JPS6160871B2 - - Google Patents
Info
- Publication number
- JPS6160871B2 JPS6160871B2 JP55106752A JP10675280A JPS6160871B2 JP S6160871 B2 JPS6160871 B2 JP S6160871B2 JP 55106752 A JP55106752 A JP 55106752A JP 10675280 A JP10675280 A JP 10675280A JP S6160871 B2 JPS6160871 B2 JP S6160871B2
- Authority
- JP
- Japan
- Prior art keywords
- paprika
- pigment
- paprika pigment
- reaction product
- browning reaction
- 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
- 239000000049 pigment Substances 0.000 claims description 87
- 240000004160 Capsicum annuum Species 0.000 claims description 86
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 claims description 86
- 239000001511 capsicum annuum Substances 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 51
- 239000007795 chemical reaction product Substances 0.000 claims description 34
- 235000001014 amino acid Nutrition 0.000 claims description 25
- 150000001413 amino acids Chemical class 0.000 claims description 25
- 150000001720 carbohydrates Chemical class 0.000 claims description 23
- 239000003960 organic solvent Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000002016 disaccharides Chemical class 0.000 claims description 10
- 150000002772 monosaccharides Chemical class 0.000 claims description 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000284 extract Substances 0.000 claims description 8
- 244000000626 Daucus carota Species 0.000 claims description 7
- 235000002767 Daucus carota Nutrition 0.000 claims description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 6
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 6
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 5
- 239000004471 Glycine Substances 0.000 claims description 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 4
- 239000004472 Lysine Substances 0.000 claims description 3
- 235000004279 alanine Nutrition 0.000 claims description 3
- 235000003704 aspartic acid Nutrition 0.000 claims description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004475 Arginine Substances 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 235000009697 arginine Nutrition 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- 235000014304 histidine Nutrition 0.000 claims description 2
- 235000018977 lysine Nutrition 0.000 claims description 2
- 235000013930 proline Nutrition 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- 235000014393 valine Nutrition 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 229940024606 amino acid Drugs 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 229940008396 carrot extract Drugs 0.000 description 25
- 235000000346 sugar Nutrition 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 150000008163 sugars Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000000605 extraction Methods 0.000 description 13
- 239000001325 capsicum annuum l. var. longum oleoresin Substances 0.000 description 12
- 238000005562 fading Methods 0.000 description 12
- 235000012658 paprika extract Nutrition 0.000 description 12
- DYUUPIKEWLHQGQ-SDXBLLFJSA-N paprika oleoresin Chemical compound C(\[C@]12[C@@](O1)(C)C[C@@H](O)CC2(C)C)=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=C[C@H]1C(C)=C[C@H](O)CC1(C)C DYUUPIKEWLHQGQ-SDXBLLFJSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000003513 alkali Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- -1 aliphatic alcohols Chemical class 0.000 description 7
- 239000000084 colloidal system Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 244000215068 Acacia senegal Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- 229920000084 Gum arabic Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000010489 acacia gum Nutrition 0.000 description 6
- 239000000205 acacia gum Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000005720 sucrose Substances 0.000 description 6
- 229930091371 Fructose Natural products 0.000 description 5
- 239000005715 Fructose Substances 0.000 description 5
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 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 5
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000011648 beta-carotene Substances 0.000 description 5
- 235000013734 beta-carotene Nutrition 0.000 description 5
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 5
- 229960002747 betacarotene Drugs 0.000 description 5
- 235000013361 beverage Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- 238000000638 solvent extraction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000019864 coconut oil Nutrition 0.000 description 4
- 239000003240 coconut oil Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 3
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 3
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 3
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- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 235000015203 fruit juice Nutrition 0.000 description 3
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 3
- 229960002989 glutamic acid Drugs 0.000 description 3
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- 239000004615 ingredient Substances 0.000 description 3
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
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- 235000005875 quercetin Nutrition 0.000 description 3
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- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 3
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 3
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 3
- 235000005493 rutin Nutrition 0.000 description 3
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
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- 238000005119 centrifugation Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
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- 239000000796 flavoring agent Substances 0.000 description 2
