WO2015009181A1 - A microemulsion consisting of an oil phase, an aqueous phase and a surfactant - Google Patents
A microemulsion consisting of an oil phase, an aqueous phase and a surfactant Download PDFInfo
- Publication number
- WO2015009181A1 WO2015009181A1 PCT/PL2014/050042 PL2014050042W WO2015009181A1 WO 2015009181 A1 WO2015009181 A1 WO 2015009181A1 PL 2014050042 W PL2014050042 W PL 2014050042W WO 2015009181 A1 WO2015009181 A1 WO 2015009181A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- microemulsion
- surfactant
- fish oil
- oil
- grams
- Prior art date
Links
- 239000004530 micro-emulsion Substances 0.000 title claims abstract description 43
- 239000004094 surface-active agent Substances 0.000 title claims description 21
- 239000012071 phase Substances 0.000 title claims description 17
- 239000008346 aqueous phase Substances 0.000 title claims description 5
- 235000021323 fish oil Nutrition 0.000 claims abstract description 33
- 239000003921 oil Substances 0.000 claims description 17
- 235000019198 oils Nutrition 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 9
- 235000013618 yogurt Nutrition 0.000 claims description 7
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 235000013376 functional food Nutrition 0.000 claims description 5
- 235000013365 dairy product Nutrition 0.000 claims description 3
- 235000015872 dietary supplement Nutrition 0.000 claims description 3
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 2
- 239000008157 edible vegetable oil Substances 0.000 claims description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000016709 nutrition Nutrition 0.000 abstract description 10
- 235000013305 food Nutrition 0.000 abstract description 7
- 239000013067 intermediate product Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 21
- 238000009472 formulation Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 8
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 8
- 229920000053 polysorbate 80 Polymers 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 7
- 230000035764 nutrition Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 6
- 229940093471 ethyl oleate Drugs 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000004907 Macro-emulsion Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 230000009469 supplementation Effects 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- -1 Prostaglandins Leukotrienes Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 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 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 208000026278 immune system disease Diseases 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 150000002888 oleic acid derivatives Chemical class 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- ZPVGIKNDGJGLCO-VGAMQAOUSA-N [(2s,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)O[C@@]1([C@]2(CO)[C@H]([C@H](O)[C@@H](CO)O2)O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O ZPVGIKNDGJGLCO-VGAMQAOUSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000037365 barrier function of the epidermis Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000003293 cardioprotective effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 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
- 239000005428 food component Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000036449 good health Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 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
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229940012843 omega-3 fatty acid Drugs 0.000 description 1
- 239000006014 omega-3 oil Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 238000009928 pasteurization Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
- A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
- A23C9/1315—Non-milk proteins or fats; Seeds, pulses, cereals or soja; Fatty acids, phospholipids, mono- or diglycerides or derivatives therefrom; Egg products
-
- 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
- A23D7/003—Compositions other than spreads
-
- 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
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0053—Compositions other than spreads
-
- 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- a microemulsion consisting of an oil phase, an aqueous phase and a surfactant
- the present invention relates to the edible microemulsion constituting a carrier for fish oil and being an intermediate product intended to be introduced into foodstuffs to increase the nutritional value of foodstuffs and thereby increase their commercial value.
- Fish oil is widely recognized as the best source of supplementation of eicosapentaenoic acid (EPA, C20:5) and docosahexaenoic acid (DHA, C22:6)- the most bioactive compounds of the group of long-chain polyunsaturated fatty acids omega-3 (n-3), necessary for a proper functioning of the body. It is also a source of vitamins A and D, squalene and alkoxyglycerol which are valuable for the health. Dietary intake of fish oil allows to increase the levels of DHA and EPA and, thus, affects the normal development of children and the maintenance of good health in adults.
- fish oil has a beneficial effect on prevention and management of cardiovascular diseases, immunological disorders, type 2 diabetes, colorectal, breast and prostate cancers, and ulcerative colitis. It can also alleviate symptoms of many diseases including osteoporosis and rheumatoid arthritis (RA). It exhibits a beneficial effect on the prevention of obesity and delays the aging process. It has the effect of reducing the levels of triglycerides and total cholesterol in the blood, prevents dementia and improves concentration. Other reports describe also the positive effect of fish oil supplementation in pregnant and breastfeeding women, as it may protect against the emergence of allergic diseases and favorably affect the course of sleep in infancy.
