JP2023111879A - Method for producing purified lemon balm extract - Google Patents
Method for producing purified lemon balm extract Download PDFInfo
- Publication number
- JP2023111879A JP2023111879A JP2023009310A JP2023009310A JP2023111879A JP 2023111879 A JP2023111879 A JP 2023111879A JP 2023009310 A JP2023009310 A JP 2023009310A JP 2023009310 A JP2023009310 A JP 2023009310A JP 2023111879 A JP2023111879 A JP 2023111879A
- Authority
- JP
- Japan
- Prior art keywords
- lemon balm
- balm extract
- mass
- peak area
- rosmarinic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000284 extract Substances 0.000 title claims abstract description 172
- 244000062730 Melissa officinalis Species 0.000 title claims abstract description 170
- 235000010654 Melissa officinalis Nutrition 0.000 title claims abstract description 167
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 31
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 claims abstract description 163
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 claims abstract description 81
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 claims abstract description 81
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 claims abstract description 81
- 235000013361 beverage Nutrition 0.000 claims abstract description 47
- 125000003118 aryl group Chemical group 0.000 claims abstract description 43
- 239000003463 adsorbent Substances 0.000 claims abstract description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 59
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 36
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 claims description 30
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 20
- 235000013305 food Nutrition 0.000 claims description 19
- 238000009472 formulation Methods 0.000 claims description 18
- 238000004062 sedimentation Methods 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 13
- 239000002537 cosmetic Substances 0.000 claims description 13
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims description 11
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 11
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- SGAWOGXMMPSZPB-UHFFFAOYSA-N safranal Chemical compound CC1=C(C=O)C(C)(C)CC=C1 SGAWOGXMMPSZPB-UHFFFAOYSA-N 0.000 claims description 10
- HPMSQLYFMOOLKS-UHFFFAOYSA-N 1-ethoxy-3-methylbut-2-ene Chemical compound CCOCC=C(C)C HPMSQLYFMOOLKS-UHFFFAOYSA-N 0.000 claims description 7
- DDGBOLJFAMEBOE-UHFFFAOYSA-N Isovaleraldehyde diethyl acetal Chemical compound CCOC(CC(C)C)OCC DDGBOLJFAMEBOE-UHFFFAOYSA-N 0.000 claims description 7
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 claims description 5
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 claims description 5
- 229940088601 alpha-terpineol Drugs 0.000 claims description 5
- 235000017509 safranal Nutrition 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 244000178231 Rosmarinus officinalis Species 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 abstract description 16
- 238000012360 testing method Methods 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 32
- 238000011282 treatment Methods 0.000 description 32
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 25
- 239000003795 chemical substances by application Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000000287 crude extract Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- 238000000746 purification Methods 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 13
- 239000000796 flavoring agent Substances 0.000 description 13
- 235000019634 flavors Nutrition 0.000 description 13
- 210000004209 hair Anatomy 0.000 description 13
- 244000025254 Cannabis sativa Species 0.000 description 12
- -1 composed of styrene Chemical class 0.000 description 12
- 238000000605 extraction Methods 0.000 description 12
- 239000013049 sediment Substances 0.000 description 12
- 235000019606 astringent taste Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000002835 absorbance Methods 0.000 description 9
- 230000001747 exhibiting effect Effects 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 230000001953 sensory effect Effects 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000006071 cream Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000009508 confectionery Nutrition 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 150000003440 styrenes Chemical class 0.000 description 5
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 4
- 235000004347 Perilla Nutrition 0.000 description 4
- 244000124853 Perilla frutescens Species 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- WQNHWIYLCRZRLR-UHFFFAOYSA-N 2-(3-hydroxy-2,5-dioxooxolan-3-yl)acetic acid Chemical compound OC(=O)CC1(O)CC(=O)OC1=O WQNHWIYLCRZRLR-UHFFFAOYSA-N 0.000 description 3
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(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)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 compound 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 3
- 238000004040 coloring Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000002324 mouth wash Substances 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 239000001509 sodium citrate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000002470 solid-phase micro-extraction Methods 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 235000015961 tonic Nutrition 0.000 description 3
- 230000001256 tonic effect Effects 0.000 description 3
- 229960000716 tonics Drugs 0.000 description 3
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 3
- 229940038773 trisodium citrate Drugs 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- HRXBASQEKDCGPX-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene 2-bromoethenylbenzene Chemical compound BrC=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C HRXBASQEKDCGPX-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 241000207923 Lamiaceae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 2
- 235000013334 alcoholic beverage Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 235000011850 desserts Nutrition 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 235000013325 dietary fiber Nutrition 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 235000015203 fruit juice Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000000118 hair dye Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 235000021067 refined food Nutrition 0.000 description 2
- 235000014102 seafood Nutrition 0.000 description 2
- 235000014214 soft drink Nutrition 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000000606 toothpaste Substances 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- ZJQIXGGEADDPQB-UHFFFAOYSA-N 1,2-bis(ethenyl)-3,4-dimethylbenzene Chemical group CC1=CC=C(C=C)C(C=C)=C1C ZJQIXGGEADDPQB-UHFFFAOYSA-N 0.000 description 1
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- XIRPMPKSZHNMST-UHFFFAOYSA-N 1-ethenyl-2-phenylbenzene Chemical group C=CC1=CC=CC=C1C1=CC=CC=C1 XIRPMPKSZHNMST-UHFFFAOYSA-N 0.000 description 1
- IYSVFZBXZVPIFA-UHFFFAOYSA-N 1-ethenyl-4-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC=C(C=C)C=C1 IYSVFZBXZVPIFA-UHFFFAOYSA-N 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-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
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 description 1
- RNIXGGRLMOEPFG-UHFFFAOYSA-N 3-phenylpenta-1,4-dien-3-ylbenzene Chemical compound C=1C=CC=CC=1C(C=C)(C=C)C1=CC=CC=C1 RNIXGGRLMOEPFG-UHFFFAOYSA-N 0.000 description 1
- AIMDYNJRXHEXEL-UHFFFAOYSA-N 3-phenylprop-1-enylbenzene Chemical compound C=1C=CC=CC=1CC=CC1=CC=CC=C1 AIMDYNJRXHEXEL-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-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
- 241001237961 Amanita rubescens Species 0.000 description 1
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 108010013050 Endo180 Proteins 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 102100025353 G-protein coupled bile acid receptor 1 Human genes 0.000 description 1
- 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 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 101000857733 Homo sapiens G-protein coupled bile acid receptor 1 Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 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
- 240000005856 Lyophyllum decastes Species 0.000 description 1
- 235000013194 Lyophyllum decastes Nutrition 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
- 229920001100 Polydextrose Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 229920002642 Polysorbate 65 Polymers 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 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 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
- 238000004061 bleaching Methods 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000010957 calcium stearoyl-2-lactylate Nutrition 0.000 description 1
- OEUVSBXAMBLPES-UHFFFAOYSA-L calcium stearoyl-2-lactylate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O.CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O OEUVSBXAMBLPES-UHFFFAOYSA-L 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000008294 cold cream Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000012869 ethanol precipitation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000005484 gravity Effects 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
- 239000003676 hair preparation Substances 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 239000008123 high-intensity sweetener Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000000832 lactitol Substances 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007934 lip balm Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019449 other food additives Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001259 polydextrose Substances 0.000 description 1
- 235000013856 polydextrose Nutrition 0.000 description 1
- 229940035035 polydextrose Drugs 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229940099511 polysorbate 65 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000020991 processed meat Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 230000014860 sensory perception of taste Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229940080352 sodium stearoyl lactylate Drugs 0.000 description 1
- ODFAPIRLUPAQCQ-UHFFFAOYSA-M sodium stearoyl lactylate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O ODFAPIRLUPAQCQ-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 230000037373 wrinkle formation Effects 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Preparation Of Fruits And Vegetables (AREA)
- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
- Fodder In General (AREA)
Abstract
Description
本発明は、精製レモンバーム抽出物の製造方法、精製レモンバーム抽出物、及び、レモンバームの飲料添加の際の濁り又は沈殿を低減する方法に関する。 The present invention relates to a method for producing a purified lemon balm extract, a purified lemon balm extract, and a method for reducing cloudiness or sedimentation during the addition of lemon balm to beverages.
シソ科の多年生ハーブであるレモンバーム(Melissa officinalis、和名はコウスイハッカ、セイヨウヤマハッカ)は、フローラルなレモンを思わせる香りを有し、記憶力向上、慢性気管支炎、発熱、頭痛等に効果があると言われている。さらに、レモンバーム抽出物を調製して、新たな生理活性を探索した事例が複数報告されている。特許文献1にはレモンバーム抽出物がTGR5活性化作用をもたらすこと、特許文献2には皮膚のシワ形成を改善するEndo180発現を促進する作用をもたらすことが記載されている。 Lemon balm (Melissa officinalis), a perennial herb belonging to the Lamiaceae family, has a scent reminiscent of floral lemons, and is said to be effective in improving memory, chronic bronchitis, fever, headache, etc. It is said. Furthermore, several cases have been reported in which lemon balm extracts were prepared to search for new physiological activities. Patent Document 1 describes that a lemon balm extract has a TGR5 activating effect, and Patent Document 2 describes that it has an effect of promoting Endo180 expression that improves skin wrinkle formation.
一方、これら特許文献には、レモンバーム抽出物の精製方法については一般的な手法が記載されているにとどまる。例えば、特許文献2には、レモンバーム抽出物が特有の匂いを有しているため、生理活性の低下を招かない範囲で脱色、脱臭等を目的とする精製を行うことも可能であること、精製方法として、例えば活性炭処理、吸着樹脂処理、イオン交換樹脂処理等によって行うことができることは記載されているが、製法についての具体的な実施例は記載されていない。 On the other hand, these patent documents only describe general methods for purifying lemon balm extracts. For example, in Patent Document 2, since lemon balm extract has a peculiar smell, it is possible to perform purification for the purpose of decolorization, deodorization, etc. within a range that does not cause a decrease in physiological activity. As a method, it is described that it can be carried out by, for example, activated carbon treatment, adsorption resin treatment, ion exchange resin treatment, etc., but no specific examples of the production method are described.
レモンバーム抽出物には、生理活性成分として、ロスマリン酸等を含有することが知られている。ロスマリン酸(CAS登録番号20283-92-5)は、シソ科植物に含まれる水に対して難溶なポリフェノール類の一種であり、抗酸化作用、抗炎症作用、アレルギー症状の緩和作用等が知られている。 Lemon balm extract is known to contain rosmarinic acid and the like as physiologically active components. Rosmarinic acid (CAS registration number 20283-92-5) is a kind of water-insoluble polyphenols contained in Labiatae plants, and is known to have antioxidant, anti-inflammatory, and allergy symptom-relieving effects. It is
特許文献3には、ロスマリン酸の精製処理方法として一般的な手法が列記され、脱臭処理方法として、蒸留処理、水蒸気蒸留処理、活性炭処理、吸着樹脂処理、イオン交換樹脂処理、超臨界流体抽出、溶剤洗浄、再結晶化等の方法をとりうることが記載されている。 Patent Document 3 lists general techniques as a purification treatment method for rosmarinic acid, and deodorizing treatment methods include distillation treatment, steam distillation treatment, activated carbon treatment, adsorption resin treatment, ion exchange resin treatment, supercritical fluid extraction, It is described that methods such as solvent washing and recrystallization can be used.
特許文献4には、塩蔵赤シソの葉に含まれるロスマリン酸等のフェノール類を高濃度に含有する赤シソエキスもしくはその粉末の効率的な製造法として、塩蔵赤シソ葉を酸性条件下、かつ加熱条件下に親水性溶媒で抽出し、得られた抽出液を吸着性樹脂を用いるクロマトグラフィーにかけてエキスを得、次いで必要に応じ当該エキスを濃縮、粉末化することを特徴とするフェノール類含有エキスの製造法が記載されている。具体的には、実施例1において、熱水抽出により得られた抽出液を濾過した後に、芳香族系吸着剤に吸着させたこと、非吸着性成分を洗浄により除去した後で目的物を溶出することで、ロスマリン酸を含有する赤シソエキスを得たことが記載されている。 In Patent Document 4, as an efficient method for producing a red perilla extract containing a high concentration of phenols such as rosmarinic acid contained in salted red perilla leaves or a powder thereof, salted red perilla leaves are heated under acidic conditions. A phenol-containing extract characterized by extracting with a hydrophilic solvent under conditions, subjecting the resulting extract to chromatography using an adsorptive resin to obtain an extract, and then concentrating and pulverizing the extract as necessary. A manufacturing method is described. Specifically, in Example 1, after filtering the extract obtained by hot water extraction, it was adsorbed on an aromatic adsorbent, and the target substance was eluted after removing the non-adsorbable components by washing. By doing so, it is described that a red perilla extract containing rosmarinic acid was obtained.
本発明者らは、レモンバーム抽出物を飲料に添加した場合、濁り又は澱(オリ)のような沈殿が添加直後又は経時的に生じ、飲料の外観が悪化することを見出した。さらに、これらの濁りや沈殿の原因は、水難溶性のロスマリン酸とは異なる物質であることが判明した。そして、生理活性に優れたレモンバーム抽出物を得るためにレモンバーム抽出物中のロスマリン酸の濃度を上げようとすると、上記の濁りや沈殿が生じやすい傾向があった。 The present inventors found that when a lemon balm extract is added to a beverage, turbidity or sedimentation such as sedimentation occurs immediately after addition or over time, and the appearance of the beverage deteriorates. Furthermore, it was found that the cause of these turbidity and precipitation is a substance different from the sparingly water-soluble rosmarinic acid. When the concentration of rosmarinic acid in the lemon balm extract is increased in order to obtain a lemon balm extract with excellent bioactivity, the turbidity and precipitation described above tend to occur.
そこで、ロスマリン酸を含有し、飲料に添加した際の濁り又は沈殿が低減されたレモンバーム抽出物を提供することを本発明の課題とする。 Therefore, an object of the present invention is to provide a lemon balm extract containing rosmarinic acid and having reduced turbidity or precipitation when added to a beverage.