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- 150000008282 halocarbons Chemical class 0.000 description 2
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- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 235000010983 sucrose acetate isobutyrate Nutrition 0.000 description 2
- UVGUPMLLGBCFEJ-SWTLDUCYSA-N sucrose acetate isobutyrate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(C)=O)O1 UVGUPMLLGBCFEJ-SWTLDUCYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000019154 vitamin C Nutrition 0.000 description 2
- 239000011718 vitamin C Substances 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000555678 Citrus unshiu Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 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
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-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
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- 239000004158 L-cystine Substances 0.000 description 1
- 235000019393 L-cystine Nutrition 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- 229930182844 L-isoleucine Natural products 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000113306 Monascus purpureus Species 0.000 description 1
- 235000002322 Monascus purpureus Nutrition 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 150000001447 alkali salts Chemical group 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 235000015190 carrot juice Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance 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
- 239000011521 glass Substances 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 229960002743 glutamine Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 239000010651 grapefruit oil Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229940057059 monascus purpureus Drugs 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000029219 regulation of pH Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
Description
本発明は酸素及び/又は光に対して、安定性の
すぐれたパプリカ色素組成物に関する。
従来からパプリカの果実もしくはその乾燥物を
溶剤抽出することにより得られるパプリカオレオ
レジン、或いはパプリカオレオレジンを精製して
色素含有量を高くしたいわゆる精製パプリカ色素
は、何れもそのまゝの形態で、或いは乳化液、粉
末、顆粒などの製剤の形態で赤色系天然色素とし
て飲食物、医薬などに利用されている。
これらパプリカ色素(本発明においては、パプ
リカオレオレジンの如きパプリカ色素含有物か
ら、これから導かれた精製色素にわたるパプリカ
色素及びその含有物を包含する呼称である)は、
赤色から橙色乃至黄橙色にわたる赤色系の色調を
呈する天然色素であつて、例えば水性媒体中で比
較的高濃度で赤色調を、比較的低濃度で黄橙色調
を示し、又、例えば乾燥状態では、その含量が比
較的低い場合でも赤色乃至赤橙色調を示すのが普
通である。そして、良く知られているように、天
然色素であるパプリカ色素は、多くの天然色素に
おいて見られる如く、酸素及び/又は光、更には
水分の存在下などにおいては可成り不安定で貯蔵
安定性が悪く、経済的に比較的容易に褪色すると
いう宿命的なトラブルがある。パプリカ色素にお
けるこのトラブルは比較的大きく、とくに水性飲
食物類、たとえば広義の飲料や水気の多い食品類
に於ては、溶存酸素(空気)及び光などによつて
その褪色劣化が促進される傾向があり、経時的に
赤色調から黄橙色調へ、そして遂には殆んど無色
になるまで褪色劣化する。又、粉末状や顆粒状な
どの形態のパプリカ色素製剤においても、乾燥状
態、貯蔵条件などにより程度の差こそあれ、同様
な褪色劣化を生ずる。
このようなパプリカ色素が本来的に有する褪色
のトラブルを克服しようとして、パプリカ色素に
ケルセチン及び/又はその配糖体であるルチンを
添加することを特徴とする飲料以外をパプリカ色
素で着色する場合についてのパプリカ色素の褪色
防止法(特公昭54―10568号)、及びパプリカ色素
飲料に上記ケルセチン及び/又はルチンを
600ppm以下の濃度になる量において添加するこ
とを特徴とするパプリカ色素着色飲料の褪色防止
法(特公昭52―31947号)が知られている。ケル
セチン及び又はルチン水溶液は翠緑乃至翠黄色を
呈するが、上記後者の提案においては、600〜
250ppmの濃度では極く僅かに翠緑乃至翠黄色を
示すことを記載している。
又、他の提案として、モナスカス属に属する微
生物、たとえばモナスカス・アンカやモナスカ
ス・プルプレウスが生産する色素に該色素の劣化
防止のために糖とアミノ酸との褐変反応生成物を
添加する提案が知られている(特開昭51―
180428)。この提案は上記微生物の生産色素につ
いてのみ特定的に開示しており、他の色素に対す
る該褐変反応生成物の作用に関しては、勿論、全
く言及していない。例えば、ビタミンCはβ―カ
ロチン色素に対しては安定化効果を示すが、該ビ
タミンCはパプリカ色素に対しては利用し得る安
定化効果を示さないように、色素の相違によつ
て、該色素に対する同一化合物の示す安定化作用
は異なり、予測し得ないのが普通であり、上記提
案が上記微生物生産色素についてのみ、該褐変反
応生成物の劣化防止作用を開示しているのは至当
なことである。
本発明者等はパプリカ色素の赤色系色調に対し
て、その色相を変化させることなく、しかも安定
性のすぐれたパプリカ色素組成物を開発すべく研
究を行つた。
その結果、酸素及び/又は光の存在下における
パプリカ色素の褪色に、にんじんの有機溶媒抽出
物(以下、にんじん抽出物と略記することがあ
る)が、単糖類及び二糖類からえらばれた少なく
とも一種の糖類の褐変反応生成物及び/又は該糖
類とアミノ酸類との褐変反応生成物の共存下に、
優れた褪色防止作用効果を示すことを発見した。
にんじん抽出物が含有するカロチノイド系色素
も、酸素及び/又は光の存在下に褪色し易いこと
が知られているにも拘わらず、上記三者の共存条
件下に、パプリカ色素の安定化に優れた効果を示
すことがわかつた。にんじん抽出物は多種類の成
分を含有しているため、安定化有効成分が何であ
るかは未だ明らかではないが、少くともにんじん
抽出物の一成分であるβ―カロチンについては、
明らかにパプリカ色素の褪色防止作用を有してい
る事実が判明した。しかしながら、にんじん抽出
物中のβ―カロチンと同一色素量の合成β−カロ
チンをパプリカ色素に添加して、その褪色防止効
果を検討したところ、にんじん抽出物の方が、は
るかにすぐれた結果を示した。従つて、にんじん
抽出物中には、パプリカ色素の褪色防止に役立つ
成分としてβ―カロチン以外の有効成分が存在し
ていることは明らかである。
また糖類の褐変反応生成物及び/又は糖類とア
ミノ酸類との褐変反応生成物がパプリカ色素の褪
色防止に効果的作用を及ぼすことが同一発明者等
によりすでに提案されている〔特開昭56―41259
号(特願54―115120)〕。
更に本発明者等は、にんじんの有機溶媒抽出物
と単糖類及び二糖類からえらばれた少なくとも一
種の糖類の褐変反応生成物及び/又は該糖類とア
ミノ酸類との褐変反応生成物を、パプリカ色素と
共存させると、夫々を単独に共存させた場合に比
べて驚くべき相乗効果を示し、安定性のすぐれた
パプリカ色素組成物が得られることを発見した。
従つて本発明の目的は、安定性のすぐれたパプ
リカ色素組成物を提供するにある。
本発明の安定性のすぐれたパプリカ色素組成物
は、パプリカ色素及びにんじんの有機溶媒抽出物
と単糖類及び二糖類からえらばれた少なくとも一
種の糖類の褐変反応生成物及び/又は該糖類とア
ミノ酸類との褐変反応生成物を有効成分として含
有する。該組成物に使用するパプリカ色素は、パ
プリカオレオレジン、或いは精製パプリカ色素の
何れであつても良い。
パプリカオレオレジンは、よく知られているよ
うに、例えば、パプリカ果実の乾燥粉砕物にアセ
トン、n―ペンタン、n―ヘキサン、メチレンク
ロライド、エチレンジクロライドなどの有機溶剤
を加えて抽出した後、有機溶剤相を分離し、常圧
乃至減圧下で該有機溶剤を留去させるなどの手段
で得ることができる。
また精製パプリカ色素としては、例えばパプリ
カオレオレジンを溶剤抽出、或いは水蒸気蒸留す
ることによりパプリカの香味成分を除去したパプ
リカオレオレジン処理物を挙げることができる。
溶剤抽出を採用する場合は、パプリカオレオレジ
ンを低級脂肪族アルコール、例えば、メタノー
ル、エタノール、n―プロピルアルコール、イソ
プロピルアルコールの如きC1〜C3の脂肪族アル
コールで抽出することができる。好ましくはエタ
ノールが利用できる。
またこれらの脂肪族アルコール類は含水系、例
えば水分含有率約1〜約30重量%で用いることも
できる。
抽出操作及び抽出条件は種々選択できるが、例
えばパプリカオレオレジンに、約0.5〜約20倍重
量の脂肪族アルコールを添加し、室温乃至使用し
た低級脂肪族アルコールの沸点温度で約5分〜約
10時間撹拌して行うことができる。
このようにして抽出操作を行つたのち例えば静
置してアルコール相とパプリカ色素含有相とを分
離させることができる。遠心分離その他の液―液
分離手段を利用することもできる。必要ならば、
更に分離したパプリカ色素含有相に脂肪族アルコ
ールを添加して同様の操作をくり返し、パプリカ
色素含有相のパプリカ臭を更に充分に除去するこ
ともできる。
又、水蒸気蒸留手段を採用する場合には、大気
圧条件のほかに加圧もしくは減圧条件を採用する
こともできる。
更にまた、精製パプリカ色素として、パプリカ
オレオレジンを低級脂肪族アルコールもしくはそ
の含水物で抽出してアルコール層(パプリカ香味
成分含有相)と分離したパプリカ色素含有相をア
ルカリ処理した後、系のPHを酸性側に調節し、該
PH調節された系を該系に含有される脂肪酸類を水
難溶性乃至不溶性の塩に転化し得る形成剤で処理
し、得られた処理物を有機溶媒で抽出することに
より得られたパプリカ色素の利用が推奨できる。
本発明で利用するパプリカ色素の好適態様にお
いては、上述のようにして得られるパプリカ色素
含有相をアルカリ処理する。この処理に利用する
アルカリの例としては、例えば、水酸化カリウ
ム、水酸化ナトリウム、炭酸カリウム、炭酸ナト
リウム、ナトリウムアルコラート、カリウムアル
コラート、これらの併用等を例示することができ
る。パプリカ色素含有相は、そのまま利用しても
よいし、或は又、蒸留により少量含有され得るア
ルコールを留去したのち用いることもできる。
又、アルカリは固体の状態で添加してもよいし或
は又水、アルコール類、もしくはこれらの混合溶
液の形で添加してもよい。アルカリ処理系におけ
るアルカリ濃度が約5%〜約30%程度となるよう
なアルカリ条件の採用がよい。
上記アルカリ処理操作及びアルカリ処理条件は
適宜に選択してよい。例えばパプリカ色素含有相
