WO2011061995A1 - 精製卵黄リン脂質組成物の製造方法およびこれにより得られた精製卵黄リン脂質組成物を用いた医薬品組成物、化粧品組成物、または食品組成物 - Google Patents
精製卵黄リン脂質組成物の製造方法およびこれにより得られた精製卵黄リン脂質組成物を用いた医薬品組成物、化粧品組成物、または食品組成物 Download PDFInfo
- Publication number
- WO2011061995A1 WO2011061995A1 PCT/JP2010/066511 JP2010066511W WO2011061995A1 WO 2011061995 A1 WO2011061995 A1 WO 2011061995A1 JP 2010066511 W JP2010066511 W JP 2010066511W WO 2011061995 A1 WO2011061995 A1 WO 2011061995A1
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- WIPO (PCT)
- Prior art keywords
- composition
- egg yolk
- yolk phospholipid
- content
- phospholipid composition
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 172
- 239000008345 purified egg yolk phospholipid Substances 0.000 title claims abstract description 82
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 32
- 235000013305 food Nutrition 0.000 title claims abstract description 17
- 239000002537 cosmetic Substances 0.000 title claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title abstract description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 202
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 67
- 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 claims abstract description 66
- 239000008344 egg yolk phospholipid Substances 0.000 claims abstract description 45
- 229940068998 egg yolk phospholipid Drugs 0.000 claims abstract description 45
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 45
- 238000011282 treatment Methods 0.000 claims abstract description 38
- 235000012000 cholesterol Nutrition 0.000 claims abstract description 33
- 230000007935 neutral effect Effects 0.000 claims abstract description 20
- 238000000746 purification Methods 0.000 abstract description 5
- 235000013345 egg yolk Nutrition 0.000 description 25
- 210000002969 egg yolk Anatomy 0.000 description 25
- 102000002322 Egg Proteins Human genes 0.000 description 20
- 108010000912 Egg Proteins Proteins 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000605 extraction Methods 0.000 description 13
- 150000002632 lipids Chemical class 0.000 description 13
- 239000002904 solvent Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 239000004375 Dextrin Substances 0.000 description 3
- 229920001353 Dextrin Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 235000019425 dextrin Nutrition 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000002960 lipid emulsion Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000006228 supernatant Substances 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
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 229930091371 Fructose Natural products 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
- 239000005715 Fructose Substances 0.000 description 2
- 102000015439 Phospholipases Human genes 0.000 description 2
- 108010064785 Phospholipases Proteins 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- -1 Polyoxyethylene Polymers 0.000 description 2
- 108010073771 Soybean Proteins Proteins 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 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 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 235000021568 protein beverage Nutrition 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 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
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-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
- 241000287828 Gallus gallus Species 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
- 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
- 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
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940093430 polyethylene glycol 1500 Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000013547 stew Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
- A61K8/981—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of mammals or bird
- A61K8/982—Reproductive organs; Embryos, Eggs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/01—Other fatty acid esters, e.g. phosphatides
- A23D7/011—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
- A61K8/553—Phospholipids, e.g. lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
Definitions
- the present invention relates to a method for producing a purified egg yolk phospholipid composition having a reduced cholesterol content, and a pharmaceutical composition, a cosmetic composition, or a food composition using the purified egg yolk phospholipid composition obtained thereby.
- Egg yolk phospholipid has a hydrophilic group and a hydrophobic group in the molecule, and thus has been widely used as an emulsifier in the food, cosmetic and pharmaceutical fields.
- egg yolk phospholipids having a phospholipid content of 80% or more and a neutral phospholipid content of 60% or more are excellent in emulsifiability and safety. It is used as an additive and as a cosmetic raw material such as an emulsifier for skin cosmetics such as emulsion.
- Non-Patent Document 1 When an egg yolk phospholipid composition extracted from egg yolk is mixed with acetone, the egg yolk phospholipid which is hardly soluble in acetone becomes a precipitate, and the egg yolk phospholipid can be purified by removing acetone in which impurities such as neutral lipid are dissolved. it can.
- the purified phospholipid is dissolved in a nonpolar solvent, the resulting solution is contacted with silica gel, the silica gel is removed, and then the nonpolar solvent is distilled off from this solution.