- RA osteoporosis and rheumatoid arthritis
- SCC squamous cell carcinoma
- microcapsules whose shell is composed of gelatin, may dissolve and lose their properties when introduced into drinks or dairy products.
- the selection of a suitable encapsulating material whose nature significantly affects the stability of the microcapsules, may be difficult.
- the shell is required to effectively protect the core of a microcapsule from the harmful impact of environmental factors without reacting with food components or affecting the odor or taste of the final product.
- Micro-encapsulation of oils is also significantly limited by the growing intensity of their characteristic odor during storage, which in turn shortens their shelf life.
- Microemulsions which are thermodynamically stable dispersions of oil and aqueous phase, in which one or more of the surfactants/co-surfactants are used to transform them into a macroscopically single-phase system, are also known.
- the diameter of particles in the dispersed phase of the microemulsion is less than 140 nm.
- the particle size in the macroemulsion is typically > 1 ⁇ .
- Such a small particle size determines the transparency of microemulsion systems, because the wavelength of visible light (400 nm-700 nm) is longer, and thereby rays of white light do not refract while passing through a microemulsion.
- a decrease of the particle diameter to sizes expressed in nanometers positively affects the thermodynamic stability of the microemulsion.
- Said stability is ensured by a very low tension on the interface oil-water, which equals 10 "3 mN/m.
- a low surface tension value is reached by the use of surfactants and co-surfactants. It facilitates the mixing of hydrophilic and lipophilic ingredients, so that no phase separation is observed, and the process of forming a microemulsion occurs spontaneously in the absence or a very low share of mechanical energy.
- micro-encapsulation process does not provide as high bioavailability of active substances as microemulsion systems.
- microemulsions results from a spontaneous mutual penetration of hydrophilic and hydrophobic areas in contrary to macroemulsions in which the droplets of internal and external phases are clearly separated.
- Another important difference is the stability of both systems. Macroemulsions are unstable systems. The most common symptoms of their instability are the following phenomena: creaming, flocculation, coalescence and phase separation.
- microemulsions are characterized by a high stability. In addition, they provide a protection against hydrolysis and oxidation of active substances.
- the advantage of microemulsions justifying the use of these systems for foodstuffs is their transparency.
- microemulsion systems are also characterized by a much smaller particle size, which is important for improving the bioavailability and facilitates the absorption of active ingredients.
- Difficulties in application of microemulsion systems comprise, however, a necessity to use a high concentration of surfactants, which are toxic and may cause irritation once a certain concentration limit is exceeded.
- the purpose of the invention is to provide such a form of oil, which once introduced into foodstuffs, would not significantly influence its sensory qualities and long-term storage stability.
- Another purpose of the invention is to provide an optimal composition and form of a food formulation comprising fish oil, both qualitatively and quantitatively, so as to obtain a stable form of fish oil as a bioactive ingredient.
- the present invention relates to a microemulsion comprising an oil phase, an aqueous phase and a surfactant characterized in that it comprises about 30% of the surfactant suitable for use in foodstuffs and at least 7% of edible oil, particularly fish oil.
- the microemulsion according to present invention comprises only one surfactant and does not comprise a co-surfactant.
- the surfactant suitable for the preparation of microemulsions may be any surfactant approved for use in foodstuffs, for example: lecithins, esters of sucrose and fatty acids, esters of fatty acids and polyglycerol, esters of fatty acids and propylene glycol, esters of polyoxyethylene sorbate and fatty acids, esters of sorbitol and fatty acids.
- the microemulsion of the invention comprises polyoxyethylene sorbitan monooleate.
- the carrier for fish oil is a microemulsion system, which allows maintaining its stability. It was found that the stability of the formulations is achieved if they comprise not more than 30% of the surfactant and at least 7% of fish oil.
- the microemulsion of the invention comprises the above oil in amounts greater than it was previously possible in this type of systems.
- the used fish oil does not contain less than 70% of DHA and less than 17% of EPA.
- the food microemulsion of the invention does not comprise a co-surfactant and/or a cosolvent.
- the transparency of the present invention determines the lack of impact on the appearance of the final product.
- the novel product comprising a formulation with the microemulsion developed according to the present invention is characterized by an acceptable taste profile. The appearance and odor remain unchanged.
- the present invention can provide an effective method of maintaining the stability and acceptable sensory qualities of foodstuffs enriched with fish oil.
- the prepared edible microemulsion systems are characterized by a new improved composition selected for a possible application of the formulations created with their content in food industry.