に約0.5乃至約5倍重量の水酸化ナトリウム水溶
液(約20%濃度の場合)を加えて約50乃至約100
℃にて約30分乃至約12時間撹拌することにより行
うことができる。
アルカリ処理後、処理系のPHを酸性側、好まし
くは約4〜約6.5程度のPHの酸性側に調節する。
PH調節剤の例としては、例えば、塩酸、硫酸、リ
ン酸、酢酸、乳酸、クエン酸などの如き無機もし
くは有機酸類を例示することができる。
このアルカリ処理後のPH調節処理によつて、パ
プリカ色素含有相に含有されていた脂肪酸類は、
その水可溶性アルカリ塩の形から一旦遊離の脂肪
酸類の形に転化する。次いで、このPH調節した系
を、該系に含有される脂肪類を水難溶性ないし不
溶性塩類に転化し得る塩形成剤で処理する。この
処理によつて、一旦遊離の脂肪酸類の形に転化し
た脂肪酸類は、その水難溶性ないし不溶性塩類に
転化する。
この塩形成処理は、例えば以下のような操作及
び条件で行うことができる。例えばPH調節処理物
に使用した原料オレオレジン量の約0.2乃至約3
倍重量の塩形成剤を徐々に加えて行うことができ
る。反応は室温で行うことができ、所望により冷
却もしくは加熱条件を採用することもでき、例え
ば0〜約100℃の如き温度を例示できる。このよ
うな塩形成剤の例としては、アルカリ土類金属の
水酸化物たとえば水酸化カルシウム、水酸化マグ
ネシウム、水酸化パリウムなどを好ましく例示で
きる。その他、Al、Fe、Zn、Cuその他の金属の
水酸化物も利用可能である。このようにして塩形
成剤で処理した系は、例えば、過、遠心分離な
どの固―液分離手段によつて固形物相を採取し、
所望により、水洗、脱水などの手段を施したの
ち、有機溶媒抽出することができる。
上述のようにして、PH調節処理及び塩形成処理
された固形物相は、従来提案における石けん様固
形物相に比して、有機溶媒抽出操作が著しく容易
であつて、且つ抽出効率も優れている。この抽出
に用いる溶媒としては、円滑且つ効率的な色素抽
出を妨害するトリグリセリドが充分に除去されて
いるため、広汎な有機溶媒が利用可能である。こ
のような有機溶媒の例としては、アセトン、メチ
ルエチルケトンの如きケトン類;酢酸メチル、酢
酸エチルの如きエステル類;メタノール、エタノ
ール、イソプロパノールの如きアルコール類;n
―ペンタン、iso―ペンタン、シクロヘキサン、
n―ヘキサン、ベンゼン、トルエンの如き炭化水
素類;メチレンクロライド、エチレンジクロライ
ド、四塩化炭素、クロロホルムの如きハロゲン化
炭化水素類;ジエチルエーテル、イソプロピルエ
ーテルの如きエーテル類;これらの任意の混合物
などを例示することができる。
抽出操作及び抽出条件も適宜に選択でき、例え
ば、得られた上記固形物相に約0.5乃至約20倍重
量の有機溶媒を添加して室温乃至使用した溶剤の
沸点温度で約15分乃至約15時間色素成分を抽出し
て行うことができる。上記抽出に際して、カラム
状にした上記固形物相中を上記有機溶媒を流下さ
せることにより行うことができる。
有機溶媒抽出操作後、有機溶媒相(パプリカ色
素含有相)と固形物残渣とを分離し、更に有機溶
剤相を大気圧乃至減圧下で蒸留して溶剤を留去さ
せることにより、約30万〜約60万のカラーバリユ
ーを有するパプリカ色素を得ることができる。
また本発明で用いるにんじん抽出物は、産地・
品種に特に限定はなく、新鮮なにんじん、その乾
燥物、新鮮なにんじんの搾汁液、或いはその搾汁
残渣などを有機溶剤で抽出することにより得るこ
とができる。
有機溶剤としては、アセトン、メチルエチルケ
トンの如きケトン類、酢酸メチル、酢酸エチルの
如きエステル類、n―ペンタン、イソペンタン、
シクロヘキサン、n―ヘキサン、ベンゼン、トル
エンの如き炭化水素類、メチレンクロライド、エ
チレンジクロライドの如きハロゲン化炭化水素
類、ジエチルエーテル、イソプロピルエーテルの
如きエーテル類、これらの任意の混合物などを例
示できる。抽出温度・時間には特別な制約はない
が、例えば室温乃至使用溶剤の沸点温度で約5分
乃至約150時間抽出して行うことができる。抽出
液を常圧乃至減圧下で蒸留して溶剤を完全に除去
することによりにんじん抽出物を得ることができ
る。
更にまた本発明で用いる単糖類及び二糖類から
えらばれた少なくとも一種の糖類及び/又は該糖
類とアミノ酸類の褐変反応生成物に利用する糖類
の例としては、たとえば、グルコース、フラクト
ース、キシロース、カラクトース、マンノース、
ラムノース、グルクロン酸、アラビノースなどの
如き単糖類;たとえば、シユクロース、ラクトー
ス、マルトース、などの如き二糖類;シユクロー
スを酵素で加水分解して得られる転化糖及びこれ
らの少なくとも二種の混合物を、好ましく例示で
きる。これらの中でも、グルコース、フラクトー
ス、シユクロース、キシロースの利用がより好ま
しい。
主成分量の単糖類及び二糖類からえらばれた少
なくとも一種の糖類のほかに、副成分量の三糖類
その他のオリゴ糖類を含有していても差支えな
い。
又、アミノ酸類の例としては、グリシン、L―
アラニン、L―イソロイシン、L―バリン、L―
リジン、L―グルタミン酸、L―アスパラギン
酸、L―グルタミン、L―アスパラギン、L―プ
ロリン、L―アルギニン、L―トリプトフアン、
L―ヒスチジン、L―シスチン、これらの塩類及
びこれらの少なくとも二種の混合物よりなる群か
らえらばれたアミノ酸類を好ましく例示できる。
とくに光学活性体である必要はなく、同様に利用
できる。これらの中でも、グリシン、アラニン、
バリン、リジン、グルタミン酸、アスパラギン
酸、プロリン、アルギニン、ヒスチジン、これら
の塩類及びこれらの少なくとも二種の混合物より
なる群から選ばれたアミノ酸類がより好ましい。
反応条件は、利用する糖類の種類、アミノ酸類
の種類、これらの組み合せの種類、反応系の状態
などによつても、適宜に選択できる。
種類の褐変反応を、例えば、溶融状態で行う場
合には、例えば約120℃〜約200℃の温度に約0.5
時間〜約5時間加熱して行うことができる。又例
えば、溶液状態で褐変反応を行う場合には、例え
ば、約0.1乃至約90重量パーセントの糖類溶液を
約80℃〜約160℃の温度に約0.5時間〜約48時間加
熱して行なうことができる。糖類を溶解・分散せ
しめる溶剤としては、水及び/又はプロピレング
リコール、グリセリンの如き多価アルコール類を
用いることができる。又、この反応に際して、糖
類のほかにたとえばアンモニア、亜硫酸アンモ
ン、硫酸、塩酸、水酸化ナトリウム、炭酸ナトリ
ウムの如きカラメル化触媒を共存させて反応を行
うこともできる。又、糖類とアミノ酸類との褐変
反応の場合には、例えば、反応を溶融状態で行う
態様に於ては、糖類のみをあらかじめ約120℃〜
約200℃の温度に約0.5時間〜約2時間加熱して溶
融させたのち、アミノ酸を添加し、更に約120℃
〜約200℃の温度に約0.5時間〜約5時間加熱して
行なうことができる。又、たとえば水溶液状態で
反応を行う場合には、系のPHを特に限定する必要
はないが好ましくはPH約8〜約13の如きアルカリ
PH条件に調節して行うのがよく、とくにアミノ酸
類としてパリンやダルタミン酸、アスパラギン酸
を利用する場合には、そのようなPH条件に調節し
て行うのが好ましく、アミノ酸の溶解度を高め、
反応速度を速めて、短縮された反応時間で褐変反
応生成物を高収率で得るのに役立つ。
このようなPH調節に利用する調節剤の例として
は、水酸化カリウム、水酸化ナトリウム、炭酸カ
リウム、炭酸ナトリウム、炭酸水素ナトリウム、
アンモニアなどを例示することができる。又、糖
類とアミノ酸類との反応モル比も適宜に選択でき
るが、ほぼ等モル付近で行うのが普通である。溶
液状態での反応では、通常、約0.1乃至約90重量
パーセントの糖類とアミノ酸の混合物溶液を約80
℃〜約160℃の温度に、約0.5時間〜約48時間加熱
して目的とする褐変反応生成物を得ることができ
る。反応時の溶剤としては水及び/又はプロピレ
ン・グリコール、グリセリンの如き多価アルコー
ル類を用いることができる。
本発明で用いるパプリカ色素及びにんじん抽出
物の混合比は、パプリカ色素のカラーバリユーに
よつても異るが、1:0.005乃至0.001:1、好ま
しくは1:0.01乃至0.01:1の範囲を挙げること
ができる。
また単糖類及び二糖類からえらばれた少なくと
も一種の糖類及び/又は該糖類とアミノ酸類との
褐変反応生成物は、上記パプリカ色素及びにんじ
ん抽出物の混合物に対して0.01乃至150倍重量、
好ましくは0.1乃至50倍重量の範囲で用いること
ができる。
本発明によるパプリカ色素組成物は、上述のよ
うにして得られたパプリカ色素及びにんじん抽出
物と単糖類及び二糖類からえらばれた少なくとも
一種の糖類及び/又は該糖類とアミノ酸類との褐
変反応生成物を混合することにより得ることがで
きるが、該組成物は乳化液もしくは粉末の剤形に
形成するのが好ましい。
例えばパプリカ色素とにんじん抽出物との混合
物を界面活性剤及び/又は保護コロイドの水溶液
で常法により乳化後、或いは乳化前に単糖類及び
二糖類からえらばれた少なくとも一種の糖類及
び/又は該糖類とアミノ酸類との褐変反応生成物
を添加することにより乳化状パプリカ色素組成物
を得ることができる。またパプリカ色素とにんじ
ん抽出物の混合系に更に香料、たとえばオレンジ
油、グレープフルーツ油、シモネンなどの如き精
油類、動植物性油脂類、天然樹脂類、ビタミン
類、多価アルコール類、シユークロースアセテー
トヘキサイソブチレート(SAIB)などを添加
後、同様に乳化することができる。
本発明に於いて用いられる界面活性剤として
は、例えば、しよ糖脂肪酸エステル、ソルビタン
脂肪酸エステル、大豆リン脂質、プロピレングリ
コール脂肪酸エステル、グリセリン脂肪酸エステ
ルなどの如き非イオン性界面活性剤が好ましくは
利用でき、更に陰イオン性界面活性剤あるいは陽
イオン性界面活性剤あるいは両性界面活性剤など
も使用することができる。これら界面活性剤の使
用量としては、パプリカ色素及びにんじん抽出物
の総重量に対して、例えば約0.5〜約150重量%、
より好ましくは約1〜約70重量%の範囲の使用量
が例示できる。
又、保護コロイドの具体例としては、アラビア
ガム、キサンタンガム、グアーガム、ローカスト
ビーンガム、トラガントガムなど天然ガム質類;
デキストリン、サイクロデキストリンなどの多糖
類;ゼラチン、カゼインなどの蛋白質類;などを
例示できる。これらの保護コロイドは、通常水溶
液の状態で使用され、その濃度は、使用する保護
コロイドの種類および乾燥工程に不都合を生じな
い程度の任意の濃度で良いが、例えば約0.05〜約
50%(重量)の濃度範囲が例示できる。又、保護
コロイド含有水性系の使用量は、保護コロイドの
種類により任意に選択できるが、例えば、パプリ
カ色素及びにんじん抽出物の総重量に対して約1
〜約50倍重量の使用量が挙げられる。これら界面
活性剤および保護コロイドは単種の使用あるいは
2種以上の併用も許される。上記水性系は、更
に、ソルビトール、グリセリン、プロピレングリ
コールの如き多価アルコール類を含有することが
できる。
また本発明のパプリカ色素組成物は、上述の乳
化液を噴霧乾燥、真空乾燥、凍結乾燥などの乾燥
手段によつて粉末化物とすることができる。更に
また該組成物の乳化液もしくは粉末を造粒機或い
は顆粒機を用いて、粒状ないし顆粒状にすること
も可能である。
本発明の安定性のすぐれたパプリカ色素組成物
は、例えば無果汁飲料、果汁入飲料、乳酸菌飲
料、乳飲料、粉末飲料の如き飲料類、アイスクリ
ーム、シヤーベツトの如き冷菓類、プリン、ゼリ
ー、ヨーグルトの如きデザート食品類、ドロツ
プ、キヤンデイーなどの菓子類、海産物類、加工
野菜類、保健医薬品類、石けん、洗剤、シヤンプ
ーの如き香粧品類などの着色に有用である。
以下、実施例により、本発明の安定性のすぐれ
たパプリカ色素組成物の数例について例示する。
参考例1(パプリカ色素の製造)
パプリカオレオレジン1Kgに85%エタノール10
Kgを添加して60℃で1時間撹拌する。静置後、パ
プリカ色素含有相を分離し、これに更に85%エタ
ノール5Kgを加えて60℃、30分撹拌する。同様に
して分離したパプリカ色素含有相に20%水酸化ナ
トリウムエタノール溶液2Kgを加えて70℃5時間
加熱撹拌する。冷却後10%塩酸溶液を添加してPH
6.5に調整後水酸化カルシウム500gを徐々に添加
する。次いで遠心分離して固形物2.7Kgを得た。
この固形物を減圧乾燥して含有水分を除去した
後、これにアセトン5Kgを加えて50℃にて2時間
撹拌して色素成分を抽出する。溶剤相を分離し、
これを減圧下で蒸留してアセトンを留去し、にお
いのないパプリカ色素248gを得た(カラーバリ
ユー400000)。
参考例2(パプリカ色素の製造)
パプリカオレオレジン500gに90%エタノール
溶液2Kgを加えて45℃にて3時間撹拌する。冷却
後静置してパプリカ色素含有相を分離し、これを
減圧下60―65℃にて蒸留して含有しているエタノ
ールを除去してにおいのないパプリカ色素470g
を得た(カラーバリユー110000)。
参考例3(にんじん抽出物の製造)
市販のにんじん10Kgを粉砕したのちプレスにて
ジユースと固形分とを分離し、ジユース7Kg固形
物3Kgを得た。固形物3Kgのヘキサン6Kgを加え
還流条件下、3時間抽出後、固液分離し、固形物
にはさらにヘキサン6Kgを加え同様に還流条件下