- a method is known (Patent Document 1).
- an object of the present invention is to produce a purified egg yolk phospholipid composition that can efficiently reduce the cholesterol content when producing a purified egg yolk phospholipid composition, and a purified egg yolk phosphorus obtained thereby.
- the present invention provides a pharmaceutical composition, a cosmetic composition, or a food composition using the lipid composition.
- the present inventors have refined the egg yolk phospholipid composition in the production method of the purified egg yolk phospholipid composition.
- a purified egg yolk phospholipid composition with reduced cholesterol content can be obtained by treatment with hydrous alcohol-containing acetone having an acetone content of 80% by volume or more, and the present invention has been completed. It was.
- the present invention (1) A method for producing a purified egg yolk phospholipid composition having a phospholipid content of 80% or more and a neutral phospholipid content of 60% or more, and in the purification of the egg yolk phospholipid composition, acetone A method for producing a purified egg yolk phospholipid composition, which is treated with hydrous alcohol-containing acetone having a content of 80% by volume or more, (2) The method for producing a purified egg yolk phospholipid composition according to (1), wherein the alcohol content of the water-containing alcohol-containing acetone is 0.3 to 3% by volume, (3) The method for producing a purified egg yolk phospholipid composition according to (1) or (2), wherein the water-containing alcohol-containing acetone has a water content of 0.3 to 6% by volume, (4) The method for producing a purified egg yolk phospholipid composition according to any one of (1) to (3), wherein the treatment with water-containing alcohol-containing acetone is performed twice or more, (5) The method for producing the purified egg yolk phospholipid composition according to
- the present applicant treated the crude egg yolk phospholipid composition obtained by extraction from egg yolk with water-containing acetone, and removed the water-containing acetone from the obtained acetone insoluble material, thereby improving the color tone of purified egg yolk phosphorus.
- the manufacturing method of a lipid composition is disclosed (patent document 2). Although the purified egg yolk phospholipid composition obtained by this method certainly improved in color tone, the cholesterol-reducing effect was not satisfactory.
- the present invention it is possible to provide a purified egg yolk phospholipid composition having a reduced cholesterol content, and a pharmaceutical composition, cosmetic composition, or food composition using the same, and the demand for further phospholipid compositions is expanded. There is expected.
- Purified egg yolk phospholipid composition The present invention relates to a method for producing a purified egg yolk phospholipid composition in order to obtain a purified egg yolk phospholipid composition having a reduced cholesterol content.
- a water-containing alcohol-containing acetone treatment with a content of 80% by volume or more is performed.
- the “purified egg yolk phospholipid composition” refers to a composition having a phospholipid content of 80% or more and a neutral phospholipid content of 60% or more. Including those that are mixed.
- the “phospholipid” of the present invention refers to a phospholipid derived from egg yolk, or a phospholipid obtained by exchanging or removing a base bonded to a phosphate group of the phospholipid.
- the “neutral phospholipid” indicates neutral properties among the phospholipids, and examples thereof include phosphatidylcholine, lysophosphatidylcholine, and sphingomyelin.
- the content of cholesterol as an impurity is preferably low.
- the cholesterol content of the purified egg yolk phospholipid composition is preferably 1.5% or less, and more preferably 1% or less.
- the phospholipid content, the neutral phospholipid content, and the cholesterol content are determined by TLC-FID method using a purified egg yolk phospholipid composition. Obtained by measuring at That is, 0.1 g of the obtained purified egg yolk phospholipid composition sample was dissolved in a chloroform: methanol (2 parts by volume: 1 part by volume) solution using Iatroscan (TH-10: manufactured by Mitsubishi Chemical Yatron Corporation).
- Raw material The raw material in the manufacturing method of the refined egg yolk phospholipid composition of this invention will not be specifically limited if it is a composition containing egg yolk phospholipid.
- an egg yolk phospholipid composition obtained by extracting egg yolk with an organic solvent may be used, and the above-mentioned “purified egg yolk phospholipid composition” is used as a raw material to further reduce the cholesterol content.
- a “purified egg yolk phospholipid composition” may be produced.
