JP4458893B2 - Process for producing purified egg yolk phospholipid composition, and pharmaceutical composition, cosmetic composition, or food composition using the same - Google Patents
Process for producing purified egg yolk phospholipid composition, and pharmaceutical composition, cosmetic composition, or food composition using the same Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims description 149
- 239000008345 purified egg yolk phospholipid Substances 0.000 title claims description 67
- 238000000034 method Methods 0.000 title claims description 19
- 235000013305 food Nutrition 0.000 title claims description 18
- 239000002537 cosmetic Substances 0.000 title claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 166
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 67
- 150000003904 phospholipids Chemical class 0.000 claims description 35
- 210000002969 egg yolk Anatomy 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 239000008344 egg yolk phospholipid Substances 0.000 claims description 24
- 229940068998 egg yolk phospholipid Drugs 0.000 claims description 24
- 238000005406 washing Methods 0.000 claims description 20
- 102000002322 Egg Proteins Human genes 0.000 claims description 18
- 108010000912 Egg Proteins Proteins 0.000 claims description 18
- 235000013345 egg yolk Nutrition 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 238000002835 absorbance Methods 0.000 claims description 12
- 238000000746 purification Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 8
- 230000000052 comparative effect Effects 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000002960 lipid emulsion Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 235000015872 dietary supplement Nutrition 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004375 Dextrin Substances 0.000 description 3
- 229920001353 Dextrin Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 235000019425 dextrin Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 2
- 102000011632 Caseins Human genes 0.000 description 2
- 108010076119 Caseins Proteins 0.000 description 2
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 102000015439 Phospholipases Human genes 0.000 description 2
- 108010064785 Phospholipases Proteins 0.000 description 2
- -1 Polyoxyethylene Polymers 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 108010046377 Whey Proteins Proteins 0.000 description 2
- 102000007544 Whey Proteins Human genes 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 235000010350 erythorbic acid Nutrition 0.000 description 2
- 239000004318 erythorbic acid Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229940026239 isoascorbic acid Drugs 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 235000021119 whey protein Nutrition 0.000 description 2
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940093430 polyethylene glycol 1500 Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080237 sodium caseinate Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000020712 soy bean extract Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000013547 stew Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Landscapes
- General Preparation And Processing Of Foods (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Description
本発明は、簡便な方法で色調が改善された精製卵黄リン脂質組成物の製造方法、及びこれを用いた医薬品組成物、化粧品組成物、又は食品組成物に関する。 The present invention relates to a method for producing a purified egg yolk phospholipid composition whose color tone has been improved by a simple method, and a pharmaceutical composition, cosmetic composition, or food composition using the same.
精製卵黄リン脂質組成物は医薬品用添加物として、例えば静脈投与に供する脂肪乳剤製剤用の乳化剤として、また化粧品原料として、例えば乳液等の皮膚用化粧料の乳化剤として用いられている。また食品原料や食品添加物として広く加工食品に用いられている。しかし、従来より使用されている精製卵黄リン脂質組成物は卵黄由来の色素が残存し、一般的には黄色味を帯びた色調を呈している。従って精製卵黄リン脂質組成物を配合することにより特に透明もしくは白色の医薬品組成物、化粧品組成物、食品組成物は精製卵黄リン脂質組成物由来の色調を帯びるという不都合が生じた。 The purified egg yolk phospholipid composition is used as a pharmaceutical additive, for example, as an emulsifier for fat emulsion preparations for intravenous administration, and as a cosmetic raw material, for example, as an emulsifier for skin cosmetics such as emulsions. It is also widely used in processed foods as food ingredients and food additives. However, conventionally used purified egg yolk phospholipid compositions have yolk-derived pigments remaining and generally have a yellowish color tone. Therefore, by blending the purified egg yolk phospholipid composition, in particular, a transparent or white pharmaceutical composition, cosmetic composition, or food composition has a disadvantage that it has a color tone derived from the purified egg yolk phospholipid composition.
この問題を解決する方法として特許文献１（特開昭５５−５７５９５号公報）には、リン脂質組成物を製造するに際し、大豆抽出油滓をアスコルビン酸又はエリソルビン酸の水溶液で洗浄することによりリン脂質組成物の風味及び色を改善する方法が開示されている。
しかしアスコルビン酸又はエリソルビン酸の水溶液を添加するとこれらを完全に除去することは困難で、得られるリン脂質組成物に残存することにより、リン脂質組成物のｐHや乳化特性に影響を及ぼすという課題があった。
As a method for solving this problem, Patent Document 1 (Japanese Patent Application Laid-Open No. 55-57595) discloses that when producing a phospholipid composition, a soybean extract oil cake is washed with an aqueous solution of ascorbic acid or erythorbic acid. A method for improving the flavor and color of a lipid composition is disclosed.
However, when an aqueous solution of ascorbic acid or erythorbic acid is added, it is difficult to completely remove them, and there is a problem that the pH and emulsification characteristics of the phospholipid composition are affected by remaining in the resulting phospholipid composition. there were.
この他にも、リン脂質組成物の色調を改善する方法として、活性炭を接触させ、色素を吸着させることにより脱色する方法が知られているが、吸着後の活性炭を製品に混入することなく完全に除去するには、高度なろ過技術を要するという問題がある。
本発明は、簡便な方法で色調が改善された、精製卵黄リン脂質組成物の製造方法、及びこの精製卵黄リン脂質組成物を含有する医薬品組成物、化粧品組成物、又は食品組成物を提供することを目的とする。 The present invention provides a method for producing a purified egg yolk phospholipid composition whose color tone is improved by a simple method, and a pharmaceutical composition, cosmetic composition, or food composition containing the purified egg yolk phospholipid composition. For the purpose.
本発明者は、上記目的を達成すべく精製工程の様々な諸条件について鋭意研究を重ねた結果、精製工程において通常洗浄に用いていたアセトンに単に水を添加することにより、つまりは含水アセトンにより洗浄することにより、容易に色調が改善された精製卵黄リン脂質組成物が得られることを見出し、本発明を完成するに至った。 As a result of intensive research on various conditions of the purification process in order to achieve the above-mentioned object, the present inventor simply added water to acetone that was normally used for washing in the purification process, that is, with water-containing acetone. It has been found that a purified egg yolk phospholipid composition having an improved color tone can be easily obtained by washing, and the present invention has been completed.