で3時間抽出する。得られた抽出液のヘキサンは
回収し、キヤロツト抽出物10g(カラーバリユー
88000)を得た。
参考例4(にんじん抽出物の製造)
乾燥にんじん粉砕物1Kgにアセトン5Kgを加え
還流条件下、1時間抽出後、固溶分離し、固形物
に更にアセトン3Kgを加え同様に還流条件下で1
時間抽出した。得られた抽出液を合せてアセトン
を回収し、にんじん抽出物13gを得た。
参考例5(糖類の褐変反応生成物の製造)
シユクロース100g、グルコース50g、フラク
トース50gからなる糖混合物を硫酸にてPH3.5に
調整したのち、加熱を行ない、徐々に加熱温度を
高め、糖を溶融させ、160℃で30分間保持する。
その後更に温度を180℃まで上昇させた時点で水
200gを加えて急冷する。得られた褐変反応生成
物の溶液をソーダ灰で中和後、置し赤褐色の液
体を得た。
参考例6糖類とアミノ酸類との褐変反応生成物の
製造)
グルコース90g、キシロース75g、L―グルタ
ミン酸105g、L―バリン36gからなる糖―アミ
ノ酸混合物に水200gを加え、水酸化ナトリウム
にて該混合物のPHを11に調整する。この混合物を
100℃で6時間加熱反応を行なつたのち冷却後
置し分光光度計のO.D430mμにおける吸光度が
250の褐変反応生成物を得た。
参考例 7
シユークロース90g、フラクトース90g、L―
アラニン68g、グリセリン300g、水200gからな
る混合物を、炭酸ソーダにて該混合物のPHを9.5
に調整する。この混合物を115℃で3時間加熱反
応を行つたのち冷却し、分光光度計のOD430mμ
における吸光度が380の褐変反応生成物を得た。
参考例 8
シユークロース20g、グルコース40g、L―リ
ジン35g、L―プロリン5g、L―アルギニン5
g、からなる糖―アミノ酸混合物に水200g、グ
リセリン200gを加え、水酸化カリウムにて該混
合物のPHを9に調整する。この混合物を110℃で
4時間加熱反応を行つたのち冷却し、次いで過
を行つたOD480mμにおける吸光度が220の褐変
反応生成物を得た。
参考例 9
グルコース300g、フラクトース100g、グリシ
ン150g、L―アスパラギン酸ナトリウム20g、
L―ヒスチジン30gからなる糖―アミノ酸混合物
に水1000gを加え、水酸化ナトリウムを用いて該
混合物のPHを10に調整した。
この混合物を100℃で4時間加熱反応した後冷
却し、過を行つて分光光度計のOD430mμにお
ける吸光度が200の褐変反応生成物を得た。
比較例 1
参考例1で製造したパプリカ色素(カラーパリ
ユー400000)3部、ヤシ油2部を加熱混合したも
のに、30%アラビアガム水溶液95部を加えて乳化
機で乳化し、パプリカ色素組成物を得た。
比較例 2
参考例2で得られた脱臭パプリカ色素0.2部、
オレンジ油0.1部及び精製ヤシ油0.7部の混合油に
35%アラビアガム水溶液60部及びプロピレングリ
コール40部を混合して乳化処理し、パプリカ色素
乳化物を調製した。
実施例 1
参考例1で製造したパプリカ色素3部、参考例
3で製造したにんじん抽出物0.3部、ヤシ油1.7部
を加熱混合したものに30%アラビアガム水溶液90
部、参考例6で製造した糖類とアミノ酸類の褐変
反応生成物5部、を加えて乳化機で乳化し、安定
性のすぐれたパプリカ色素組成物を得た。
実施例 2
参考例1で製造したパプリカ色素6部、参考例
3で製造したにんじん抽出物2部、SAIB1部、ヤ
シ油1部を加熱混合したものに35%アラビアガム
水溶液160部を加えて乳化後、参考例6で製造し
た糖類とアミノ酸類との褐変反応生成物20部、水
10部を上記乳化液に加えて混合撹拌し、安定性の
すぐれたパプリカ色素組成物を得た。
実施例 3
実施例1、実施例2及び比較例1で得られたそ
れぞれのパプリカ色素組成物1gを砂糖110g、
温州みかん1/5濃縮果汁20g、クエン酸2g、オ
レンジエツセンス1mlと混合し、その混合物を水
にて1に希釈して90℃、15分加熱殺菌後、
200ml容の無色透明ガラスびんに熱時充填し、日
光照射試験用試料を調製した。
冷却後直ちに、各1本を開栓し、色差計(日本
電色工業ND―101D型)にて、L、a、b値を測
定した。残りの試料を4日間直射日光に暴露した
〔積算光量計(スガ試験機PH―51―T型)による
照射光量は1980ラングレー(cal/cm2)であつ
た〕。
日光照射後の試料を再び色差計を用いて測定
し、夫々の試料の日光照射前後における色差△E
を算出した。その結果を第1表に示す。
The present invention relates to a paprika pigment composition having excellent stability against oxygen and/or light. Conventionally, paprika oleoresin, which is obtained by solvent extraction of paprika fruit or its dried product, or so-called purified paprika pigment, which is obtained by refining paprika oleoresin to increase the pigment content, are both in their original form. Alternatively, it is used as a red natural pigment in foods, drinks, medicines, etc. in the form of preparations such as emulsions, powders, and granules. These paprika pigments (in the present invention, the term encompasses paprika pigments and their containing materials ranging from paprika pigment-containing materials such as paprika oleoresin to purified pigments derived therefrom),
A natural pigment that exhibits a red color tone ranging from red to orange to yellow-orange; for example, it exhibits a red tone at a relatively high concentration in an aqueous medium, and a yellow-orange tone at a relatively low concentration, and, for example, in a dry state. Even when its content is relatively low, it usually exhibits a red to reddish-orange color tone. As is well known, paprika pigment, which is a natural pigment, is quite unstable and storage stable in the presence of oxygen and/or light, and even moisture, as seen in many natural pigments. It has the fateful trouble of being bad and fading relatively easily economically. This problem with paprika pigments is relatively serious, and fading and deterioration tends to be accelerated by dissolved oxygen (air) and light, especially in aqueous foods and beverages, such as beverages in a broad sense and foods with a high water content. Over time, the color fades and deteriorates from red to yellow-orange, and finally to almost colorless. In addition, paprika pigment preparations in the form of powder or granules also suffer from similar fading and deterioration, although the degree varies depending on drying conditions, storage conditions, etc. Regarding the case of coloring beverages other than those characterized by adding quercetin and/or its glycoside rutin to paprika pigment with paprika pigment in order to overcome the problem of fading that paprika pigment inherently has. The method for preventing fading of paprika pigment (Special Publication No. 10568/1983), and the use of the above quercetin and/or rutin in paprika pigment drinks.
A method for preventing fading of paprika-colored beverages (Japanese Patent Publication No. 31947/1983) is known, which is characterized in that paprika is added in an amount to achieve a concentration of 600 ppm or less. Quercetin and/or rutin aqueous solution exhibits a green to green yellow color, but in the latter proposal above,
It is stated that at a concentration of 250 ppm, it exhibits a very slight green to green yellow color. Another known proposal is to add a browning reaction product of sugar and amino acids to pigments produced by microorganisms belonging to the genus Monascus, such as Monascus anchora and Monascus purpureus, in order to prevent the pigments from deteriorating. (Unexamined Japanese Patent Publication 1973-
180428). This proposal specifically discloses only the pigment produced by the above-mentioned microorganism, and of course makes no mention of the effect of the browning reaction product on other pigments. For example, vitamin C has a stabilizing effect on β-carotene pigment, but vitamin C has no usable stabilizing effect on paprika pigment; Since the stabilizing effects of the same compound on pigments are usually different and unpredictable, it is reasonable that the above proposal discloses the deterioration prevention effect of the browning reaction product only for the microorganism-produced pigments. That's true. The present inventors conducted research to develop a paprika pigment composition that does not change the hue of paprika pigments and has excellent stability. As a result, at least one type of carrot organic solvent extract (hereinafter sometimes abbreviated as carrot extract) selected from monosaccharides and disaccharides is effective against fading of paprika pigment in the presence of oxygen and/or light. In the coexistence of a browning reaction product of a saccharide and/or a browning reaction product of the saccharide and an amino acid,