- those obtained by treating these egg yolk phospholipid compositions with an enzyme such as phospholipase and hydrolyzing fatty acid residues may be used.
- Examples of egg yolks used in the present invention include raw raw egg yolks that can be separated from avian eggs such as chicken eggs, frozen egg yolks that are preserved, dried egg yolks, enzyme-treated egg yolks treated with protease, phospholipase, or cholesterol.
- Examples thereof include egg yolk processed by a supercritical gas extraction method in order to reduce the content.
- it is preferable to use dried 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” means a product having a moisture content of 10% or less and manufactured in the food industry by spray drying, freeze drying, drum drying, vacuum continuous drying, etc. Treatment with flipase or the like, supercritical gas extraction or the like may be performed to reduce the cholesterol content.
- an egg yolk phospholipid composition is first extracted from egg yolk as a raw material. Specifically, when dry egg yolk is used as a raw material, an organic solvent is added to the dried egg yolk (water content 4%), and the mixture is stirred using a high-speed mixer such as a high-speed mixer. After the solid-liquid separation by filtration, the solvent can be removed from the filtrate using a vacuum distillation apparatus to obtain an egg yolk phospholipid composition.
- Examples of the organic solvent used for the extraction of the egg yolk phospholipid composition in the present invention include alcohols such as methanol, ethanol, n-propanol, 2-propanol, 2-methyl-1-propanol, denatured alcohol, hexane, heptane, chloroform, and the like. Among these, lower alcohols having 1 to 3 carbon atoms are preferable, and ethanol is more preferable in consideration of use in food applications.
- water-containing alcohol mixed with water that can be used for industrial use such as distilled water is also included in the alcohol. By changing the water content of the alcohol, the phospholipid content of the egg yolk phospholipid composition obtained can be reduced. Since it can be adjusted, a water-containing alcohol having a water content according to the purpose is usually used.
- the water content of the hydrous alcohol used for the extraction of the egg yolk phospholipid composition is preferably 0.5 to 20% by volume, more preferably 1 to 10% by volume from the viewpoint of improving the extraction efficiency of the egg yolk phospholipid composition.
- the amount of the organic solvent used for the extraction of the egg yolk phospholipid composition is preferably 2 to 20 parts, more preferably 5 to 10 parts with respect to 1 part of the dried egg yolk from the viewpoint of improving the extraction efficiency.
- Step of treating egg yolk phospholipid composition with hydrous alcohol-containing acetone the egg yolk phospholipid composition is purified.
- the cholesterol content of the purified egg yolk phospholipid composition can be reduced by treatment with water-containing alcohol-containing acetone. Specifically, hydrated alcohol-containing acetone is added to the egg yolk phospholipid composition obtained in the above extraction step, and after homogenous dispersion with a high-speed stirrer or the like, the phospholipid composition is precipitated by allowing to stand, Remove the solvent.
- the water-containing alcohol-containing acetone of the present invention is a mixture of acetone and water that can be used for industrial purposes such as distilled water and alcohol.
- examples of the alcohol include methanol, ethanol, n-propanol, 2-propanol, 2-methyl-1-propanol, denatured alcohol, etc., but lower alcohols having 1 to 3 carbon atoms are preferable and are used for food applications. In view of this, ethanol is more preferable.
- the acetone content of the hydrous alcohol-containing acetone is 80% by volume or more, preferably 90 to 99.4% by volume. If the acetone content is lower than the above range, part of the egg yolk phospholipid is dissolved in the hydrous alcohol-containing acetone, or the yield of the purified egg yolk phospholipid composition tends to decrease.
- the hydrous alcohol-containing acetone of this invention may contain organic solvents, such as hexane and a heptane, in the range which does not impair the effect of this invention other than acetone, water, and alcohol.
- the alcohol content of water-containing alcohol-containing acetone is 0.3 to 3% by volume, preferably 0.5 to 2.5% by volume. If the alcohol content is lower than the above range, the cholesterol content of the purified egg yolk phospholipid composition is difficult to reduce. In addition, when the alcohol content is higher than the above range, part of the egg yolk phospholipid is dissolved in the water-containing alcohol-containing acetone, or the yield of the purified egg yolk phospholipid composition tends to decrease.