- microemulsions obtained according to the invention are formulations in which a relatively large amount of water can be dispersed in oil.
- the cost of preparation of said invention is relatively low and limited mainly to the purchase of raw materials, without a necessity of using any specialized devices, apart from the ones which are typically applied, which may influence a price of the final foodstuff for the benefit of producers and consumers.
- Optimal edible microemulsion systems were obtained by a qualitative and quantitative selection of the surfactant and phases of the system, as well as by determining the order of adding the ingredients. The assumption was to introduce the best formulation to products eagerly consumed by the consumers, so that the kind of enriched product was not a limitation, but encouraged its consumption.
- the manufactured product is a dairy product, particularly a yogurt.
- the invention offers an opportunity to increase the intake of EPA and DHA acids without a radical change of dietary habits. It was assumed that there is a possibility of supplementing the diet with EPA and DHA acids through the regular use of the newly developed foodstuff.
- the present invention shall provide a food additive as a mean to support the care and protection of skin. Thanks to its numerous health-promoting properties it can also provide an alternative to traditional dietary supplements intended for the prevention of obesity, type 2 diabetes or immunological disorders.
- An interesting use of functional food comprising the present invention may be also a consumption of these products in order to reduce the susceptibility to stress, prevent depression, dementia or alleviate symptoms of the Attention Deficit Hyperactivity Disorder (ADHD) in children.
- ADHD Attention Deficit Hyperactivity Disorder
- the procedure for preparing the microemulsions of the present invention is simple and practical. It is important to follow the appropriate order of adding the ingredients.
- the method for preparing microemulsion systems of the invention is carried out at room temperature and comprises the following steps:
- Step 1 Preparation of the oil phase. This step can be performed by mixing the oil phase ingredients e.g. fish oil and lipophilic solvent e.g. oleic acid esters, using a mechanical stirrer. Step 1 can be omitted if the formulation does not comprise oleic acid esters.
- oil phase ingredients e.g. fish oil and lipophilic solvent e.g. oleic acid esters, using a mechanical stirrer.
- Step 1 can be omitted if the formulation does not comprise oleic acid esters.
- a liquid emulsion system with the internal phase droplet diameter of 140 nm is obtained.
- a liquid emulsion system with the internal phase droplet diameter of above 900 nm is obtained.
- Example 4 To 20.00 grams of 70% solution of fish oil in a lipophilic solvent e.g. ethyl oleate, 80.0 grams of polyoxyethylene sorbitan monooleate is added. Subsequently, 100.0 grams of distilled water is gradually added to this mixture.
- a lipophilic solvent e.g. ethyl oleate
- a solid transparent emulsion system is obtained.
- a liquid emulsion system with the internal phase droplet diameter of below 150 nm is obtained.
- a semisolid emulsion system which solidifies after a while is obtained.
- microemulsions obtained in the examples 1-5 were subjected to tests intended to analyze their stability. The evaluation was conducted based on visual observations of samples stored both at room temperature and in a refrigerator at +9°C. Observations were conducted sequentially 24 h, 48 h and 7, 14, 30 days after preparing the microemulsions. Stability of the formulation was also tested with a centrifugal test (3000 rpm for 10 min.). All the analyzed formulations were homogenous, and no phase separation was observed.
- the newly developed foodstuff was tested for its sensory qualities.
- the conducted consumer trial demonstrated a possibility to enrich yogurts with microemulsion formulations.
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Microbiology (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- General Preparation And Processing Of Foods (AREA)
Abstract
A food microemulsion constituting a carrier for fish oil and being an intermediate product intended to be introduced into foodstuff to increase the nutritional value of foodstuff is disclosed.
Description
A microemulsion consisting of an oil phase, an aqueous phase and a surfactant
The present invention relates to the edible microemulsion constituting a carrier for fish oil and being an intermediate product intended to be introduced into foodstuffs to increase the nutritional value of foodstuffs and thereby increase their commercial value.
Fish oil is widely recognized as the best source of supplementation of eicosapentaenoic acid (EPA, C20:5) and docosahexaenoic acid (DHA, C22:6)- the most bioactive compounds of the group of long-chain polyunsaturated fatty acids omega-3 (n-3), necessary for a proper functioning of the body. It is also a source of vitamins A and D, squalene and alkoxyglycerol which are valuable for the health. Dietary intake of fish oil allows to increase the levels of DHA and EPA and, thus, affects the normal development of children and the maintenance of good health in adults.