すなわち、本発明は、
（１）卵黄から抽出して得られる粗製卵黄リン脂質組成物を更に精製する精製卵黄リン脂質組成物の製造方法であって、前記精製工程において、以下の工程を少なくとも含み、含水アセトンの含水含量が０．３〜６容量％であることを特徴とする精製卵黄リン脂質組成物の製造方法、
粗製卵黄リン脂質組成物を含水アセトンで処理し、得られたアセトン不溶物から含水アセトンを除去する、含水アセトン洗浄工程
（２）乾燥卵黄からアルコールで抽出し、その抽出液からアルコールを除去して得られる粗製卵黄リン脂質組成物を更に精製する精製卵黄リン脂質組成物の製造方法であって、前記精製工程において、以下の工程を少なくとも含み、含水アセトンの含水含量が０．３〜６容量％であることを特徴とする精製卵黄リン脂質組成物の製造方法、
粗製卵黄リン脂質組成物を含水アセトンで処理し、得られたアセトン不溶物から含水アセトンを除去する、含水アセトン洗浄工程
（３）得られた精製卵黄リン脂質組成物１質量部をクロロホルム１０容量部に溶解した際の波長４５５ｎｍでの吸光度が０．３以下である（１）又は（２）の精製卵黄リン脂質組成物の製造方法、
（４）前記含水アセトンの洗浄工程を、２回以上行う（１）乃至（３）のいずれかの精製卵黄リン脂質組成物の製造方法、
（５）（１）乃至（４）のいずれかに記載の製造方法で得られる精製卵黄リン脂質組成物を配合させる医薬品組成物の製造方法
（６）（１）乃至（４）のいずれかに記載の製造方法で得られる精製卵黄リン脂質組成物を配合させる化粧品組成物の製造方法、
（７）（１）乃至（４）のいずれかに記載の製造方法で得られる精製卵黄リン脂質組成物を配合させる食品組成物の製造方法、
である。
That is, the present invention
(1) A method for producing purified egg yolk phospholipid composition further purification the crude yolk phospholipid composition obtained by extracting from egg yolk, in the purification step, at least viewed including the steps of hydrous aqueous acetone A method for producing a purified egg yolk phospholipid composition, wherein the content is 0.3 to 6% by volume ,
A crude egg yolk phospholipid composition is treated with water-containing acetone, and water-containing acetone is removed from the obtained acetone insoluble matter. Water-containing acetone washing step (2) Extraction from dried egg yolk with alcohol and alcohol is removed from the extract crude yolk phospholipid composition obtained by a method of manufacturing a purified egg yolk phospholipid composition purified in the purification step, the following steps at least seen including, water content of the hydrous acetone 0.3 to 6 volume %, A method for producing a purified egg yolk phospholipid composition,
A crude egg yolk phospholipid composition is treated with water-containing acetone, and water-containing acetone is removed from the obtained acetone insoluble matter. Water-containing acetone washing step (3) 1 part by mass of the purified egg yolk phospholipid composition obtained is 10 parts by volume of chloroform. (1) or (2) a method for producing a purified egg yolk phospholipid composition having an absorbance at a wavelength of 455 nm of 0.3 or less when dissolved in
( 4 ) The method for producing a purified egg yolk phospholipid composition according to any one of (1) to ( 3 ), wherein the washing step of the water-containing acetone is performed twice or more,
(5) (1) through any of a method of manufacturing a pharmaceutical composition for blending the purified yolk phospholipid composition obtained by the production method according to any one of (4) (6) (1) to (4) A method for producing a cosmetic composition comprising a purified egg yolk phospholipid composition obtained by the production method described above ,
(7) (1) to (4) a method of manufacturing a food composition for blending the purified yolk phospholipid composition obtained by the production method according to any one of,
It is.
本発明の製造方法は、従来製造方法で行われたアセトンによる洗浄工程において、アセトンに単に水を添加した含水アセトンを用いることで、精製卵黄リン脂質組成物の色調を容易に改善させることから簡便性に優れている。また、本発明により得られる精製卵黄リン脂質組成物は、色調が改善された精製卵黄リン脂質組成物であるため、医薬品組成物、化粧品組成物、又は食品組成物の原料として使用した場合、各製品本来の色調を損なうことなく、良好な色調の医薬品組成物、化粧品組成物、又は食品組成物を提供することを可能とするため、精製卵黄リン脂質組成物及びその用途の更なる利用拡大が期待される。 The production method of the present invention is simple because it can easily improve the color tone of the purified egg yolk phospholipid composition by using water-containing acetone obtained by simply adding water to acetone in the washing step with acetone performed in the conventional production method. Excellent in properties. Moreover, since the purified egg yolk phospholipid composition obtained by the present invention is a purified egg yolk phospholipid composition having an improved color tone, when used as a raw material for a pharmaceutical composition, a cosmetic composition, or a food composition, In order to make it possible to provide a pharmaceutical composition, cosmetic composition, or food composition having a good color without impairing the original color of the product, further expansion of the use of the purified egg yolk phospholipid composition and its application Be expected.
以下本発明を詳細に説明する。
本発明は、精製卵黄リン脂質組成物を得るために、原料である卵黄リン脂質を含有する卵黄から抽出して得られる粗製卵黄リン脂質組成物を精製する際、含水アセトンで処理して得られるアセトン不溶物から含水アセトンを除去する、含水アセトン洗浄工程を少なくとも含むことを特徴とする。
The present invention will be described in detail below.
The present invention is obtained by treating with water-containing acetone when purifying a crude egg yolk phospholipid composition obtained by extraction from egg yolk containing egg yolk phospholipid as a raw material in order to obtain a purified egg yolk phospholipid composition. It includes at least a water-containing acetone washing step for removing water-containing acetone from the acetone insoluble matter.
