JP2010507630A - 2−ヒドロキシ−4−メチルセレノ酪酸単独の製造方法、又はその硫黄含有アナログとの混合物としての製造方法、及びそれらの栄養食品としての使用、特に動物用の栄養食品としての使用 - Google Patents
2−ヒドロキシ−4−メチルセレノ酪酸単独の製造方法、又はその硫黄含有アナログとの混合物としての製造方法、及びそれらの栄養食品としての使用、特に動物用の栄養食品としての使用 Download PDFInfo
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- JP2010507630A JP2010507630A JP2009533870A JP2009533870A JP2010507630A JP 2010507630 A JP2010507630 A JP 2010507630A JP 2009533870 A JP2009533870 A JP 2009533870A JP 2009533870 A JP2009533870 A JP 2009533870A JP 2010507630 A JP2010507630 A JP 2010507630A
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005891 transamination reaction Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
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- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- A23L33/16—Inorganic salts, minerals or trace elements
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- A—HUMAN NECESSITIES
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/04—Sulfur, selenium or tellurium; Compounds thereof
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Abstract
【選択図】なし
Description
式(II):
式(I):
で予期された化合物を導く工程を含むことで、特徴付けられる。
式(II)の2−ヒドロキシ−4−メチルセレノブチロニトリル及び式(IIa)の2−ヒドロキシ−4−メチルチオブチロニトリル:
式(I)の3−メチルセレノプロピオンアルデヒド及び式(Ia)の3−メチルチオプロピオンアルデヒド(3−methylthioprionaldehyde):
*水溶液、アルコール溶液、又は油剤、
*水/油又は油/水エマルジョン、マイクロエマルジョン、
*水性ゲル、
*ビヒクル、マイクロカプセル、マイクロ粒子又はナノ粒子の分散物、
*ビタミン類、天然の抗酸化剤、鉱物塩類、単糖類、二糖類又は多糖類、特に葉酸、ビタミンB6、E又はC、ラクトース、デンプン、から選択されてもよい、1種以上の添加物及び/又は賦形剤からなる固形溶媒。上記に定義した1種以上の添加物及び/又は賦形剤を含んでなる、そして一般式(I)の少なくとも一つの化合物を含む、この固形溶媒は、ゼラチンカプセル剤、錠剤又は粉末剤として製剤化されてもよい。これらの組成物の、式(IV)及び(IVa)の化合物以外の異なる構成成分の量は、種々の適用で示されたように通常使用されている量である。
−L(+)−セレノメチオニン前駆体。直接、あるいは酵素的加水分解後いずれかの、インビボにおける酸化及びトランスアミノ化;
あるいは:
−セレンの部分的又は全体的な欠乏を補完するためのセレン源として;
あるいは:
−動物(特に、ウシ、ヒツジ、ブタ、ウマ、ネコ及びイヌ並びに家畜)食品用の栄養組成物を製造するための食品成分、食品補完物又は食品添加物として。
Rf(SiO2,シクロヘキサン/酢酸エチル、50/50):0.22.
RMN−1H(CDCl3,300MHz):
δ(ppm)=2.06(s,3H);2.27(m,2H);2.73(m,2H);3.20(bs,1H,OH);4.74(t,J=8Hz,α−H).
MS(IE,70eV):m/z(%)=179(80,M+);164(90);153(100);123(50);109(80).
Rf(SiO2,シクロヘキサン/酢酸エチル、50/50+1%CF3COOH):0.26.
RMN−1H(CDCl3,300MHz):
δ(ppm)=2.02(s,3H,SeCH3);2.08(m,1H);2.22(m,1H);2.70(m(sym.),2H);4.41(dd,J=8Hz,J=4Hz,1H,α−H).
Rf(SiO2,シクロヘキサン/メタノール、90/10):0.13.
RMN−1H(CDCl3,300MHz):
δ(ppm)=2.06(s,3H,SeCH3);2.08(m,1H);2.30(m,1H);2.75(m(sym.),2H);3.25(bs,1H,OH);4.36(dd,J=8Hz,J=4Hz,1H,α−H);5.5(bs,1H,NH2);
6.5(bs,1H,NH2).
MS(IC,NH):m/z(%)=215(40,M+NH4)+;198(100,M+H)+;181(20);102(25).
RMN−1H(CDCl3,300MHz):
δ(ppm)=2.06(s,SeCH3);2.16(s,SCH3),2.10−2.35(m);2.50−2.65(m);2.64−2.90(m);3.20(bs,OH);4.74(t,J=8Hz,2−H,Se混成);4.76(t,J=8Hz,2−H,S混成).
ES(LC−MS):tR=1.69分:148.9(M[C5H10O3S]−H+);
tR=2.24分:196.8(M[C5H10O3Se]−H+).