The most widely investigated property of fish oil is its anti-inflammatory and cardioprotective activity. This oil has a beneficial effect on prevention and management of cardiovascular diseases, immunological disorders, type 2 diabetes, colorectal, breast and prostate cancers, and ulcerative colitis. It can also alleviate symptoms of many diseases including osteoporosis and rheumatoid arthritis (RA). It exhibits a beneficial effect on the prevention of obesity and delays the aging process. It has the effect of reducing the levels of triglycerides and total cholesterol in the blood, prevents dementia and improves concentration. Other reports describe also the positive effect of fish oil supplementation in pregnant and breastfeeding women, as it may protect against the emergence of allergic diseases and favorably affect the course of sleep in infancy. (Judge M.P., Cong X., Harel O., Courville A.B., Lammi-Keefe C.J., Early Human Development, 2012, 88(7), 531-537; Furuhjelm C, Warstedt K., Fagerias M., Falth-Magnusson K., Larsson J., Fredriksson M., Duchen K., Pediatric Allergy and Immunology, 2011, 22, 505- 514; Kremmyda L.S., Vlachawa M, Noakes P.S., Diaper N.D., Miles E.A., Calder P.C., A systematic review, Clinical Reviews in Allergy and Immunology, 2011, 41, 36-66; Cleland L.G., James M.J., Proudman S., Arthritis Research & Therapy, 2006, 8, 1-9; Furst P., Kuhn K.S., Clinical Nutrition, 2000, 19, 7-14; Lewis M.D., Bailes J., Military Medicine, 2011, 176, 1120- 1127; Marciniak-Lukasiak K., ZYWNOSC. Nauka. Technologia. Jakosc, 2011, 6 (79), 24-35; Simopoulos A., American Journal of Clinical Nutrition, 1999, 70, 560-569).
Fish oil has also a number of advantages in maintaining optimal skin condition, among others it exhibits photoprotective activity and strengthens the epidermal barrier. Attempts to use EPA and DHA acids for alleviating symptoms of psoriasis are also made. It was found that 8 week fish oil
supplementation reduces scaling, itching and erythema and limits the area of skin covered by the disease (Brittiner S.B., Tucker W.F., Cartwright L, Bleehen S.S., The Lancet, 1988, 1, 378-380; Grimminger S., Mayser P., Prostaglandins Leukotrienes and Essential Fatty Acids, 1995, 52, 1- 15; Ziboh V.A., Cohen H.A., Ellis C.N., Miller C, Hamilton T.A., Kraqballe K., Hydrick C.R., Voorhees J.J., Archives of Dermatology, 1986, 122, 1277-1282). A reduction in the risk of squamous cell carcinoma (SCC) development, associated with an increased intake of n-3 acids was also demonstrated (Hakim I. A., Harris R. B., Ritenbaugh Ch., Nutrition and Cancer, 2000, 36, 155-162).
Unfortunately, despite numerous health-promoting properties of fish oil, its intense flavor and odor effectively discourage consumers from consuming it in its pure form. Neither traditional supplementation is much appreciated (Kolanowski W., Nutrition Research, 2008, 28, 245-250). Therefore, the attempts to introduce fish oil into foodstuffs resulting in products of functional foods category as an alternative for people who do not consume fish are advisable.
The largest problem resulting from the introduction of fish oil into foodstuffs is its high sensitivity to oxidation and hydrolysis, which alters the odor and taste of the final product. Sensitivity of n-3 acids (present in said oil) to oxidation is at the same time several hundred times greater in comparison to other fatty acids. Therefore consumers cannot store the foodstuffs comprising n-3 acids for too long once it is opened to avoid emission of fishy smell arising due to oxidation. In the production of milk enriched with n-3 acids it is practiced to add them in the form of an emulsion, while the addition of omega-3 fatty acids into yogurts requires their gradual introduction into the product prior to homogenization and pasteurization.