本発明において「精製卵黄リン脂質組成物」とは、卵黄由来のリン脂質、又は当該リン脂質のリン酸基に結合した塩基を交換あるいは除いたリン脂質、例えばホスファチジルコリン、ホスファチジルエタノールアミン、ホスファチジルイノシトール、ホスファチジルセリン、ホスファチジン酸、これらのリゾ化物、およびスフィンゴミエリン等の１種又は２種以上を主成分とするもので、前記リン脂質含有率が８０質量％以上の組成物をいい、その他の成分として中性脂質やコレステロール等を含むこともある。
前記リン脂質含有率は、精製卵黄リン脂質組成物をＴＬＣ−ＦＩＤ法にて測定し、求める。つまり、イアトロスキャン（ＴＨ−１０：(株)三菱化学ヤトロン製）を用い、得られた精製卵黄リン脂質組成物の試料０．１ｇをクロロホルム：メタノール（２：１）溶液に溶解し、これをクロマロッドにインジェクションし、クロロホルム：メタノール：水（７０：３０：３）溶液で展開し乾燥後、次にヘキサン：ジエチルエーテル：蟻酸（９０：１０：０．１）溶液で展開する。これをスキャンスピード３０にて脂質組成の分析を行い、リン脂質含有率を算出する。
In the present invention, the term “purified egg yolk phospholipid composition” means phospholipid derived from egg yolk, or a phospholipid obtained by exchanging or excluding the base bound to the phosphate group of the phospholipid, such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, One or two or more of phosphatidylserine, phosphatidic acid, lysates thereof, sphingomyelin, etc. as a main component, refers to a composition having a phospholipid content of 80% by mass or more, and other components May contain neutral lipids and cholesterol.
The phospholipid content is determined by measuring the purified egg yolk phospholipid composition by the TLC-FID method. That is, 0.1 g of the obtained purified egg yolk phospholipid composition sample was dissolved in chloroform: methanol (2: 1) solution using Iatroscan (TH-10: Mitsubishi Chemical Yatron Co., Ltd.) Is injected into a chroma rod, developed with a chloroform: methanol: water (70: 30: 3) solution, dried, and then developed with a hexane: diethyl ether: formic acid (90: 10: 0.1) solution. This is analyzed for the lipid composition at a scan speed of 30, and the phospholipid content is calculated.
原料として使用する「卵黄」としては、鶏卵等鳥類の卵から分別され得られる未加工の生卵黄、保存を考慮した冷凍卵黄、乾燥卵黄、プロテアーゼやホスフォリパーゼ等で処理した酵素処理卵黄、又はコレステロール含有量を低減させるため超臨界ガス抽出法により処した卵黄等が挙げられる。特に本発明を実施するにあたり、原料の卵黄の水分含量が小さいほど抽出溶剤の量が低減され、また抽出溶剤を効率よく除去できるため、乾燥卵黄を用いることが好ましい。「乾燥卵黄」とは水分含量５質量％以下であって、スプレードライ法、フリーズドライ法、ドラムドライ法、真空連続乾燥法等により食品工業的に製されるものをいい、前処理としてプロテアーゼやホスフォリパーゼ等での処理、コレステロール含有量を低減させるため超臨界ガス抽出等を行っても良い。 As the “yolk” used as a raw material, raw raw egg yolk obtained by separation from avian eggs such as chicken eggs, frozen egg yolk, dried egg yolk considered for storage, enzyme-treated egg yolk treated with protease or phospholipase, or Examples include egg yolk treated by a supercritical gas extraction method to reduce the cholesterol content. In particular, when the present invention is carried out, it is preferable to use dry egg yolk because the lower the moisture content of the raw material egg yolk, the more the amount of extraction solvent is reduced and the extraction solvent can be removed efficiently. “Dried egg yolk” refers to those having a water content of 5% by mass or less and manufactured in the food industry by spray drying, freeze drying, drum drying, continuous vacuum drying, etc. Treatment with phospholipase or the like, supercritical gas extraction or the like may be performed to reduce the cholesterol content.
「アルコール」とはメタノール、エタノール、イソプロピルアルコール等が挙げられるが、食品用途に使用されることを考慮するとエタノールが好ましい。また、本発明においては蒸留水等工業用に用いることのできる水を混合した含水アルコールも「アルコール」に含まれ、アルコールの含水率を変えることにより、得られる粗製の卵黄リン脂質組成物のリン脂質含量を調節することができるため、通常目的に応じた含水率の含水アルコールが用いられる。 Examples of the “alcohol” include methanol, ethanol, isopropyl alcohol and the like, and ethanol is preferable in consideration of use in food applications. In the present invention, water-containing alcohol mixed with water that can be used for industrial purposes such as distilled water is also included in the “alcohol”, and the phosphorous content of the crude egg yolk phospholipid composition obtained by changing the water content of the alcohol. Since the lipid content can be adjusted, a water-containing alcohol having a water content according to the purpose is usually used.
「含水アセトン」とはアセトンに、蒸留水等工業用に用いることのできる水を混合したもので、水の配合割合は、得られる精製卵黄リン脂質組成物の色調改善効果から、好ましくは０．３〜６容量％、より好ましくは０．５〜４容量％、最も好ましくは０．８〜２．５容量％である。 “Water-containing acetone” is a mixture of acetone and water that can be used for industrial purposes such as distilled water. The blending ratio of water is preferably from the viewpoint of the color tone improving effect of the obtained purified egg yolk phospholipid composition. It is 3 to 6% by volume, more preferably 0.5 to 4% by volume, and most preferably 0.8 to 2.5% by volume.
「吸光度」の測定においては、精製卵黄リン脂質組成物特有の黄色の色調を評価するため、波長４５５ｎｍでの吸光度を測定し、色調評価の方法とした。
つまり、得られた精製卵黄リン脂質組成物１質量部を１０容量部のクロロホルムに溶解し、実際には試料１ｇを１０ｍｌのクロロホルムに溶解し、メンブレンフィルターＦＲ−４０（フジフィルム(株)製）にてろ過後、クロロホルムをブランクとして、吸光度計にて吸光度（OD４５５ｎｍ）を測定する。
In the measurement of “absorbance”, in order to evaluate the yellow color tone peculiar to the purified egg yolk phospholipid composition, the absorbance at a wavelength of 455 nm was measured and used as a color tone evaluation method.
