrier selected from the group consisting of calcium hydrogen phosphate, calcium carbonate, silica, ground corn cobs, and powdered sugar or a mixture of any of the above.
7. A neutral complex of a trace element selected from the group consisting of:
zinc, copper and manganese and an alpha amino acid selected from the group consisting of aspartic acid and glutamic acid.
8. A neutral complex of claim 7 wherein the trace element is selected from the group consisting of zinc, copper and manganese and the alpha amino acid is aspartic acid.
9. A neutral complex of claim 7 wherein the trace element is selected from the group consisting of zinc, copper and manganese and the alpha amino acid is glutamic acid.
10. A neutral complex of claim 8 combined with a suitable animal feed carrier selected from the group consisting of aspartic acid and glutamic acid.
11. A neutral complex of claim 8 combined with a suitable animal feed carrier selected from the group consisting of zinc, copper and manganese and the alpha amino acid is glutamic acid.
12. A method of nutritional supplementation of animals, comprising: feeding a small but nutritional supplementation effective amount, a neutral complex of an essential trace element and a dicarboxylic alpha amino acid to an animal.
13. The method of claim 12 wherein the animal is a domesticated livestock or poultry animal.
14. A method of preparing a neutral complex of essential trace elements and a dicarboxylic alpha amino acid, comprising: mixing a water soluble monobasic and amino acid dicarboxylic acid with a water soluble metal salt of the trace element in salt form;
adjusting the pH to neutral in a manner to avoid formation of insoluble metal hydroxides;
and, quickly cooling the reactants to form small crystals of the neutral complexes.
CA2488696A 2002-10-16 2003-08-25 Metal complexes of alpha amino dicarboxylic acids Expired - Lifetime CA2488696C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/272,382 2002-10-16
US10/272,382 US7129375B2 (en) 2002-10-16 2002-10-16 Metal complexes of α amino dicarboxylic acids
PCT/US2003/026672 WO2004035524A1 (en) 2002-10-16 2003-08-25 Metal complexes of alpha amino dicarboxylic acids

Publications (2)

Publication Number Publication Date
CA2488696A1 true CA2488696A1 (en) 2004-04-29
CA2488696C CA2488696C (en) 2010-05-18

Family

ID=32092598

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2488696A Expired - Lifetime CA2488696C (en) 2002-10-16 2003-08-25 Metal complexes of alpha amino dicarboxylic acids

Country Status (22)