本発明者らは、鋭意検討を重ねた結果、レモンバーム抽出物を芳香族系合成吸着剤と接触させて非吸着画分を得る工程を含む製造方法によって、飲料に添加した際の濁り又は沈殿が低減された精製レモンバーム抽出物が得られることを見出し、本発明を完成させた。 As a result of extensive studies, the present inventors found that a production method comprising a step of contacting a lemon balm extract with an aromatic synthetic adsorbent to obtain a non-adsorbed fraction causes turbidity or precipitation when added to a beverage. The present invention was completed by finding that a reduced purified lemon balm extract can be obtained.
即ち、本発明は以下の態様を含む。
[1]
(a)レモンバーム抽出物を芳香族系合成吸着剤と接触させて、非吸着画分を得る工程を含む、精製レモンバーム抽出物の製造方法。
[2]
前記工程(a)のレモンバーム抽出物が低級アルコールを10~90%(v/v)含有する、[1]に記載の精製レモンバーム抽出物の製造方法。
[3]
前記工程(a)の芳香族系合成吸着剤の体積量が、レモンバーム抽出物の体積量に対して0.01~10倍である、[1]又は[2]に記載の精製レモンバーム抽出物の製造方法。
[4]
(b)レモンバーム抽出物を、活性炭と接触させ、非吸着画分を得る工程をさらに含む、[1]~[3]のいずれか1に記載の精製レモンバーム抽出物の製造方法。
[5]
前記精製レモンバーム抽出物をロスマリン酸換算量で225ppm、砂糖8質量%、クエン酸無水物0.12質量%、及びクエン酸三ナトリウム0.08質量%を含有する水溶液の波長700nmにおける濁度(OD700)が、0.05以下である、[1]~[4]のいずれか1に記載の精製レモンバーム抽出物の製造方法。
[6]
ロスマリン酸を0.01~20質量%含有する、精製レモンバーム抽出物であって、
前記精製レモンバーム抽出物をロスマリン酸換算量で225ppm、砂糖8質量%、クエン酸無水物0.12質量%、及びクエン酸三ナトリウム0.08質量%を含有する水溶液の波長700nmにおける濁度(OD700)が、0.05以下である、精製レモンバーム抽出物。
[7]
前記精製レモンバーム抽出物3gに内部標準物質として0.5mg/mLの3-ヘプタノールのエタノール溶液を1μL添加してガスクロマトグラフィー質量分析法(GC/MS)で測定した場合に、下記の(A)~(F)の少なくとも1つを満たす、[6]に記載の精製レモンバーム抽出物:
(A)酢酸エチルのロスマリン酸1質量%当たりピーク面積比が、0.24以下;
(B)イソバレルアルデヒドのロスマリン酸1質量%当たりピーク面積比が、0.35以下;
(C)イソバレルアルデヒドジエチルアセタールのロスマリン酸1質量%当たりピーク面積比が、0.53以下;
(D)α-テルピネオールのロスマリン酸1質量%当たりピーク面積比が、0.26以下;
(E)プレニルエチルエーテルのロスマリン酸1質量%当たりピーク面積比が、0.05以下;
(F)サフラナールのロスマリン酸1質量%当たりピーク面積比が、1.72以下:
ここで、特定の香気成分のロスマリン酸1質量%当たりピーク面積比は、該精製レモンバーム抽出物中のロスマリン酸含有量をc質量%とした場合に、GC/MSピークの面積から下記式により算出される;
ロスマリン酸1質量%当たりピーク面積比=
〔(前記特定の香気成分のピーク面積)/(3-ヘプタノールのピーク面積)〕×1/c。
[8]
前記精製レモンバーム抽出物3gに内部標準物質として0.5mg/mLの3-ヘプタノールのエタノール溶液を1μL添加してガスクロマトグラフィー質量分析法(GC/MS)で測定した場合に、イソ吉草酸のロスマリン酸1質量%当たりピーク面積比が、0.083以下である、[6]又は[7]に記載の精製レモンバーム抽出物;
ここで、特定の香気成分のロスマリン酸1質量%当たりピーク面積比は、該精製レモンバーム抽出物中のロスマリン酸含有量をc質量%とした場合に、GC/MSピークの面積から下記式により算出される;
ロスマリン酸1質量%当たりピーク面積比=
〔(前記特定の香気成分のピーク面積)/(3-ヘプタノールのピーク面積)〕×1/c。
[9]
[1]~[8]のいずれか1に記載の精製レモンバーム抽出物を含有する、製剤。
[10]
[1]~[8]のいずれか1に記載の精製レモンバーム抽出物を含有し、飲食品、医薬品、医薬部外品、化粧品又は飼料である、組成物。
[11]
(a)レモンバーム抽出物を芳香族系合成吸着剤と接触させて、非吸着画分を得る工程を含む、レモンバーム抽出物の飲料添加の際の濁り又は沈殿を低減する方法。
That is, the present invention includes the following aspects.
[1]
(a) A method for producing a purified lemon balm extract, comprising the step of contacting a lemon balm extract with an aromatic synthetic adsorbent to obtain a non-adsorbed fraction.
[2]
The method for producing a purified lemon balm extract according to [1], wherein the lemon balm extract in step (a) contains 10 to 90% (v/v) of lower alcohol.
[3]
The purified lemon balm extract according to [1] or [2], wherein the volume of the aromatic synthetic adsorbent in step (a) is 0.01 to 10 times the volume of the lemon balm extract. Production method.
[4]
(b) The method for producing the purified lemon balm extract according to any one of [1] to [3], further comprising the step of contacting the lemon balm extract with activated carbon to obtain a non-adsorbed fraction.
[5]
The turbidity at a wavelength of 700 nm (OD700 ) is 0.05 or less, the method for producing a purified lemon balm extract according to any one of [1] to [4].
[6]
A purified lemon balm extract containing 0.01 to 20% by mass of rosmarinic acid,
The turbidity at a wavelength of 700 nm (OD700 ) is 0.05 or less.
[7]
When 1 μL of an ethanol solution of 0.5 mg/mL 3-heptanol was added as an internal standard substance to 3 g of the purified lemon balm extract and measured by gas chromatography mass spectrometry (GC/MS), the following (A) The purified lemon balm extract according to [6], which satisfies at least one of (F):
(A) the peak area ratio of ethyl acetate per 1% by mass of rosmarinic acid is 0.24 or less;
(B) the peak area ratio of isovaleraldehyde per 1% by mass of rosmarinic acid is 0.35 or less;
(C) the peak area ratio of isovaleraldehyde diethyl acetal per 1% by mass of rosmarinic acid is 0.53 or less;
(D) the peak area ratio of α-terpineol per 1% by mass of rosmarinic acid is 0.26 or less;
(E) the peak area ratio of prenyl ethyl ether per 1% by mass of rosmarinic acid is 0.05 or less;
(F) The peak area ratio of safranal per 1% by mass of rosmarinic acid is 1.72 or less:
Here, the peak area ratio per 1% by mass of rosmarinic acid of a specific aromatic component is calculated from the area of the GC/MS peak by the following formula, where c% by mass is the rosmarinic acid content in the purified lemon balm extract. to be;
Peak area ratio per 1% by mass of rosmarinic acid =
[(Peak area of the specific aroma component)/(Peak area of 3-heptanol)]×1/c.
[8]
When 1 μL of an ethanol solution of 0.5 mg/mL 3-heptanol was added as an internal standard substance to 3 g of the purified lemon balm extract and measured by gas chromatography mass spectrometry (GC/MS), rosmarin of isovaleric acid The purified lemon balm extract according to [6] or [7], which has a peak area ratio of 0.083 or less per 1% by mass of acid;
Here, the peak area ratio per 1% by mass of rosmarinic acid of a specific aromatic component is calculated from the area of the GC/MS peak by the following formula, where c% by mass is the rosmarinic acid content in the purified lemon balm extract. to be;
Peak area ratio per 1% by mass of rosmarinic acid =
[(Peak area of the specific aroma component)/(Peak area of 3-heptanol)]×1/c.
[9]
A formulation containing the purified lemon balm extract according to any one of [1] to [8].
[10]
A composition, which contains the purified lemon balm extract according to any one of [1] to [8], and is a food or beverage, a pharmaceutical, a quasi-drug, a cosmetic or a feed.
[11]
(a) A method of reducing turbidity or sedimentation upon addition of lemon balm extract to beverages comprising the step of contacting lemon balm extract with a synthetic aromatic adsorbent to obtain a non-adsorbed fraction.
本発明の製造方法によれば、ロスマリン酸を含有し、飲料に添加した際の濁り又は沈殿が低減されたレモンバーム抽出物を提供することができる。 According to the production method of the present invention, it is possible to provide a lemon balm extract containing rosmarinic acid and having reduced turbidity or precipitation when added to a beverage.
本明細書において、体積%又は%(v/v)はmL/100mLと、%(w/v)は、g/100mLと同義である。また、ppmは質量当たりの百万分率である。 As used herein, volume % or % (v/v) is synonymous with mL/100 mL, and % (w/v) is synonymous with g/100 mL. Also, ppm is parts per million per mass.
[精製レモンバーム抽出物の製造方法]
本発明の精製レモンバーム抽出物の製造方法は、
(a)レモンバーム抽出物を芳香族系合成吸着剤と接触させて、非吸着画分を得る工程(以下、工程(a)と呼ぶ場合がある)、を含む。
[Method for producing purified lemon balm extract]
The method for producing the purified lemon balm extract of the present invention comprises
(a) a step of contacting a lemon balm extract with an aromatic synthetic adsorbent to obtain a non-adsorbed fraction (hereinafter sometimes referred to as step (a)).
(工程(a):芳香族系合成吸着剤処理工程)
前記芳香族系合成吸着剤と接触させるレモンバーム抽出物は、レモンバーム抽出原液に由来し、ロスマリン酸を少なくとも含有する、液体である。レモンバーム抽出物としては、例えば、レモンバーム抽出原液、レモンバーム抽出原液の加工物、又はそれらの混合物が挙げられる。
(Step (a): Aromatic Synthetic Adsorbent Treatment Step)
The lemon balm extract to be brought into contact with the synthetic aromatic adsorbent is a liquid derived from a lemon balm extract undiluted solution and containing at least rosmarinic acid. The lemon balm extract includes, for example, a lemon balm extract undiluted solution, a processed lemon balm extract undiluted solution, or a mixture thereof.
本明細書において、「レモンバーム抽出原液」はレモンバームの植物体から溶媒抽出操作を行って得られ、その後に精製、濾過等による不溶物除去、溶媒添加、濃縮及び乾燥等の操作を経ていないものを表す。
本明細書において、レモンバーム抽出原液の「加工物」は、レモンバーム抽出原液に対して精製、濾過等による不溶物除去、溶媒添加、濃縮及び乾燥等のうちの少なくとも1種の操作を経たものを表す。
In the present specification, the "lemon balm extract undiluted solution" is obtained by subjecting the lemon balm plant to solvent extraction, followed by purification, removal of insoluble matter by filtration, addition of a solvent, concentration, drying, and other operations. represent.
In the present specification, the “processed product” of lemon balm extract undiluted solution refers to a lemon balm extract undiluted solution that has undergone at least one operation of purification, removal of insoluble matter by filtration or the like, addition of a solvent, concentration, drying, and the like. .
前記レモンバーム抽出原液の調製に用いられるレモンバームの植物体は、例えば、全草、葉部、茎部、根部、樹皮、果実、種子及び花部からなる群より選択される少なくとも1種を含み、好ましくは少なくとも葉部を含む。レモンバームの植物体は、そのまま(生)若しくは破砕物として抽出操作に付してもよく、また乾燥後、必要に応じて粉砕若しくは粉体状として抽出操作に付してもよい。 The lemon balm plant body used for the preparation of the lemon balm extract stock solution includes, for example, at least one selected from the group consisting of whole grass, leaves, stems, roots, bark, fruits, seeds and flowers, and preferably contains at least the leaf part. The lemon balm plant body may be subjected to the extraction operation as it is (raw) or as a crushed product, and after drying, it may be subjected to the extraction operation after being pulverized or powdered as necessary.
前記レモンバーム抽出原液の調製に用いられる抽出溶媒は、例えば、水;メタノール、エタノール、プロパノール、ブタノール等の炭素数1~4である、低級アルコール;酢酸エチル等の低級アルキルエステル;エチレングリコール、ブチレングリコール、プロピレングリコール、グリセリン等のグリコール類;その他エチルエーテル、アセトン、酢酸等の極性溶媒、又は、これらの溶媒から選択される2種以上の混合物であり得る。中でも抽出溶媒は、水、低級アルコール又はそれらの混合物が好ましく、レモンバーム特有の不快な風味と着色を抑制する観点から、水と低級アルコールの混合物がより好ましく、水とエタノールの混合物が更に好ましい。 Extraction solvents used in the preparation of the lemon balm extract stock solution include, for example, water; lower alcohols having 1 to 4 carbon atoms such as methanol, ethanol, propanol and butanol; lower alkyl esters such as ethyl acetate; ethylene glycol and butylene glycol. , propylene glycol, glycerin, and other polar solvents such as ethyl ether, acetone, and acetic acid, or a mixture of two or more selected from these solvents. Among them, the extraction solvent is preferably water, a lower alcohol, or a mixture thereof, more preferably a mixture of water and a lower alcohol, and a mixture of water and ethanol from the viewpoint of suppressing the unpleasant flavor and coloration peculiar to lemon balm.
前記抽出溶媒として、水と低級アルコールの混合物を用いる場合、低級アルコールの含有量は、抽出溶媒全量に対して、例えば、10%(v/v)以上であり、ロスマリン酸の収率を高める観点から、好ましくは30%(v/v)以上、より好ましくは40%(v/v)以上、更に好ましくは50%(v/v)以上であり、そして、低級アルコールの使用量を抑える観点から、例えば90%(v/v)以下であり、好ましくは80%(v/v)以下、より好ましくは70%(v/v)以下、更に好ましくは60%(v/v)以下であり得る。 When a mixture of water and a lower alcohol is used as the extraction solvent, the content of the lower alcohol is, for example, 10% (v / v) or more with respect to the total amount of the extraction solvent, from the viewpoint of increasing the yield of rosmarinic acid. Therefore, it is preferably 30% (v / v) or more, more preferably 40% (v / v) or more, still more preferably 50% (v / v) or more, and from the viewpoint of suppressing the amount of lower alcohol used , for example 90% (v/v) or less, preferably 80% (v/v) or less, more preferably 70% (v/v) or less, even more preferably 60% (v/v) or less .