That is, 1 part by mass of the obtained purified egg yolk phospholipid composition was dissolved in 10 parts by volume of chloroform, and actually 1 g of a sample was dissolved in 10 ml of chloroform, and membrane filter FR-40 (manufactured by Fuji Film Co., Ltd.) After filtration, the absorbance (OD455 nm) is measured with an absorptiometer using chloroform as a blank.
次に本発明の代表的な製造方法について詳述する。尚、本発明はこれに限定するものではない。
乾燥卵黄（卵黄液をスプレードライにて乾燥して得られる、水分含量４質量％のもの）１質量部に対し、５〜１０容量部の含水エタノール（水分含量１〜１０容量％）を加え、ホモミクサー等の高回転可能な攪拌装置を用い攪拌する。これをろ過による固液分離後、ろ液より減圧蒸留装置を用い溶剤を除去し、粗製の原料卵黄リン脂質組成物を得る。
この粗製の原料卵黄リン脂質組成物１質量部に対し、２〜５容量部の含水アセトン（含水率０．３〜６容量％）を仕込み、ホモミクサー等で均質に分散後、静置することによりリン脂質組成物を沈殿させ、上澄みの溶媒を除去する。さらに精製するためにはこの工程を繰り返すことが効果的である。この間極性溶媒例えばメタノール、エタノール、ジクロロメタン、また非極性溶媒ｎ−ペンタン、ｎ−ヘキサン、クロロホルム、酢酸エチル、エーテル、あるいはこれらの混合物等に溶解し、精密ろ過を行えば更に効果的である。この場合最後に濃縮を行い、濃縮物を同様の方法で含水アセトンによる洗浄を行い、真空下で脱溶剤することにより、精製した原料卵黄リン脂質組成物を得る。
Next, a typical production method of the present invention will be described in detail. Note that the present invention is not limited to this.
5 to 10 parts by volume of water-containing ethanol (water content 1 to 10% by volume) is added to 1 part by weight of dried egg yolk (obtained by drying the egg yolk liquid by spray drying and having a water content of 4% by weight), Stir using a stirrer capable of high rotation such as a homomixer. After the solid-liquid separation by filtration, the solvent is removed from the filtrate using a vacuum distillation apparatus to obtain a crude raw material egg yolk phospholipid composition.
By charging 2 to 5 parts by volume of water-containing acetone (water content 0.3 to 6% by volume) with respect to 1 part by mass of this crude raw material egg yolk phospholipid composition, and dispersing the mixture homogenously with a homomixer, etc. The phospholipid composition is precipitated and the supernatant solvent is removed. It is effective to repeat this process for further purification. During this time, it is more effective if it is dissolved in a polar solvent such as methanol, ethanol, dichloromethane or a nonpolar solvent n-pentane, n-hexane, chloroform, ethyl acetate, ether, or a mixture thereof and subjected to microfiltration. In this case, concentration is finally performed, the concentrate is washed with water-containing acetone in the same manner, and the solvent is removed under vacuum to obtain a purified raw material egg yolk phospholipid composition.
また、本発明は上述した製造方法で得られた精製卵黄リン脂質組成物を含有する医薬品組成物、化粧品組成物、又は食品組成物である。具体的には、例えば脂肪乳剤やリポ化製剤等の医薬品組成物、皮膚用乳液やスキンクリーム等の化粧品組成物、ココアやホワイトシチュー、流動食等の食品組成物、もしくはこれらを製するための中間原料も各組成物に含まれる。
上述した製造方法で得られた精製卵黄リン脂質組成物は、色調が改善されていることから、前記各組成物は、製品本来の色調を損なうことなく良好な色調の組成物が得られる。
Moreover, this invention is a pharmaceutical composition, a cosmetic composition, or a food composition containing the refined egg yolk phospholipid composition obtained by the manufacturing method mentioned above. Specifically, for example, a pharmaceutical composition such as a fat emulsion or a lipogenized preparation, a cosmetic composition such as a skin emulsion or skin cream, a food composition such as cocoa, white stew, or liquid food, or for producing these Intermediate materials are also included in each composition.
Since the color tone of the purified egg yolk phospholipid composition obtained by the above-described production method is improved, a composition having a good color tone can be obtained without impairing the original color tone of the product.
以下、本発明の精製卵黄リン脂質組成物の製造方法及びこれを用いた各組成物について、実施例及び試験例に基づき具体的に説明する。尚、本発明はこれら実施例及び試験例に限定するものではない。 Hereinafter, the manufacturing method of the refined egg yolk phospholipid composition of this invention and each composition using the same are demonstrated concretely based on an Example and a test example. The present invention is not limited to these examples and test examples.
［実施例１］
乾燥卵黄（卵黄液をスプレードライにて乾燥させて得られる、水分含量３質量％のもの）より含水エタノール（水分含量５容量％）を用い抽出し、粗製卵黄リン脂質組成物を得た。
これにはリン脂質が総計約６０質量％含まれていた。
この粗製卵黄リン脂質組成物５０ｇに、アセトン１４８．５ｍｌと蒸留水１．５ｍｌの混合溶媒（水分含量１．０容量％の含水アセトン）を加え、高速攪拌器（ヒスコトロンＮＳ−５０：(株)日音医理科器械製作所製、目盛り３０）を用い、室温（２０〜２５℃）にて５分間攪拌を行った。これを静置し、アセトン不溶物（主に卵黄リン脂質）を沈殿させ、上澄みの含水アセトンをデカンテーションする。この操作を４回繰り返す。得られたアセトン不溶物を真空状態で脱溶剤を行い、ほぼ白色の、色調の改善された精製リン脂質組成物２６ｇを得た。
[Example 1]
Extraction was performed from dried egg yolk (obtained by drying egg yolk liquid by spray drying, having a water content of 3% by mass) using hydrous ethanol (water content of 5% by volume) to obtain a crude egg yolk phospholipid composition.
This contained a total of about 60% by weight of phospholipids.
A mixed solvent of 148.5 ml of acetone and 1.5 ml of distilled water (hydrous acetone having a water content of 1.0% by volume) was added to 50 g of this crude egg yolk phospholipid composition, and a high-speed stirrer (Hiscotron NS-50: Co., Ltd.) was added. Stirring was carried out for 5 minutes at room temperature (20 to 25 ° C.) using a scale 30) manufactured by Nissin Medical Science Instruments. This is allowed to stand, and acetone insoluble matter (mainly egg yolk phospholipid) is precipitated, and the supernatant water-containing acetone is decanted. This operation is repeated 4 times. The obtained acetone insolubles were desolvated in a vacuum state to obtain 26 g of a purified phospholipid composition with almost white color and improved color tone.