Country Link
US (3) US7129375B2 (en)
EP (1) EP1556336B1 (en)
JP (1) JP2006503092A (en)
KR (1) KR100609526B1 (en)
CN (1) CN1328245C (en)
AT (1) ATE420849T1 (en)
AU (1) AU2003262869B2 (en)
BR (1) BR0311654A (en)
CA (1) CA2488696C (en)
DE (1) DE60325878D1 (en)
DK (1) DK1556336T3 (en)
ES (1) ES2318199T3 (en)
HK (1) HK1073647A1 (en)
IL (1) IL164894A (en)
MX (1) MXPA05003809A (en)
NZ (1) NZ536677A (en)
PL (1) PL209541B1 (en)
PT (1) PT1556336E (en)
TR (1) TR200403625T2 (en)
TW (1) TWI298016B (en)
WO (1) WO2004035524A1 (en)
ZA (1) ZA200408841B (en)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7129375B2 (en) 2002-10-16 2006-10-31 Zinpro Corporation Metal complexes of α amino dicarboxylic acids
CN100549015C (en) * 2002-12-05 2009-10-14 Md白奥阿尔法有限公司 The preparation method of amino-acid chelate
KR100481326B1 (en) * 2004-06-22 2005-04-07 주식회사 동암비티 Producing process for organic chelate
US7687650B2 (en) 2006-02-03 2010-03-30 Jr Chem, Llc Chemical compositions and methods of making them
US7897800B2 (en) * 2006-02-03 2011-03-01 Jr Chem, Llc Chemical compositions and methods of making them
US20070269495A1 (en) * 2006-05-18 2007-11-22 Ashmead H Dewayne Compositions and methods for enhancing mineral levels in animals with reduced environmental impact
US7495117B2 (en) * 2006-08-04 2009-02-24 Kemin Industries, Inc. Metal carboxylate salts
US7341708B1 (en) 2006-10-20 2008-03-11 Oleksandr Miroshnychenko Methods for producing pure amino acid chelate complexes, and uses thereof
US20080096804A1 (en) * 2006-10-20 2008-04-24 Viva Pharmaceuticals Inc. Pure amino acid chelate complexes and uses thereof
BRPI0812774A2 (en) * 2007-06-06 2014-12-02 Novus Int Inc FOOD SUPPLEMENTS FOR PROMOTING GROWTH, REPAIR AND MAINTENANCE OF BONE AND JOINTS
US20160184354A1 (en) 2009-01-23 2016-06-30 Jr Chem, Llc Rosacea treatments and kits for performing them
CN101503415A (en) * 2009-03-10 2009-08-12 深圳市危险废物处理站有限公司 Preparation and use of amino acid chelated hydroxy copper chloride crystal
KR101828418B1 (en) * 2009-10-30 2018-02-12 아크조 노벨 케미칼즈 인터내셔널 비.브이. Use of a metal supplement in animal feed
CN101785534B (en) * 2010-03-12 2013-06-12 广州英赛特生物技术有限公司 Application of zinc glutamate and derivatives thereof as animal feed additive for promoting growth
CN101822316A (en) * 2010-03-12 2010-09-08 广州英赛特生物技术有限公司 Application of glutamic acid microelement chelate as animal feed additive
CN101756042B (en) * 2010-03-12 2012-07-04 广州英赛特生物技术有限公司 Application of cupric glutamate or derivatives thereof as feed additive for promoting animal growth
CN102578393A (en) * 2010-03-12 2012-07-18 广州英赛特生物技术有限公司 Use of cupric glutamate or derivative thereof as growth-promoting feed additive for animals
CN102578394A (en) * 2010-03-12 2012-07-18 广州英赛特生物技术有限公司 Application of cupric glutamate or derivative of cupric glutamate serving as feed additive for promoting animal growth
US8952057B2 (en) 2011-01-11 2015-02-10 Jr Chem, Llc Compositions for anorectal use and methods for treating anorectal disorders
US9149057B2 (en) * 2011-03-01 2015-10-06 Zinpro Corporation Enhanced bioavailable iodine molecules
US8741375B2 (en) 2011-06-07 2014-06-03 Zinpro Corporation Mixed amino acid metal salt complexes
FR2990205B1 (en) * 2012-05-02 2014-08-22 Pancosma S A ORGANOMETALLIC COMPLEX, POWDER FOR ANIMAL FEEDING AND METHODS OF PREPARATION
WO2014179353A1 (en) 2013-05-02 2014-11-06 Karandikar Bhalchandra M Antimicrobial compositions and methods of making the same
CN104326932A (en) * 2014-10-09 2015-02-04 中国食品发酵工业研究院 Method for low temperature solid-phase synthesis of zinc aspartate
CN104387143A (en) * 2014-10-16 2015-03-04 郑州瑞普生物工程有限公司 Copper ammonium citrate preparation method
CN104311317A (en) * 2014-10-16 2015-01-28 郑州瑞普生物工程有限公司 Preparation method of ammonia manganese citrate
CN104402750A (en) * 2014-12-09 2015-03-11 芜湖莱博生物医药有限公司 Dicarboxylic amino acid-chromium complex and preparation method thereof
EP3966193A4 (en) * 2019-06-05 2023-06-28 Asklepion Pharmaceuticals, LLC Improved method of synthesis and purification of citrulline
CN113170837A (en) * 2021-04-07 2021-07-27 彭险峰 Copper aspartate complex and application thereof
CN113666836A (en) * 2021-08-03 2021-11-19 四川吉隆达生物科技集团有限公司 Production process of feed-grade zinc glutamate
CA3233715A1 (en) * 2021-10-05 2023-04-13 I-Chen Li A cobalt-containing acidic amino acid complex and its use for treating cancer
CN113845435A (en) * 2021-10-14 2021-12-28 四川吉隆达生物科技集团有限公司 Production process of feed-grade manganese glutamate