Numerous reports describe attempts to create functional foods comprising pure fish oil, without developing any special carrier. Among others, odor and taste of the products manufactured in this way were analyzed. It has been shown that the addition of fish oil does not result in significant differences in their appearance or sensory quality (Kolanowski W., Swiderski F., Lis E., Berger S., International Journal of Food Sciences and Nutrition, 52, 2001, 469-476, 37; Lovegrove J.A., Brooks C.N., Murphy M.C., Gould B.J., Williams CM., British Journal of Nutrition, 1997, 78, 223-236, Let M.B., Jacobsen Ch., Meyer A.S., Journal of Agricultural and Food Chemistry, 2007, 55, 7802-7809; Kolanowski W., Swiderski F., Berger S., International Journal of Food Science and Nutrition, 1999, 50, 39-49). Yet, the question remains unanswered, what is the actual impact of the presence of pure oil in the foodstuff on its stability during storage.
Attempts have been made to develop specific formulations based on fish oil, in most cases based on the preparation of an emulsion or micro-encapsulation of said oil. However, it should be
noted that microcapsules, whose shell is composed of gelatin, may dissolve and lose their properties when introduced into drinks or dairy products. The selection of a suitable encapsulating material, whose nature significantly affects the stability of the microcapsules, may be difficult. The shell is required to effectively protect the core of a microcapsule from the harmful impact of environmental factors without reacting with food components or affecting the odor or taste of the final product. Micro-encapsulation of oils is also significantly limited by the growing intensity of their characteristic odor during storage, which in turn shortens their shelf life.
Microemulsions which are thermodynamically stable dispersions of oil and aqueous phase, in which one or more of the surfactants/co-surfactants are used to transform them into a macroscopically single-phase system, are also known. The diameter of particles in the dispersed phase of the microemulsion is less than 140 nm. To compare, the particle size in the macroemulsion is typically > 1 μπι. Such a small particle size determines the transparency of microemulsion systems, because the wavelength of visible light (400 nm-700 nm) is longer, and thereby rays of white light do not refract while passing through a microemulsion. A decrease of the particle diameter to sizes expressed in nanometers positively affects the thermodynamic stability of the microemulsion. Said stability is ensured by a very low tension on the interface oil-water, which equals 10"3 mN/m. A low surface tension value is reached by the use of surfactants and co-surfactants. It facilitates the mixing of hydrophilic and lipophilic ingredients, so that no phase separation is observed, and the process of forming a microemulsion occurs spontaneously in the absence or a very low share of mechanical energy.
It is believed that the micro-encapsulation process does not provide as high bioavailability of active substances as microemulsion systems.
In turn, the advantage of microemulsion over macroemulsions results from a spontaneous mutual penetration of hydrophilic and hydrophobic areas in contrary to macroemulsions in which the droplets of internal and external phases are clearly separated. Another important difference is the stability of both systems. Macroemulsions are unstable systems. The most common symptoms of their instability are the following phenomena: creaming, flocculation, coalescence and phase separation. In contrast, microemulsions are characterized by a high stability. In addition, they provide a protection against hydrolysis and oxidation of active substances. The advantage of microemulsions justifying the use of these systems for foodstuffs is their transparency. As compared to milky macroemulsions, this feature is advantageous for esthetic reasons and helpful in, among others, quality control of foodstuffs. Compared with the traditional emulsion,
microemulsion systems are also characterized by a much smaller particle size, which is important for improving the bioavailability and facilitates the absorption of active ingredients.
Difficulties in application of microemulsion systems comprise, however, a necessity to use a high concentration of surfactants, which are toxic and may cause irritation once a certain concentration limit is exceeded.
The problem of developing a fish oil-based formulations, ensuring its stability and neutralizing the intense taste and odor of the oil remains open, since it is important to optimize the content of fish oil while limiting excipients to their necessary minimum.
The purpose of the invention is to provide such a form of oil, which once introduced into foodstuffs, would not significantly influence its sensory qualities and long-term storage stability. Another purpose of the invention is to provide an optimal composition and form of a food formulation comprising fish oil, both qualitatively and quantitatively, so as to obtain a stable form of fish oil as a bioactive ingredient.
It is also desirable to find a suitable foodstuff, which after enriching with the present invention would gain a higher nutritional value while maintaining acceptable taste.
The present invention relates to a microemulsion comprising an oil phase, an aqueous phase and a surfactant characterized in that it comprises about 30% of the surfactant suitable for use in foodstuffs and at least 7% of edible oil, particularly fish oil.
Preferably, the microemulsion according to present invention comprises only one surfactant and does not comprise a co-surfactant.