- the water content of the hydrous alcohol-containing acetone is preferably 0.3 to 6% by volume, more preferably 0.5 to 4% by volume. If the water content is lower than the above range, the cholesterol content of the purified egg yolk phospholipid composition is difficult to reduce, which is not preferable. Moreover, when the water content is higher than the above range, it is not preferable because part of the egg yolk phospholipid is dissolved in the hydrous alcohol-containing acetone or the yield of the purified egg yolk phospholipid composition tends to decrease. In addition, it is preferable to treat the egg yolk phospholipid composition with water-containing alcohol-containing acetone whose water content is in the above range because the content of free fatty acids can be effectively reduced.
- the amount of water-containing alcohol-containing acetone used for the treatment with water-containing alcohol-containing acetone is preferably 1 to 10 parts, more preferably 2 to 5 parts with respect to 1 part of egg yolk phospholipid composition as a raw material from the viewpoint of improving the treatment efficiency. .
- the hydrous alcohol-containing acetone treatment By repeating the hydrous alcohol-containing acetone treatment, impurities such as cholesterol and neutral lipid can be further removed, which is effective.
- the number of repetitions of the hydroalcoholic acetone treatment is preferably 2 or more, more preferably 3 to 5 in consideration of the degree of purification of the egg yolk phospholipid composition and the cost and time required for the treatment process.
- treatments using other solvents such as acetone and hydrous acetone may be performed between each treatment. Good.
- the hydroalcoholic acetone treatment is preferably performed under a temperature condition of ⁇ 10 to 35 ° C., more preferably under a temperature condition of 0 to 20 ° C.
- a temperature higher than the above range is not preferable because the yield of the purified egg yolk phospholipid composition tends to decrease.
- the temperature is lower than the above range, the dispersibility of the phospholipid during the treatment is lowered and the treatment efficiency is lowered, which is not preferable.
- Step of drying egg yolk phospholipid composition In the method for producing a purified egg yolk phospholipid composition of the present invention, the egg yolk phospholipid composition obtained by removing the supernatant solvent after the treatment with the hydrous alcohol-containing acetone described above is used. A drying step can be included.
- the purified egg yolk phospholipid composition in the step of drying the egg yolk phospholipid composition, can be obtained by removing the solvent from the egg yolk phospholipid composition obtained by removing the supernatant solvent under vacuum. it can.
- this invention is a pharmaceutical composition, cosmetic composition, or food composition containing the refined egg yolk phospholipid composition obtained by the manufacturing method mentioned above.
- 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 purified egg yolk phospholipid composition obtained by the production method described above has a reduced cholesterol content, each of the compositions is more excellent in safety.
- Example 1 Extraction was performed from dried egg yolk (obtained by drying egg yolk liquid by spray drying, having a water content of 3%) using water-containing ethanol (water content 5% by volume) to obtain an egg yolk phospholipid composition.
- the phospholipid content of the obtained egg yolk phospholipid composition was about 60%.
- a mixed solvent of 192 mL of acetone, 4 mL of distilled water and 4 mL of ethanol water-containing ethanol acetone having a water content of 2% by volume and an ethanol content of 2% by volume
- Hiscotron NS high-speed stirrer
- the obtained purified egg yolk phospholipid composition was analyzed for lipid composition by the TLC-FID method.
- the phospholipid content was 95%, the neutral phospholipid content was 78%, and the cholesterol content. was 0.5%.
- Example 1 In the water-containing alcohol-containing acetone treatment step, the following test was conducted in order to investigate the influence of the water content of the mixed solvent used and the alcohol content on the cholesterol-reducing action of the purified egg yolk phospholipid composition. Specifically, the purified egg yolk phospholipid composition was obtained in the same manner as in Example 1 except that the water-containing ethanol acetone used in Example 1 was changed to an acetone solvent having the water content and ethanol content shown in Table 1. I got a thing. The lipid composition of the obtained purified egg yolk phospholipid composition was analyzed in the same manner as in Example 1.
- the amount of acetone or a mixed solvent obtained by mixing water and alcohol in acetone was 200 mL, and the treatment was performed four times.
- the phospholipid content of all the purified egg yolk phospholipid compositions obtained was 80% or more, and the neutral phospholipid content was 60% or more.