抽出方法としては、一般に用いられる方法が採用でき、例えばエキス剤、エリキシル剤、浸剤、煎剤、流エキス剤、チンキ剤等の各種生薬製剤の調製に用いられる抽出方法を広く挙げることができる。特に限定されないが、例えば、前記抽出溶媒中に上記の植物(そのまま(生)若しくは粗末、細切物)、又はそれらの乾燥破砕物(粉末等)を冷浸(通常1~25℃)や温浸(通常35~45℃)等によって浸漬する方法、加温し撹拌しながら抽出を行い、ろ過して抽出液を得る方法、又はパーコレーション法(通常1~30℃程度)等を挙げることができる。 As the extraction method, commonly used methods can be employed, and examples include a wide range of extraction methods used for preparing various crude drug preparations such as extracts, elixirs, infusions, decoctions, liquid extracts and tinctures. Although not particularly limited, for example, the above plants (as is (raw), coarse powder, chopped), or their dried crushed products (powder, etc.) are cold soaked (usually 1 to 25 ° C.) or warm in the extraction solvent. A method of immersion by immersion (usually 35 to 45° C.) or the like, a method of performing extraction while heating and stirring and filtering to obtain an extract, or a percolation method (usually about 1 to 30° C.) can be mentioned. .
前記抽出溶媒として水と低級アルコールの混合物を用いる場合、抽出温度は、ロスマリン酸の収率を高める観点から、5~100℃、好ましくは25~80℃、より好ましくは60~80℃である。 When a mixture of water and a lower alcohol is used as the extraction solvent, the extraction temperature is 5 to 100°C, preferably 25 to 80°C, more preferably 60 to 80°C, from the viewpoint of increasing the yield of rosmarinic acid.
前記レモンバーム抽出原液は、前記芳香族系合成吸着剤と接触させる前に、後述の別の処理剤による精製、濾過等による不溶物除去、溶媒添加、濃縮及び乾燥からなる群より選ばれる少なくとも1つの工程を経てもよいが、植物体残渣を除く観点から、少なくとも不溶物除去工程を含むことが好ましい。 Before contacting the lemon balm extract stock solution with the aromatic synthetic adsorbent, at least one selected from the group consisting of purification with another treatment agent described later, removal of insoluble matter by filtration or the like, addition of a solvent, concentration and drying Although a process may be performed, it is preferable to include at least an insoluble matter removal process from the viewpoint of removing plant residue.
工程(a)に供されるレモンバーム抽出物のロスマリン酸の含有量は、特に限定されず、抽出物の全量に対して、例えば、0.01~20質量%、0.1~10質量%又は0.5~5質量%であり得る。 The content of rosmarinic acid in the lemon balm extract to be subjected to step (a) is not particularly limited, and is, for example, 0.01 to 20% by mass, 0.1 to 10% by mass, or It can be from 0.5 to 5% by weight.
工程(a)に供されるレモンバーム抽出物は、本発明の効果を顕著に奏する観点から、低級アルコールを含有することが好ましく、エタノールを含有することがより好ましい。低級アルコールの含有量は、レモンバーム抽出物全量に対して、例えば、10%(v/v)以上であり、抽出液量の増加を抑制する観点から、好ましくは30%(v/v)以上、より好ましくは40%(v/v)以上、更に好ましくは50%(v/v)以上であり、そして、本発明の効果を顕著に奏する観点から、例えば90%(v/v)以下であり、好ましくは80%(v/v)以下、より好ましくは70%(v/v)以下、更に好ましくは60%(v/v)以下であり得る。 The lemon balm extract to be subjected to step (a) preferably contains a lower alcohol, more preferably ethanol, from the viewpoint of significantly exhibiting the effects of the present invention. The content of lower alcohol is, for example, 10% (v/v) or more relative to the total amount of lemon balm extract, and from the viewpoint of suppressing an increase in the amount of extract, preferably 30% (v/v) or more, More preferably 40% (v/v) or more, still more preferably 50% (v/v) or more, and from the viewpoint of significantly exhibiting the effects of the present invention, for example, 90% (v/v) or less , preferably 80% (v/v) or less, more preferably 70% (v/v) or less, even more preferably 60% (v/v) or less.
前記芳香族系合成吸着剤の樹脂母体は、芳香族環を含み、イオン交換基を有しない合成樹脂が挙げられ、好ましくは、モノビニル芳香族モノマーと架橋性芳香族モノマーの共重合体であり、より好ましくは、モノビニル芳香族モノマーと架橋性芳香族モノマーの共重合で得られる架橋構造骨格を有する多孔質架橋重合体粒子が挙げられる。 The resin matrix of the aromatic synthetic adsorbent includes a synthetic resin containing an aromatic ring and having no ion exchange group, preferably a copolymer of a monovinyl aromatic monomer and a crosslinkable aromatic monomer, More preferred are porous crosslinked polymer particles having a crosslinked structural skeleton obtained by copolymerization of a monovinyl aromatic monomer and a crosslinkable aromatic monomer.
前記モノビニル芳香族モノマーとしては、(i)ブロモスチレン等のハロゲン置換スチレン類、メチルスチレン、エチルスチレン等のアルキル置換スチレン類、等のスチレンを主体とする化学修飾型スチレン類;(ii)スチレン;(iii)モノビニルビフェニル、ベンジルスチレン、モノビニルナフタレン、モノビニルアントラセン等の多環芳香族モノビニルモノマー類が挙げられる。中でも、前記モノビニル芳香族モノマーは、本発明の効果を顕著に奏する観点から、(i)の化学修飾型スチレン類が好ましく、ハロゲン置換スチレン類がより好ましく、ブロモスチレンが更に好ましい。
前記架橋性芳香族モノマーとしては、ジビニルベンゼン、トリビニルベンゼン、ジビニルトルエン、ジビニルナフタレン、ジビニルキシレン、ジビニルビフェニル、ジビニルジフェニルメタン等が挙げられ、本発明の効果を顕著に奏する観点から、ジビニルベンゼンが好ましい。
Examples of the monovinyl aromatic monomer include (i) chemically modified styrenes mainly composed of styrene, such as halogen-substituted styrenes such as bromostyrene, alkyl-substituted styrenes such as methylstyrene and ethylstyrene; (ii) styrene; (iii) polycyclic aromatic monovinyl monomers such as monovinylbiphenyl, benzylstyrene, monovinylnaphthalene and monovinylanthracene; Among them, the monovinyl aromatic monomer is preferably the chemically modified styrenes of (i), more preferably halogen-substituted styrenes, and still more preferably bromostyrene, from the viewpoint of significantly exhibiting the effects of the present invention.
Examples of the crosslinkable aromatic monomer include divinylbenzene, trivinylbenzene, divinyltoluene, divinylnaphthalene, divinylxylene, divinylbiphenyl, and divinyldiphenylmethane. Divinylbenzene is preferred from the viewpoint of exhibiting the effects of the present invention remarkably. .
前記芳香族系合成吸着剤の樹脂母体は、本発明の効果を顕著に奏する観点から、好ましくは化学修飾型スチレン類-ジビニルベンゼン架橋共重合体であり、好ましくはハロゲン置換スチレン類-ジビニルベンゼン架橋共重合体であり、より好ましくはブロモスチレン-ジビニルベンゼン架橋共重合体であり、更により好ましくは下記の化学式(I)を構造単位とするブロモスチレン-ジビニルベンゼン架橋共重合体である。 The resin matrix of the aromatic synthetic adsorbent is preferably a chemically modified styrenes-divinylbenzene crosslinked copolymer, preferably a halogen-substituted styrenes-divinylbenzene crosslinked copolymer, from the viewpoint of remarkably exhibiting the effects of the present invention. It is a copolymer, more preferably a bromostyrene-divinylbenzene crosslinked copolymer, still more preferably a bromostyrene-divinylbenzene crosslinked copolymer having the following chemical formula (I) as a structural unit.
前記芳香族系合成吸着剤の比表面積(specific surface area)は、好ましくは300m2/g以上、より好ましくは500m2/g以上である。 The specific surface area of the synthetic aromatic adsorbent is preferably 300 m 2 /g or more, more preferably 500 m 2 /g or more.
前記芳香族系合成吸着剤の細孔半径(pore radius)は、好ましくは約10~500Å、より好ましくは約20~200Åである。 The pore radius of the synthetic aromatic adsorbent is preferably about 10-500 Å, more preferably about 20-200 Å.
前記芳香族系合成吸着剤の具体例としては、例えば、セパビーズSP樹脂(セパビーズTM SP207、SP207SS、SP825L、SP850、SP70、SP700等)、MCI GEL樹脂(MCI GELTM CHP20/P20、CHP20/P30、CHP20/P50、CHP20/P70、CHP20/P120、CHP50/P20、CHP50/P30、CSP50/P10、CHP07/P120、CHP85/P120、CHP87/P120、CSP800、SFP08/P25等)、ダイヤイオンHP樹脂(DIAIONTM HP20、HP20SS、HP21等)、(以上、三菱ケミカル(株)製);アンバーライトXAD樹脂(アンバーライトTM XADTM2000、XAD4、XAD1180N、XAD-2等)、アンバーライトFPX樹脂(アンバーライトTM FPX66、FPX68等)(以上、オルガノ(株)製);ピュロライトPAD樹脂(PAD350、PAD400、PAD500、PAD550、PAD600、PAD700、PAD900、PAD910、PAD1200等)、マクロネット樹脂(MacronetTM MN(MN200、MN202、MN250、MN270等)(以上、ピュロライト(株)製))等を例示することができる。本発明に用いられる前記芳香族系合成吸着剤としては、中でもセパビーズSP207、セパビーズSP207SS、セパビーズSP825L、セパビーズSP850、セパビーズSP70、セパビーズSP700又はアンバーライトXAD1180Nが好ましく、セパビーズSP207又はセパビーズSP207SSがより好ましく、セパビーズSP207が更に好ましい。 Specific examples of the aromatic synthetic adsorbent include Sepabeads SP resin (Sepabeads TM SP207, SP207SS, SP825L, SP850, SP70, SP700, etc.), MCI GEL resin (MCI GEL TM CHP20/P20, CHP20/P30, CHP20/P50, CHP20/P70, CHP20/P120, CHP50/P20, CHP50/P30, CSP50/P10, CHP07/P120, CHP85/P120, CHP87/P120, CSP800, SFP08/P25, etc.), Diaion HP resin (DIAION TM HP20, HP20SS, HP21, etc.), (manufactured by Mitsubishi Chemical Corporation); Amberlite XAD resin (Amberlite TM XAD TM 2000, XAD4, XAD1180N, XAD-2, etc.), Amberlite FPX resin (Amberlite TM FPX66, FPX68 , etc.) (manufactured by Organo Co., Ltd.); , MN250, MN270, etc.) (manufactured by Purolite Co., Ltd.). The aromatic synthetic adsorbent used in the present invention is preferably Sepabeads SP207, Sepabeads SP207SS, Sepabeads SP825L, Sepabeads SP850, Sepabeads SP70, Sepabeads SP700 or Amberlite XAD1180N, more preferably Sepabeads SP207 or Sepabeads SP207SS, and Sepabeads SP207SS. SP207 is more preferred.
工程(a)において、前記芳香族系合成吸着剤の量は、特に限定されず、合成吸着剤のモノマー組成や形態、精製条件等によって適宜調整し得る。前記芳香族系合成吸着剤の体積量は、レモンバーム抽出物の体積量に対して、例えば0.001~10倍であり、本発明の効果をより顕著に奏する観点から、好ましくは0.01~10倍であり、より好ましくは0.01~1倍である。 In the step (a), the amount of the aromatic synthetic adsorbent is not particularly limited, and can be appropriately adjusted depending on the monomer composition and form of the synthetic adsorbent, purification conditions, and the like. The volume of the aromatic synthetic adsorbent is, for example, 0.001 to 10 times the volume of the lemon balm extract, and from the viewpoint of achieving a more pronounced effect of the present invention, preferably 0.01 to 10 times, more preferably 0.01 to 1 times.
工程(a)において前記芳香族系合成吸着剤とレモンバーム抽出物を接触させる態様については特に限定されず、例えば、カラム法、バッチ法等が挙げられるが、カラム法がより好ましい。カラム法の場合、レモンバーム抽出物は、前記芳香族系合成吸着剤を充填したカラムに通液し、その通過液と、場合によって押し出し液を回収する。抽出物を通液する際、SV(space velocity)を適度に調節することが好ましい。SVは、特に限定されないが、通常SV0.5~10程度、好ましくはSV1~6程度の条件を例示することができる。次いで、同様のSV条件でカラムの吸着剤から非吸着画分を押し出す。押し出しに用いる液は、水、又はレモンバーム抽出物と同じかそれ以下の含有量の低級アルコール(好ましくはエタノール)を含有する含水アルコールを使用することができる。なお、工程(a)は、例えば、5~80℃、25~80℃などの温度で実施することができる。 The manner in which the synthetic aromatic adsorbent and the lemon balm extract are brought into contact in step (a) is not particularly limited, and examples thereof include a column method and a batch method, with the column method being more preferable. In the case of the column method, the lemon balm extract is passed through a column filled with the aromatic synthetic adsorbent, and the passing liquid and optionally the extruded liquid are recovered. It is preferable to moderately adjust the SV (space velocity) when passing the extract. Although the SV is not particularly limited, conditions of about SV 0.5 to 10, preferably about SV 1 to 6 can be exemplified. The non-adsorbed fraction is then pushed out of the column adsorbent under similar SV conditions. The liquid used for extrusion can be water or a hydrous alcohol containing a lower alcohol (preferably ethanol) in a content equal to or less than that of the lemon balm extract. Incidentally, the step (a) can be carried out at a temperature of, for example, 5 to 80°C, 25 to 80°C.
