JPH07216383A - Fish oil with reduced odor and its production - Google Patents
Fish oil with reduced odor and its productionInfo
- Publication number
- JPH07216383A JPH07216383A JP6024750A JP2475094A JPH07216383A JP H07216383 A JPH07216383 A JP H07216383A JP 6024750 A JP6024750 A JP 6024750A JP 2475094 A JP2475094 A JP 2475094A JP H07216383 A JPH07216383 A JP H07216383A
- Authority
- JP
- Japan
- Prior art keywords
- fish oil
- fish
- oil
- hydrogenation
- odor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 235000021323 fish oil Nutrition 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 12
- 239000011630 iodine Substances 0.000 claims abstract description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 46
- 241000251468 Actinopterygii Species 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 13
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 11
- 230000009467 reduction Effects 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 8
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products 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 abstract description 43
- 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 abstract description 24
- 235000020673 eicosapentaenoic acid Nutrition 0.000 abstract description 24
- 229960005135 eicosapentaenoic acid Drugs 0.000 abstract description 24
- 235000020669 docosahexaenoic acid Nutrition 0.000 abstract description 23
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 abstract description 23
- 229940090949 docosahexaenoic acid Drugs 0.000 abstract description 22
- 235000013305 food Nutrition 0.000 abstract description 21
- 239000000463 material Substances 0.000 abstract description 12
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 7
- 229930195729 fatty acid Natural products 0.000 abstract description 7
- 239000000194 fatty acid Substances 0.000 abstract description 7
- 150000004665 fatty acids Chemical class 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract 1
- QAPAPLIQQTVEJZ-UHFFFAOYSA-N n-[(3-fluorophenyl)methyl]ethanamine Chemical compound CCNCC1=CC=CC(F)=C1 QAPAPLIQQTVEJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 44
- 235000019198 oils Nutrition 0.000 description 44
- 235000019688 fish Nutrition 0.000 description 38
- 235000019645 odor Nutrition 0.000 description 36
- 239000003925 fat Substances 0.000 description 23
- 235000019197 fats Nutrition 0.000 description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
- 235000019512 sardine Nutrition 0.000 description 12
- 241001125048 Sardina Species 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 241000962514 Alosa chrysochloris Species 0.000 description 7
- 230000001953 sensory effect Effects 0.000 description 7
- 239000004927 clay Substances 0.000 description 6
- 235000014593 oils and fats Nutrition 0.000 description 6
- 241000269851 Sarda sarda Species 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 241000283153 Cetacea Species 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000035790 physiological processes and functions Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- 241000555825 Clupeidae Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001125831 Istiophoridae Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 241001504592 Trachurus trachurus Species 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 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
- 239000000470 constituent Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000004626 essential fatty acids Nutrition 0.000 description 2
- 229940013317 fish oils Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- 235000019149 tocopherols Nutrition 0.000 description 2
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 2
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 1
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 241001149724 Cololabis adocetus Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000736160 Cynoscion regalis Species 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 235000015429 Mirabilis expansa Nutrition 0.000 description 1
- 244000294411 Mirabilis expansa Species 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 241000276699 Seriola Species 0.000 description 1
- 208000006981 Skin Abnormalities Diseases 0.000 description 1
- 206010047531 Visual acuity reduced Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013332 fish product Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- -1 icosapentaenoic acid Chemical class 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000007087 memory ability Effects 0.000 description 1
- 239000002207 metabolite 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
- 235000020166 milkshake Nutrition 0.000 description 1
- 235000013536 miso Nutrition 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、魚臭の発生を低減した
魚油及びその製造法に関する。本発明の方法により製造
した魚油は、魚臭が低減されていると共にドコサヘキサ
エン酸やエイコサペンタエン酸などの高度不飽和脂肪酸
が相当量残存しているので、一般食品や医療食などの素
材として有用である。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to fish oil having reduced fish odor and a method for producing the same. The fish oil produced by the method of the present invention has a reduced fish odor and also contains a considerable amount of highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid, which is useful as a material for general food and medical food. is there.
【０００２】[0002]
【従来の技術】油脂は、タンパク質、炭水化物と並び食
品の三大栄養素の一つであって、エネルギー源として重
要な役割を果たしており、日本人においては、食事中の
総エネルギーに占める脂肪エネルギーの比率が約２５％
に達している現状にある。また、油脂は生体を構成する
重要な成分でもあり、食物からの脂肪摂取が欠乏すると
様々な症状や障害が現れることが多数報告されている。BACKGROUND OF THE INVENTION Oils and fats are one of the three major nutrients in foods, along with proteins and carbohydrates, and play an important role as an energy source. Ratio is about 25%
The current situation has reached. In addition, fats and oils are also important constituents of the living body, and it has been reported that various symptoms and disorders appear when the intake of fats from food is deficient.
【０００３】また、油脂はグリセロール骨格に脂肪酸３
分子がエステル結合した構造を有しており、脂肪酸の種
類や組合せによって、性状や生体内での役割が大きく左
右される。そして、この脂肪酸の中でも、高度不飽和脂
肪酸には、それ自体あるいはその代謝生産物に生体内で
有用な生理機能を示すものが多い。例えば、リノール酸
やα−リノレン酸が欠乏すると、皮膚異常、組織再生力
の減退、病気感染に対する感受性の増加などの症状をも
たらし、かつ、これらの脂肪酸は生体内で合成されず食
事から摂取しなければならないので、必須脂肪酸とされ
ている。Fats and oils are fatty acids 3 in the glycerol skeleton.
