JPS6231902B2 - - Google Patents
Info
- Publication number
- JPS6231902B2 JPS6231902B2 JP57154020A JP15402082A JPS6231902B2 JP S6231902 B2 JPS6231902 B2 JP S6231902B2 JP 57154020 A JP57154020 A JP 57154020A JP 15402082 A JP15402082 A JP 15402082A JP S6231902 B2 JPS6231902 B2 JP S6231902B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- tocopherol
- antioxidant
- acid
- monoglyceride
- 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.)
- Expired
Links
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 26
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000003963 antioxidant agent Substances 0.000 claims description 21
- 235000006708 antioxidants Nutrition 0.000 claims description 21
- 230000003078 antioxidant effect Effects 0.000 claims description 20
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 16
- 239000011732 tocopherol Substances 0.000 claims description 16
- 229930003799 tocopherol Natural products 0.000 claims description 16
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 16
- 239000002211 L-ascorbic acid Substances 0.000 claims description 13
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 13
- 229960005070 ascorbic acid Drugs 0.000 claims description 13
- 235000004515 gallic acid Nutrition 0.000 claims description 13
- 229940074391 gallic acid Drugs 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 10
- 235000010384 tocopherol Nutrition 0.000 claims description 9
- 229960001295 tocopherol Drugs 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 7
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 4
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 claims description 2
- 235000014593 oils and fats Nutrition 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 16
- 238000009472 formulation Methods 0.000 description 15
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 8
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 7
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 7
- 229960000984 tocofersolan Drugs 0.000 description 7
- 235000019149 tocopherols Nutrition 0.000 description 7
- 239000000230 xanthan gum Substances 0.000 description 7
- 235000010493 xanthan gum Nutrition 0.000 description 7
- 229920001285 xanthan gum Polymers 0.000 description 7
- 229940082509 xanthan gum Drugs 0.000 description 7
- 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 7
- 238000004945 emulsification Methods 0.000 description 6
- 235000019484 Rapeseed oil Nutrition 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 241000555825 Clupeidae Species 0.000 description 4
- 235000019512 sardine Nutrition 0.000 description 4
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 3
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 3
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 3
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 3
- -1 glycerin fatty acid Chemical class 0.000 description 3
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 235000019688 fish Nutrition 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000014102 seafood Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 235000010389 delta-tocopherol Nutrition 0.000 description 1
- ORYOIBJWFDNIPD-UHFFFAOYSA-N diacetyl 2,3-dihydroxybutanedioate Chemical compound CC(=O)OC(=O)C(O)C(O)C(=O)OC(C)=O ORYOIBJWFDNIPD-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/90—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in food processing or handling, e.g. food conservation
Landscapes
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57154020A JPS5945860A (ja) | 1982-09-06 | 1982-09-06 | 乳液状酸化防止製剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57154020A JPS5945860A (ja) | 1982-09-06 | 1982-09-06 | 乳液状酸化防止製剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5945860A JPS5945860A (ja) | 1984-03-14 |
| JPS6231902B2 true JPS6231902B2 (enrdf_load_stackoverflow) | 1987-07-10 |
Family
ID=15575148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57154020A Granted JPS5945860A (ja) | 1982-09-06 | 1982-09-06 | 乳液状酸化防止製剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5945860A (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60221032A (ja) * | 1984-04-16 | 1985-11-05 | Nippon Oil & Fats Co Ltd | 魚介類の鮮度保持剤 |
| JPS63137639A (ja) * | 1986-11-28 | 1988-06-09 | Riken Vitamin Co Ltd | 節類の品質改良法 |
| JPH01137934A (ja) * | 1987-11-19 | 1989-05-30 | Nippon Oil & Fats Co Ltd | 煮干し用酸化防止製剤 |
| JPH01171465A (ja) * | 1987-12-28 | 1989-07-06 | Takara Shuzo Co Ltd | 食品の鮮度保持剤 |
| CH676470A5 (enrdf_load_stackoverflow) * | 1988-02-03 | 1991-01-31 | Nestle Sa | |
| JPH01265870A (ja) * | 1988-04-16 | 1989-10-23 | Nisshin Oil Mills Ltd:The | 油脂組成物 |
| JP2701897B2 (ja) * | 1988-12-16 | 1998-01-21 | 宇野醤油株式会社 | 天然トコフェロール含有ｏ／ｗ型乳化物の製造方法 |
| JPH03259034A (ja) * | 1990-03-09 | 1991-11-19 | Nippon Light Metal Co Ltd | 食品の鮮度保持液並びにその使用方法 |
| US20040195549A1 (en) | 2003-04-04 | 2004-10-07 | Clifford Adams | Lipid-soluble formulations containing mixtures of antioxidants |
| CN1930269B (zh) * | 2004-03-19 | 2011-09-21 | 三菱化学株式会社 | 劣化防止剂 |
| JP5623959B2 (ja) * | 2011-03-30 | 2014-11-12 | 森永乳業株式会社 | 調製粉乳及びその製造方法、並びに酸化抑制剤 |
-
1982
- 1982-09-06 JP JP57154020A patent/JPS5945860A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5945860A (ja) | 1984-03-14 |
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