- the purified egg yolk phospholipid composition obtained by treatment with hydrous alcohol-containing acetone having a water content of 0.3 to 6% by volume and an alcohol content of 0.3 to 3% by volume is cholesterol. It is obtained by treatment with hydrous alcohol-containing acetone with reduced content, high yield, water content of 0.5-4% by volume, and alcohol content of 0.5-2.5% by volume. It can be understood that the purified egg yolk phospholipid composition has a lower cholesterol content and a higher yield.
- Example 2 In the water-containing alcohol-containing acetone treatment step, the following test was conducted in order to examine the effect of the number of times of the water-containing alcohol-containing acetone treatment on the cholesterol reducing effect of the purified egg yolk phospholipid composition. Specifically, in the method for producing a purified egg yolk phospholipid composition of Example 1, after changing the number of hydrous alcohol-containing acetone treatments to the number shown in Table 2, the total number of solvent treatments is 4 times. A purified egg yolk phospholipid composition was obtained in the same manner as in Example 1 except that the same treatment was performed using a mixed solvent of 196 mL of acetone and 4 mL of distilled water (water-containing acetone having a water content of 2% by volume). .
- the lipid composition of the obtained purified egg yolk phospholipid composition was analyzed in the same manner as in Example 1.
- the phospholipid content of all the obtained purified egg yolk phospholipid compositions was 80% or more, and the neutral phospholipid content was 60% or more.
- Example 2 In Example 1, purification was performed in the same manner as in Example 1 except that the mixture was treated with water-containing ethanol acetone by stirring for 5 minutes while maintaining the temperature of the mixture of egg yolk phospholipid composition and water-containing ethanol acetone at 35 ° C. 42 g of phospholipid composition was obtained.
- the phospholipid content was 94%
- the neutral phospholipid content was 77%
- the cholesterol content was 0.5%.
- Example 3 Except that the water-containing ethanol acetone used in Example 1 was changed to a mixed solvent of 192 mL of acetone, 4 mL of distilled water and 4 mL of methanol (water-containing methanol acetone having a water content of 2% by volume and a methanol content of 2% by volume). In the same manner as in Example 1, 46 g of a purified phospholipid composition was obtained.
- the lipid composition of the obtained purified egg yolk phospholipid composition was analyzed by the same method as in Example 1, the phospholipid content was 96%, the neutral phospholipid content was 78%, and the cholesterol content was 0.4%.
- Example 4 Using the purified egg yolk phospholipid composition obtained in Example 1 as an emulsifier, a fat emulsion (an example of a pharmaceutical composition) having the following formulation was prepared. Specifically, the purified egg yolk phospholipid composition (Example 1) is 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 ° C.) using a high-speed stirrer (Hiscotron NS-50: manufactured by Nisshin Medical Science Instrument Co., Ltd., scale 30), and then uniformly with a TK homomixer (Primix). Emulsified to prepare a fat emulsion.
- a high-speed stirrer Hiscotron NS-50: manufactured by Nisshin Medical Science Instrument Co., Ltd., scale 30
- Example 5 Using the purified egg yolk phospholipid composition obtained in Example 1 as an emulsifier, a cosmetic composition for skin having the following formulation was prepared. Specifically, in the following formulation, polyethylene glycol, triethanolamine, and a purified egg yolk phospholipid composition (Example 1) are added to purified water and 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). An oil phase was added to the aqueous phase to perform preliminary emulsification, and the mixture was uniformly emulsified with a TK homomixer (manufactured by Primemics). After emulsification, the emulsion was cooled to 30 ° C. to prepare a skin cosmetic composition.
- a TK homomixer manufactured by Primemics
- 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 (Example 1) 20 Purified water 725 Fragrance 5 Preservative appropriate amount
- Example 6 Using the purified egg yolk phospholipid composition obtained in Example 1 as an emulsifier, a protein beverage (food composition) having the following formulation was prepared. Specifically, in the following formulation, while stirring purified water with a TK homomixer, separated soybean protein, fructose / glucose liquid sugar, dextrin, purified egg yolk phospholipid composition (Example 1), flavor, emulsifier, Add viscosity stabilizer and dissolve completely. Refined soybean oil was gradually added to this to perform primary emulsification. This liquid was heated to 80 ° C. and subjected to secondary emulsification with a high-pressure homogenizer (manufactured by Izumi Food Machinery Co., Ltd.) to prepare a protein beverage (food composition).