It was discovered that it exhibits an excellent anti-fading effect. Although it is known that the carotenoid pigments contained in carrot extract tend to discolor in the presence of oxygen and/or light, paprika pigments are excellently stabilized under the coexistence conditions of the three above. It was found that the effect of Carrot extract contains many types of ingredients, so it is not yet clear what the stabilizing active ingredient is, but at least one component of carrot extract, β-carotene, is known.
It was found that the paprika pigment clearly has an anti-fading effect. However, when we added synthetic β-carotene in the same amount as the β-carotene in carrot extract to paprika pigment and examined its anti-fading effect, carrot extract showed much better results. Ta. Therefore, it is clear that active ingredients other than β-carotene are present in the carrot extract as ingredients that help prevent fading of paprika pigment. In addition, the same inventors have already proposed that browning reaction products of sugars and/or browning reaction products of sugars and amino acids have an effective effect on preventing fading of paprika pigments [JP-A-56-1996] 41259
No. (Patent Application No. 54-115120)]. Furthermore, the present inventors used a browning reaction product of an organic solvent extract of carrot and at least one saccharide selected from monosaccharides and disaccharides and/or a browning reaction product of the saccharide and an amino acid as paprika pigment. It has been discovered that when these pigments are co-existed with each other, a paprika pigment composition exhibits a surprising synergistic effect and has excellent stability compared to when each of them coexists alone. Therefore, an object of the present invention is to provide a paprika pigment composition with excellent stability. The highly stable paprika pigment composition of the present invention is a browning reaction product of a paprika pigment, an organic solvent extract of carrot, and at least one saccharide selected from monosaccharides and disaccharides, and/or a browning reaction product of the saccharide and an amino acid. Contains a browning reaction product with as an active ingredient. The paprika color used in the composition may be either paprika oleoresin or purified paprika color. As is well known, paprika oleoresin is produced by adding an organic solvent such as acetone, n-pentane, n-hexane, methylene chloride, or ethylene dichloride to a dried and crushed paprika fruit, and then extracting the resulting product. It can be obtained by separating the phases and distilling off the organic solvent under normal pressure to reduced pressure. Examples of purified paprika pigments include paprika oleoresin-treated products obtained by removing the flavor components of paprika by solvent extraction or steam distillation of paprika oleoresin.
If solvent extraction is employed, paprika oleoresin can be extracted with lower aliphatic alcohols, such as C1 - C3 aliphatic alcohols such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol. Preferably ethanol can be used. These aliphatic alcohols can also be used in a hydrous system, for example in a water content of about 1 to about 30% by weight. Various extraction operations and extraction conditions can be selected, but for example, about 0.5 to about 20 times the weight of aliphatic alcohol is added to paprika oleoresin, and the mixture is heated at room temperature or the boiling point temperature of the lower aliphatic alcohol used for about 5 minutes to about
This can be done by stirring for 10 hours. After performing the extraction operation in this manner, the alcohol phase and the paprika pigment-containing phase can be separated, for example, by allowing the mixture to stand still. Centrifugation or other liquid-liquid separation means may also be used. If necessary,
Furthermore, the paprika odor of the paprika pigment-containing phase can be further sufficiently removed by adding an aliphatic alcohol to the separated paprika pigment-containing phase and repeating the same operation. Further, when a steam distillation means is employed, pressurized or reduced pressure conditions may be employed in addition to atmospheric pressure conditions. Furthermore, as a purified paprika pigment, paprika oleoresin is extracted with a lower aliphatic alcohol or its water content, and the paprika pigment-containing phase separated from the alcohol layer (paprika flavor component-containing phase) is treated with an alkali, and then the pH of the system is adjusted. Adjust to the acidic side and
A paprika pigment obtained by treating a pH-controlled system with a forming agent that can convert fatty acids contained in the system into poorly water-soluble or insoluble salts and extracting the resulting treated product with an organic solvent. Its use is recommended. In a preferred embodiment of the paprika pigment used in the present invention, the paprika pigment-containing phase obtained as described above is treated with an alkali. Examples of the alkali used in this treatment include potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium alcoholate, potassium alcoholate, and combinations thereof. The paprika pigment-containing phase may be used as it is, or it may be used after distilling off the alcohol that may be contained in a small amount.