L−2−ヒドロキシ−4−メチルセレノ酪酸 0.2mg
L−2−ヒドロキシ−4−メチルチオ酪酸 200mg
賦形剤*及び外皮**
合計1000mgのゼラチンカプセル
(*コーンスターチ、ラクトース、ステアリン酸マグネシウム、ラウリル硫酸ナトリウム、
**ゼラチン、二酸化チタン、着色剤)。
L−2−ヒドロキシ−4−メチルセレノ酪酸 0.05mg
L−2−ヒドロキシ−4−メチルチオ酪酸 50mg
賦形剤*及び外皮**
合計1000mgのゼラチンカプセル
(*コーンスターチ、ラクトース、ステアリン酸マグネシウム、ラウリル硫酸ナトナトリウム、
**ゼラチン、二酸化チタン、着色剤)。
L−2−ヒドロキシ−4−メチルセレノ酪酸 10mg
L−2−ヒドロキシ−4−メチルチオ酪酸 10g
水 合計1000mL
Claims (13)
- 以下の工程を含むことを特徴とする、2−ヒドロキシ−4−メチルセレノ酪酸の製造方法:
(式(II):
の化合物である、2−ヒドロキシ−4−メチルセレノブチロ−ニトリルを導くために、
式(I):
の3−メチルセレノプロピオンアルデヒドを、プロトン性極性溶媒中、好ましくは式M+HSO3 −(式中、Mは、アルカリ金属原子を表す)の亜硫酸水素アルカリの存在下で、式M+CN−(式中、Mは、アルカリ金属原子を表す)のシアン化アルカリと反応させる工程、
式(II)の化合物を、プロトン性極性溶媒中、熱濃強酸溶媒で加水分解して、式(IV)で予期された化合物を導く工程:
(ここで、生理学的に許容可能な塩基を添加した後に、その塩のうちの一つに転換されていてもよい))。 - 請求項1に記載の製造方法であって、式(II)の化合物が、式(III):
の化合物を導くために、プロトン性極性溶媒中、熱濃硫酸溶媒で加水分解され、式(III)の化合物は、それ自身が熱濃強酸溶媒で加水分解して、式(IV)の化合物を導くことを特徴とする方法。 - シアン化アルカリ試薬が、シアン化ナトリウム、シアン化カリウム、及びシアン化リチウムから選択されることを特徴とする、請求項1又は2のいずれか一項に記載の方法。
- プロトン性極性溶媒が水であることを特徴とする、請求項1から3のいずれか一項に記載の製造方法。
- 2−ヒドロキシ−4−メチルセレノ酪酸及び2−ヒドロキシ−4−メチルチオ酪酸の混合物の製造方法であって、以下の工程:
式(II)の2−ヒドロキシ−4−メチルセレノブチロニトリル及び式(IIa)の2−ヒドロキシ−4−メチルチオブチロニトリル:
の混合物を導くために、
式(I)の3−メチルセレノ−プロピオンアルデヒド及び式(Ia)の3−メチル−チオプロピオンアルデヒド:
の混合物を、プロトン性極性溶媒中、好ましくは式M+HSO3 −(式中、Mは、アルカリ金属原子を表す)の亜硫酸水素アルカリの存在下、式M+CN−(式中、Mは、アルカリ金属原子を表す)のシアン化アルカリと反応させる工程、
式(II)及び式(IIa)の化合物を、プロトン性極性溶媒中、熱濃強酸溶媒で加水分解して、式(IV)及び(IVa):
(ここで、生理学的に許容可能な塩基を添加した後に、これらの塩の混合物に転換されていてもよい)で予期された化合物である、2つの化合物の混合物を導く工程
(化合物(IV)及び(IVa)両方の相対割合については、当該方法の最初に、化合物(I)及び(Ia)の相対量により設定されており、前記製造方法の全体にわたって変わりないことが理解される)を含むことを特徴とする、方法。 - シアン化アルカリ試薬が、シアン化ナトリウム、シアン化カリウム及びシアン化リチウムから選択されることを特徴とする、請求項5に記載の方法。
- プロトン性極性溶媒が水であることを特徴とする、請求項5又は6のいずれか一項に記載の製造方法。
- 化合物(IV)及び化合物(IVa)の比率が、0.01重量%〜1.0重量%の間であり、好ましくは0.05重量%〜0.5重量%の間で変化することを特徴とする、請求項5から7のいずれか一項に記載の製造方法。
- 式(II):
の2−ヒドロキシ−4−メチルセレノブチロニトリル化合物、並びにそのエナンチオマー。 - ヒト又は動物における、セレノメチオニン及び/又はセレン源としての、請求項9に定義した式(II)の化合物、あるいはそのエナンチオマーの使用。
- 活性成分としての、式(IV)の2−ヒドロキシ−4−メチルセレノ酪酸及び式(IVa)の2−ヒドロキシ−4−メチルチオ酪酸の混合物、並びに生理学的に許容可能な溶媒を含む、栄養組成物。
- 化合物(IV)及び化合物(IVa)間の比率が、0.01重量%〜1.0重量%の間であり、好ましくは0.05重量%〜0.5重量%の間で変化することを特徴とする、請求項11に記載の組成物。
- 食品成分、食品補完物又は食品添加物としての、式(IV)の2−ヒドロキシ−4−メチルセレノ酪酸及び式(IVa)の2−ヒドロキシ−4−メチルチオ酪酸の混合物の使用。
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FR0609451A FR2907785B1 (fr) | 2006-10-27 | 2006-10-27 | Procede de preparation de l'acide 2-hydroxy-4-methylselenobutyrique, seul ou en melange avec son analogue soufre, ainsi que leurs utilisations en nutrition, en particulier en nutrition animale |
PCT/EP2007/061567 WO2008049927A1 (fr) | 2006-10-27 | 2007-10-26 | Procédé de préparation de l'acide 2-hydroxy-4-méthylsélénobutyrique, seul ou en mélange avec son analogue soufré, ainsi que leurs utilisations en nutrition, en particulier en nutrition animale |
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US20100055291A1 (en) | 2010-03-04 |
ES2399360T3 (es) | 2013-03-27 |
EP2089405A1 (fr) | 2009-08-19 |
RU2009118374A (ru) | 2010-12-10 |
KR20090086082A (ko) | 2009-08-10 |
FR2907785A1 (fr) | 2008-05-02 |
CN101573367A (zh) | 2009-11-04 |
US8309763B2 (en) | 2012-11-13 |
WO2008049927A1 (fr) | 2008-05-02 |
KR101440979B1 (ko) | 2014-09-17 |
JP5350256B2 (ja) | 2013-11-27 |
EP2089405B1 (fr) | 2012-11-28 |
RU2453537C2 (ru) | 2012-06-20 |
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