- a high-pressure homogenizer manufactured by Izumi Food Machinery Co., Ltd.
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Abstract
Description
(1)リン脂質含有量が80%以上であり、中性リン脂質含有量が60%以上である精製卵黄リン脂質組成物の製造方法であって、卵黄リン脂質組成物の精製の際、アセトン含有率が80容量%以上である含水含アルコールアセトン処理を行う精製卵黄リン脂質組成物の製造方法、
(2)前記含水含アルコールアセトンのアルコール含有率が0.3~3容量%である(1)記載の精製卵黄リン脂質組成物の製造方法、
(3)前記含水含アルコールアセトンの水含有率が0.3~6容量%である(1)または(2)に記載の精製卵黄リン脂質組成物の製造方法、
(4)含水含アルコールアセトン処理を2回以上行う(1)乃至(3)のいずれかに記載の精製卵黄リン脂質組成物の製造方法、
(5)含水含アルコールアセトン処理を-10~35℃の温度条件下で行う(1)乃至(4)のいずれかに記載の精製卵黄リン脂質組成物の製造方法、
(6)コレステロールの含有量が1.5%以下である(1)乃至(5)のいずれかに記載の精製卵黄リン脂質組成物の製造方法、
(7)(1)乃至(6)のいずれかに記載の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、
(8)(1)乃至(6)のいずれかに記載の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化粧品組成物、
(9)(1)乃至(6)のいずれかに記載の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食品組成物、
である。
本発明は、コレステロール含有量が低減された精製卵黄リン脂質組成物を得るために、精製卵黄リン脂質組成物の製造方法において、卵黄リン脂質組成物の精製の際、アセトン含有率が80容量%以上である含水含アルコールアセトン処理を行うことを特徴とする。
本発明において、リン脂質含有量、中性リン脂質含有量およびコレステロール含有量は、精製卵黄リン脂質組成物をTLC-FID法にて測定して求める。つまり、イアトロスキャン(TH-10:三菱化学ヤトロン社製)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容量部:1容量部)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容量部:30容量部:3容量部)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容量部:10容量部:0.1容量部)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、リン脂質含有量、中性リン脂質含有量およびコレステロール含有量を算出する。
本発明の精製卵黄リン脂質組成物の製造方法における原料は、卵黄リン脂質を含有する組成物であれば特に限定するものではない。通常、卵黄を有機溶媒を用いて抽出して得られた卵黄リン脂質組成物を用いればよく、また、上述した「精製卵黄リン脂質組成物」を原料として用いて、よりコレステロール含有量が低減された「精製卵黄リン脂質組成物」を製造してもよい。更に、これら卵黄リン脂質組成物をホスフォリパーゼ等の酵素で処理し、脂肪酸残基が加水分解されたものを用いてもよい。
4.1.卵黄リン脂質組成物の抽出工程
本発明では、まず原料となる卵黄から卵黄リン脂質組成物を抽出する。具体的には、原料として乾燥卵黄を用いる場合、乾燥卵黄(水分含量4%)に有機溶媒を加え、高速ミキ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媒を除去し、卵黄リン脂質組成物を得ることができる。
次に、抽出された卵黄リン脂質組成物のリン脂質含有量を高めるため、卵黄リン脂質組成物の精製を行う。この際、含水含アルコールアセトン処理を行うことで、精製卵黄リン脂質組成物のコレステロール含有量を低減することができる。具体的には、上記抽出工程で得られた卵黄リン脂質組成物に含水含アルコールアセトンを加え、高速攪拌器等で均質に分散後、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。
本発明の精製卵黄リン脂質組成物の製造方法において、上述した含水含アルコールアセトン処理の後に、前記上澄みの溶媒を除去して得られた卵黄リン脂質組成物を乾燥する工程を含むことができる。
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、コレステロール含有量が低減されていることから、前記各組成物は、より安全性に優れたものとなる。
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%のもの)より含水エタノール(水含有率5容量%)を用い抽出し、卵黄リン脂質組成物を得た。得られた卵黄リン脂質組成物のリン脂質含有量は約60%であった。