Further, the alkali may be added in a solid state, or in the form of water, alcohol, or a mixed solution thereof. It is preferable to adopt alkaline conditions such that the alkaline concentration in the alkaline treatment system is about 5% to about 30%. The above alkali treatment operation and alkali treatment conditions may be selected as appropriate. For example, add about 0.5 to about 5 times the weight of an aqueous sodium hydroxide solution (for a concentration of about 20%) to the paprika pigment-containing phase to give a solution of about 50 to about 100%.
This can be carried out by stirring at a temperature of about 30 minutes to about 12 hours. After the alkali treatment, the pH of the treatment system is adjusted to the acidic side, preferably about 4 to about 6.5.
Examples of PH regulators include inorganic or organic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, lactic acid, and citric acid. Through this PH adjustment treatment after the alkali treatment, the fatty acids contained in the paprika pigment-containing phase were
The water-soluble alkali salt form is once converted into free fatty acids. This PH-adjusted system is then treated with a salt-forming agent capable of converting the fats contained in the system into poorly water-soluble to insoluble salts. By this treatment, fatty acids that have been once converted into free fatty acids are converted into their sparingly water-soluble or insoluble salts. This salt formation treatment can be performed, for example, under the following operations and conditions. For example, about 0.2 to about 3 of the amount of raw material oleoresin used in the PH-adjusted product
This can be done by gradually adding twice the weight of the salt former. The reaction can be carried out at room temperature, and if desired, cooling or heating conditions can be employed, such as temperatures of 0 to about 100°C. Preferred examples of such salt forming agents include alkaline earth metal hydroxides such as calcium hydroxide, magnesium hydroxide, and pallium hydroxide. In addition, hydroxides of other metals such as Al, Fe, Zn, and Cu can also be used. The solid phase of the system thus treated with the salt forming agent is collected by solid-liquid separation means such as filtration or centrifugation, and
If desired, after washing with water, dehydration, etc., extraction with an organic solvent can be performed. As described above, the solid phase subjected to the pH adjustment treatment and the salt formation treatment is much easier to perform organic solvent extraction than the soap-like solid phase proposed in the past, and has excellent extraction efficiency. There is. As the solvent used for this extraction, a wide variety of organic solvents can be used since triglycerides that interfere with smooth and efficient dye extraction are sufficiently removed. Examples of such organic solvents include ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, and isopropanol;
-Pentane, iso-pentane, cyclohexane,
Examples include hydrocarbons such as n-hexane, benzene, and toluene; halogenated hydrocarbons such as methylene chloride, ethylene dichloride, carbon tetrachloride, and chloroform; ethers such as diethyl ether and isopropyl ether; and arbitrary mixtures thereof. can do. The extraction operation and extraction conditions can be selected as appropriate. For example, about 0.5 to about 20 times the weight of an organic solvent is added to the obtained solid phase and the mixture is heated at room temperature to the boiling point of the solvent used for about 15 minutes to about 15 minutes. This can be done by extracting the temporal pigment component. The extraction can be carried out by flowing the organic solvent down through the solid phase formed into a column. After the organic solvent extraction operation, the organic solvent phase (paprika pigment-containing phase) and solid residue are separated, and the organic solvent phase is further distilled under atmospheric pressure or reduced pressure to remove the solvent. Paprika pigments with approximately 600,000 color variations can be obtained. In addition, the carrot extract used in the present invention is
There is no particular limitation on the variety, and it can be obtained by extracting fresh carrots, dried carrots, fresh carrot juice, juice residue, etc. with an organic solvent. Examples of organic solvents include acetone, ketones such as methyl ethyl ketone, esters such as methyl acetate and ethyl acetate, n-pentane, isopentane,
Examples include hydrocarbons such as cyclohexane, n-hexane, benzene and toluene, halogenated hydrocarbons such as methylene chloride and ethylene dichloride, ethers such as diethyl ether and isopropyl ether, and arbitrary mixtures thereof. Although there are no particular restrictions on the extraction temperature and time, for example, extraction can be carried out at room temperature to the boiling point temperature of the solvent used for about 5 minutes to about 150 hours. A carrot extract can be obtained by distilling the extract under normal pressure to reduced pressure to completely remove the solvent. Furthermore, examples of the saccharide used in the browning reaction product of at least one saccharide selected from monosaccharides and disaccharides and/or the saccharide and amino acids used in the present invention include, for example, glucose, fructose, xylose, and caractose. , mannose,
Preferred examples include monosaccharides such as rhamnose, glucuronic acid, arabinose, etc.; disaccharides such as sucrose, lactose, maltose, etc.; invert sugars obtained by enzymatic hydrolysis of sucrose, and mixtures of at least two thereof. can. Among these, it is more preferable to use glucose, fructose, sucrose, and xylose. In addition to at least one type of saccharide selected from monosaccharides and disaccharides as the main component, it may contain trisaccharides and other oligosaccharides as subcomponents. In addition, examples of amino acids include glycine, L-
Alanine, L-isoleucine, L-valine, L-
Lysine, L-glutamic acid, L-aspartic acid, L-glutamine, L-asparagine, L-proline, L-arginine, L-tryptophan,
Preferred examples include amino acids selected from the group consisting of L-histidine, L-cystine, salts thereof, and mixtures of at least two thereof.
It does not need to be an optically active substance and can be used in the same way. Among these, glycine, alanine,
More preferred are amino acids selected from the group consisting of valine, lysine, glutamic acid, aspartic acid, proline, arginine, histidine, salts thereof, and mixtures of at least two thereof. Reaction conditions can be appropriately selected depending on the type of saccharide used, the type of amino acid, the type of combination thereof, the state of the reaction system, etc. For example, when carrying out a browning reaction in the molten state, for example, at a temperature of about 120°C to about 200°C, about 0.5
This can be done by heating for 5 hours to about 5 hours. For example, when carrying out the browning reaction in a solution state, it can be carried out by heating a saccharide solution of about 0.1 to about 90% by weight to a temperature of about 80°C to about 160°C for about 0.5 to about 48 hours. can. As a solvent for dissolving and dispersing sugars, water and/or polyhydric alcohols such as propylene glycol and glycerin can be used. Further, in addition to sugars, a caramelization catalyst such as ammonia, ammonium sulfite, sulfuric acid, hydrochloric acid, sodium hydroxide, or sodium carbonate may be present in the presence of this reaction. In addition, in the case of a browning reaction between sugars and amino acids, for example, in embodiments in which the reaction is carried out in a molten state, only the sugars are heated in advance at about 120°C to
After heating and melting at a temperature of about 200°C for about 0.5 to about 2 hours, the amino acid is added, and then heated to about 120°C.
This can be carried out by heating at a temperature of about 200° C. for about 0.5 hours to about 5 hours. For example, when carrying out the reaction in an aqueous solution state, it is not necessary to particularly limit the pH of the system, but it is preferable to use an alkaline solution with a pH of about 8 to about 13.
It is best to adjust the PH conditions. Particularly when using parin, daltamic acid, or aspartic acid as amino acids, it is preferable to adjust the PH conditions to increase the solubility of the amino acids.
It helps to speed up the reaction rate and obtain a high yield of browning reaction product in a shortened reaction time. Examples of regulators used for such pH regulation include potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium hydrogen carbonate,
Examples include ammonia. Further, the molar ratio of the reaction between sugars and amino acids can be selected as appropriate, but it is common to perform the reaction at approximately equimolar ratios. For reactions in solution, a solution of a mixture of sugars and amino acids of about 0.1 to about 90 percent by weight is typically added to about 80 percent by weight.