The molecule has an ester-bonded structure, and its properties and role in the living body are greatly influenced by the type and combination of fatty acids. Of these fatty acids, many of the polyunsaturated fatty acids have useful physiological functions in vivo for themselves or their metabolites. For example, deficiency of linoleic acid or α-linolenic acid causes symptoms such as skin abnormalities, decrease in tissue regeneration power, and increased susceptibility to disease infection, and these fatty acids are not synthesized in vivo and are ingested from the diet. It is considered an essential fatty acid because it must be present.
【０００４】これらの必須脂肪酸と並んで、ドコサヘキ
サエン酸（ＤＨＡ）やエイコサペンタエン酸（ＥＰＡ）
は、循環器系疾患やその他の成人病の予防及び治療に有
効であるとされており、近年、注目を集めている高度不
飽和脂肪酸である。そして、特に血小板凝集能低下、血
中コレステロール低下、血糖値低下などの血液循環器系
への作用、肝中性脂肪低下やリウマチの治療及び予防効
果、各種悪性腫瘍発生率低下作用、アトピー、喘息、花
粉症などに対する免疫調整作用、さらには、最近注目さ
れている作用として、学習機能や記憶力の向上及び改
善、痴呆症抑制、視力の向上あるいは低下の抑制などの
神経系に対する作用が報告されている〔「機能性脂質の
開発と応用」、佐藤清隆他監修、シーエムシー、「食品
と開発」１９９２年８月号、健康産業新聞社〕。Along with these essential fatty acids, docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA)
Is a polyunsaturated fatty acid, which is said to be effective for the prevention and treatment of cardiovascular diseases and other adult diseases, and has been attracting attention in recent years. And, in particular, the effects on the blood circulation system such as a decrease in platelet aggregation ability, a decrease in blood cholesterol, and a decrease in blood sugar level, a therapeutic and preventive effect on a decrease in hepatic triglyceride and rheumatism, an effect of reducing the incidence of various malignant tumors, atopy, asthma , An effect on the nervous system such as an immunomodulatory action against hay fever, etc., and further, an action which has recently been attracting attention, such as improvement and improvement of learning function and memory ability, suppression of dementia, suppression of improvement or deterioration of visual acuity. ("Development and application of functional lipids", supervised by Kiyotaka Sato et al., CMC, "Food and Development" August 1992 issue, Kenko Sangyo Shimbun).
【０００５】このように各種の生理機能が報告されてい
るドコサヘキサエン酸やエイコサペンタエン酸は、多く
の魚類や鯨の油脂中に存在しており、魚種や鯨種、また
は、それらの部位により、あるいは漁獲の場所や時期に
より、これらの含有量が異なる。そして、イワシ、アジ
などの小型魚の油脂中にはエイコサペンタエン酸が、カ
ツオ、カジキ、カンパチ、サメなどの大型魚の油脂中に
はドコサヘキサエン酸が、それぞれ多量に含まれている
ことが知られている〔油脂化学便覧第４版〕。Docosahexaenoic acid and eicosapentaenoic acid, which have been reported to have various physiological functions as described above, are present in oils and fats of many fishes and whales, and depending on fish species, whale species, or their parts, Alternatively, the contents of these differ depending on the location and time of catch. It is known that the fats and oils of small fish such as sardines and horse mackerels contain a large amount of eicosapentaenoic acid, and the fats and oils of large fish such as skipjack, marlin, amberjack, and shark contain a large amount of docosahexaenoic acid. [Oil and Fat Chemistry Handbook 4th Edition].
【０００６】そして、ドコサヘキサエン酸やエイコサペ
ンタエン酸を含有している魚油は、魚体全体もしくは魚
体の一部分から搾汁され、デカンテーションや遠心分離
などの処理により水溶性画分を除去して得られる。さら
に、この魚油に分別やウィンタリングなどの処理を施す
ことにより、ドコサヘキサエン酸やエイコサペンタエン
酸を濃縮し、それらの含有量を上昇させることも可能で
ある。The fish oil containing docosahexaenoic acid and eicosapentaenoic acid is obtained by squeezing the whole fish body or a part of the fish body and removing the water-soluble fraction by a treatment such as decantation or centrifugation. Furthermore, it is possible to concentrate docosahexaenoic acid and eicosapentaenoic acid and increase their contents by subjecting this fish oil to treatments such as fractionation and wintering.
【０００７】ところで、食品素材として香りは重要な因
子の一つであるが、魚油は特有の臭気（魚臭）を有して
おり、食品素材としての利用が制限されている。現在、
活性炭や活性白土などへの吸着、あるいは、分子蒸留や
水蒸気蒸留により、魚臭の除去が試みられている。しか
しながら、脱臭した魚油もしくはこの魚油を配合した食
品を保存しておくと、魚臭が発生する。これらの魚臭
は、高度不飽和脂肪酸であるドコサヘキサエン酸やエイ
コサペンタエン酸などが酸化劣化を受けて発生するもの
であって、臭気成分としては、ノナジエナール、デカト
リエナール、ヘキセナール、ヘプテナールなどのアルデ
ヒド及びオクタジエノンなどのケトンであるとの報告が
なされている〔Ｋａｒａｈａｄｉａｎ ａｎｄ Ｌｉｎ
ｓａｙ，Ｊ．ｏｆ Ａｍ．Ｏｉｌ Ｃｈｅｍｉｓｔｓ’
Ｓｏｃｉｅｔｙ，Ｖｏｌ．６６，ｎｏ．７，ｐ．９５
３，１９８９〕。したがって、魚油を食品素材として利
用するに際しては、魚臭の発生が大きな問題となってお
り、これらの臭気成分の除去及び発生抑制が重要な技術
的課題となっている。Although scent is one of the important factors as a food material, fish oil has a specific odor (fish odor), and its use as a food material is limited. Current,
Attempts have been made to remove fishy odor by adsorption on activated carbon or activated clay, or by molecular distillation or steam distillation. However, when deodorized fish oil or foods containing this fish oil is stored, fish odor is generated. These fish odors are generated by oxidative deterioration of highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid. It has been reported to be a ketone such as octadienone [Karahadian and Lin.
say, J. et al. of Am. Oil Chemist's
Society, Vol. 66, no. 7, p. 95
3, 1989]. Therefore, when fish oil is used as a food material, the generation of fish odor has become a serious problem, and the removal of these odorous components and the suppression of their generation have become important technical issues.