工程(a)によって、飲料に添加した際の濁り、沈殿が低減された精製レモンバーム抽出物を得ることができる。加えて、得られた精製レモンバーム抽出物は、後述のレモンバーム抽出物特有の不快な風味(青臭さ、枯草臭、渋み、油臭等)、着色、及び特定の香気成分の含有量も低減される。 Through step (a), a purified lemon balm extract with reduced turbidity and sedimentation when added to a beverage can be obtained. In addition, the resulting purified lemon balm extract has reduced unpleasant flavors (grass odor, dry grass odor, astringent taste, oily odor, etc.), coloration, and the content of specific aromatic components peculiar to the lemon balm extract described later. .
(工程(b):活性炭処理工程)
本発明の製造方法には、さらに(b)レモンバーム抽出物を、活性炭と接触させ、非吸着画分を得る工程(以下、工程(b)と呼ぶ場合がある)を含むことが好ましい。工程(a)に加えて活性炭を使用した工程(b)を行うことにより、レモンバームの不快な風味及び着色が大きく低減する。さらに、飲料の風味を損ない得る香気成分(例えば、酢酸エチル、イソバレルアルデヒド、イソバレルアルデヒドジエチルアセタール、α-テルピネオール、プレニルエチルエーテル、サフラナール等)や、レモンバーム抽出物特有の油臭の原因であるイソ吉草酸も、工程(a)単独又は工程(b)単独を経た場合に比べて大幅に減少し、風味が改善する。
(Step (b): activated carbon treatment step)
The production method of the present invention preferably further includes (b) a step of contacting the lemon balm extract with activated carbon to obtain a non-adsorbed fraction (hereinafter sometimes referred to as step (b)). By performing step (b) using activated charcoal in addition to step (a), the unpleasant flavor and coloration of lemon balm are greatly reduced. Furthermore, it is the cause of aroma components that can impair the flavor of beverages (e.g., ethyl acetate, isovaleraldehyde, isovaleraldehyde diethyl acetal, α-terpineol, prenylethyl ether, safranal, etc.) and the oily odor peculiar to lemon balm extracts. Isovaleric acid is also significantly reduced as compared with the case where step (a) alone or step (b) alone is performed, and the flavor is improved.
工程(b)に供されるレモンバーム抽出物のロスマリン酸の含有量は、特に限定されず、抽出物の全量に対して、例えば、0.01~20質量%とすることができ、本発明の効果をより顕著に奏する観点から、好ましくは0.1~20質量%であり、さらにレモンバーム抽出物の着色を低減する観点から、0.5~20質量%(例えば0.5~5質量%)であり得る。 The content of rosmarinic acid in the lemon balm extract to be subjected to step (b) is not particularly limited, and can be, for example, 0.01 to 20% by mass with respect to the total amount of the extract. It is preferably 0.1 to 20% by mass from the viewpoint of achieving a more pronounced effect, and 0.5 to 20% by mass (for example, 0.5 to 5% by mass) from the viewpoint of reducing coloring of the lemon balm extract. can be
工程(b)に供されるレモンバーム抽出物は、本発明の効果を顕著に奏する観点から、低級アルコールを含有することが好ましく、エタノールを含有することがより好ましい。低級アルコールの含有量は、レモンバーム抽出物全量に対して、例えば、10%(v/v)以上であり、抽出液量の増加を抑制する観点から、好ましくは30%(v/v)以上、より好ましくは40%(v/v)以上、更に好ましくは50%(v/v)以上であり、そして、本発明の効果を顕著に奏する観点から、例えば90%(v/v)以下であり、好ましくは80%(v/v)以下、より好ましくは70%(v/v)以下、更に好ましくは60%(v/v)以下であり得る。 The lemon balm extract to be subjected to step (b) preferably contains a lower alcohol, more preferably ethanol, from the viewpoint of significantly exhibiting the effects of the present invention. The content of lower alcohol is, for example, 10% (v/v) or more relative to the total amount of lemon balm extract, and from the viewpoint of suppressing an increase in the amount of extract, preferably 30% (v/v) or more, More preferably 40% (v/v) or more, still more preferably 50% (v/v) or more, and from the viewpoint of significantly exhibiting the effects of the present invention, for example, 90% (v/v) or less , preferably 80% (v/v) or less, more preferably 70% (v/v) or less, even more preferably 60% (v/v) or less.
前記活性炭の由来は、特に限定されず、例えば、石炭、ヤシ殻、おがくず等が挙げられる。また、活性炭の形状も特に限定されず、粒状、粉末状、繊維状等のものを使用することができる。前記活性炭の好適な例としては、おがくず又はヤシ殻由来の活性炭が挙げられ、より好ましくはタケコール50WG-T又は白鷺DO-2(いずれも大阪ガスケミカル(株)製)が挙げられる。 The origin of the activated carbon is not particularly limited, and examples thereof include coal, coconut shells, and sawdust. Also, the shape of the activated carbon is not particularly limited, and granular, powdery, fibrous, or the like can be used. Preferable examples of the activated carbon include sawdust- or coconut-shell-derived activated carbon, more preferably TAKECOL 50WG-T or Shirasagi DO-2 (both manufactured by Osaka Gas Chemicals Co., Ltd.).
工程(b)においてレモンバーム抽出物を活性炭と接触させる態様については特に限定されず、例えば、カラム法、バッチ法等が挙げられる。非吸着画分を得る方法は、例えば、上記の工程(a)に記載したカラム法による精製方法と同じ方法を用いることができる。 The manner in which the lemon balm extract is brought into contact with activated carbon in step (b) is not particularly limited, and examples thereof include a column method and a batch method. As a method for obtaining the non-adsorbed fraction, for example, the same method as the purification method by the column method described in step (a) above can be used.
活性炭の量は、特に限定されず、活性炭の由来や形態、精製条件によって適宜調整し得るが、上記の効果を奏する観点から、レモンバーム抽出物100質量部に対して、好ましくは0.1質量部以上、より好ましくは0.5質量部以上、更に好ましくは1質量部以上、更により好ましくは2質量部以上であり、そして例えば10質量部以下である。 The amount of activated carbon is not particularly limited, and can be appropriately adjusted depending on the origin and form of the activated carbon and the purification conditions. Above, more preferably 0.5 parts by mass or more, still more preferably 1 part by mass or more, still more preferably 2 parts by mass or more, and for example 10 parts by mass or less.
工程(a)と工程(b)の順序は特に限定されず、工程(a)を経てから工程(b)を経てもよいし、工程(b)を経てから工程(a)を経てもよい。 The order of steps (a) and (b) is not particularly limited, and step (a) may be followed by step (b), or step (b) may be followed by step (a).
(その他工程)
本発明の製造工程は、上記工程(a)、工程(b)の他、上記のレモンバーム抽出原液の調製、別の処理剤による精製、濾過等による不溶物除去、溶媒添加、濃縮、乾燥及び殺菌等の工程から選ばれる1種以上を含み得る。
(Other processes)
In addition to the above steps (a) and (b), the production process of the present invention includes preparation of the above lemon balm extract undiluted solution, purification with another treatment agent, removal of insoluble matter by filtration, addition of a solvent, concentration, drying and sterilization. It may include one or more selected from steps such as
前記別の処理剤による精製工程は、例えば、別の処理剤と接触させ、吸着画分又は非吸着画分を得ることを含む。前記別の処理剤との接触は、例えばバッチ法又はカラムクロマトグラフィーが挙げられる。前記別の処理剤としては、特に限定されないが、シリカゲル、ゼオライト、ポリビニルピロリドン、活性白土、珪藻土、酸性白土、イオン交換樹脂、前記芳香族系合成吸着剤以外の合成吸着剤等が挙げられる。これら処理剤としては、商業的に入手可能なものを用いることができる。 The purification step with another treating agent includes, for example, contacting with another treating agent to obtain an adsorbed fraction or a non-adsorbed fraction. Contacting with another treating agent includes, for example, a batch method or column chromatography. Examples of the other treatment agent include, but are not limited to, silica gel, zeolite, polyvinylpyrrolidone, activated clay, diatomaceous earth, acid clay, ion exchange resins, and synthetic adsorbents other than the aromatic synthetic adsorbents. As these processing agents, commercially available ones can be used.
前記不溶物除去工程は、例えば、多孔質媒体(濾材)を用いた濾過、遠心分離等が挙げられる。 Examples of the insoluble matter removing step include filtration using a porous medium (filter medium), centrifugation, and the like.
前記濃縮工程又は乾燥工程では、例えば、エバポレーター等を用いた減圧濃縮法、限外濾過法、逆浸透膜法、アルコール沈殿法(エタノール沈殿法等)、噴霧乾燥法、凍結乾燥法等を用いることができる。 In the concentration step or drying step, for example, a vacuum concentration method using an evaporator or the like, an ultrafiltration method, a reverse osmosis membrane method, an alcohol precipitation method (ethanol precipitation method, etc.), a spray drying method, a freeze drying method, or the like can be used. can be done.
[精製レモンバーム抽出物]
本発明の製造方法によって得られる精製レモンバーム抽出物は、飲料に添加した際の濁り及び沈殿が低減されている。例えば、前記精製レモンバーム抽出物をロスマリン酸換算量で225ppm、砂糖8質量%、クエン酸無水物0.12質量%、及びクエン酸三ナトリウム0.08質量%を含有する水溶液の波長700nmにおける濁度(OD700)は、好ましくは0.05以下であり、より好ましくは0.02以下、更に好ましくは0.01以下である。飲料の前記濁度が0.05以下の場合は、飲料の透明感が顕著に感じられるため、好ましい。
[Purified lemon balm extract]
The purified lemon balm extract obtained by the production method of the present invention has reduced turbidity and sedimentation when added to beverages. For example, the turbidity at a wavelength of 700 nm of an aqueous solution containing 225 ppm of the purified lemon balm extract in terms of rosmarinic acid, 8% by weight of sugar, 0.12% by weight of citric acid anhydride, and 0.08% by weight of trisodium citrate (OD700) is preferably 0.05 or less, more preferably 0.02 or less, and still more preferably 0.01 or less. When the turbidity of the beverage is 0.05 or less, it is preferable because the transparency of the beverage can be felt remarkably.
本発明の製造方法によって得られる精製レモンバーム抽出物は、レモンバーム特有の不快な風味が低減され、改善した風味を有する。ここで、レモンバーム特有の不快な風味は、レモンバーム抽出原液を摂取した際に味覚及び/又は嗅覚により知覚されるものであり、具体的には、例えば、「青臭さ」、「枯草臭」、「渋み」、「油臭」等で表される感覚である。 The purified lemon balm extract obtained by the production method of the present invention has an improved flavor with reduced unpleasant flavor peculiar to lemon balm. Here, the unpleasant flavor peculiar to lemon balm is perceived by the sense of taste and/or smell when the undiluted lemon balm extract is ingested. It is a feeling represented by "astringency", "oily smell", and the like.
さらに、本発明の製造方法によって得られる精製レモンバーム抽出物は、例えば、着色が低減されている。前記精製レモンバーム抽出物をロスマリン酸換算量で225ppm、砂糖8質量%、クエン酸無水物0.12質量%、及びクエン酸三ナトリウム0.08質量%を含有する水溶液の波長400nmにおける吸光度は、好ましくは1以下、より好ましくは0.6以下であり、更により好ましくは0.2以下とすることができる。 Furthermore, the purified lemon balm extract obtained by the production method of the present invention has, for example, reduced coloring. The absorbance at a wavelength of 400 nm of an aqueous solution containing 225 ppm in terms of rosmarinic acid of the purified lemon balm extract, 8% by mass of sugar, 0.12% by mass of citric anhydride, and 0.08% by mass of trisodium citrate is preferably is 1 or less, more preferably 0.6 or less, and even more preferably 0.2 or less.
さらに、本発明の製造方法によって得られる精製レモンバーム抽出物は、不快な風味の原因となり得る特定の香気成分が低減されている。特定の香気成分としては、例えば、酢酸エチル、イソバレルアルデヒド(CAS登録番号590-86-3)、イソバレルアルデヒドジエチルアセタール(1,1-ジエトキシ-3-メチルブタン;CAS登録番号3842-03-3)、α-テルピネオール(CAS登録番号98-55-5)、プレニルエチルエーテル(1-エトキシ-3-メチル-2-ブテン;CAS登録番号22094-00-4)又はサフラナール(CAS登録番号:116-26-7)が挙げられる。 Furthermore, the purified lemon balm extract obtained by the production method of the present invention has reduced specific aroma components that may cause an unpleasant flavor. Specific aroma components include, for example, ethyl acetate, isovaleraldehyde (CAS registration number 590-86-3), isovaleraldehyde diethyl acetal (1,1-diethoxy-3-methylbutane; CAS registration number 3842-03-3 ), α-terpineol (CAS Registry Number 98-55-5), prenyl ethyl ether (1-ethoxy-3-methyl-2-butene; CAS Registry Number 22094-00-4) or safranal (CAS Registry Number: 116- 26-7).