Family Cites Families (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE535350A (en) 1954-02-01
US2810754A (en) 1955-06-29 1957-10-22 Gen Mills Inc Synthesis of l-glutamine from l-glutamic acid
US2915540A (en) 1955-06-29 1959-12-01 Gen Mills Inc Complexes of gamma glutamyl mono-esters
US3084189A (en) 1958-11-24 1963-04-02 Gen Mills Inc Nickel complex of glutamine dihydrate and method for purification of glutamine
GB994517A (en) 1961-06-21 1965-06-10 Ajinomoto Kk Process for resolving racemic glutamic acid
US3168541A (en) 1962-03-06 1965-02-02 Int Minerals & Chem Corp Ferrous glutamate
US3463858A (en) 1965-05-06 1969-08-26 Dean R Anderson Organic zinc feed additive and method of making same
IT943160B (en) 1971-02-19 1973-04-02 Rohm & Haas PRESSURE-SENSITIVE ADHESIVE SHEET WITHOUT SUPPORT AND SUBSTANTIVE THICKNESS ESPECIALLY FOR FIXING RIGID OBJECTS ON LARGER SURFACES
US3911117A (en) 1971-12-20 1975-10-07 Fredrik Ender Raw fish and iron chelated with glutamic or ribonucleic acid in a mink diet
US4021569A (en) 1973-08-20 1977-05-03 Zinpro Corporation Method of nutritional supplementation for zinc and methionine by ingesting 1:1 zinc methionine complexes
US4039681A (en) 1973-08-20 1977-08-02 Zinpro Corporation Zinc methionine complex for acne treatment
US3941818A (en) 1973-08-20 1976-03-02 Zinpro Corporation 1:1 Zinc methionine complexes
US3925433A (en) 1973-09-10 1975-12-09 Zinpro Corp 1:1 And 2:1 chromium, alpha amino acid complex salts
US3950372A (en) 1974-07-03 1976-04-13 Zinpro Corporation 1:1 Manganese alpha amino acid complexes
US4167564A (en) 1974-09-23 1979-09-11 Albion Laboratories, Inc. Biological assimilation of metals
US4067994A (en) 1976-03-26 1978-01-10 Zinpro Corporation Iron methionine complex salts
US4216144A (en) 1977-10-20 1980-08-05 Ashmead H H Soluble iron proteinates
US4216143A (en) 1977-10-20 1980-08-05 Ashmead H H Soluble non-ferrous metal proteinates
SE7903359L (en) 1978-04-20 1979-10-21 Johnson Matthey Co Ltd COMPOSITIONS CONTAINING PLATINUM
US5409905A (en) 1981-01-05 1995-04-25 Eby, Iii; George A. Cure for commond cold
US4425280A (en) 1981-03-30 1984-01-10 Ferro Corporation Metal amino acids
US4517330A (en) 1983-03-30 1985-05-14 Rohm And Haas Company Floor polish composition having improved durability
US4460734A (en) 1983-04-19 1984-07-17 Rohm And Haas Company Self-leveling floor polish compositions
JPS6078950A (en) * 1983-10-14 1985-05-04 フエルラーフアルム アルツナイミツテルフアブリーク アポテーケル ハー.ヤー.フオン エーリツヒ ゲゼルシヤフト ミツト ベシユレンクテル ハフツンク ウント コンパニー カーゲー Manufacture of aminodicarboxylic acid-divalent matal-halogencomplex salts and novel complex salts thereby
EP0183840B1 (en) * 1984-06-11 1994-03-02 GODFREY SCIENCE & DESIGN, INC. Improvement in the flavor of zinc supplements for oral use
US4599152A (en) 1985-05-24 1986-07-08 Albion Laboratories Pure amino acid chelates
US4670269A (en) 1985-06-26 1987-06-02 Zinpro Corporation Cobalt complexes and their use as nutritional supplements
DE3532860C1 (en) * 1985-09-14 1987-03-12 Blendax Werke Schneider Co Oral hygiene products
US4830716B1 (en) 1986-07-03 1999-12-07 Albion Int Preparation of pharmaceutical grade amino acid chelates
US4678854A (en) 1986-11-25 1987-07-07 Zinpro Corporation Cobalt complexes and their use as nutritional supplements
US4764633A (en) 1987-08-31 1988-08-16 Zinpro Corporation Ferric ion catalyzed complexation of zinc and/or manganese with alpha amino acids
US5061815A (en) 1988-07-06 1991-10-29 Zinpro Corporation Metal lysine complexes and method for producing metal lysine complexes
US4956188A (en) 1988-10-20 1990-09-11 Zinpro Corporation Copper complexes with alpha hydroxy organic acids and their use as nutritional supplements
US4948594A (en) 1989-01-03 1990-08-14 Zinpro Corporation Copper complexes of alpha-amino acids that contain terminal amino groups, and their use as nutritional supplements
US4900561A (en) 1989-01-03 1990-02-13 Zinpro Corporation Copper complexes of alpha-amino acids that contain terminal amino groups, and their use as nutritional supplements
HU207800B (en) * 1990-05-10 1993-06-28 Andras Sikter Process for producing composition for improving condition and for treating different illnesses
DE4028906A1 (en) 1990-09-12 1992-03-19 Paz Arzneimittelentwicklung MEDICINAL PRODUCTS AND THEIR PREPARATION AND THEIR USE IN THE CONTROL OF PAIN AND / OR DEFENSE AND / OR FEVER OF ANIMALS AND PEOPLE
JPH0578243A (en) 1990-12-11 1993-03-30 Shiseido Co Ltd Antipruritic agent and antipruritic composition
US5460972A (en) 1991-04-08 1995-10-24 Research Foundation Of The State University Of New York Ionized magnesium2+ concentrations in biological samples
US5278329A (en) 1992-02-21 1994-01-11 Zinpro Corporation L-form 1:1 metal methionine complexes
US5505968A (en) 1993-07-02 1996-04-09 Her Majesty The Queen In Right Of Canada, As Represented By The Department Of Agriculture Antemortem nutrient supplement for livestock
US5504055A (en) 1994-03-15 1996-04-02 J.H. Biotech, Inc. Metal amino acid chelate
IT1272994B (en) 1994-05-25 1997-07-01 Giampiero Valletta USE OF PRODUCTS CONTAINING MAGNESIUM IN THE THERAPY AND PROPHYLAXIS OF NEOPLASTIC DISEASES AND SELF-IMMUNITARY DISEASES.-
US6352713B1 (en) * 1999-12-01 2002-03-05 Drugtech Corporation Nutritional composition
US5516925A (en) 1994-08-23 1996-05-14 Albion International, Inc. Amino acid chelates having improved palatability
US5569458A (en) 1994-09-14 1996-10-29 Greenberg; Mike Nutritional formula
US5430164A (en) 1994-10-18 1995-07-04 Zinpro Corporation Enhanced solubilization of zinc and manganese methionine complex salts by addition of ferric ion
US5583243A (en) 1995-05-19 1996-12-10 Zinpro Corporation Salts of alpha-hydroxy aliphatic carboxylic acids and uses thereof
WO1997015201A1 (en) * 1995-10-27 1997-05-01 The Procter & Gamble Company Color stable iron, zinc and vitamin fortified dry drink mixes
US5698724A (en) 1996-04-30 1997-12-16 Zinpro Corporation Amino acid metal complexes using hydrolyzed protein as the amino acid source and methods re same
TW427911B (en) 1997-03-04 2001-04-01 Shiseido Co Ltd Water-in-oil type emulsified composition
US5885610A (en) 1997-03-04 1999-03-23 Zinpro Corporation By-pass rumen product
US6169118B1 (en) 1998-11-12 2001-01-02 Block Drug Company, Inc. Flavor blend for masking unpleasant taste of zinc compounds
US6242009B1 (en) 1999-04-20 2001-06-05 Kareem I. Batarseh Microbicidal formulations and methods to control microorganisms
US6126928A (en) 1999-08-24 2000-10-03 The Procter & Gamble Company Compositions containing solubilized, acid-enhanced antiperspirant active
US6166071A (en) 2000-03-13 2000-12-26 Albion International, Inc. Zinc amino acid chelates having ligands comprised of glycine and a sulfur-containing amino acids
US6323354B1 (en) 2001-03-16 2001-11-27 Agri-Nutrients Technology Group, Inc. Amino acid chelates from lipoproteins
US7129375B2 (en) 2002-10-16 2006-10-31 Zinpro Corporation Metal complexes of α amino dicarboxylic acids