C. to about 160.degree. C. for about 0.5 hours to about 48 hours to obtain the desired browning reaction product. As a solvent during the reaction, water and/or polyhydric alcohols such as propylene glycol and glycerin can be used. The mixing ratio of the paprika pigment and carrot extract used in the present invention varies depending on the color value of the paprika pigment, but is in the range of 1:0.005 to 0.001:1, preferably 1:0.01 to 0.01:1. be able to. In addition, at least one saccharide selected from monosaccharides and disaccharides and/or a browning reaction product of the saccharide and amino acids is 0.01 to 150 times the weight of the mixture of paprika pigment and carrot extract,
Preferably, it can be used in a range of 0.1 to 50 times the weight. The paprika pigment composition according to the present invention is produced by a browning reaction between the paprika pigment and carrot extract obtained as described above, at least one saccharide selected from monosaccharides and disaccharides, and/or the saccharide and amino acids. Although the composition can be obtained by mixing the ingredients, it is preferable to form the composition into an emulsion or powder form. For example, after emulsifying a mixture of paprika color and carrot extract with an aqueous solution of a surfactant and/or protective colloid by a conventional method, or before emulsifying, at least one saccharide selected from monosaccharides and disaccharides and/or the saccharide is added. An emulsified paprika pigment composition can be obtained by adding a browning reaction product between In addition, in addition to the mixture of paprika color and carrot extract, fragrances such as orange oil, grapefruit oil, essential oils such as simonene, animal and vegetable fats and oils, natural resins, vitamins, polyhydric alcohols, sucrose acetate hexane, etc. After adding isobutyrate (SAIB), etc., it can be emulsified in the same way. As the surfactant used in the present invention, nonionic surfactants such as sucrose fatty acid ester, sorbitan fatty acid ester, soybean phospholipid, propylene glycol fatty acid ester, glycerin fatty acid ester, etc. are preferably used. Furthermore, anionic surfactants, cationic surfactants, amphoteric surfactants, etc. can also be used. The amount of these surfactants used is, for example, about 0.5 to about 150% by weight, based on the total weight of paprika pigment and carrot extract.
More preferably, the amount used is in the range of about 1 to about 70% by weight. Specific examples of protective colloids include natural gums such as gum arabic, xanthan gum, guar gum, locust bean gum, and gum tragacanth;
Examples include polysaccharides such as dextrin and cyclodextrin; proteins such as gelatin and casein; and the like. These protective colloids are usually used in the form of an aqueous solution, and the concentration may be any concentration that does not cause any inconvenience to the type of protective colloid used and the drying process, but for example, from about 0.05 to about
An example is a concentration range of 50% (by weight). The amount of the protective colloid-containing aqueous system to be used can be arbitrarily selected depending on the type of protective colloid, but for example, approximately 1% of the total weight of paprika pigment and carrot extract is used.
The amount used is approximately 50 times the weight. These surfactants and protective colloids may be used alone or in combination of two or more. The aqueous system may further contain polyhydric alcohols such as sorbitol, glycerin, propylene glycol. Moreover, the paprika pigment composition of the present invention can be made into a powder by drying the above-mentioned emulsion by drying means such as spray drying, vacuum drying, and freeze drying. Furthermore, it is also possible to make the emulsion or powder of the composition into granules or granules using a granulator or a granulator. The highly stable paprika color composition of the present invention can be used, for example, in beverages such as non-fruit juice drinks, fruit juice-containing drinks, lactic acid bacteria drinks, milk drinks, and powder drinks, ice creams, frozen desserts such as sherbet, puddings, jellies, and yogurts. It is useful for coloring dessert foods such as, confectionery such as drops and candy, seafood, processed vegetables, health pharmaceuticals, and cosmetics such as soap, detergent, and shampoo. Hereinafter, several examples of the paprika pigment composition of the present invention with excellent stability will be illustrated by way of Examples. Reference Example 1 (Manufacture of paprika pigment) 1 kg of paprika oleoresin and 10 parts of 85% ethanol
Kg and stirred at 60°C for 1 hour. After standing still, the paprika pigment-containing phase is separated, and 5 kg of 85% ethanol is added thereto, followed by stirring at 60°C for 30 minutes. Add 2 kg of a 20% sodium hydroxide ethanol solution to the similarly separated paprika pigment-containing phase, and heat and stir at 70°C for 5 hours. After cooling, add 10% hydrochloric acid solution to adjust the pH.
After adjusting to 6.5, gradually add 500g of calcium hydroxide. Then, it was centrifuged to obtain 2.7 kg of solid material.
After drying this solid under reduced pressure to remove the water content, 5 kg of acetone is added thereto and stirred at 50° C. for 2 hours to extract the pigment component. Separate the solvent phase;
This was distilled under reduced pressure to remove acetone, yielding 248 g of odorless paprika pigment (color value 400,000). Reference Example 2 (Manufacture of paprika pigment) 2 kg of 90% ethanol solution was added to 500 g of paprika oleoresin and stirred at 45°C for 3 hours. After cooling, the paprika pigment-containing phase is separated by standing and distilled under reduced pressure at 60-65℃ to remove the ethanol contained in it, producing 470 g of odorless paprika pigment.
(color value 110000). Reference Example 3 (Manufacture of Carrot Extract) After pulverizing 10 kg of commercially available carrots, the green juice and solid content were separated using a press to obtain 7 kg of green juice and 3 kg of solid matter. After adding 3 kg of solid matter to 6 kg of hexane and extracting under reflux conditions for 3 hours, solid-liquid separation is carried out. To the solid matter, 6 kg of hexane is further added and extraction is similarly carried out under reflux conditions for 3 hours. The hexane of the obtained extract was collected, and 10 g of carrot extract (color value) was collected.
88000). Reference Example 4 (Manufacture of Carrot Extract) Add 5 kg of acetone to 1 kg of dried carrot extract, extract under reflux conditions for 1 hour, perform solid solution separation, add 3 kg of acetone to the solid, and add 1 kg of acetone under reflux conditions.
Time extracted. The obtained extracts were combined to recover acetone, and 13 g of carrot extract was obtained. Reference Example 5 (Production of browning reaction product of sugars) A sugar mixture consisting of 100 g of sucrose, 50 g of glucose, and 50 g of fructose was adjusted to pH 3.5 with sulfuric acid, heated, and the heating temperature was gradually increased to Melt and hold at 160 °C for 30 minutes.
After that, when the temperature was further increased to 180℃, the water
Add 200g and cool quickly. The resulting solution of the browning reaction product was neutralized with soda ash and then allowed to stand to obtain a reddish-brown liquid. Reference Example 6 Production of browning reaction product between sugars and amino acids) Add 200 g of water to a sugar-amino acid mixture consisting of 90 g of glucose, 75 g of xylose, 105 g of L-glutamic acid, and 36 g of L-valine, and stir the mixture with sodium hydroxide. Adjust the PH to 11. this mixture
After heating the reaction at 100℃ for 6 hours, the absorbance at O.D430mμ of the spectrophotometer was measured after cooling.
250 browning reaction products were obtained. Reference example 7 Syuucrose 90g, fructose 90g, L-
A mixture of 68 g of alanine, 300 g of glycerin, and 200 g of water was brought to a pH of 9.5 with soda carbonate.
Adjust to. This mixture was heated at 115°C for 3 hours, cooled, and measured at OD430mμ on a spectrophotometer.
A browning reaction product with an absorbance of 380 was obtained. Reference example 8 Syuucrose 20g, glucose 40g, L-lysine 35g, L-proline 5g, L-arginine 5
200 g of water and 200 g of glycerin are added to the sugar-amino acid mixture consisting of g, and the pH of the mixture is adjusted to 9 with potassium hydroxide. This mixture was reacted by heating at 110° C. for 4 hours, cooled, and then filtered to obtain a browned reaction product having an absorbance of 220 at OD480 mμ. Reference example 9 Glucose 300g, fructose 100g, glycine 150g, L-sodium aspartate 20g,
1000 g of water was added to a sugar-amino acid mixture consisting of 30 g of L-histidine, and the pH of the mixture was adjusted to 10 using sodium hydroxide. This mixture was reacted by heating at 100°C for 4 hours, then cooled and filtered to obtain a browning reaction product having an absorbance of 200 at OD430mμ on a spectrophotometer. Comparative Example 1 95 parts of a 30% gum arabic aqueous solution was added to a heated mixture of 3 parts of the paprika pigment (Color Pariyu 400000) produced in Reference Example 1 and 2 parts of coconut oil, and emulsified with an emulsifier to obtain the paprika pigment composition. I got something. Comparative Example 2 0.2 parts of deodorized paprika dye obtained in Reference Example 2,
Mixed oil of 0.1 part orange oil and 0.7 part refined coconut oil
60 parts of a 35% aqueous gum arabic solution and 40 parts of propylene glycol were mixed and emulsified to prepare a paprika pigment emulsion. Example 1 3 parts of the paprika color produced in Reference Example 1, 0.3 parts of the carrot extract produced in Reference Example 3, and 1.7 parts of coconut oil were heated and mixed with 90% of a 30% gum arabic aqueous solution.