得られた精製卵黄リン脂質組成物の吸光度は０．１７、リン脂質含有率は９８％であった。 The obtained purified egg yolk phospholipid composition had an absorbance of 0.17 and a phospholipid content of 98%.
［実施例２］
実施例１で得た粗製卵黄リン脂質組成物（リン脂質総計含量約６０質量％）５０ｇを原料とし、これにアセトン１４８．５ｍｌと蒸留水１．５ｍｌの混合溶媒（水分含量１．０容量％の含水アセトン）を加え、高速攪拌器（ヒスコトロンＮＳ−５０：(株)日音医理科器械製作所製、目盛り３０）を用い、室温（２０〜２５℃）にて５分間攪拌を行った。これを静置し、アセトン不溶物（主に卵黄リン脂質）を沈殿させ、上澄みの含水アセトンをデカンテーションする。この操作を２回繰り返す。得られたアセトン不溶物をｎ−ヘキサン１５０ｍｌに溶解し、精密ろ過膜にて吸引ろ過を行い、ろ液を減圧下で濃縮する。これに同様の含水率１．０容量％の含水アセトンにてさらに２回洗浄を繰り返し、真空状態で脱溶剤を行った結果、ほぼ白色の、色調の改善された精製卵黄リン脂質組成物２４ｇを得た。
[Example 2]
50 g of the crude egg yolk phospholipid composition (total phospholipid content of about 60% by mass) obtained in Example 1 was used as a raw material, and a mixed solvent of 148.5 ml of acetone and 1.5 ml of distilled water (water content: 1.0% by volume). Was added, and the mixture was stirred at room temperature (20 to 25 ° C.) for 5 minutes using a high-speed stirrer (Hiscotron NS-50: manufactured by Nisshin Medical Science Instrument Co., Ltd., scale 30). This is allowed to stand to precipitate acetone-insoluble matter (mainly egg yolk phospholipid), and the supernatant water-containing acetone is decanted. This operation is repeated twice. The obtained acetone insoluble matter is dissolved in 150 ml of n-hexane, suction filtration is performed with a microfiltration membrane, and the filtrate is concentrated under reduced pressure. As a result of repeating washing twice with the same water-containing acetone having a water content of 1.0% by volume and removing the solvent in a vacuum state, 24 g of purified egg yolk phospholipid composition with almost white color and improved color tone was obtained. Obtained.
得られた精製卵黄リン脂質組成物の吸光度は０．１５、リン脂質含有率は９８％であった。 The obtained purified egg yolk phospholipid composition had an absorbance of 0.15 and a phospholipid content of 98%.
［実施例３］
実施例１で得られた粗製卵黄リン脂質組成物（リン脂質総計含量約６０質量％）５０ｇを原料とし、これにアセトン１４８．５ｍｌと蒸留水１．５ｍｌの混合溶媒（水分含量１．０容量％の含水アセトン）を加え、高速攪拌器（ヒスコトロンＮＳ−５０：(株)日音医理科器械製作所製、目盛り３０）を用い、室温（２０〜２５℃）にて５分間攪拌を行った。これを静置し、アセトン不溶物（主に卵黄リン脂質）を沈殿させ、上澄みの含水アセトンをデカンテーションする。この操作を２回繰り返す。得られたアセトン不溶物をｎ−ヘキサン１５０ｍｌに溶解し、珪藻土４ｇを用い吸引ろ過し、ろ液を減圧下で濃縮する。これに同様の含水率１．０容量％の含水アセトンにてさらに２回洗浄を繰り返し、真空状態で脱溶剤を行った結果、ほぼ白色の、色調の改善された精製リン脂質組成物２３ｇを得た。
[Example 3]
50 g of the crude egg yolk phospholipid composition (total phospholipid content of about 60% by mass) obtained in Example 1 was used as a raw material, and a mixed solvent of 148.5 ml of acetone and 1.5 ml of distilled water (water content 1.0 volume). % Water-containing acetone) was added, and the mixture was stirred at room temperature (20 to 25 ° C.) for 5 minutes using a high-speed stirrer (Hiscotron NS-50: manufactured by Nissan Medical Science Instrument Co., Ltd., scale 30). This is allowed to stand to precipitate acetone-insoluble matter (mainly egg yolk phospholipid), and the supernatant water-containing acetone is decanted. This operation is repeated twice. The obtained acetone insoluble matter is dissolved in 150 ml of n-hexane, suction filtered using 4 g of diatomaceous earth, and the filtrate is concentrated under reduced pressure. This was further washed twice with water-containing acetone having a water content of 1.0% by volume, and the solvent was removed in a vacuum state. As a result, 23 g of a purified phospholipid composition with almost white color and improved color tone was obtained. It was.
得られた精製卵黄リン脂質組成物の吸光度は０．１５、リン脂質含有率は９８％であった。 The obtained purified egg yolk phospholipid composition had an absorbance of 0.15 and a phospholipid content of 98%.
［比較例１］
実施例１で得られた粗製卵黄リン脂質組成物（リン脂質総計含量約６０質量％）５０ｇを原料とし、これにアセトン１５０ｍｌを加え、高速攪拌器（ヒスコトロンＮＳ−５０：(株)日音医理科器械製作所製、目盛り３０）を用い、室温（２０〜２５℃）にて５分間攪拌を行った。これを静置し、アセトン不溶物（主に卵黄リン脂質）を沈殿させ、上澄みの含水アセトンをデカンテーションする。この操作を４回繰り返す。これを真空状態で脱溶剤を行った結果、黄味を帯びた色調の精製卵黄リン脂質組成物２４ｇを得た。
[Comparative Example 1]
Using 50 g of the crude egg yolk phospholipid composition (total phospholipid content of about 60% by mass) obtained in Example 1 as a raw material, 150 ml of acetone was added thereto, and a high-speed stirrer (Hiscotron NS-50: Nissin Medical Co., Ltd.) Stirring was performed for 5 minutes at room temperature (20 to 25 ° C.) using a scale 30) manufactured by Science Instruments Co., Ltd. This is allowed to stand to precipitate acetone-insoluble matter (mainly egg yolk phospholipid), and the supernatant water-containing acetone is decanted. This operation is repeated 4 times. As a result of removing the solvent in a vacuum state, 24 g of a purified egg yolk phospholipid composition having a yellowish color tone was obtained.