【０００８】一方、油脂の水素添加（以下、水添と略記
する）は、エステル交換や分別と並んで加工油脂製造に
関わる代表的な技術であり、水添により得られる硬化油
は分別油と並んで有用な加工油脂であって、油脂食品を
製造する上で重要な役割を果たしている。一般的に水添
は、反応温度１２０〜２００℃、水素雰囲気下、触媒存
在下で液状油脂を撹拌して行われる。この際、水素圧力
は常圧から５ｋｇ／ｃｍ2 程度であり、触媒としては還
元ニッケル、ギ酸ニッケル、ラネーニッケル、ホウ化ニ
ッケルなどのニッケル触媒が用いられることが多い。こ
の水添により、油脂を構成する脂肪酸中の炭素−炭素の
二重結合が水素化される。ここで、水添により得られる
硬化油の特性を以下に挙げる。 （１）油脂の融点が上昇し、可塑性油脂として使用でき
る。 （２）二重結合（不飽和結合）が減少し、油脂の酸化安
定性が向上する。 （３）選択的水添により固体脂含量（ＳＦＣ）の対温度
曲線がシャープな縦型となり、他の油脂との混合や分別
の処理を行うことにより、チョコレート、マーガリン、
ショートニングなどの食品への適性の良い油脂となる。On the other hand, hydrogenation of oils and fats (hereinafter abbreviated as hydrogenation) is a typical technique related to the production of processed oils and fats, along with transesterification and fractionation, and hydrogenated oils obtained by hydrogenation are fractionated oils. It is also a useful processed fat and oil, and plays an important role in producing fat and oil foods. Generally, hydrogenation is performed by stirring liquid oils and fats in the presence of a catalyst under a hydrogen atmosphere at a reaction temperature of 120 to 200 ° C. At this time, the hydrogen pressure is from normal pressure to about 5 kg / cm 2 , and a nickel catalyst such as reduced nickel, nickel formate, Raney nickel or nickel boride is often used as the catalyst. By this hydrogenation, the carbon-carbon double bond in the fatty acid that constitutes the fat is hydrogenated. Here, the characteristics of the hydrogenated oil obtained by hydrogenation are listed below. (1) The melting point of the oil / fat is increased, and the oil / fat can be used as a plastic oil / fat. (2) Double bonds (unsaturated bonds) are reduced, and the oxidative stability of fats and oils is improved. (3) By selective hydrogenation, the solid fat content (SFC) has a sharp vertical curve with respect to temperature, and by mixing with other fats and oils and fractionation, chocolate, margarine,
It becomes an oil and fat with good suitability for foods such as shortening.
【０００９】従来、魚油を水添して硬化魚油とすること
により、酸化安定性を向上させて魚臭の発生を抑制する
ことが行われており、魚油を食品素材として利用するた
めの常法となっている。なお、食品素材としては、融点
が２０〜４５℃、好ましくは３５℃以上に上昇した硬化
魚油が使用し易いとされている〔油脂・油糧ハンドブッ
ク、阿部芳郎監修、幸書房〕。しかしながら、魚油中に
含まれるドコサヘキサエン酸やエイコサペンタエン酸な
どの高度不飽和脂肪酸は、魚油の水添により還元されて
消失する。したがって、現在、入手可能な硬化魚油に
は、ドコサヘキサエン酸やエイコサペンタエン酸などの
高度不飽和脂肪酸は含まれていないか、あるいは、ごく
僅かに残存しているのみである。そして、ドコサヘキサ
エン酸やエイコサペンタエン酸などの高度不飽和脂肪酸
を相当量残存させたまま、水添により魚臭の発生を抑制
せしめて官能的に問題のない魚油を調製する試みについ
ては報告されていない現状にある。[0009] Conventionally, hydrogenation of fish oil into hardened fish oil has been carried out to improve the oxidative stability and suppress the generation of fish odor. The conventional method for utilizing fish oil as a food material. Has become. As a food material, it is said that hardened fish oil having a melting point of 20 to 45 ° C., preferably 35 ° C. or higher is easy to use [Fat and Oil Handbook, supervised by Yoshiro Abe, Shoshobo]. However, highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid contained in fish oil are reduced and disappear by hydrogenation of fish oil. Therefore, currently available hydrogenated fish oils do not contain, or only very little remain, highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid. Then, while leaving a considerable amount of highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid, no attempt has been made to prepare a sensory fish oil by suppressing the generation of fish odor by hydrogenation. It is in the present condition.
【００１０】[0010]
【発明が解決しようとする課題】本発明は、上記の問題
に鑑みなされたものであって、その目的は、多くの生理
機能を有するので有用な食品素材となり得るが、特有の
臭気を発生するが故に食品素材としての利用が困難であ
るか、もしくは、その利用が限定されている魚油を、非
選択的条件下で水添処理することにより、魚臭の発生を
低減せしめると共にドコサヘキサエン酸やエイコサペン
タエン酸などの高度不飽和脂肪酸を相当量含有する魚油
及び該魚油を調製する方法を提供することにある。SUMMARY OF THE INVENTION The present invention has been made in view of the above problems, and its purpose is to be a useful food material because it has many physiological functions, but it produces a peculiar odor. Therefore, it is difficult to use it as a food material, or by subjecting fish oil whose use is limited to hydrogenation treatment under non-selective conditions, the generation of fish odor can be reduced and docosahexaenoic acid and ethanol can be reduced. (EN) It is intended to provide a fish oil containing a considerable amount of a highly unsaturated fatty acid such as icosapentaenoic acid, and a method for preparing the fish oil.