前記精製レモンバーム抽出物は、該精製レモンバーム抽出物3gに内部標準物質として0.5mg/mLの3-ヘプタノールのエタノール溶液を1μL添加してガスクロマトグラフィー質量分析法(GC/MS)で測定した場合に、好ましくは下記の(A)~(F)の少なくとも1つを満たし、より好ましくは(A)~(F)の全てを満たす:
(A)酢酸エチルのロスマリン酸1質量%当たりピーク面積比が、0.24以下、好ましくは0.07以下;
(B)イソバレルアルデヒドのロスマリン酸1質量%当たりピーク面積比が、0.35以下、好ましくは0.19以下;
(C)イソバレルアルデヒドジエチルアセタールのロスマリン酸1質量%当たりピーク面積比が、0.53以下、好ましくは0.16以下;
(D)α-テルピネオールのロスマリン酸1質量%当たりピーク面積比が、0.26以下、好ましくは0.04以下;
(E)プレニルエチルエーテルのロスマリン酸1質量%当たりピーク面積比が、0.05以下、好ましくは0.01以下;
(F)サフラナールのロスマリン酸1質量%当たりピーク面積比が、1.72以下、好ましくは0.39以下:
ここで、特定の香気成分のロスマリン酸1質量%当たりピーク面積比は、該精製レモンバーム抽出物中のロスマリン酸含有量をc質量%とした場合に、GC/MSピークの面積から下記式により算出される;
ロスマリン酸1質量%当たりピーク面積比=
〔(前記特定の香気成分のピーク面積)/(3-ヘプタノールのピーク面積)〕×1/c。
ここで、前記GC/MSによる測定は、具体的には、実施例の項に記載した測定方法により行われるものとする。
The purified lemon balm extract was measured by gas chromatography mass spectrometry (GC/MS) by adding 1 μL of an ethanol solution of 0.5 mg/mL 3-heptanol as an internal standard substance to 3 g of the purified lemon balm extract. , preferably at least one of the following (A) to (F), more preferably all of (A) to (F):
(A) the peak area ratio of ethyl acetate per 1% by mass of rosmarinic acid is 0.24 or less, preferably 0.07 or less;
(B) the peak area ratio of isovaleraldehyde per 1% by mass of rosmarinic acid is 0.35 or less, preferably 0.19 or less;
(C) the peak area ratio of isovaleraldehyde diethyl acetal per 1% by mass of rosmarinic acid is 0.53 or less, preferably 0.16 or less;
(D) the peak area ratio of α-terpineol per 1% by mass of rosmarinic acid is 0.26 or less, preferably 0.04 or less;
(E) the peak area ratio of prenyl ethyl ether per 1% by mass of rosmarinic acid is 0.05 or less, preferably 0.01 or less;
(F) The peak area ratio of safranal per 1% by mass of rosmarinic acid is 1.72 or less, preferably 0.39 or less:
Here, the peak area ratio per 1% by mass of rosmarinic acid of a specific aromatic component is calculated from the area of the GC/MS peak by the following formula, where c% by mass is the rosmarinic acid content in the purified lemon balm extract. to be;
Peak area ratio per 1% by mass of rosmarinic acid =
[(Peak area of the specific aroma component)/(Peak area of 3-heptanol)]×1/c.
Here, the measurement by GC/MS is specifically performed by the measurement method described in the section of Examples.
さらに、前記精製レモンバーム抽出物は、イソ吉草酸が低減され、それによりレモンバーム抽出物特有の油臭が低減されている。
前記精製レモンバーム抽出物は、該精製レモンバーム抽出物3gに内部標準物質として0.5mg/mLの3-ヘプタノールのエタノール溶液を1μL添加してガスクロマトグラフィー質量分析法(GC/MS)で測定した場合に、イソ吉草酸のロスマリン酸1質量%当たりピーク面積比は、例えば0.083以下、好ましくは0.040以下である。ここで、特定の香気成分のロスマリン酸1質量%当たりピーク面積比の定義及びGC/MSによる測定条件は、上記の酢酸エチル等のものに準じる。
Furthermore, the purified lemon balm extract has reduced isovaleric acid, thereby reducing the oily smell peculiar to lemon balm extracts.
The purified lemon balm extract was measured by gas chromatography mass spectrometry (GC/MS) by adding 1 μL of an ethanol solution of 0.5 mg/mL 3-heptanol as an internal standard substance to 3 g of the purified lemon balm extract. In addition, the peak area ratio of isovaleric acid per 1% by mass of rosmarinic acid is, for example, 0.083 or less, preferably 0.040 or less. Here, the definition of the peak area ratio per 1% by mass of rosmarinic acid of a specific aroma component and the measurement conditions by GC/MS conform to those of ethyl acetate and the like described above.
前記精製レモンバーム抽出物は、ロスマリン酸を、抽出物全量に対して、例えば0.01~20質量%、好ましくは0.1~10質量%、より好ましくは0.5~5質量%含有する。 The purified lemon balm extract contains, for example, 0.01 to 20% by mass, preferably 0.1 to 10% by mass, and more preferably 0.5 to 5% by mass of rosmarinic acid relative to the total amount of the extract.
前記精製レモンバーム抽出物は、例えば、製剤の製造に使用され得る。前記製剤には、例えば、飲食品、医薬品、医薬部外品、化粧品又は飼料に添加される製剤が挙げられる。 Said purified lemon balm extract can be used, for example, in the manufacture of pharmaceuticals. Examples of the formulations include formulations added to foods and drinks, pharmaceuticals, quasi-drugs, cosmetics, and feeds.
前記製剤の形態は、例えば、液体状(溶液、乳化液、分散液等)、半固形状(ペースト状、クリーム状等)、又は固形状(粉末状、顆粒状等)が挙げられる。 Examples of the form of the formulation include liquid (solution, emulsion, dispersion, etc.), semi-solid (paste, cream, etc.), or solid (powder, granule, etc.).
また、前記精製レモンバーム抽出物は、例えば、飲食品、医薬品、医薬部外品、化粧品又は飼料の製造に使用され得る。中でも、前記精製レモンバーム抽出物は、飲食品の製造に使用されることが好ましく、本発明の効果を顕著に奏する観点から、飲料の製造に使用されることがより好ましい。 In addition, the purified lemon balm extract can be used, for example, in the production of food and drink, pharmaceuticals, quasi-drugs, cosmetics, or feed. Above all, the purified lemon balm extract is preferably used for the production of food and drink, and more preferably used for the production of beverages from the viewpoint of significantly exhibiting the effects of the present invention.
前記飲食品としては、特に限定されないが、例えば、清涼飲料(フレーバーウォーター、炭酸飲料、果汁飲料、乳性飲料、茶系飲料等のアルコール度数1度未満の飲料);アルコール飲料(酎ハイ、カクテル等のアルコール度数1度以上の飲料);ゼリー、プリン、ババロア、ケーキ、クッキー、マカロン等のパティスリー;アイスクリーム、アイスミルク、ラクトアイス、氷菓等の冷菓;ヨーグルト、チーズ等の乳製品;タブレット、カプセル菓子、フィルム菓子、キャンディー、チューインガム、チョコレート、焼菓子等の菓子類;団子、カステラ等の和菓子類;調理食品(カレー、パスタ、唐揚げ等)、畜肉類加工品、魚介類加工品、野菜加工品、果物加工品、海産物加工品、穀物加工品等の加工食品;ソース、ドレッシング、食用油、スパイス等の調味料;シロップ、ジャム等を挙げることができる。中でも、本発明の効果を顕著に奏する観点から、前記飲食品としては、飲料(清涼飲料、アルコール飲料)が好ましい。また、前記飲食品は、精製レモンバーム抽出物のロスマリン酸の生理活性を利用する点において、機能性表示食品、特定保健用食品、特別用途食品、栄養機能食品、サプリメント等の機能性食品であることが好ましい。 The food and drink are not particularly limited, but for example, soft drinks (flavored water, carbonated drinks, fruit juice drinks, milky drinks, tea beverages, etc. with an alcohol content of less than 1 degree); patisserie such as jelly, pudding, bavarois, cakes, cookies, macaroons; frozen desserts such as ice cream, ice milk, lacto ice, ice desserts; dairy products such as yogurt and cheese; tablets, capsules Confectionery such as confectionery, film confectionery, candy, chewing gum, chocolate, baked confectionery; Japanese confectionery such as dumplings and castella; Cooked foods (curry, pasta, fried chicken, etc.), processed meat products, processed seafood products, processed vegetables processed foods such as processed foods, processed fruits, processed seafood, and processed grains; seasonings such as sauces, dressings, edible oils, and spices; syrups, jams, and the like. Among them, beverages (soft drinks, alcoholic beverages) are preferable as the food and drink from the viewpoint of exhibiting the effects of the present invention remarkably. In addition, the food and drink is a functional food such as a food with function claims, a food for specified health uses, a food for special dietary uses, a food with nutrient function claims, and a supplement, in that it utilizes the physiological activity of rosmarinic acid in the purified lemon balm extract. is preferred.
前記医薬品としては、特に限定されないが、例えば、錠剤(たとえば、糖衣錠)、顆粒剤、液剤、カプセル剤、トローチ剤、及びうがい薬等の経口医薬品、ハップ剤、軟膏剤等の皮膚外用剤等が挙げられる。 Examples of the pharmaceuticals include, but are not limited to, oral pharmaceuticals such as tablets (e.g., sugar-coated tablets), granules, liquids, capsules, lozenges, and mouthwashes; mentioned.
前記医薬部外品としては、特に限定されないが、例えば、口中清涼剤、のど清涼剤、健胃清涼剤、ビタミン剤、カルシウム剤、ビタミン含有保健剤(ドリンク剤等を含む)、育毛剤(養毛剤)、除毛剤、染毛剤(染毛、脱色又は脱染に用いるものを含む)、薬用歯磨き類(洗口剤等を含む)等が挙げられる。 Examples of the quasi-drugs include, but are not limited to, mouth fresheners, throat refreshers, stomach refreshers, vitamins, calcium preparations, vitamin-containing health care preparations (including health drinks, etc.), hair restorers (hair tonics). ), hair removers, hair dyes (including those used for hair dyeing, bleaching, or destaining), medicated toothpastes (including mouthwashes, etc.), and the like.
前記化粧品としては、特に限定されないが、例えば、香水等のフレグランス製品、基礎化粧品(洗顔クリーム、バニシングクリーム、クレンジングクリーム、コールドクリーム、マッサージクリーム、乳液、化粧水、美容液、パック、メイク落とし等)、仕上げ化粧品(ファンデーション、タルカムパウダー、口紅、リップクリーム、頬紅、アイライナー、マスカラ、アイシャドウ、眉墨、アイパック、ネイルエナメル、エナメルリムバー等)、頭髪化粧品(ポマード、ブリランチン、セットローション、ヘアーステック、ヘアーソリッド、ヘアーオイル、ヘアートリートメント、ヘアークリーム、ヘアートニック、ヘアーリキッド、ヘアースプレー、ヘアワックス、バンドリン、養毛料、染毛料等)、日焼け化粧品(サンタン製品、サンスクリーン製品等)、ハンドクリーム、オーラルケア用品(洗口液、歯磨き等)等が挙げられる。 Examples of the cosmetics include, but are not limited to, fragrance products such as perfumes, basic cosmetics (face wash cream, vanishing cream, cleansing cream, cold cream, massage cream, milky lotion, lotion, serum, mask, makeup remover, etc.). , finishing cosmetics (foundation, talcum powder, lipstick, lip balm, blusher, eyeliner, mascara, eye shadow, eyebrow, eye pack, nail enamel, enamel remover, etc.), hair cosmetics (pomade, brilantin, set lotion, hair stick, Hair solids, hair oils, hair treatments, hair creams, hair tonics, hair liquids, hair sprays, hair waxes, bandolins, hair tonics, hair dyes, etc.), tanning cosmetics (suntan products, sunscreen products, etc.), hand creams, Examples include oral care products (mouthwash, toothpaste, etc.).
飲食品、医薬品、医薬部外品、化粧品又は飼料において、前記精製レモンバーム抽出物は、それら組成物の全量に対して、例えば、ロスマリン酸を45~450ppm含有するように添加される。かかるロスマリン酸濃度は、組成物にロスマリン酸が有する生理活性機能を付与することができる点で、好ましい。 The purified lemon balm extract is added to food and drink, pharmaceuticals, quasi-drugs, cosmetics, or feed so as to contain, for example, 45 to 450 ppm of rosmarinic acid with respect to the total amount of the composition. Such a concentration of rosmarinic acid is preferable in terms of imparting the physiologically active function of rosmarinic acid to the composition.
[精製レモンバーム抽出物を含有する製剤]
本発明には、精製レモンバーム抽出物を含有する製剤、好ましくは飲食品、医薬品、医薬部外品、化粧品又は飼料に用いられる製剤が含まれる。
[Preparation containing purified lemon balm extract]
The present invention includes formulations containing a purified lemon balm extract, preferably formulations used for food and drink, pharmaceuticals, quasi-drugs, cosmetics, or feeds.
精製レモンバーム抽出物、製剤形態、飲食品等の具体的な態様は、上記[精製レモンバーム抽出物]の項の記載に準じる。 Specific aspects of the purified lemon balm extract, formulation forms, food and drink, and the like conform to the description in the section [Purified lemon balm extract] above.
前記製剤中の精製レモンバーム抽出物の含有量は、特に限定されず、製剤の用途、形態等に応じて適宜調整され得るが、製剤の全量に対して、例えば、0.1~100質量%又は1~80質量%である。 The content of the purified lemon balm extract in the formulation is not particularly limited, and can be appropriately adjusted according to the application, form, etc. of the formulation. 1 to 80% by mass.
前記製剤中のロスマリン酸の含有量は、特に限定されず、製剤の用途、形態等に応じて適宜調整され得るが、製造後の濃縮工程を省略できる点から、製剤の全量に対して、例えば、0.01~20質量%であり、好ましくは0.1~20質量%(例えば、0.1~10質量%又は0.5~5質量%)である。 The content of rosmarinic acid in the formulation is not particularly limited, and can be appropriately adjusted according to the application, form, etc. of the formulation. , 0.01 to 20% by mass, preferably 0.1 to 20% by mass (eg, 0.1 to 10% by mass or 0.5 to 5% by mass).