The surfactant suitable for the preparation of microemulsions may be any surfactant approved for use in foodstuffs, for example: lecithins, esters of sucrose and fatty acids, esters of fatty acids and polyglycerol, esters of fatty acids and propylene glycol, esters of polyoxyethylene sorbate and fatty acids, esters of sorbitol and fatty acids. Preferably the microemulsion of the invention comprises polyoxyethylene sorbitan monooleate.
According to the invention the carrier for fish oil is a microemulsion system, which allows maintaining its stability. It was found that the stability of the formulations is achieved if they comprise not more than 30% of the surfactant and at least 7% of fish oil. The microemulsion of the invention comprises the above oil in amounts greater than it was previously possible in this type of systems.
Preferably, the used fish oil does not contain less than 70% of DHA and less than 17% of EPA.
Preferably, the food microemulsion of the invention does not comprise a co-surfactant and/or a cosolvent.
Preferably, the transparency of the present invention determines the lack of impact on the appearance of the final product. Preferably, the novel product comprising a formulation with the microemulsion developed according to the present invention is characterized by an acceptable taste profile. The appearance and odor remain unchanged.
The present invention can provide an effective method of maintaining the stability and acceptable sensory qualities of foodstuffs enriched with fish oil. The prepared edible microemulsion systems are characterized by a new improved composition selected for a possible application of the formulations created with their content in food industry.
The microemulsions obtained according to the invention are formulations in which a relatively large amount of water can be dispersed in oil.
Preferably, the cost of preparation of said invention is relatively low and limited mainly to the purchase of raw materials, without a necessity of using any specialized devices, apart from the ones which are typically applied, which may influence a price of the final foodstuff for the benefit of producers and consumers.
Optimal edible microemulsion systems were obtained by a qualitative and quantitative selection of the surfactant and phases of the system, as well as by determining the order of adding the ingredients. The assumption was to introduce the best formulation to products eagerly consumed by the consumers, so that the kind of enriched product was not a limitation, but encouraged its consumption.
Another subject of the invention is the application of the microemulsion as defined above according to the invention for the preparation of dietary supplements or functional food. Preferably, the manufactured product is a dairy product, particularly a yogurt.
The invention offers an opportunity to increase the intake of EPA and DHA acids without a radical change of dietary habits. It was assumed that there is a possibility of supplementing the diet with EPA and DHA acids through the regular use of the newly developed foodstuff. The present invention shall provide a food additive as a mean to support the care and protection of skin. Thanks to its numerous health-promoting properties it can also provide an alternative to traditional dietary supplements intended for the prevention of obesity, type 2 diabetes or immunological disorders. An interesting use of functional food comprising the present invention
may be also a consumption of these products in order to reduce the susceptibility to stress, prevent depression, dementia or alleviate symptoms of the Attention Deficit Hyperactivity Disorder (ADHD) in children.
The subject of the invention is described below with the help of selected examples.
Method of preparing a microemulsion of the invention
The procedure for preparing the microemulsions of the present invention is simple and practical. It is important to follow the appropriate order of adding the ingredients. The method for preparing microemulsion systems of the invention is carried out at room temperature and comprises the following steps:
1) Preparation of the oil phase. This step can be performed by mixing the oil phase ingredients e.g. fish oil and lipophilic solvent e.g. oleic acid esters, using a mechanical stirrer. Step 1 can be omitted if the formulation does not comprise oleic acid esters.
2) Addition of the surfactant, approved for the use in foodstuffs, to the oil phase. For this purpose, polyoxyethylene sorbitan monooleate shall be mixed with the oil phase (point 1).
Mixing with the use of a low speed mechanical stirrer should be continued until the homogenous system is obtained.
3) Gradual addition of water to the anhydrous microemulsion. For this purpose water should be added to the system described in point 2 in portions, e.g. measured using a peristaltic pump with continuous stirring.
Example 1
To 14.3 grams of 60% solution of fish oil in a lipophilic solvent e.g. ethyl oleate, 85.7 grams of polyoxyethylene sorbitan monooleate is added. Subsequently, 160.0 grams of distilled water is gradually added to this mixture.
A liquid emulsion system with the internal phase droplet diameter of 140 nm is obtained.
Example 2
To 14.3 grams of 60% solution of fish oil in a lipophilic solvent e.g. ethyl oleate, 42.9 grams of polyoxyethylene sorbitan monooleate is added. Subsequently, 80.0 grams of distilled water is gradually added to this mixture.
A liquid emulsion system with the internal phase droplet diameter of 150 nm is obtained.