得られた精製卵黄リン脂質組成物の吸光度は０．４２、リン脂質含有率は９８％であった。 The obtained purified egg yolk phospholipid composition had an absorbance of 0.42 and a phospholipid content of 98%.
［試験例１］
精製工程で行うアセトン洗浄工程による、精製卵黄リン脂質組成物の色調への影響を調べるため、次の試験を行った。つまり、実施例１に記載した方法に従い、粗製卵黄リン脂質組成物（リン脂質総計含量約６０質量％）５０ｇを原料とし、アセトン洗浄の条件として、アセトンに各種溶剤を規定量加え１５０ｍｌとする。洗浄回数は４回行う。得られた精製卵黄リン脂質組成物の吸光度（波長４５５ｎｍ）、及びリン脂質組成を実施例１記載の方法にて分析した。
その結果を表１に記す。
[Test Example 1]
In order to investigate the influence on the color tone of the purified egg yolk phospholipid composition by the acetone washing step performed in the purification step, the following test was performed. That is, according to the method described in Example 1, 50 g of a crude egg yolk phospholipid composition (total content of phospholipids of about 60% by mass) is used as a raw material. Wash 4 times. The absorbance (wavelength 455 nm) and phospholipid composition of the obtained purified egg yolk phospholipid composition were analyzed by the method described in Example 1.
The results are shown in Table 1.
試験例１の結果より、精製卵黄リン脂質組成物のアセトン洗浄工程において、アセトンに水を添加して、すなわち含水アセトンにて洗浄を行うことにより、アセトン単独で、もしくはエタノールまたはヘキサンを加えたアセトンで洗浄するより、効果的に色調が改善されることがわかった。 From the results of Test Example 1, in the acetone washing step of the purified egg yolk phospholipid composition, by adding water to acetone, that is, by washing with water-containing acetone, acetone alone or acetone added with ethanol or hexane It was found that the color tone was more effectively improved than by washing with s.
［試験例２］
精製工程で行うアセトン洗浄工程の添加溶媒と洗浄回数による、精製卵黄リン脂質組成物の色調への影響を調べるため、次の試験を行った。つまり、試験例１と同様に、粗製卵黄リン脂質組成物（リン脂質総計含量約６０質量％）５０ｇを原料とし、洗浄条件として、アセトンに各種溶剤を規定量加え１５０ｍｌとする。実施例１と同様の方法により、洗浄を１〜４回繰り返し行った結果、得られた精製リン脂質組成物の吸光度（波長４５５ｎｍ）を実施例１記載の方法にて分析した。
その結果を表２に記す。
[Test Example 2]
In order to investigate the influence of the added solvent and the number of washings in the acetone washing step performed in the purification step on the color tone of the purified egg yolk phospholipid composition, the following test was conducted. That is, in the same manner as in Test Example 1, 50 g of a crude egg yolk phospholipid composition (total phospholipid content of about 60% by mass) is used as a raw material, and as a washing condition, various solvents are added in prescribed amounts to 150 ml. As a result of repeating washing 1 to 4 times by the same method as in Example 1, the absorbance (wavelength 455 nm) of the obtained purified phospholipid composition was analyzed by the method described in Example 1.
The results are shown in Table 2.
サンプル４、５では含水アセトン洗浄工程を２回繰り返すことで、サンプル３、６では３回繰り返すことで、サンプル２、７では４回繰り返すことで吸光度（OD455nm）を０．３以下とすることができた。これに対しサンプル１、８、９，１０ではいずれも０．３以上であった。（※サンプル９ではリン脂質が液状となり、固液分離が不可能であったため、精製リン脂質組成物が得られなかった。） Absorbance (OD455nm) can be reduced to 0.3 or less by repeating the water-containing acetone washing process twice for samples 4 and 5, repeating 3 times for samples 3 and 6, and repeating 4 times for samples 2 and 7. did it. In contrast, Samples 1, 8, 9, and 10 all had 0.3 or more. (* In sample 9, the phospholipid became liquid and solid-liquid separation was impossible, so a purified phospholipid composition could not be obtained.)
［試験例３］
実施例１〜３及び比較例１で得られた精製卵黄リン脂質組成物４種を乳化剤とし、以下に記す処方で脂肪乳剤（医薬品組成物の一例）を調製し、得られた脂肪乳剤の色調を評価した。
〔処方〕 精製卵黄リン脂質組成物※ １２（ｇ）
精製大豆油 ２００
濃グリセリン ２５
注射用蒸留水 （全量で１０００に）
（※精製卵黄リン脂質組成物は実施例１〜３、比較例１で得たもの。）
実施例１〜３及び比較例１で得られた精製卵黄リン脂質組成物を、精製大豆油に分散させ、６０℃に加温する。次に注射用蒸留水に濃グリセリンを加え、６０℃に加温する。両者を高速攪拌器（ヒスコトロンＮＳ−５０：(株)日音医理科器械製作所製、目盛り３０）を用い、室温（２０〜２５℃）にて３０分間攪拌し、脂肪乳剤を調製した。
得られた脂肪乳剤１５０ｍｌを１６５ｍｌ容耐熱ガラス瓶に充填し、ゴム栓にて密封後、オートクレーブにて１２１℃で２０分間の加熱滅菌処理を行った。室温（２０〜２５℃）に冷却後、脂肪乳剤の色調を評価した。その結果を表３に記す。
[Test Example 3]
A fat emulsion (an example of a pharmaceutical composition) was prepared according to the formulation described below, using the four purified egg yolk phospholipid compositions obtained in Examples 1 to 3 and Comparative Example 1 as emulsifiers, and the color tone of the resulting fat emulsion Evaluated.