【００１１】[0011]
【課題を解決するための手段】係る目的を達成するため
の本発明は、原料となる魚油に還元触媒を添加し、水素
雰囲気下で微水添反応を行うことにより、魚臭の発生を
低減せしめると共にドコサヘキサエン酸やエイコサペン
タエン酸などの高度不飽和脂肪酸を相当量含有させるも
のである。なお、ここで言う微水添とは、ヨウ素価の減
少率が１５％以内の水添を意味する。[Means for Solving the Problems] In order to achieve the above object, the present invention reduces the generation of fish odor by adding a reducing catalyst to fish oil as a raw material and performing a slight hydrogenation reaction in a hydrogen atmosphere. It also contains a considerable amount of highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid. The slight hydrogenation referred to here means hydrogenation in which the reduction rate of the iodine value is within 15%.
【００１２】本発明では、魚油の微水添を非選択的条件
で実施することにより、魚臭の発生を低減すると共に、
魚油中のドコサヘキサエン酸やエイコサペンタエン酸な
どの高度不飽和脂肪酸の消失を最低限に抑制することが
できる。なお、本発明で言う微水添の非選択的条件と
は、ヨウ素価の減少率が１５％以内で、かつ、ドコサヘ
キサエン酸やエイコサペンタエン酸などの高度不飽和脂
肪酸の減少率が３３％以内であるような条件を意味し、
水添処理の水素圧力、反応温度及び反応時間、触媒種及
び触媒量、撹拌強度などを変化させることにより、最適
化を図ることができる。In the present invention, the slight hydrogenation of fish oil is carried out under non-selective conditions to reduce the generation of fish odor and
It is possible to minimize the loss of highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid in fish oil. In addition, the non-selective condition of slight hydrogenation referred to in the present invention means that the reduction rate of iodine value is within 15% and the reduction rate of highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid is within 33%. Means some condition,
Optimization can be achieved by changing the hydrogen pressure, the reaction temperature and the reaction time of the hydrogenation treatment, the catalyst species and the amount of catalyst, the stirring strength, and the like.
【００１３】本発明の方法により得られる微水添魚油
は、官能的に悪影響を及ぼす魚臭の発生が少なく、か
つ、魚油中のドコサヘキサエン酸やエイコサペンタエン
酸などの高度不飽和脂肪酸の消失が最低限に抑制されて
いるので、食品素材として利用するのに適したものであ
り、また、医薬品にも適用が可能である。さらには、本
発明の方法により得られる微水添魚油に、抗酸化剤を併
用したり、他の精製油脂を配合することにより、魚臭の
低減効果を増強せしめることが可能であり、風味が良好
で安定な油脂として利用され得る。The slightly hydrogenated fish oil obtained by the method of the present invention produces less fish odor that has a sensory adverse effect, and has a minimum loss of highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid in the fish oil. Since it is suppressed to the maximum, it is suitable for use as a food material, and can be applied to medicines. Furthermore, the slightly hydrogenated fish oil obtained by the method of the present invention, in combination with an antioxidant, or by blending other refined fats and oils, it is possible to enhance the effect of reducing fish odor, and the flavor is It can be used as a good and stable fat.
【００１４】本発明で原料となる魚油は、イワシ、サン
マ、アジ、サバなどの小型もしくは中型青背魚やマグ
ロ、カツオ、カジキなどの大型青背魚の魚体から採取さ
れるものであるが、これらに限定されるものではなく、
鮫、鯨、イカなどから採取されたものでも良い。また、
魚体全体からではなく、肝臓などの臓器部分や頭部、眼
部など、部分を限定して採取された魚油でも構わない。
なお、本発明では、これらの魚油をそのまま微水添する
ことも可能であるが、リン脂質に代表される複合脂質や
蛋白質が魚油に混在すると微水添に用いる触媒を被毒
し、触媒活性を低下させて微水添の進行を妨げるので、
微水添に供する魚油は、可能な限り精製されていること
が望ましい。The fish oil used as a raw material in the present invention is obtained from fish bodies of small or medium-sized blue-backed fish such as sardines, saury, horse mackerel, and mackerel, and large-sized blue-backed fish such as tuna, bonito, and marlin. Not limited to
It may be a shark, whale, squid, etc. Also,
Instead of the whole fish body, fish oil collected by limiting the parts such as the liver and other organs, the head, and the eyes may be used.
Incidentally, in the present invention, it is also possible to microhydrogenate these fish oils as they are, but if complex lipids and proteins typified by phospholipids are mixed in the fish oil, they poison the catalyst used for microhydrogenation and have catalytic activity. To lower the progress of fine hydrogenation,
It is desirable that the fish oil to be subjected to slight hydrogenation be purified as much as possible.