前記製剤は、例えば、澱粉分解物(デキストリン、粉飴等)、糖類〔単糖(グルコース、フルクトース等)、二糖(例えば、ショ糖、乳糖、麦芽糖、トレハロース等)〕、オリゴ糖(セロオリゴ糖、マルトオリゴ糖、フラクトオリゴ糖等)、糖アルコール(キシリトール、ソルビトール、ラクチトール、マルチトール等)、還元澱粉糖化物、食物繊維(例えば、難消化性デキストリン、ポリデキストロース、グァーガム酵素分解物等)等のうちの1種単独又は2種以上の組み合わせを含有してもよい。これらの成分の使用目的は特に限定されず、例えば、賦形、比重調整、安定化等の目的で使用される。 The formulations include, for example, starch hydrolysates (dextrin, powdered syrup, etc.), saccharides [monosaccharides (glucose, fructose, etc.), disaccharides (e.g., sucrose, lactose, maltose, trehalose, etc.)], oligosaccharides (cellooligosaccharides), , malto-oligosaccharides, fructo-oligosaccharides, etc.), sugar alcohols (xylitol, sorbitol, lactitol, maltitol, etc.), reduced starch saccharification products, dietary fibers (e.g., indigestible dextrin, polydextrose, guar gum enzymatic decomposition products, etc.), etc. It may contain one type alone or a combination of two or more types. The purpose of use of these components is not particularly limited, and for example, they are used for purposes such as shaping, specific gravity adjustment, and stabilization.
前記製剤は、製剤化をしやすくする観点から、さらに乳化剤を含有することができる。乳化剤の種類は、特に限定されないが、例えば、ショ糖脂肪酸エステル、グリセリン脂肪酸エステル(例えば、モノグリセリン脂肪酸エステル、ポリグリセリン脂肪酸エステル、ポリグリセリン縮合リシノール酸エステル、有機酸モノグリセリド等)、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、レシチン、酵素分解レシチン、酵素処理レシチン、ステアロイル乳酸ナトリウム、ステアロイル乳酸カルシウム、キラヤ抽出物、サポニン、ポリソルベート(例、ポリソルベート20、ポリソルベート60、ポリソルベート65、ポリソルベート80)等が挙げられる。これらの乳化剤は、1種単独で用いても、2種以上を組み合わせて用いてもよい。 The formulation may further contain an emulsifier from the viewpoint of facilitating formulation. The type of emulsifier is not particularly limited, but for example, sucrose fatty acid ester, glycerin fatty acid ester (e.g., monoglycerin fatty acid ester, polyglycerin fatty acid ester, polyglycerin condensed ricinoleic acid ester, organic acid monoglyceride, etc.), propylene glycol fatty acid ester , sorbitan fatty acid ester, lecithin, enzymatically decomposed lecithin, enzymatically treated lecithin, sodium stearoyl lactylate, calcium stearoyl lactylate, quillaya extract, saponin, polysorbate (e.g., polysorbate 20, polysorbate 60, polysorbate 65, polysorbate 80) and the like. These emulsifiers may be used singly or in combination of two or more.
さらに、前記製剤は、本発明の効果を損なわない限りにおいて、精製レモンバーム抽出物及び上記成分以外に、その他成分として、栄養成分、アルコール、酒類、塩類、呈味成分、果汁、果肉、野菜、野菜汁、ピューレ、エキス(動物、植物、微生物等由来)、香辛料、甘味料、高甘味度甘味料、苦味料、酸味料、香料、着色料、その他食品添加物(食物繊維、pH調整剤、保存料、酸化防止剤、増粘剤、安定化剤等);医薬品、医薬部外品又は化粧品の有効成分又は添加剤;その他の防腐剤、防カビ剤、界面活性剤、ゲル化剤、溶剤、香料、殺菌剤等を1種以上配合することができる。 In addition to the purified lemon balm extract and the above ingredients, the formulation may contain nutritional ingredients, alcohol, alcoholic beverages, salts, taste ingredients, fruit juice, pulp, vegetables, and vegetables, as long as the effects of the present invention are not impaired. Juice, puree, extract (derived from animals, plants, microorganisms, etc.), spices, sweeteners, high-intensity sweeteners, bittering agents, acidulants, flavors, coloring agents, other food additives (dietary fiber, pH adjusters, preservatives) ingredients, antioxidants, thickeners, stabilizers, etc.); active ingredients or additives for pharmaceuticals, quasi-drugs or cosmetics; other preservatives, antifungal agents, surfactants, gelling agents, solvents One or more kinds of perfumes, bactericides, etc. can be blended.
製剤化方法は、特に限定されないが、例えば水、有機溶媒(アルコール、グリセリン、プロピレングリコール)又はそれらの混合物等の所望の溶媒に溶解させて液剤とする方法;液剤にデキストリン等の賦形剤を配合してペースト状製剤にする方法;ペースト状製剤をさらに顆粒化又は打錠して顆粒剤又は錠剤にする方法;上記液剤を噴霧乾燥又は凍結乾燥することでパウダー状製剤(粉末製剤)とする方法;さらに上記液剤に乳化剤とともに油脂類を添加し分散・乳化させることでエマルジョン製剤とする方法等を挙げることができ、用途に応じて所望の剤型を適宜選択採用することができる。 The formulation method is not particularly limited, for example, a method of dissolving in a desired solvent such as water, an organic solvent (alcohol, glycerin, propylene glycol) or a mixture thereof to form a liquid formulation; A method of blending to form a paste-like preparation; a method of further granulating or compressing the paste-like preparation into granules or tablets; a method of spray-drying or freeze-drying the liquid preparation to obtain a powder-like preparation (powder preparation). Method; Further, a method of adding oils and fats to the above liquid formulation together with an emulsifier and dispersing and emulsifying the mixture to form an emulsion formulation can be exemplified.
[精製レモンバーム抽出物を含有する、飲食品、医薬品、医薬部外品、化粧品又は飼料]
本発明には、精製レモンバーム抽出物を含有し、飲食品、医薬品、医薬部外品、化粧品又は飼料である、組成物が含まれる。本組成物の構成のより具体的な態様は、上記[精製レモンバーム抽出物]の記載に準じる。
[Food and drink, pharmaceuticals, quasi-drugs, cosmetics or feed containing purified lemon balm extract]
The present invention includes a composition that contains a purified lemon balm extract and is food or beverage, pharmaceutical, quasi-drug, cosmetic or feed. A more specific embodiment of the composition of the present composition conforms to the description of [Purified lemon balm extract] above.
[レモンバーム抽出物の飲料添加の際の濁り又は沈殿を低減する方法]
本発明は、(a)レモンバーム抽出物を芳香族系合成吸着剤と接触させて、非吸着画分を得る工程を含む、レモンバーム抽出物の飲料添加の際の濁り又は沈殿を低減する方法、を含む。本方法のより具体的な態様は、上記[精製レモンバーム抽出物の製造方法]の記載に準じる。
[Method for Reducing Turbidity or Precipitation During Addition of Lemon Balm Extract to Beverage]
The present invention provides (a) a method of reducing turbidity or sedimentation upon addition of lemon balm extract to a beverage comprising the step of contacting the lemon balm extract with a synthetic aromatic adsorbent to obtain a non-adsorbed fraction. include. A more specific embodiment of the present method conforms to the above [Method for producing purified lemon balm extract].
以下、本発明を実験例及び実施例に基づいてさらに詳細に説明するが、本発明はこれらの実施例によって何ら制限されるものではない。なお、実施例中の「部」「%」は、特に記載がない限り、それぞれ「質量部」「質量%」を意味する。 Hereinafter, the present invention will be described in more detail based on experimental examples and examples, but the present invention is not limited by these examples. "Parts" and "%" in the examples mean "parts by mass" and "% by mass", respectively, unless otherwise specified.
[レモンバーム粗抽出物の調製]
57%(v/v)エタノール水溶液2Lに対してレモンバーム葉(AmorosNature社製、ロスマリン酸約3質量%含有)100gを加え、60℃で3時間抽出処理した後、No.2濾紙で濾過し、ロスマリン酸を含有する粗抽出物(レモンバーム抽出原液)を調製し、各試験例に用いた。
[Preparation of Lemon Balm Crude Extract]
100 g of lemon balm leaves (manufactured by AmorosNature, containing about 3% by mass of rosmarinic acid) were added to 2 L of a 57% (v/v) aqueous ethanol solution, and extracted at 60° C. for 3 hours. 2 filter paper to prepare a crude extract containing rosmarinic acid (lemon balm extract undiluted solution) and used in each test example.
[試験例1]
[試験例1-1.精製レモンバーム抽出物の調製]
上記レモンバーム粗抽出物に対して、下記工程(a)及び/又は工程(b)による精製処理を経たレモンバーム抽出物(比較例1-2~4、実施例1-1~2)を調製した。比較例1-1は、対照サンプルであり、精製処理を行わなかったレモンバーム粗抽出物である。各サンプルの調製で使用した処理剤、工程(a)の有無及び使用した処理剤、並びに工程(b)の有無は表1に示した。いずれのサンプルも、ロスマリン酸含有量はサンプル全量に対して2.0質量%であった。
<工程>
工程(a):表1の各処理剤に上記粗抽出物を通液し、その通過画分(非吸着画分)を得る。ここで各処理剤は通液2Lに対して200mLの割合で使用した。
工程(b):活性炭(タケコール50WG-T、大阪ガスケミカル(株)製)に上記粗抽出物又は工程(a)で処理した液を通液し、その通過画分を得る。ここで、活性炭は通液2L(約1.9kg)に対して16gの割合で使用した。
[Test Example 1]
[Test Example 1-1. Preparation of purified lemon balm extract]
Lemon balm extracts (Comparative Examples 1-2 to 1-4, Examples 1-1 to 2) were prepared by subjecting the crude lemon balm extract to the following step (a) and/or step (b). Comparative Example 1-1 is a control sample, which is a lemon balm crude extract that has not undergone any purification treatment. Table 1 shows the processing agents used in the preparation of each sample, the presence or absence of step (a), the processing agents used, and the presence or absence of step (b). Each sample had a rosmarinic acid content of 2.0% by mass relative to the total amount of the sample.
<Process>
Step (a): The above crude extract is passed through each treatment agent in Table 1 to obtain a passing fraction (non-adsorbed fraction). Here, each treatment agent was used at a rate of 200 mL per 2 L of liquid.
Step (b): The crude extract or the liquid treated in step (a) is passed through activated carbon (Takecoal 50WG-T, manufactured by Osaka Gas Chemicals Co., Ltd.) to obtain a passing fraction. Here, 16 g of activated carbon was used per 2 L (approximately 1.9 kg) of liquid flow.
[試験例1-2.精製レモンバーム抽出物の飲料の外観に及ぼす影響の検討]
得られた精製レモンバーム抽出物を用いて下記試験飲料を調製したときの沈殿や澱(オリ)の有無を目視による外観観察で評価した。
<試験飲料の調製>
砂糖8質量部、クエン酸無水物0.12質量部、クエン酸三ナトリウム0.08質量部、レモンバーム抽出物1.13質量部に対して、水を加えて全量を100質量部としたものを加熱し、93℃達温後密栓して、速やかに冷却して調製した。飲料中のロスマリン酸含有量は225ppmとなる。
[Test Example 1-2. Examination of the effect of purified lemon balm extract on the appearance of beverages]
The purified lemon balm extract was used to prepare the following test beverages, and the presence or absence of precipitates and sediments was visually observed to evaluate the appearance.
<Preparation of test beverage>
Water was added to 8 parts by mass of sugar, 0.12 parts by mass of citric anhydride, 0.08 parts by mass of trisodium citrate, and 1.13 parts by mass of lemon balm extract to make the total amount 100 parts by mass. It was heated, sealed after reaching 93° C., and rapidly cooled to prepare. The rosmarinic acid content in the beverage is 225 ppm.
その結果、表1に示されるように、芳香族系合成吸着剤の非吸着画分から得られる実施例サンプルでは試験飲料に沈殿又は澱は見られなかったが、未処理又は合成吸着剤以外の吸着剤で処理を行った比較例サンプルでは、沈殿又は澱が発生した。 As a result, as shown in Table 1, no sediment or sediment was observed in the test beverages of the example samples obtained from the non-adsorbed fractions of the synthetic aromatic adsorbents, whereas the non-treated or non-synthetic adsorbents did not exhibit any sedimentation or sedimentation. Precipitation or sediment occurred in the comparative samples treated with the agent.
さらに、沈殿又は澱が見られなかった実施例サンプルについて、それぞれの試験飲料の波長700nmでの吸光度を測定して、濁りを評価した。表1に示されるように、芳香族系合成吸着剤の非吸着画分をさらに活性炭処理した実施例1-2では、活性炭処理を行わない実施例1-1に比べて、濁りが大幅に減少した。 Furthermore, for example samples in which no precipitate or sediment was observed, the absorbance of each test beverage was measured at a wavelength of 700 nm to evaluate turbidity. As shown in Table 1, in Example 1-2 in which the non-adsorbed fraction of the synthetic aromatic adsorbent was further treated with activated carbon, turbidity was significantly reduced compared to Example 1-1 in which no activated carbon treatment was performed. did.
さらに、それぞれの試験飲料の波長400nmでの吸光度を測定して、着色を評価した。表1に示されるように、実施例1-1でも着色の減少が見られたが、さらに活性炭処理を行った実施例1-2では、着色が大幅に減少した。 In addition, coloration was evaluated by measuring the absorbance of each test beverage at a wavelength of 400 nm. As shown in Table 1, a reduction in coloration was observed in Example 1-1, but a significant reduction in coloration was observed in Example 1-2, which was further treated with activated carbon.
[試験例1-3.精製レモンバーム抽出物の不快風味の比較]
食品の研究開発に従事し、官能評価に熟練した9名によって構成される官能評価パネルにより、上記の精製レモンバーム抽出物含有飲料の青臭さ、枯草臭、渋みを官能評価した。これらの青臭さ、枯草臭及び渋みは、レモンバーム抽出物特有の不快な風味の一部を構成する官能特性である。各パネリストは、ロスマリン酸を1.4質量%含有する市販のレモンバーム抽出物(市販品A)をロスマリン酸含有量が225ppmとなるように添加した上記の試験飲料の評点を3として、それぞれの官能特性を下記の基準により5段階評価した。評価サンプルには、試験例1-2の試験飲料と同じ組成の飲料を使用した。最終的に、パネリストの評点の単純平均を各官能特性の評価値とした。
<青臭さ/枯草臭/渋みの評価基準>
5:青臭さ/枯草臭/渋みがとても強く感じられる
4:青臭さ/枯草臭/渋みが強く感じられる
3:青臭さ/枯草臭/渋みが感じられる(市販品A含有飲料と同程度に感じられる)
2:青臭さ/枯草臭/渋みが低減されている
1:青臭さ/枯草臭/渋みがかなり低減されている
[Test Example 1-3. Comparison of unpleasant flavor of purified lemon balm extract]
A sensory evaluation panel consisting of 9 persons engaged in food research and development and skilled in sensory evaluation performed sensory evaluations of grassy odor, dry grass odor, and astringency of the beverage containing the purified lemon balm extract. These grassy, withered and astringent are organoleptic properties that form part of the unpleasant flavor characteristic of lemon balm extracts. Each panelist gave a score of 3 for the above test beverage in which a commercially available lemon balm extract (commercial product A) containing 1.4% by mass of rosmarinic acid was added so that the rosmarinic acid content was 225 ppm. The properties were evaluated in 5 grades according to the following criteria. A beverage having the same composition as the test beverage of Test Example 1-2 was used as an evaluation sample. Finally, the simple average of the scores of the panelists was used as the evaluation value for each sensory characteristic.