この卵黄リン脂質組成物90gに、アセトン192mL、蒸留水4mLおよびエタノール4mLの混合溶媒(水含有率2容量%、エタノール含有率2容量%の含水含エタノールアセトン)を加え、高速攪拌器(ヒスコトロンNS-50:日音医理科器械製作所製、目盛り30)を用い、混合物の温度を10℃に保持しながら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、上澄みの含水含エタノールアセトンをデカンテーションした。この操作を4回繰り返した後、得られたアセトン不溶物を真空状態で脱溶媒を行い、精製卵黄リン脂質組成物47gを得た。
含水含アルコールアセトン処理工程において、用いる混合溶媒の水含有率、およびアルコール含有率による、精製卵黄リン脂質組成物のコレステロールの低減作用への影響を調べるため、次の試験を行った。具体的には、実施例1で用いた含水含エタノールアセトンを表1に記載した水含有率、エタノール含有率のアセトン溶媒に変更した以外は、実施例1と同様の方法で精製卵黄リン脂質組成物を得た。得られた精製卵黄リン脂質組成物の脂質組成を実施例1と同様の方法で分析した。なお、アセトン処理の条件として、アセトンまたはアセトンに水、アルコールを混合した混合溶媒の使用量を200mLとし、処理回数は4回行った。また、得られた全ての精製卵黄リン脂質組成物のリン脂質含有量は80%以上であり、中性リン脂質含有量は60%以上であった。
含水含アルコールアセトン処理工程において、含水含アルコールアセトン処理の回数による、精製卵黄リン脂質組成物のコレステロールの低減作用への影響を調べるため、次の試験を行った。具体的には、実施例1の精製卵黄リン脂質組成物の製造方法において、含水含アルコールアセトン処理の回数を表2に示す回数に変更した後、溶媒処理回数の合計が4回となるように、アセトン196mLと蒸留水4mLの混合溶媒(水含有率2容量%の含水アセトン)を用いて同様の処理を行った以外は、実施例1と同様の方法で精製卵黄リン脂質組成物を得た。得られた精製卵黄リン脂質組成物の脂質組成を実施例1と同様の方法で分析した。なお、得られた全ての精製卵黄リン脂質組成物のリン脂質含有量は80%以上であり、中性リン脂質含有量は60%以上であった。
実施例1において、卵黄リン脂質組成物と含水含エタノールアセトンの混合物の温度を35℃に保持しながら5分間攪拌を行って含水含エタノールアセトン処理した以外は、実施例1と同様の方法で精製リン脂質組成物42gを得た。
実施例1で用いた含水含エタノールアセトンをアセトン192mL、蒸留水4mLおよびメタノール4mLの混合溶媒(水含有率2容量%、メタノール含有率2容量%の含水含メタノールアセトン)に変更した以外は、実施例1と同様の方法で精製リン脂質組成物46gを得た。
実施例1で得られた精製卵黄リン脂質組成物を乳化剤とし、下記の処方の脂肪乳剤(医薬品組成物の一例)を調製した。具体的には、精製卵黄リン脂質組成物(実施例1)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: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分間攪拌した後、TKホモミクサー(プライミクス社製)で均一に乳化し、脂肪乳剤を調製した。
精製大豆油 200
濃グリセリン 25
注射用蒸留水 (全量で1000に)
実施例1で得られた精製卵黄リン脂質組成物を乳化剤とし、下記の処方の皮膚用化粧品組成物を調製した。具体的には、下記処方において、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、精製卵黄リン脂質組成物(実施例1)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(プライミクス社製)で均一に乳化し、乳化後30℃まで冷却し、皮膚用化粧品組成物を調製した。
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(実施例1) 20
精製水 725
香料 5
防腐剤 適量
実施例1で得られた精製卵黄リン脂質組成物を乳化剤とし、下記の処方のプロテイン飲料(食品組成物)を調製した。具体的には、下記処方において、精製水をTKホモミクサーにて攪拌しながら、分離状大豆蛋白質、果糖・ブドウ糖液糖、デキストリン、精製卵黄リン脂質組成物(実施例1)、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次乳化を行った。この液を80℃まで加熱し、高圧ホモゲナイザー(イズミフードマシナリ社製)にて2次乳化を行い、プロテイン飲料(食品組成物)を調製した。
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(実施例1) 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 (全量で1000に)
Claims (9)
- リン脂質含有量が80%以上であり、中性リン脂質含有量が60%以上である精製卵黄リン脂質組成物の製造方法であって、卵黄リン脂質組成物の精製の際、アセトン含有率が80容量%以上である含水含アルコールアセトン処理を行うことを特徴とする精製卵黄リン脂質組成物の製造方法。