1 part, and 5 parts of the browning reaction product of sugars and amino acids produced in Reference Example 6 were added and emulsified using an emulsifier to obtain a paprika pigment composition with excellent stability. Example 2 160 parts of a 35% gum arabic aqueous solution was added to a heated mixture of 6 parts of paprika color produced in Reference Example 1, 2 parts of carrot extract produced in Reference Example 3, 1 part of SAIB, and 1 part of coconut oil to emulsify. Then, add 20 parts of the browning reaction product of sugars and amino acids produced in Reference Example 6, and water.
10 parts were added to the above emulsion and mixed and stirred to obtain a paprika pigment composition with excellent stability. Example 3 1 g of each paprika color composition obtained in Example 1, Example 2, and Comparative Example 1 was mixed with 110 g of sugar,
Mix 20g of Satsuma mandarin 1/5 concentrated fruit juice, 2g of citric acid, and 1ml of orange essence, dilute the mixture to 1 with water and heat sterilize it at 90℃ for 15 minutes.
A sample for sunlight irradiation test was prepared by hot filling a 200 ml colorless transparent glass bottle. Immediately after cooling, each bottle was opened and the L, a, and b values were measured using a color difference meter (Nippon Denshoku Kogyo Model ND-101D). The remaining sample was exposed to direct sunlight for 4 days (the amount of irradiation light measured by an integrated light meter (Suga Test Instruments Model PH-51-T) was 1980 Langley (cal/cm 2 )). The samples after sunlight irradiation were measured again using a color difference meter, and the color difference △E of each sample before and after sunlight irradiation was measured.
was calculated. The results are shown in Table 1.
【表】
第1表の結果から明かな通り、実施例1及び実
施例2のパプリカ色素組成物を用いたものは依然
として橙赤色を保持していたや、無添加の比較例
1は淡黄色に褪色してしまつた。
実施例 4
参考例2で得られたパプリカ色素0.15部、参考
例4で得られたにんじん抽出物0.05部、オレンジ
油0.1部、の混合油に35%アラビアガム水溶液60
部、プロピレングリコール25部及び参考例5で得
られた糖類の褐変反応生成物15部を加えて乳化
し、パプリカ色素組成物を得た。
実施例 5〜7
実施例4において参考例5で得られた糖類の褐
変反応生成物に替えて、同量の参考例7で得られ
た糖類とアミノ酸類の褐変反応生成物を添加(実
施例5)、参考例8で得られた反応生成物を添加
(実施例6)、及び参考例9で得られた反応生成物
を添加(実施例7)した以外は実施例4と同様の
方法によつて夫々のパプリカ色素組成物を調製し
た。
実施例 8
実施例4〜7及び比較例2で得られたパプリカ
色素組成物を夫々PH3.0、Brix12〓の糖液に0.1%
添加して着色シロツプを調製し、実施例3と同じ
方法で4日間日光照射試験を行つた。その結果を
第2表に示す。[Table] As is clear from the results in Table 1, those using the paprika pigment compositions of Examples 1 and 2 still maintained an orange-red color, and Comparative Example 1 without additives turned pale yellow. It has faded. Example 4 A 35% gum arabic aqueous solution was added to a mixed oil of 0.15 part of paprika color obtained in Reference Example 2, 0.05 part of carrot extract obtained in Reference Example 4, and 0.1 part of orange oil.
1 part, 25 parts of propylene glycol, and 15 parts of the saccharide browning reaction product obtained in Reference Example 5 were added and emulsified to obtain a paprika pigment composition. Examples 5 to 7 In Example 4, instead of the browning reaction product of sugars obtained in Reference Example 5, the same amount of the browning reaction product of sugars and amino acids obtained in Reference Example 7 was added (Example 5), the same method as Example 4 except that the reaction product obtained in Reference Example 8 was added (Example 6), and the reaction product obtained in Reference Example 9 was added (Example 7). Thus, each paprika pigment composition was prepared. Example 8 Each of the paprika pigment compositions obtained in Examples 4 to 7 and Comparative Example 2 was added at 0.1% to a sugar solution with a pH of 3.0 and a Brix of 12.
A colored syrup was prepared, and a 4-day sunlight irradiation test was conducted in the same manner as in Example 3. The results are shown in Table 2.
【表】
第2表の結果から明らかな如く、にんじん抽出
物と糖類しくは糖類とアミノ酸類との褐変反応生
成物を添加した本発明の実施例4〜7は好ましい
橙赤色を保持していたが、無添加の比較例2は淡
黄色に退色してしまつた。[Table] As is clear from the results in Table 2, Examples 4 to 7 of the present invention, in which the browning reaction product of carrot extract and saccharides or saccharides and amino acids was added, maintained a preferable orange-red color. However, in Comparative Example 2 without additives, the color faded to pale yellow.
Claims (1)
と、単糖類及び二糖類からえらばれた少なくとも
一種の糖類の褐変反応生成物及び/又は該糖類と
アミノ酸類との褐変反応生成物を含有することを
特徴とする安定性のすぐれたパプリカ色素組成
物。 2 該アミノ酸類がグリシン、アラニン、バリ
ン、リジン、グルタミン酸、アスパラギン酸、プ
ロリン、アルギニン、ヒスチジン、これらの塩類
及びこれらの少なくとも二種の混合物よりなる群
から選ばれたアミノ酸類であることを特徴とする
特許請求の範囲第1項記載のパプリカ色素組成
物。[Claims] 1. A browning reaction product of paprika pigment and an organic solvent extract of carrot and at least one saccharide selected from monosaccharides and disaccharides and/or a browning reaction product of the saccharide and amino acids. A highly stable paprika pigment composition characterized by containing. 2. The amino acids are selected from the group consisting of glycine, alanine, valine, lysine, glutamic acid, aspartic acid, proline, arginine, histidine, salts thereof, and mixtures of at least two of these. The paprika pigment composition according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10675280A JPS5731962A (en) | 1980-08-05 | 1980-08-05 | Paprika coloring matter composition having excellent stability |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10675280A JPS5731962A (en) | 1980-08-05 | 1980-08-05 | Paprika coloring matter composition having excellent stability |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5731962A JPS5731962A (en) | 1982-02-20 |
JPS6160871B2 true JPS6160871B2 (en) | 1986-12-23 |
Family
ID=14441637
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10675280A Granted JPS5731962A (en) | 1980-08-05 | 1980-08-05 | Paprika coloring matter composition having excellent stability |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5731962A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2010110269A1 (en) * | 2009-03-26 | 2012-09-27 | キッコーマン株式会社 | Browning reaction product and oil and fat food |
US11851734B2 (en) | 2015-01-12 | 2023-12-26 | Ati Properties Llc | Titanium alloy |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60137261A (en) * | 1983-12-27 | 1985-07-20 | Seiwa Kasei Kk | Prevention of browning of edible coloring matter |
JPH0759181B2 (en) * | 1985-11-29 | 1995-06-28 | 長谷川香料株式会社 | Anti-fading agent for carotenoid pigments |
US7097867B2 (en) | 2003-03-24 | 2006-08-29 | Council Of Scientific And Industrial Research | Process of extracting chili (capsicum) oleoresin |
-
1980
- 1980-08-05 JP JP10675280A patent/JPS5731962A/en active Granted
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2010110269A1 (en) * | 2009-03-26 | 2012-09-27 | キッコーマン株式会社 | Browning reaction product and oil and fat food |
JP5734839B2 (en) * | 2009-03-26 | 2015-06-17 | キッコーマン株式会社 | Emulsifier, oil and fat food and method for producing oil and fat food |
US11851734B2 (en) | 2015-01-12 | 2023-12-26 | Ati Properties Llc | Titanium alloy |
Also Published As
Publication number | Publication date |
---|---|
JPS5731962A (en) | 1982-02-20 |
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