<Evaluation Criteria for Grassy Smell/Dry Grass Smell/Astringency>
5: Grassy odor / dry grass odor / astringency is felt very strongly 4: Grassy odor / dry grass odor / astringency is felt strongly 3: Grassy odor / dry grass odor / astringency is felt can be)
2: grassy odor / dry grass odor / astringency is reduced 1: grassy odor / dry grass odor / astringency is considerably reduced
得られた各官能特性の評価値を表2に示した。芳香族系合成吸着剤で処理した実施例1-1を含有する試験飲料では、未処理の比較例1-1に比べて青臭さ、枯草臭、渋みのいずれも改善が見られ、市販品Aと比べても風味が改善していた。活性炭処理を行った実施例1-2を含有する試験飲料では、さらに大幅な改善が見られ、他の樹脂による精製と活性炭処理の両方を行った比較例1-3又は比較例1-4を含有する試験飲料と比べても、青臭さ、枯草臭、渋みが顕著に低減していた。 Table 2 shows the obtained evaluation values for each sensory property. In the test beverage containing Example 1-1 treated with the aromatic synthetic adsorbent, improvement was observed in all of the grassy odor, dry grass odor, and astringency compared to the untreated Comparative Example 1-1. The flavor was improved as well. Test beverages containing Example 1-2 with activated charcoal treatment showed even greater improvement, compared to Comparative Example 1-3 or Comparative Example 1-4 with both other resin purification and activated charcoal treatment. Compared to the test beverage containing the sap, grassy odor, dry grass odor, and astringency were remarkably reduced.
[試験例1-4.精製レモンバーム抽出物の香気成分の比較]
各精製レモンバーム抽出物の香気成分をガスクロマトグラフィー質量分析法(GC/MS)によって測定した。測定方法の詳細は下記のとおりである。
<測定試料の調製>
分析対象試料を撹拌し均一にした後、各分析対象試料3gをSPMEバイアルに秤量した。そこへ、内部標準物質として0.5mg/mL 3-ヘプタノール(メタノール溶液)を1μL加え、均一になるように混合し、キャップで密閉して測定試料とした。
<SPME-GC/MS分析方法>
前記測定試料を固相マイクロ抽出-ガスクロマトグラフィー質量分析法(SPME-GC/MS)に供した。分析には、Agilent Technologies社のGC/MS装置(7890A GC System,5975C inert XL MSD with Triple-Axis Detector)を使用した。SPMEとして、Gerstel社製 MPSを使用した。SPMEファイバーを、密閉したバイアル内で40℃、30分間曝露して、揮発成分を吸着させた後に、GC/MS装置へインジェクションした。分析は各試料につきn=5で行った。
<GC/MS条件>
使用カラム:DB-WAX(60m×0.25mm、0.25μm)(Agilent Technologies社製)
カラム昇温条件:(i)50℃で2分間加熱→(ii)3℃/分の条件で56.667分間加熱し220℃まで昇温させて、12分保持させて終了(昇温開始から70.667分経過)
検出器:四重極型質量分析計5975C inert XL MSD with Triple-Axis Detector(Agilent Technologies社製)
MS条件:イオン源温度350℃
<内部標準物質に対するピーク面積比の算出方法>
それぞれの香気成分及び3-ヘプタノールの代表的なMSフラグメントのm/zでイオンクロマトグラム抽出し、得られたピークの面積を使用した。ここで、各香気成分の代表的なMSフラグメントのm/zは、表3のとおりである。また、3-ヘプタノールの代表的なMSフラグメントのm/zは59である。
次に、下記計算式により、内部標準物質に対するピーク面積比(内標比)を算出した。
香気成分のピーク面積の内標比
=(香気成分のピーク面積)/(3-ヘプタノールのピーク面積)
<ロスマリン酸1質量%当たりピーク面積比の算出方法>
各GC/MS測定試料中のロスマリン酸含有量をc(質量%)とした場合に、下記計算式により、GC/MS測定試料中のロスマリン酸1質量%当たりのピーク面積比を算出した:
ロスマリン酸1質量%当たりピーク面積比=(香気成分のピーク面積の内標比)/c。
[Test Example 1-4. Comparison of aroma components of purified lemon balm extract]
The aroma components of each purified lemon balm extract were measured by gas chromatography-mass spectrometry (GC/MS). The details of the measurement method are as follows.
<Preparation of measurement sample>
After stirring and homogenizing the analytes, 3 g of each analyte was weighed into SPME vials. To this, 1 μL of 0.5 mg/mL 3-heptanol (methanol solution) was added as an internal standard substance, mixed uniformly, sealed with a cap, and used as a measurement sample.
<SPME-GC/MS analysis method>
The measurement sample was subjected to solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC/MS). A GC/MS instrument from Agilent Technologies (7890A GC System, 5975C inert XL MSD with Triple-Axis Detector) was used for analysis. As SPME, MPS manufactured by Gerstel was used. The SPME fiber was exposed to 40° C. for 30 minutes in a sealed vial to adsorb volatiles before injection into the GC/MS instrument. Analysis was performed with n=5 for each sample.
<GC/MS conditions>
Column used: DB-WAX (60 m × 0.25 mm, 0.25 μm) (manufactured by Agilent Technologies)
Column heating conditions: (i) heating at 50 ° C. for 2 minutes → (ii) heating at 3 ° C./min for 56.667 minutes, raising the temperature to 220 ° C., holding for 12 minutes, and ending (from the start of heating 70.667 minutes elapsed)
Detector: Quadrupole mass spectrometer 5975C inert XL MSD with Triple-Axis Detector (manufactured by Agilent Technologies)
MS conditions: ion source temperature 350°C
<Method for calculating peak area ratio to internal standard>
Ion chromatograms were extracted at m/z of MS fragments representative of each aroma component and 3-heptanol, and the areas of the resulting peaks were used. Here, m/z of representative MS fragments of each aroma component are as shown in Table 3. Also, the m/z of a representative MS fragment of 3-heptanol is 59.
Next, the peak area ratio (internal standard ratio) to the internal standard substance was calculated by the following formula.
Internal standard ratio of peak area of aroma component = (peak area of aroma component) / (peak area of 3-heptanol)
<Calculation method of peak area ratio per 1% by mass of rosmarinic acid>
When the rosmarinic acid content in each GC/MS measurement sample is c (% by mass), the peak area ratio per 1% by mass of rosmarinic acid in the GC/MS measurement sample was calculated by the following formula:
Peak area ratio per 1% by mass of rosmarinic acid=(internal standard ratio of peak area of aroma component)/c.
結果を表3及び図1に示す。イソバレルアルデヒドは嗅覚閾値が低い悪臭物質として知られるが、実施例1-1(合成吸着剤処理のみ)は、比較例に比べて顕著にイソバレルアルデヒド量が減少し、実施例1-2(合成吸着剤処理+活性炭処理)ではさらに顕著に減少していた。 The results are shown in Table 3 and FIG. Isovaleraldehyde is known as a malodorous substance with a low olfactory threshold. Synthetic adsorbent treatment + activated carbon treatment) showed a further significant decrease.
また、実施例1-2は、驚くべきことに、いずれの香気成分についても、比較例1-2(活性炭処理のみ)及び実施例1-1から想定される減少量を大幅に超える減少を示した。 In addition, Example 1-2 surprisingly shows a reduction that greatly exceeds the amount of reduction expected from Comparative Example 1-2 (activated carbon treatment only) and Example 1-1 for both aroma components. Ta.
評価基準以外は試験例1-4と同様の方法で、同じ官能評価パネルにより、比較例1-1、比較例1-2、実施例1-1及び実施例1-2のレモンバーム抽出物を飲料中のロスマリン酸含有量が225ppmとなるように試験飲料に添加したサンプルのレモンバーム抽出物特有の油臭を官能評価した。比較例1-1の精製レモンバーム抽出物を含有する試験飲料の評点を4として、それぞれの官能特性を下記の基準により5段階評価した。最終的に、パネリストの評点の単純平均を各官能特性の評価値とした。
<レモンバーム抽出物特有の油臭の評価基準>
5:特有の油臭がとても強く感じられる
4:特有の油臭が強く感じられる(比較例1-1含有飲料と同程度に感じられる)
3:特有の油臭が感じられる
2:特有の油臭が低減されている
1:特有の油臭がかなり低減されている
The lemon balm extracts of Comparative Example 1-1, Comparative Example 1-2, Example 1-1 and Example 1-2 were prepared as beverages by the same method as in Test Example 1-4 except for the evaluation criteria and by the same sensory evaluation panel. A sensory evaluation was made of the oily odor peculiar to the lemon balm extract of the sample added to the test beverage so that the rosmarinic acid content in the beverage was 225 ppm. The test beverage containing the purified lemon balm extract of Comparative Example 1-1 was given a score of 4, and each sensory characteristic was evaluated on a 5-point scale according to the following criteria. Finally, the simple average of the scores of the panelists was used as the evaluation value for each sensory characteristic.
<Evaluation criteria for oily odor peculiar to lemon balm extract>
5: Very strong peculiar oily odor 4: Strongly peculiar oily odor (similar to the beverage containing Comparative Example 1-1)
3: Unique oil odor is felt 2: Unique oil odor is reduced 1: Unique oil odor is considerably reduced
各サンプルの油臭の評価値を表4に示す。実施例1-1を添加した試験飲料は、比較例1-1や比較例1-2を添加した場合に比べて特有の油臭が低減した。さらに実施例1-2を添加した場合は、他の場合よりも顕著に特有の油臭が低減した。 Table 4 shows the evaluation value of the oily smell of each sample. The test beverage to which Example 1-1 was added had a reduced characteristic oily odor compared to the case of adding Comparative Example 1-1 and Comparative Example 1-2. Furthermore, when Example 1-2 was added, the characteristic oil odor was significantly reduced compared to the other cases.
次に、比較例1-1、比較例1-2、実施例1-1及び実施例1-2のレモンバーム抽出物を試験例1-4と同じ方法によりSPME-GC/MS分析を行った。各サンプルのイソ吉草酸(m/z=60、保持時間34.180(分))のロスマリン酸1質量%当たりピーク面積比を表4に示す。また、各サンプルのイソ吉草酸のロスマリン酸1質量%当たりピーク面積比を比較したグラフを図2に示す。油臭の強さとイソ吉草酸の量とは相関性があることから、イソ吉草酸は、レモンバーム抽出物に特有の油臭の原因物質であると言える。 Next, the lemon balm extracts of Comparative Examples 1-1, 1-2, Examples 1-1 and 1-2 were subjected to SPME-GC/MS analysis in the same manner as in Test Example 1-4. Table 4 shows the peak area ratio of isovaleric acid (m/z=60, retention time 34.180 (minutes)) per 1% by mass of rosmarinic acid of each sample. FIG. 2 shows a graph comparing the peak area ratio of isovaleric acid per 1% by mass of rosmarinic acid of each sample. Since there is a correlation between the strength of the oily odor and the amount of isovaleric acid, it can be said that isovaleric acid is the causative agent of the oily odor peculiar to the lemon balm extract.
[試験例2.工程(a)で用いる合成吸着剤の検討]
工程(a)の処理剤を表5の各処理剤に変更する以外は実施例1-2と同じ条件でレモンバーム粗抽出物を精製処理し、実施例2-1~6、比較例2-1を調製した。得られた精製レモンバーム抽出物を用いて試験例1-2の方法に従って試験飲料を調製し、目視による沈殿又は澱の有無の観察と波長700nmでの吸光度の測定を行った。
[Test Example 2. Examination of synthetic adsorbent used in step (a)]
The lemon balm crude extract was purified under the same conditions as in Example 1-2 except that the treatment agent in step (a) was changed to each treatment agent in Table 5, and Examples 2-1 to 2-6 and Comparative Example 2-1 were obtained. was prepared. Using the obtained purified lemon balm extract, test beverages were prepared according to the method of Test Example 1-2, and the presence or absence of precipitation or sediment was visually observed and absorbance was measured at a wavelength of 700 nm.
結果を表5に示す。処理剤の樹脂母体として芳香族系合成吸着剤を使用した実施例2-1~6は、いずれも沈殿又は澱の発生はなく、濁りも少ないことが確認された。また、処理剤の樹脂母体としては、上記化学式(I)を構造単位とする場合が優れ、中でもセパビーズSP207が特に優れていることが明らかとなった。一方、陰イオン交換樹脂を使用した比較例2-1では、比較例1-3の場合と同様に澱が発生した。 Table 5 shows the results. In Examples 2-1 to 2-6, in which an aromatic synthetic adsorbent was used as the resin base of the treatment agent, no precipitation or sediment occurred, and it was confirmed that the turbidity was low. In addition, as the resin matrix of the treatment agent, it was found that the structural unit represented by the chemical formula (I) is excellent, and Sepabeads SP207 is particularly excellent. On the other hand, in Comparative Example 2-1 using an anion exchange resin, sediment was generated as in Comparative Example 1-3.