- 前記含水含アルコールアセトンのアルコール含有率が0.3~3容量%であることを特徴とする請求項1記載の精製卵黄リン脂質組成物の製造方法。
- 前記含水含アルコールアセトンの水含有率が0.3~6容量%であることを特徴とする請求項1または2に記載の精製卵黄リン脂質組成物の製造方法。
- 含水含アルコールアセトン処理を2回以上行うことを特徴とする請求項1乃至3のいずれかに記載の精製卵黄リン脂質組成物の製造方法。
- 含水含アルコールアセトン処理を-10~35℃の温度条件下で行うことを特徴とする請求項1乃至4のいずれかに記載の精製卵黄リン脂質組成物の製造方法。
- コレステロールの含有量が1.5%以下であることを特徴とする請求項1乃至5のいずれかに記載の精製卵黄リン脂質組成物の製造方法。
- 請求項1乃至6のいずれかに記載の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ことを特徴とする医薬品組成物。
- 請求項1乃至6のいずれかに記載の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ことを特徴とする化粧品組成物。
- 請求項1乃至6のいずれかに記載の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ことを特徴とする食品組成物。
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EP10831394.1A EP2502928B1 (en) | 2009-11-20 | 2010-09-24 | Process for production of purified egg-yolk phospholipid composition, and pharmaceutical composition, cosmetic composition or food composition comprising purified egg-yolk phospholipid composition produced by the process |
JP2010545131A JP4723694B1 (ja) | 2009-11-20 | 2010-09-24 | 精製卵黄リン脂質組成物の製造方法およびこれにより得られた精製卵黄リン脂質組成物を用いた医薬品組成物、化粧品組成物、または食品組成物 |
CN201080052094.7A CN102712666B (zh) | 2009-11-20 | 2010-09-24 | 精制卵黄磷脂组合物的制造方法及使用由其得到的精制卵黄磷脂组合物的医药品组合物、化妆品组合物、或者食品组合物 |
KR1020127015848A KR101412434B1 (ko) | 2009-11-20 | 2010-09-24 | 정제 난황 인 지질 조성물의 제조 방법 및 이로써 얻어진 정제 난황 인 지질 조성물을 사용한 의약품 조성물, 화장품 조성물, 또는 식품 조성물 |
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WO2018042576A1 (ja) * | 2016-08-31 | 2018-03-08 | キユーピー株式会社 | 卵黄リン脂質組成物およびその製造方法、ならびに該卵黄リン脂質組成物を用いた脂肪乳剤およびリポ化製剤 |
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KR101958325B1 (ko) * | 2018-10-19 | 2019-03-18 | 주식회사 뉴로바이오로직스 | 스핑고미엘린 함유 기억력 개선 및 집중력 장애 치료용 조성물의 제조방법 |
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US6217926B1 (en) * | 1998-06-30 | 2001-04-17 | Michael Foods, Inc. | Aqueous extraction process to selectively remove phospholipid from egg yolks |
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EP2502928A1 (en) | 2012-09-26 |
CN102712666B (zh) | 2015-04-08 |
JPWO2011061995A1 (ja) | 2013-04-04 |
JP4723694B1 (ja) | 2011-07-13 |
EP2502928A4 (en) | 2013-07-24 |
EP2502928B1 (en) | 2017-11-08 |
KR20120096004A (ko) | 2012-08-29 |
KR101412434B1 (ko) | 2014-06-25 |
CN102712666A (zh) | 2012-10-03 |
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