【００１５】本発明では、この原料となる魚油と水添用
触媒を反応容器に供給して微水添を行えば良い。なお、
水添用の触媒としては、還元触媒が用いられ、例えば、
銅触媒、ルテニウム、白金、パラジウムなどの貴金属触
媒などが使用可能であるが、特に、還元ニッケル、ギ酸
ニッケル、ラネーニッケルなどの構成元素としてニッケ
ルを主体とするニッケル触媒を一種または二種以上選択
して使用することが好ましい。通常の水添の場合、これ
らの触媒は油脂に対して０．０２〜０．２０重量％の割
合で使用されているが、本発明では、非選択的に微水添
を進行させるために、油脂に対して０．０５重量％以上
の割合で触媒を使用する。なお、反応容器は、耐圧式で
撹拌装置が装備されているものが好ましく、その形状や
サイズは特に限定されない。また、バッチ式の反応容器
であっても構わないし、連続式の反応容器であっても構
わない。In the present invention, the fish oil as the raw material and the hydrogenation catalyst may be supplied to the reaction vessel for fine hydrogenation. In addition,
As the catalyst for hydrogenation, a reduction catalyst is used, for example,
Copper catalysts, ruthenium, platinum, precious metal catalysts such as palladium, etc. can be used, but in particular, one or more nickel catalysts containing nickel as a constituent element such as reduced nickel, nickel formate, Raney nickel are selected. Preference is given to using. In the case of ordinary hydrogenation, these catalysts are used in a proportion of 0.02 to 0.20% by weight with respect to fats and oils. However, in the present invention, in order to proceed the fine hydrogenation nonselectively, The catalyst is used in a proportion of 0.05% by weight or more based on the fat and oil. The reaction vessel is preferably pressure resistant and equipped with a stirrer, and its shape and size are not particularly limited. Further, it may be a batch reaction container or a continuous reaction container.
【００１６】本発明では、反応容器に供給された魚油及
び触媒を撹拌しながら５ｔｏｒｒ以下となるよう減圧操
作を行って魚油及び触媒の脱気、脱水を十分に行った
後、減圧状態を保ったままで所定の反応温度まで昇温す
る。そして、所定の反応温度に達した後、水素ガスを反
応容器に供給し、微水添を開始する。このとき、反応容
器の気相の水素圧力は３ｋｇ／ｃｍ2 以上に設定するこ
とが望ましい。また、微水添中にも、この水素圧力を保
つことが望ましい。本発明で、非選択的に微水添を進行
させるための反応温度としては、触媒が活性を発揮する
温度以上で、かつ、可能な限り低い温度に保つことが望
ましい。なお、最適な反応温度は触媒により異なるが、
ニッケル触媒を使用した場合においては、９０〜１５０
℃の範囲である。In the present invention, the fish oil and the catalyst supplied to the reaction vessel are agitated to reduce the pressure to 5 torr or less to sufficiently deaerate and dehydrate the fish oil and the catalyst, and then maintain the depressurized state. Up to a predetermined reaction temperature. Then, after reaching a predetermined reaction temperature, hydrogen gas is supplied to the reaction vessel to start fine hydrogenation. At this time, it is desirable to set the gas phase hydrogen pressure in the reaction vessel to 3 kg / cm 2 or more. Further, it is desirable to maintain this hydrogen pressure even during slight hydrogenation. In the present invention, the reaction temperature for non-selectively advancing the fine hydrogenation is preferably maintained at a temperature not lower than the temperature at which the catalyst exhibits its activity, and as low as possible. The optimum reaction temperature depends on the catalyst,
90 to 150 in the case of using a nickel catalyst
It is in the range of ° C.
【００１７】本発明では、水添を開始して所定の時間が
経過した後、撹拌を止め、水素ガスを反応容器から除去
することにより、水添反応を停止する。また、急激な温
度操作が可能な反応容器を使用した場合には、魚油の温
度を速やかに５０℃以下に冷却することにより、水添反
応を停止することもできる。なお、本発明で、水添の程
度を微水添の範囲に留めるためには、反応時間は５分〜
３０分以内の範囲とすることが望ましい。In the present invention, the hydrogenation reaction is stopped by stopping the stirring and removing hydrogen gas from the reaction vessel after a lapse of a predetermined time from the start of hydrogenation. Further, when a reaction vessel capable of rapid temperature control is used, the hydrogenation reaction can be stopped by rapidly cooling the temperature of fish oil to 50 ° C or lower. In the present invention, in order to keep the degree of hydrogenation within the range of slight hydrogenation, the reaction time is 5 minutes to
It is desirable to set the range within 30 minutes.
【００１８】その後、反応容器から微水添魚油を取り出
すが、その際、微水添魚油の酸化劣化を避けるために魚
油を２０℃以下に冷却することが特に望ましい。このよ
うにして、反応容器から取り出した微水添魚油に、活性
白土などの吸着剤を加えて撹拌する。なお、吸着剤は、
魚油に対して１〜５重量％の割合で使用されるが、この
範囲に限定されるものではない。また、吸着剤として
は、活性白土の他に、珪藻土を使用することもできる
し、活性白土もしくは珪藻土にシリカゲルやフロリジル
などを混合して使用することも可能である。そして、フ
ィルタープレスなどを使用して濾過を行い、触媒及び吸
着剤を除去して、微水添魚油を回収する。さらに、この
微水添魚油に、必要に応じて、水蒸気蒸留などの脱臭操
作を施すこともできる。この魚臭を低減した微水添魚油
については、酸化防止剤を添加し、不活性ガスを吹き込
んだ後、冷蔵で保存すると良い。After that, the slightly hydrogenated fish oil is taken out from the reaction vessel. At this time, it is particularly desirable to cool the fish oil to 20 ° C. or lower in order to avoid oxidative deterioration of the slightly hydrogenated fish oil. In this way, an adsorbent such as activated clay is added to the slightly hydrogenated fish oil taken out of the reaction vessel and stirred. The adsorbent is
It is used in a proportion of 1 to 5% by weight with respect to fish oil, but is not limited to this range. As the adsorbent, diatomaceous earth can be used in addition to activated clay, or silica gel, florisil, or the like can be mixed with activated clay or diatomaceous earth. Then, filtration is performed using a filter press or the like to remove the catalyst and the adsorbent, and to collect the slightly hydrogenated fish oil. Furthermore, this slightly hydrogenated fish oil can be subjected to a deodorizing operation such as steam distillation, if necessary. The slightly hydrogenated fish oil with reduced fish odor should be stored in a refrigerator after adding an antioxidant and blowing an inert gas.