[Prescription] Purified egg yolk phospholipid composition * 12 (g)
Refined soybean oil 200
Concentrated glycerin 25
Distilled water for injection (total volume is 1000)
(* Purified egg yolk phospholipid compositions were obtained in Examples 1 to 3 and Comparative Example 1.)
The purified egg yolk phospholipid compositions obtained in Examples 1 to 3 and Comparative Example 1 are dispersed in purified soybean oil and heated to 60 ° C. Next, concentrated glycerin is added to distilled water for injection and heated to 60 ° C. Both were stirred for 30 minutes at room temperature (20-25 degreeC) using the high-speed stirrer (Hiscotron NS-50: Nisshin Medical Science Instrument Co., Ltd. make, the scale 30), and the fat emulsion was prepared.
150 ml of the resulting fat emulsion was filled in a 165 ml heat-resistant glass bottle, sealed with a rubber stopper, and then heat-sterilized at 121 ° C. for 20 minutes in an autoclave. After cooling to room temperature (20-25 ° C.), the color tone of the fat emulsion was evaluated. The results are shown in Table 3.
比較例１の精製卵黄リン脂質組成物を乳化剤として調製した脂肪乳剤（医薬品組成物）の加熱滅菌処理後の色調は黄みを帯びた乳白色を呈しており、脂肪乳剤の色調を損なうものであったのに対し、実施例１〜３の精製卵黄リン脂質組成物を用いた脂肪乳剤（医薬品組成物）においてはいずれも加熱滅菌処理後の色調は白色であり、良好な色調を呈していることが分かった。
また、表には示していないが、得られた４種の脂肪乳剤を４５℃、湿度７５％の恒温高湿器内で１ヵ月保存したところ、比較例１では色調が黄変したのに対し、実施例１では製品として問題ない範囲内のやや黄みを帯びた白色を、実施例２、３ではほぼ白色を維持した。
The color tone after heat sterilization of the fat emulsion (pharmaceutical composition) prepared using the purified egg yolk phospholipid composition of Comparative Example 1 as an emulsifier has a yellowish milky white color, which impairs the color tone of the fat emulsion. On the other hand, in the fat emulsion (pharmaceutical composition) using the purified egg yolk phospholipid composition of Examples 1 to 3, the color tone after heat sterilization treatment is white and exhibits a good color tone. I understood.
Although not shown in the table, the four fat emulsions obtained were stored for one month in a constant temperature and high humidity chamber at 45 ° C. and 75% humidity. In Comparative Example 1, the color tone turned yellow. In Example 1, a slightly yellowish white within a range where there is no problem as a product was maintained, and in Examples 2 and 3, a substantially white color was maintained.
［試験例４］
実施例１〜３及び比較例１で得られた精製卵黄リン脂質組成物４種を乳化剤とし、以下の処方の皮膚用化粧品組成物であるO／W型の乳液に添加し、色調を評価した。
〔処方〕 ステアリン酸 ２５（ｇ）
セチルアルコール １５
ワセリン ５０
流動パラフィン １００
ポリオキシエチレン（10モル）
モノオレイン酸エステル ２０
ポリエチレングリコール１５００ ３０
トリエタノールアミン １０
精製卵黄リン脂質組成物※ ２０
精製水 ７２５
香料 ５
防腐剤 適量
（※精製卵黄リン脂質組成物は実施例１〜３、比較例１で得たもの。）
上記処方において、精製水にポリエチレングリコール、トリエタノールアミン、実施例１〜３、比較例１で得た精製卵黄リン脂質組成物を加え加熱溶解し７０℃に保つ（水相）。次に他の成分を混合し、加熱溶解して７０℃に保つ（油相）。水相に油相を加え予備乳化を行い、TKホモミクサー（特殊機化(株)）で均一に乳化し、乳化後３０℃まで冷却する。
これをキャップ付きガラス瓶に充填し、キャップを密閉後、色調を評価した。その結果を表４に記す。
[Test Example 4]
Four kinds of purified egg yolk phospholipid compositions obtained in Examples 1 to 3 and Comparative Example 1 were used as emulsifiers and added to an O / W type emulsion, which is a cosmetic composition for skin having the following formulation, and the color tone was evaluated. .
[Prescription] Stearic acid 25 (g)
Cetyl alcohol 15
Vaseline 50
Liquid paraffin 100
Polyoxyethylene (10 mol)
Monooleate 20
Polyethylene glycol 1500 30
Triethanolamine 10
Purified egg yolk phospholipid composition * 20
Purified water 725
Fragrance 5
Preservative appropriate amount (* Purified egg yolk phospholipid composition obtained in Examples 1 to 3 and Comparative Example 1)
In the above formulation, polyethylene glycol, triethanolamine, the purified egg yolk phospholipid composition obtained in Examples 1 to 3 and Comparative Example 1 are added to purified water, dissolved by heating and kept at 70 ° C. (aqueous phase). Next, other components are mixed, dissolved by heating and kept at 70 ° C. (oil phase). Preliminarily emulsify by adding the oil phase to the aqueous phase, uniformly emulsify with TK homomixer (Special Machine Co., Ltd.), and cool to 30 ° C after emulsification.
This was filled in a glass bottle with a cap, and after sealing the cap, the color tone was evaluated. The results are shown in Table 4.
比較例１の精製卵黄リン脂質組成物を乳化剤として調製した乳液（化粧品組成物）においては黄みを帯びた乳白色を呈しており、乳液の色調を損なうものであったのに対し、実施例１〜３の精製卵黄リン脂質組成物を用いた乳液（化粧品組成物）においてはいずれも調製後の色調は白色であり、良好な色調を呈していることが分かった。 In the milky lotion (cosmetic composition) prepared using the purified egg yolk phospholipid composition of Comparative Example 1 as an emulsifier, the yellowish milky white color was exhibited and the color tone of the milky milk was impaired. It was found that in the emulsion (cosmetic composition) using the purified egg yolk phospholipid composition of 3 to 3, the color tone after preparation was white and exhibited a good color tone.