Example 3
To 14.3 grams of 60% solution of fish oil in a lipophilic solvent e.g. ethyl oleate, 20.0-25.0 grams of polyoxyethylene sorbitan monooleate is added. Subsequently, 160.0 grams of distilled water is gradually added to this mixture.
A liquid emulsion system with the internal phase droplet diameter of above 900 nm is obtained.
Example 4 To 20.00 grams of 70% solution of fish oil in a lipophilic solvent e.g. ethyl oleate, 80.0 grams of polyoxyethylene sorbitan monooleate is added. Subsequently, 100.0 grams of distilled water is gradually added to this mixture.
A solid transparent emulsion system is obtained.
Example 5
42.9 grams of polyoxyethylene sorbitan monooleate is added to 10.0 grams of fish oil. 80.0 grams of distilled water is gradually added to this mixture.
A liquid emulsion system with the internal phase droplet diameter of below 150 nm is obtained.
Example 6
To 11.1 grams of 80% solution of fish oil in a lipophilic solvent e.g. ethyl oleate, 88.9 grams of polyoxyethylene sorbitan monooleate is added. 80.0 grams of distilled water is gradually added to this mixture.
A semisolid emulsion system which solidifies after a while is obtained.
Example 7
To 2.0 grams of 15% solution of fish oil in a lipophilic solvent e.g. ethyl oleate, 18.0 grams of sucrose palmitate is added. 50.0 grams of distilled water is gradually added to this mixture.
A liquid emulsion system with the internal phase droplet diameter of above 900 nm is obtained.
Example 8
The microemulsions obtained in the examples 1-5 were subjected to tests intended to analyze their stability. The evaluation was conducted based on visual observations of samples stored both at room temperature and in a refrigerator at +9°C. Observations were conducted sequentially 24 h, 48 h and 7, 14, 30 days after preparing the microemulsions. Stability of the formulation was also tested with a centrifugal test (3000 rpm for 10 min.). All the analyzed formulations were homogenous, and no phase separation was observed.
In a further step of the study the effect of adding the microemulsions into yogurts of different flavors on the taste and odor of the final product was analyzed. For this purpose 15.0 grams of yogurt and from 0.5 to 1.0 grams of microemulsion were mixed. The sealed samples were stored at + 9°C for 7 days. After the period of storage, no negative impact of microemulsion on organoleptic properties of the yogurt was observed.
The newly developed foodstuff was tested for its sensory qualities. The conducted consumer trial demonstrated a possibility to enrich yogurts with microemulsion formulations.
Claims
1. A microemulsion consisting of an oil phase, an aqueous phase and a surfactant, characterized in that it comprises about 30% of the surfactant applicable for use in foodstuff and at least 7% of edible oil, particularly fish oil.
2. The microemulsion according to claim 1, characterized in that it comprises only one surfactant.
3. The microemulsion according to claim 1, characterized in that it does not comprise a co- surfactant.
4. The microemulsion according to claim 1 characterized in that the fish oil contains not less than 70%) of docosahexanoic acid and not less than 17% of eicosapentanoic acid.
5. The use of the microemulsion according to claims 1-4 for preparation of dietary supplements or functional food.
6. The use according to claim 5 characterized in that the manufactured product is a dairy product, particularly a yogurt.