【００１９】上述の微水添操作により、魚臭成分及び魚
臭成分の前駆体は、還元、異性化、もしくは分解され、
魚臭を発生しない化学成分に変換される。したがって、
本発明の微水添魚油は、魚臭が消失しており、かつ、保
存中の魚臭の発生も抑制されるので、官能的に全く問題
のない魚油となる。また、本発明の微水添魚油は、ドコ
サヘキサエン酸やエイコサペンタエン酸などの高度不飽
和脂肪酸の消失が少なく、ヨウ素価の減少及び融点の上
昇も僅かである。すなわち、得られた微水添魚油におい
ては、原料魚油からのヨウ素価の減少率が１５％以内で
あれば良いが、本発明の魚臭を低減する効果を有効に発
揮し、かつ、ドコサヘキサエン酸やエイコサペンタエン
酸などの高度不飽和脂肪酸の消失を抑制するためには、
５〜１０％の範囲のヨウ素価の減少が特に好ましい。The fish odor component and the precursor of the fish odor component are reduced, isomerized or decomposed by the above-mentioned slight hydrogenation operation,
It is converted into a chemical component that does not generate fishy odor. Therefore,
The slightly hydrogenated fish oil of the present invention has no fish odor and suppresses the generation of fish odor during storage. In addition, the slightly hydrogenated fish oil of the present invention has little loss of polyunsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid, and a slight decrease in iodine value and a slight increase in melting point. That is, in the obtained slightly hydrogenated fish oil, the reduction rate of the iodine value from the raw material fish oil may be within 15%, but the effect of reducing the fish odor of the present invention is effectively exhibited, and docosahexaenoic acid is also effective. To suppress the loss of highly unsaturated fatty acids such as and eicosapentaenoic acid,
Particularly preferred is a reduction in iodine value in the range of 5-10%.
【００２０】本発明の微水添魚油は、微水添を施さない
魚油に発生する官能的な障害が少ない、もしくは全くな
いものとなるので、この微水添魚油をミルクセーキ、コ
ーヒー飲料、乳酸菌飲料などの飲料やアイスクリーム、
ゼリー、ムース、ヨーグルトなどのデザート類、さらに
は、味噌、畜肉、魚肉製品、粉ミルク類、チーズフー
ド、ファットスプレッドなどの乳製品、離乳食などのあ
らゆるタイプの食品に対する素材として利用することが
可能である。また、この微水添魚油は、医薬品の素材と
しても利用が可能である。Since the microhydrogenated fish oil of the present invention has little or no sensory obstacle generated in fish oil which is not microhydrogenated, this microhydrogenated fish oil is used as a milkshake, coffee beverage, lactic acid bacterium beverage. Such as drinks and ice cream,
It can be used as a material for desserts such as jelly, mousse and yogurt, as well as for all types of foods such as miso, meat, fish products, milk powder, cheese food, dairy products such as fat spreads and baby food. . The slightly hydrogenated fish oil can also be used as a raw material for pharmaceuticals.
【００２１】以下に実施例を示し、本発明を詳しく説明
する。The present invention will be described in detail below with reference to examples.
【００２２】[0022]
【実施例１】精製カツオ油（ヨウ素価：１８２、ドコサ
ヘキサエン酸：２３．５％、エイコサペンタエン酸：
６．２％）２ｋｇを４ｌの反応容器に充填し、還元ニッ
ケル触媒１．５ｇ（０．０７５重量％）を添加した。そ
して、撹拌しながら５ｔｏｒｒ以下となるよう脱気、脱
水操作を行った後、水素圧力が３ｋｇ／ｃｍ2 の雰囲気
下、１３０℃で１５分間、水添反応を行った。その後、
水素ガスを反応容器から除去して水添反応を停止し、２
０℃以下に冷却した後、活性白土で処理して微水添カツ
オ油１．７ｋｇを得た。この微水添カツオ油のヨウ素価
は１７１、ドコサヘキサエン酸及びエイコサペンタエン
酸の含率はそれぞれ１７．２％及び５．２％であった。Example 1 Refined skipjack oil (iodine value: 182, docosahexaenoic acid: 23.5%, eicosapentaenoic acid:
2% (6.2%) was charged into a 4 liter reaction vessel and 1.5 g (0.075% by weight) of reduced nickel catalyst was added. Then, deaeration and dehydration operations were performed with stirring to 5 torr or less, and then a hydrogenation reaction was performed at 130 ° C. for 15 minutes in an atmosphere having a hydrogen pressure of 3 kg / cm 2 . afterwards,
Hydrogen gas was removed from the reaction vessel to stop the hydrogenation reaction, and 2
After cooling to 0 ° C. or lower, it was treated with activated clay to obtain 1.7 kg of slightly hydrogenated skipjack oil. The slightly hydrogenated bonito oil had an iodine value of 171, and the contents of docosahexaenoic acid and eicosapentaenoic acid were 17.2% and 5.2%, respectively.