[試験例3.工程(a)で通液する粗抽出物の低級アルコール濃度の検討]
上記レモンバーム粗抽出物から溶媒を蒸発させて濃縮し、エタノール又は水を適量加えることにより、上記レモンバーム粗抽出物と同量、同ロスマリン酸濃度で、10%(v/v)又は90%(v/v)のエタノールを含有する粗抽出液を調製した。得られた2種類の粗抽出液に対して上記実施例1-2と同じ条件で処理剤通液による精製処理を行って、精製ロスマリン酸抽出物(実施例3-1、実施例3-2)を調製した。
[Test Example 3. Investigation of lower alcohol concentration of crude extract passed in step (a)]
By evaporating the solvent from the lemon balm crude extract and concentrating it, adding an appropriate amount of ethanol or water, the same amount as the lemon balm crude extract and the same rosmarinic acid concentration, 10% (v / v) or 90% (v /v) of ethanol was prepared. The two types of crude extracts obtained were subjected to a purification treatment by passing a treating agent under the same conditions as in Example 1-2 above to obtain purified rosmarinic acid extracts (Examples 3-1 and 3-2 ) was prepared.
得られた精製ロスマリン酸抽出物を用いて試験例1-2の方法に従って試験飲料を調製し、波長700nm及び400nmの吸光度を測定した結果を表6に示した。処理剤通液時の低級アルコールの濃度が10%(v/v)、90%(v/v)の実施例3-1及び実施例3-2は、それぞれ実施例1-2と同様に沈殿又は澱の発生はなく、濁りが大きく低減し、また着色も低減していた。 Using the obtained purified rosmarinic acid extract, a test drink was prepared according to the method of Test Example 1-2, and the absorbance at wavelengths of 700 nm and 400 nm was measured. Table 6 shows the results. Examples 3-1 and 3-2 in which the concentration of the lower alcohol is 10% (v/v) and 90% (v/v) when the treatment agent is passed are precipitated in the same manner as in Example 1-2, respectively. Or, there was no generation of sediment, turbidity was greatly reduced, and coloration was also reduced.
[試験例4.工程(a)の樹脂量の検討]
処理剤の使用体積量を通液する粗抽出物の体積量に対して0.01倍(粗抽出物2Lに対して処理剤20mL)又は0.001倍(粗抽出物2Lに対して処理剤2mL)とする以外は、上記実施例1-2と同じ条件で精製処理を行って、実施例4-1及び実施例4-2を調製した。得られた精製レモンバーム抽出物を用いて試験例1-2の方法に従って試験飲料を調製し、目視による沈殿又は澱の有無の観察と波長700nm及び400nmでの吸光度の測定を行った。
[Test Example 4. Examination of resin amount in step (a)]
0.01 times (20 mL of processing agent for 2 L of crude extract) or 0.001 times (2 L of processing agent for 2 L of crude extract) to the volume of crude extract to be passed through the volume of the processing agent used Example 4-1 and Example 4-2 were prepared by performing the purification treatment under the same conditions as in Example 1-2 above, except that the volume was 2 mL). Using the obtained purified lemon balm extract, test beverages were prepared according to the method of Test Example 1-2, and the presence or absence of precipitation or sediment was visually observed and the absorbance was measured at wavelengths of 700 nm and 400 nm.
結果を表7に示した。いずれの実施例の精製レモンバームを使用した場合も沈殿又は澱の発生はなく、濁りが低減したが、特に、接触させるレモンバーム抽出物の体積量に対する処理剤の体積量が0.01倍である実施例4-1では、波長700nmでの吸光度が0.05を下回り、顕著に高い透明性を有していた。また、実施例4-1では、着色も大きく抑えられていた。 The results are shown in Table 7. When the purified lemon balm of any example was used, there was no precipitation or sedimentation, and the turbidity was reduced. Example 4-1 had an absorbance of less than 0.05 at a wavelength of 700 nm and had remarkably high transparency. Further, in Example 4-1, coloring was greatly suppressed.
[試験例5.工程(b)の活性炭の検討]
工程(b)で使用する活性炭を白鷺DO-2(ヤシ殻由来;大阪ガスケミカル製)とする以外は、実施例1-2と同じ条件で精製処理を行って実施例5を調製した。得られた精製レモンバーム抽出物を用いて試験例1-2の方法に従って試験飲料を調製し、目視による沈殿又は澱の有無の観察と波長700nm及び400nmでの吸光度の測定を行った。
[Test Example 5. Examination of activated carbon in step (b)]
Example 5 was prepared by refining under the same conditions as in Example 1-2, except that Shirasagi DO-2 (derived from coconut shells; manufactured by Osaka Gas Chemicals) was used as the activated carbon in step (b). Using the obtained purified lemon balm extract, test beverages were prepared according to the method of Test Example 1-2, and the presence or absence of precipitation or sediment was visually observed and the absorbance was measured at wavelengths of 700 nm and 400 nm.
結果を表8に示した。実施例1-2とは異なる活性炭を使用した実施例5でも、実施例1-2と同様に飲料中の沈殿又は澱の発生はなく、濁り低減と着色の低減が確認された。 Table 8 shows the results. In Example 5, which used activated carbon different from Example 1-2, there was no precipitation or sedimentation in the beverage as in Example 1-2, and it was confirmed that turbidity and coloration were reduced.
[試験例6.通液する粗抽出液のロスマリン酸濃度の検討]
次の手順で精製レモンバーム抽出物を調製し、評価した。
(1)(i)上記レモンバーム粗抽出物を57%(v/v)で20倍希釈したもの、(ii)上記レモンバーム粗抽出物から溶媒を蒸発させて濃縮し、液量を1/10倍量としたものを調製した。
(2)試験例1-1と同じ液量の上記(i)、(ii)を実施例1-2と同様に処理して、試験例1-1で得られるサンプルに対してロスマリン酸濃度が1/20倍(0.1質量%)及び10倍(20質量%)の精製レモンバーム抽出物(実施例6-1、実施例6-2)を調製した。
(3)精製レモンバーム抽出物を用いて試験例1-2の方法に従って試験飲料を調製し、目視による沈殿又は澱の有無の観察と波長700nm及び400nmでの吸光度の測定を行った。
[Test Example 6. Investigation of Rosmarinic Acid Concentration of Crude Extract Liquid Passed]
A purified lemon balm extract was prepared and evaluated by the following procedure.
(1) (i) 20-fold dilution of the lemon balm crude extract at 57% (v/v), (ii) concentration by evaporating the solvent from the lemon balm crude extract to 1/10 times the liquid volume Quantities were prepared.
(2) The same liquid volumes of (i) and (ii) as in Test Example 1-1 are treated in the same manner as in Example 1-2, and the rosmarinic acid concentration is increased with respect to the sample obtained in Test Example 1-1. 1/20-fold (0.1% by mass) and 10-fold (20% by mass) purified lemon balm extracts (Example 6-1, Example 6-2) were prepared.
(3) Using the purified lemon balm extract, test beverages were prepared according to the method of Test Example 1-2, and the presence or absence of precipitation or sediment was visually observed and absorbance was measured at wavelengths of 700 nm and 400 nm.
結果を表9に示した。いずれの実施例でも飲料の沈殿又は澱の発生はなく、濁り、着色が低減されていた。実施例1-2の結果も踏まえると、通液して得られる精製レモンバーム抽出物のロスマリン酸濃度が0.1質量%よりも大きい値の場合は、これらの低減効果がより顕著となることが明らかとなった。 The results are shown in Table 9. In any of the Examples, there was no sedimentation or sedimentation of the beverage, and turbidity and coloration were reduced. Considering the results of Example 1-2, when the concentration of rosmarinic acid in the purified lemon balm extract obtained by passing the solution is greater than 0.1% by mass, these reduction effects are more pronounced. It became clear.
Claims (11)
前記精製レモンバーム抽出物をロスマリン酸換算量で225ppm、砂糖8質量%、クエン酸無水物0.12質量%、及びクエン酸三ナトリウム0.08質量%を含有する水溶液の波長700nmにおける濁度(OD700)が、0.05以下である、精製レモンバーム抽出物。 A purified lemon balm extract containing 0.01 to 20% by mass of rosmarinic acid,
The turbidity at a wavelength of 700 nm (OD700 ) is 0.05 or less.
(A)酢酸エチルのロスマリン酸1質量%当たりピーク面積比が、0.24以下;
(B)イソバレルアルデヒドのロスマリン酸1質量%当たりピーク面積比が、0.35以下;
(C)イソバレルアルデヒドジエチルアセタールのロスマリン酸1質量%当たりピーク面積比が、0.53以下;
(D)α-テルピネオールのロスマリン酸1質量%当たりピーク面積比が、0.26以下;
(E)プレニルエチルエーテルのロスマリン酸1質量%当たりピーク面積比が、0.05以下;
(F)サフラナールのロスマリン酸1質量%当たりピーク面積比が、1.72以下:
ここで、特定の香気成分のロスマリン酸1質量%当たりピーク面積比は、該精製レモンバーム抽出物中のロスマリン酸含有量をc質量%とした場合に、GC/MSピークの面積から下記式により算出される;
ロスマリン酸1質量%当たりピーク面積比=
〔(前記特定の香気成分のピーク面積)/(3-ヘプタノールのピーク面積)〕×1/c。 When 1 μL of an ethanol solution of 0.5 mg/mL 3-heptanol was added as an internal standard substance to 3 g of the purified lemon balm extract and measured by gas chromatography mass spectrometry (GC/MS), the following (A) Purified lemon balm extract according to claim 6, satisfying at least one of (F):
(A) the peak area ratio of ethyl acetate per 1% by mass of rosmarinic acid is 0.24 or less;
(B) the peak area ratio of isovaleraldehyde per 1% by mass of rosmarinic acid is 0.35 or less;
(C) the peak area ratio of isovaleraldehyde diethyl acetal per 1% by mass of rosmarinic acid is 0.53 or less;
(D) the peak area ratio of α-terpineol per 1% by mass of rosmarinic acid is 0.26 or less;
(E) the peak area ratio of prenyl ethyl ether per 1% by mass of rosmarinic acid is 0.05 or less;
(F) The peak area ratio of safranal per 1% by mass of rosmarinic acid is 1.72 or less:
Here, the peak area ratio per 1% by mass of rosmarinic acid of a specific aromatic component is calculated from the area of the GC/MS peak by the following formula, where c% by mass is the rosmarinic acid content in the purified lemon balm extract. to be;
Peak area ratio per 1% by mass of rosmarinic acid =
[(Peak area of the specific aroma component)/(Peak area of 3-heptanol)]×1/c.
ここで、特定の香気成分のロスマリン酸1質量%当たりピーク面積比は、該精製レモンバーム抽出物中のロスマリン酸含有量をc質量%とした場合に、GC/MSピークの面積から下記式により算出される;
ロスマリン酸1質量%当たりピーク面積比=
〔(前記特定の香気成分のピーク面積)/(3-ヘプタノールのピーク面積)〕×1/c。 When 1 μL of an ethanol solution of 0.5 mg/mL 3-heptanol was added as an internal standard substance to 3 g of the purified lemon balm extract and measured by gas chromatography mass spectrometry (GC/MS), rosmarin of isovaleric acid The purified lemon balm extract according to claim 6, wherein the peak area ratio per 1% by mass of acid is 0.083 or less;
Here, the peak area ratio per 1% by mass of rosmarinic acid of a specific aromatic component is calculated from the area of the GC/MS peak by the following formula, where c% by mass is the rosmarinic acid content in the purified lemon balm extract. to be;
Peak area ratio per 1% by mass of rosmarinic acid =
[(Peak area of the specific aroma component)/(Peak area of 3-heptanol)]×1/c.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2022012757 | 2022-01-31 | ||
JP2022012757 | 2022-01-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2023111879A true JP2023111879A (en) | 2023-08-10 |
Family
ID=87551442
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2023009310A Pending JP2023111879A (en) | 2022-01-31 | 2023-01-25 | Method for producing purified lemon balm extract |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2023111879A (en) |
-
2023
- 2023-01-25 JP JP2023009310A patent/JP2023111879A/en active Pending
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2172537B1 (en) | Flavor or fragrance deterioration inhibitor | |
EP0529962B1 (en) | Process for the preparation of a purified propolis-extract and its uses | |
JP4248571B2 (en) | Flavor improving agent, flavor improving method using the same, and food and drink | |
JP2001270881A (en) | Proanthocyanidin-containing composition | |
WO2016043276A1 (en) | Flavor deterioration inhibitor | |
JPH092917A (en) | Polyphenol preparation obtained from hop and its production | |
JP4358957B2 (en) | Agent for scavenging or reducing free radicals or active oxygen | |
JP4713324B2 (en) | Hyaluronidase inhibitor | |
JP7134976B2 (en) | Kucho tea processed product | |
JP4000283B2 (en) | Licorice oily solubilized composition, beverage, liquid seasoning, cosmetics and quasi drugs | |
JP5309301B2 (en) | Method for producing eriocitrin-containing material | |
JP4375946B2 (en) | Anti-obesity composition comprising peanut astringent skin extract as active ingredient | |
JP4837816B2 (en) | Free radical scavenger | |
JP7379055B2 (en) | Composition for suppressing thermal deterioration of citral and method for suppressing thermal deterioration | |
JP4037035B2 (en) | Flavor improver | |
JP2002371276A (en) | Antioxidant, food and cosmetic obtained by using the same | |
JP2023111879A (en) | Method for producing purified lemon balm extract | |
KR101768084B1 (en) | Extract of ginseng and method of preparing the same | |
JP2002275007A (en) | Antimicrobial agent | |
KR102252763B1 (en) | Method of Preparing Extract of Red Ginseng Having a Reduced Chromaticity | |
JP2006008571A (en) | Moisturizer, antioxidant, antiaging agent, skin cosmetic and beauty drink and food | |
WO2021175450A1 (en) | COMPOSITION OR OAT EXTRACT COMPRISING AVENANTHRAMIDE AND ß-GLUCAN | |
KR102496820B1 (en) | Method for producing Gastrodia elata with reduced unpleasant odor | |
JP2004161678A (en) | Anti-inflammatory agent and cyclic amp phosphodiesterase inhibitor | |
KR102580873B1 (en) | Method of producing extract having enhanced content of quercetin from onion |