［試験例５］
実施例１〜３及び比較例１の精製卵黄リン脂質組成物を原料として、食品組成物の一例として以下の処方の栄養補給飲料に配合し、蒸気吹き込み式高温短時間殺菌後の色調を評価した。
〔処方〕 乳清たんぱく質 ２５（ｇ）
カゼインナトリウム ２５
果糖・ブドウ糖液糖 ５０
デキストリン（DE２５） １００
精製大豆油 ４０
精製卵黄リン脂質組成物※ ２０
香料 ５
乳化剤（ショ糖脂肪酸エステル） ２
増粘安定剤 ２
精製水 全量 １０００ｍｌ
（※精製卵黄リン脂質組成物は実施例１〜３、比較例１で得たもの。）
上記処方において、精製水をTKホモミクサー（特殊機化(株)）にて攪拌しながら、乳清たんぱく質、カゼインナトリウム、果糖・ブドウ糖液糖、デキストリン、実施例１〜３、比較例１で得られた精製卵黄リン脂質組成物、香料、乳化剤、増粘安定剤を加え完全に溶解する。これに精製大豆油を徐々に加え１次乳化を行う。この液を８０℃まで加熱し、高圧ホモゲナイザー（(株)イズミフードマシナリ製）にて４００ｋｇｆ／ｃｍ２の条件で２次乳化を行う。得られた乳化液を蒸気吹き込み式高温短時間殺菌機（アセプティック殺菌機）にて１３５℃で６０秒間の加熱処理を行い、その２００ｍｌを、予め過酸化水素液にて滅菌された、アルミ層を有する多層フィルムで構成されるスタンディングパウチに充填し、無菌的に密封ヒートシールを行い、内溶液の色調を評価した。その結果を表５に記す。
[Test Example 5]
Using the purified egg yolk phospholipid composition of Examples 1 to 3 and Comparative Example 1 as a raw material, it was blended in a nutritional supplement beverage having the following prescription as an example of a food composition, and the color tone after steam blowing type high temperature short time sterilization was evaluated. .
[Prescription] Whey protein 25 (g)
Casein sodium 25
Fructose and glucose liquid sugar 50
Dextrin (DE25) 100
Refined soybean oil 40
Purified egg yolk phospholipid composition * 20
Fragrance 5
Emulsifier (sucrose fatty acid ester) 2
Thickening stabilizer 2
Purified water total 1000ml
(* Purified egg yolk phospholipid compositions were obtained in Examples 1 to 3 and Comparative Example 1.)
In the above formulation, while stirring purified water with TK homomixer (Special Mechanization), whey protein, sodium caseinate, fructose / glucose sugar, dextrin, obtained in Examples 1 to 3 and Comparative Example 1 Add the purified egg yolk phospholipid composition, flavor, emulsifier, thickening stabilizer and dissolve completely. Refined soybean oil is gradually added to this and primary emulsification is performed. This solution is heated to 80 ° C. and subjected to secondary emulsification with a high-pressure homogenizer (manufactured by Izumi Food Machinery Co., Ltd.) under the condition of 400 kgf / cm 2 . The obtained emulsion was subjected to a heat treatment at 135 ° C. for 60 seconds with a steam blow type high temperature short time sterilizer (aseptic sterilizer), and 200 ml of the aluminum layer was previously sterilized with a hydrogen peroxide solution. It was filled in a standing pouch composed of a multi-layer film, and aseptically sealed and heat sealed, and the color tone of the internal solution was evaluated. The results are shown in Table 5.
比較例１の精製卵黄リン脂質組成物を配合して調製した殺菌後の栄養補給飲料（食品組成物）においては黄みを帯びた乳白色を呈しており、栄養補給飲料の色調を損なうものであったのに対し、実施例１〜３の精製卵黄リン脂質組成物を用いた栄養補給飲料（食品組成物）においてはいずれも調製後の色調は白色であり、良好な色調を呈していることが分かった。 The sterilized nutritional supplement beverage (food composition) prepared by blending the purified egg yolk phospholipid composition of Comparative Example 1 has a yellowish milky white color and impairs the color of the nutritional supplement beverage. In contrast, in the nutritional supplement drink (food composition) using the purified egg yolk phospholipid composition of Examples 1 to 3, the color tone after preparation is white, and it exhibits a good color tone. I understood.
試験例２〜４の結果より、比較例１で得られた精製卵黄リン脂質組成物を原料として用いた医薬品組成物、化粧品組成物、食品組成物は、精製卵黄リン脂質組成物特有の色調が製品に影響し、黄色みを呈した。
これに対し、実施例１〜３により得られた精製卵黄リン脂質組成物を配合した医薬品組成物、化粧品組成物、食品組成物は、それぞれ製品固有の色調に影響を与えないことが確認できた。
From the results of Test Examples 2 to 4, the pharmaceutical composition, cosmetic composition, and food composition using the purified egg yolk phospholipid composition obtained in Comparative Example 1 as a raw material have a color tone unique to the purified egg yolk phospholipid composition. The product was affected and yellowish.
On the other hand, it was confirmed that the pharmaceutical composition, cosmetic composition, and food composition containing the purified egg yolk phospholipid composition obtained in Examples 1 to 3 did not affect the product-specific color tone. .
Claims (7)
粗製卵黄リン脂質組成物を含水アセトンで処理し、得られたアセトン不溶物から含水アセトンを除去する、含水アセトン洗浄工程 A method of manufacturing a purified egg yolk phospholipid composition further purification the crude yolk phospholipid composition obtained by extracting from egg yolk, in the purification step, at least viewed including the steps of hydrous content of aqueous acetone 0 A method for producing a purified egg yolk phospholipid composition, characterized by comprising 3 to 6% by volume .
A water-containing acetone washing step for treating a crude egg yolk phospholipid composition with water-containing acetone and removing the water-containing acetone from the obtained acetone insoluble matter
粗製卵黄リン脂質組成物を含水アセトンで処理し、得られたアセトン不溶物から含水アセトンを除去する、含水アセトン洗浄工程 A method for producing a purified egg yolk phospholipid composition that further purifies a crude egg yolk phospholipid composition obtained by extracting alcohol from the dried egg yolk and removing the alcohol from the extract. method for producing at least seen including, purified egg yolk phospholipid composition water content of the hydrous acetone, characterized in that a 0.3 to 6% by volume.
A water-containing acetone washing step for treating a crude egg yolk phospholipid composition with water-containing acetone and removing the water-containing acetone from the obtained acetone insoluble matter
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