【００２３】ここで、原料として用いた精製カツオ油と
本実施例で得られた微水添カツオ油の保存試験を実施し
た。それぞれの油脂５０ｇを容量１００ｍｌのガラス製
蓋付き容器に入れ、酸化防止剤としてトコフェロール３
０ｍｇを添加した後、５０±１℃に保持したオーブンで
保存し、強制劣化試験を行った。なお、官能評価は訓練
を受けた専門パネラー１０人により行い、魚臭の強度及
び好ましさについて表１に示す評価基準により行った。Here, a storage test was carried out on the refined skipjack oil used as a raw material and the slightly hydrogenated skipjack oil obtained in this example. Put 50 g of each fat and oil into a 100 ml capacity container with a glass lid, and use 3 tocopherols as an antioxidant.
After adding 0 mg, it was stored in an oven kept at 50 ± 1 ° C. and a forced deterioration test was conducted. The sensory evaluation was carried out by 10 trained specialized panelists, and the strength and the preference of fish odor were evaluated according to the evaluation criteria shown in Table 1.
【００２４】[0024]
【表１】 ────────────────────────────── 評価点 魚臭強度 好ましさ ────────────────────────────── ０ 全く感じない 極めて悪い １ ほとんど感じない 悪い ２ 微かに感じる やや悪い ３ 臭気を感じる どちらでもない ４ やや強く感じる 良い ５ 強く感じる 極めて良い ──────────────────────────────[Table 1] ────────────────────────────── Evaluation score Fish odor intensity Preference ──────── ────────────────────── 0 Not feeling at all Very bad 1 Almost not feeling Bad 2 Feeling slightly bad 3 Feeling odor Neither 4 Feeling stronger Good 5 Feel strongly Extremely good ───────────────────────────────
【００２５】その結果を表２に示す。なお、パネラー全
員の評価点の平均値を官能評価点として表した。The results are shown in Table 2. In addition, the average value of the evaluation points of all the panelists was expressed as a sensory evaluation point.
【００２６】[0026]
【表２】 ──────────────────────────────────── 魚臭強度 好ましさ 油脂 ────────── ────────── ０日目 ３日目 ０日目 ３日目 ──────────────────────────────────── 精製カツオ油 １．０ ３．０ ４．５ ３．０ 微水添カツオ油 ０．６ １．８ ４．８ ４．０ ────────────────────────────────────[Table 2] ──────────────────────────────────── Fish odor strength Preferability Oils and fats ─── ───────────────── Day 0 Day 3 Day 0 Day 3 ───────────────────── ─────────────── Refined skipjack oil 1.0 3.0 4.5 4.5 3.0 Finely hydrogenated skipjack oil 0.6 1.8 4.8 4.0 4.0 ──────────────────────────────────
【００２７】微水添カツオ油は、精製カツオ油に比較し
て、保存０日目で魚臭強度が弱く、好ましさの評価が高
かった。また、保存３日目においても、微水添カツオ油
では魚臭の発生が抑制されており、好ましさの評価も高
かった。The slightly hydrogenated bonito oil had a weaker fish odor intensity on day 0 of storage than the refined bonito oil, and was favorably evaluated. Further, even on the third day of storage, the generation of fishy odor was suppressed in the slightly hydrogenated bonito oil, and the favorable evaluation was also high.
【００２８】[0028]
【実施例２】精製イワシ油（ヨウ素価：１６２、ドコサ
ヘキサエン酸：８．４％、エイコサペンタエン酸：１
５．２％）６００ｇを１ｌの反応容器に充填し、ラネー
ニッケル触媒０．６ｇ（０．１重量％）を添加した。そ
して、攪拌しながら５ｔｏｒｒ以下となるよう脱気、脱
水操作を行った後、水素圧力が４ｋｇ／ｃｍ2 の雰囲気
下、１００℃で３０分間、水添反応を行った。その後、
水素ガスを反応容器から除去して水添反応を停止し、２
０℃以下に冷却した後、活性白土で処理して微水添イワ
シ油５１５ｇを得た。この微水添イワシ油のヨウ素価は
１４９、ドコサヘキサエン酸及びエイコサペンタエン酸
の含率はそれぞれ６．８％及び１２．２％であった。Example 2 Refined sardine oil (iodine value: 162, docosahexaenoic acid: 8.4%, eicosapentaenoic acid: 1)
(5.2%) 600 g was charged into a 1 liter reaction vessel, and Raney nickel catalyst 0.6 g (0.1% by weight) was added. Then, deaeration and dehydration operations were performed with stirring to 5 torr or less, and then a hydrogenation reaction was performed at 100 ° C. for 30 minutes in an atmosphere having a hydrogen pressure of 4 kg / cm 2 . afterwards,
Hydrogen gas was removed from the reaction vessel to stop the hydrogenation reaction, and 2
After cooling to 0 ° C. or lower, it was treated with activated clay to obtain 515 g of slightly hydrogenated sardine oil. The iodine value of this slightly hydrogenated sardine oil was 149, and the contents of docosahexaenoic acid and eicosapentaenoic acid were 6.8% and 12.2%, respectively.
【００２９】ここで、原料として用いた精製イワシ油と
本実施例で得られた微水添イワシ油の保存試験を実施し
た。それぞれの油脂５０ｇを容量１００ｍｌのガラス製
蓋付き容器に入れ、酸化防止剤としてトコフェロール３
０ｍｇを添加した後、３０±１℃に保持し光を遮断され
た恒温庫に保存し、安定性試験を行った。なお、官能評
価は訓練を受けた専門パネラー１０人により行い、魚臭
の強度及び好ましさについて表１に示した評価基準によ
り行った。Here, a storage test was conducted on the refined sardine oil used as a raw material and the slightly hydrogenated sardine oil obtained in this example. Put 50 g of each fat and oil into a 100 ml capacity container with a glass lid, and use 3 tocopherols as an antioxidant.