Also Published As

Publication number Publication date
KR20050037437A (en) 2005-04-21
DE60325878D1 (en) 2009-03-05
KR100609526B1 (en) 2006-08-08
US7141689B2 (en) 2006-11-28
EP1556336A1 (en) 2005-07-27
PL373067A1 (en) 2005-08-08
DK1556336T3 (en) 2009-04-14
ES2318199T3 (en) 2009-05-01
BR0311654A (en) 2005-03-15
JP2006503092A (en) 2006-01-26
TW200410639A (en) 2004-07-01
ATE420849T1 (en) 2009-01-15
US20040097748A1 (en) 2004-05-20
CA2488696C (en) 2010-05-18
US7220426B2 (en) 2007-05-22
WO2004035524A1 (en) 2004-04-29
NZ536677A (en) 2006-10-27
TR200403625T2 (en) 2005-04-21
AU2003262869A1 (en) 2004-05-04
AU2003262869B2 (en) 2006-11-23
IL164894A0 (en) 2005-12-18
HK1073647A1 (en) 2005-10-14
IL164894A (en) 2010-05-17
PT1556336E (en) 2009-04-08
CN1328245C (en) 2007-07-25
TWI298016B (en) 2008-06-21
US20040077714A1 (en) 2004-04-22
MXPA05003809A (en) 2005-06-08
US7129375B2 (en) 2006-10-31
CN1668577A (en) 2005-09-14
ZA200408841B (en) 2006-01-25
PL209541B1 (en) 2011-09-30
US20040096482A1 (en) 2004-05-20
EP1556336B1 (en) 2009-01-14

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