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080199589A1 (en) * | 2007-02-20 | 2008-08-21 | Cargill, Incorporated | Lipid Microemulsions |
WO2010091853A2 (en) * | 2009-02-11 | 2010-08-19 | Dsm Ip Assets B.V. | High concentrated pufa emulsions |
US20120058241A1 (en) * | 2010-09-07 | 2012-03-08 | Ocean Nutrition Canada Limited | Comestible emulsions |
CN102416056A (en) * | 2011-11-19 | 2012-04-18 | 西北农林科技大学 | Compound nanoemulsion oral liquid for reducing blood fat and preparation method thereof |
CN102552328A (en) * | 2011-12-15 | 2012-07-11 | 山东禹王制药有限公司 | Preparation method of compound fish oil nano-emulsion |
US20130017295A1 (en) * | 2008-03-20 | 2013-01-17 | Bromley Philip J | Compositions containing non-polar compounds |
-
2013
- 2013-07-13 PL PL404684A patent/PL227367B1/en unknown
-
2014
- 2014-07-14 WO PCT/PL2014/050042 patent/WO2015009181A1/en active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080199589A1 (en) * | 2007-02-20 | 2008-08-21 | Cargill, Incorporated | Lipid Microemulsions |
US20130017295A1 (en) * | 2008-03-20 | 2013-01-17 | Bromley Philip J | Compositions containing non-polar compounds |
WO2010091853A2 (en) * | 2009-02-11 | 2010-08-19 | Dsm Ip Assets B.V. | High concentrated pufa emulsions |
US20120058241A1 (en) * | 2010-09-07 | 2012-03-08 | Ocean Nutrition Canada Limited | Comestible emulsions |
CN102416056A (en) * | 2011-11-19 | 2012-04-18 | 西北农林科技大学 | Compound nanoemulsion oral liquid for reducing blood fat and preparation method thereof |
CN102552328A (en) * | 2011-12-15 | 2012-07-11 | 山东禹王制药有限公司 | Preparation method of compound fish oil nano-emulsion |
Non-Patent Citations (17)
Title |
---|
BRITTINER S.B.; TUCKER W.F.; CARTWRIGHT I.; BLEEHEN S.S., THE LANCET, vol. 1, 1988, pages 378 - 380 |
CLELAND L.G.; JAMES M.J.; PROUDMAN S., ARTHRITIS RESEARCH & THERAPY, vol. 8, 2006, pages 1 - 9 |
FURST P.; KUHN K.S., CLINICAL NUTRITION, vol. 19, 2000, pages 7 - 14 |
FURUHJELM C.; WARSTEDT K.; FAGERIAS M.; FALTH-MAGNUSSON K.; LARSSON J.; FREDRIKSSON M.; DUCHEN K., PEDIATRIC ALLERGY AND IMMUNOLOGY, vol. 22, 2011, pages 505 - 514 |
GRIMMINGER S.; MAYSER P., PROSTAGLANDINS LEUKOTRIENES AND ESSENTIAL FATTY ACIDS, vol. 52, 1995, pages 1 - 15 |
HAKIM 1. A.; HARRIS R. B.; RITENBAUGH CH., NUTRITION AND CANCER, vol. 36, 2000, pages 155 - 162 |
JUDGE M.P.; CONG X.; HAREL 0.; COURVILLE A.B.; LAMMI-KEEFE C.J., EARLY HUMAN DEVELOPMENT, vol. 88, no. 7, 2012, pages 531 - 537 |
KOLANOWSKI W., NUTRITION RESEARCH, vol. 28, 2008, pages 245 - 250 |
KOLANOWSKI W.; SWIDERSKI F.; BERGER S., INTERNATIONAL JOURNAL OF FOOD SCIENCE AND NUTRITION, vol. 50, 1999, pages 39 - 49 |
KOLANOWSKI W.; SWIDERSKI F.; LIS E.; BERGER S., INTERNATIONAL JOURNAL OF FOOD SCIENCES AND NUTRITION, vol. 52, no. 37, 2001, pages 469 - 476 |
KREMMYDA L.S.; VLACHAWA M.; NOAKES P.S.; DIAPER N.D.; MILES E.A.; CALDER P.C.: "A systematic review", CLINICAL REVIEWS IN ALLERGY AND IMMUNOLOGY, vol. 41, 2011, pages 36 - 66, XP019933926, DOI: doi:10.1007/s12016-009-8186-2 |
LET M.B.; JACOBSEN CH.; MEYER A.S., JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 55, 2007, pages 7802 - 7809 |
LEWIS M.D.; BAILES J., MILITARY MEDICINE, vol. 176, 2011, pages 1120 - 1127 |
LOVEGROVE J.A.; BROOKS C.N.; MURPHY M.C.; GOULD B.J.; WILLIAMS C.M., BRITISH JOURNAL OF NUTRITION, vol. 78, 1997, pages 223 - 236 |
MARCINIAK-LUKASIAK K.; ZYWNOSÉ. NAUKA, TECHNOLOGIA. JAKOSC, vol. 6, no. 79, 2011, pages 24 - 35 |
SIMOPOULOS A., AMERICAN JOURNAL OF CLINICAL NUTRITION, vol. 70, 1999, pages 560 - 569 |
ZIBOH V.A.; COHEN H.A.; ELLIS C.N.; MILLER C.; HAMILTON T.A.; KRAQBALLE K.; HYDRICK C.R.; VOORHEES J.J., ARCHIVES OF DERMATOLOGY, vol. 122, 1986, pages 1277 - 1282 |
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