After adding 0 mg, it was kept at 30 ± 1 ° C. and stored in a thermostatic chamber shielded from light to perform a stability test. The sensory evaluation was carried out by 10 trained specialized panelists, and the evaluation criteria shown in Table 1 were used for the intensity and the preference of fish odor.
【００３０】その結果を表３に示す。なお、パネラー全
員の評価点の平均値を官能評価点として表した。The results are shown in Table 3. In addition, the average value of the evaluation points of all the panelists was expressed as a sensory evaluation point.
【００３１】[0031]
【表３】 ──────────────────────────────────── 魚臭強度 好ましさ 油脂 ────────── ────────── ０日目 ７日目 ０日目 ７日目 ──────────────────────────────────── 精製イワシ油 １．５ ３．２ ３．９ ２．６ 微水添イワシ油 １．０ ２．５ ４．３ ３．１ ────────────────────────────────────[Table 3] ──────────────────────────────────── Fish odor intensity Preference Oils ─── ───────────────── Day 0 Day 7 Day 0 Day 7 ───────────────────── ─────────────── Refined sardine oil 1.5 3.2 3.9 2.6 Slightly hydrogenated sardine oil 1.0 2.5 4.3 3.1 3.1 ─── ──────────────────────────────────
【００３２】微水添イワシ油は、精製イワシ油に比較し
て、保存０日目で魚臭強度が弱く、さらに保存７日目に
おいても、魚臭強度は低く、保存中の魚臭の発生は抑制
されていた。また、微水添イワシ油は、魚臭強度の挙動
を反映し、好ましさの評価も終始高かった。Compared with refined sardine oil, the slightly hydrogenated sardine oil had a weak fish odor intensity on the 0th day of storage, and even on the 7th day of storage, the fish odor intensity was low, and fish odor was generated during storage. Was suppressed. In addition, the slightly hydrogenated sardine oil reflected the behavior of the fish odor intensity, and was highly evaluated from the beginning to the end.
【００３３】[0033]
【発明の効果】本発明の微水添魚油は、魚臭が低減され
ていると共にドコサヘキサエン酸やエイコサペンタエン
酸などの高度不飽和脂肪酸の消失を抑制されているの
で、一般食品や医療食などの素材として有用である。EFFECTS OF THE INVENTION Since the slightly hydrogenated fish oil of the present invention has reduced fish odor and suppression of loss of highly unsaturated fatty acids such as docosahexaenoic acid and eicosapentaenoic acid, it can be used for general foods and medical foods. It is useful as a material.
Claims (3)
料となる魚油に対して、微水添によるヨウ素価の減少率
が１５％以内で、かつ、高度不飽和脂肪酸の減少率が３
３％以内であることを特徴とする魚臭を低減した魚油。1. A fish oil that has been subjected to a slight hydrogenation treatment, wherein the reduction rate of the iodine value due to the slight hydrogenation is within 15% and the reduction rate of the polyunsaturated fatty acid is lower than that of the raw material fish oil. Is 3
Fish oil with reduced fish odor, characterized by being within 3%.
以内で、かつ、高度不飽和脂肪酸の減少率が３３％以内
となるよう魚油に微水添処理を施すことを特徴とする魚
臭を低減した魚油の製造法。2. The reduction rate of iodine value due to slight hydrogenation is 15%.
A method for producing fish oil having reduced fish odor, which comprises subjecting fish oil to a slight hydrogenation treatment so that the reduction rate of highly unsaturated fatty acid is within 33%.
施す請求項２記載の魚油の製造法。 （１）水添処理に用いる触媒の量が、魚油に対して０．
０５重量％以上である。 （２）水添処理開始時の気相の水素圧力が、３ｋｇ／ｃ
ｍ2 以上である。 （３）水添処理の反応温度が、９０〜１５０℃である。 （４）水添処理の反応時間が、５〜３０分である。3. The method for producing fish oil according to claim 2, wherein the fine hydrogenation treatment is performed under the following non-selective conditions. (1) The amount of the catalyst used for the hydrogenation treatment is 0.
It is at least 05% by weight. (2) Hydrogen pressure in the gas phase at the start of hydrogenation is 3 kg / c
m 2 or more. (3) The reaction temperature of the hydrogenation treatment is 90 to 150 ° C. (4) The reaction time of the hydrogenation treatment is 5 to 30 minutes.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6024750A JPH07216383A (en) | 1994-01-27 | 1994-01-27 | Fish oil with reduced odor and its production |
| US08/378,276 US5693835A (en) | 1994-01-27 | 1995-01-26 | Fish oil having decreased fish odor and a method for preparing the same |
| EP95101137A EP0665287B1 (en) | 1994-01-27 | 1995-01-27 | Fish oil having decreased fish odor and a method for preparing the same |
| DE69515919T DE69515919T2 (en) | 1994-01-27 | 1995-01-27 | Fish oil with reduced fish smell and process for its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6024750A JPH07216383A (en) | 1994-01-27 | 1994-01-27 | Fish oil with reduced odor and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07216383A true JPH07216383A (en) | 1995-08-15 |
Family
ID=12146826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6024750A Pending JPH07216383A (en) | 1994-01-27 | 1994-01-27 | Fish oil with reduced odor and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07216383A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016124963A (en) * | 2014-12-26 | 2016-07-11 | ミヨシ油脂株式会社 | Method for decreasing chloropropanol in edible oil and fat |
-
1994
- 1994-01-27 JP JP6024750A patent/JPH07216383A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016124963A (en) * | 2014-12-26 | 2016-07-11 | ミヨシ油脂株式会社 | Method for decreasing chloropropanol in edible oil and fat |
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