JP2020174651A - Citral-containing composition - Google Patents
Citral-containing composition Download PDFInfo
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- JP2020174651A JP2020174651A JP2019090977A JP2019090977A JP2020174651A JP 2020174651 A JP2020174651 A JP 2020174651A JP 2019090977 A JP2019090977 A JP 2019090977A JP 2019090977 A JP2019090977 A JP 2019090977A JP 2020174651 A JP2020174651 A JP 2020174651A
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- citral
- polyphenol
- acacia
- gum
- derived
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- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 title claims abstract description 161
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 title claims abstract description 159
- 229940043350 citral Drugs 0.000 title claims abstract description 157
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 150000008442 polyphenolic compounds Chemical class 0.000 claims abstract description 85
- 235000013824 polyphenols Nutrition 0.000 claims abstract description 85
- 229920000084 Gum arabic Polymers 0.000 claims abstract description 77
- 235000010489 acacia gum Nutrition 0.000 claims abstract description 77
- 235000013305 food Nutrition 0.000 claims abstract description 10
- 235000011194 food seasoning agent Nutrition 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 238000003860 storage Methods 0.000 claims description 29
- 244000215068 Acacia senegal Species 0.000 claims description 27
- 235000006491 Acacia senegal Nutrition 0.000 claims description 27
- 239000000839 emulsion Substances 0.000 claims description 25
- 239000000205 acacia gum Substances 0.000 abstract description 52
- 239000000463 material Substances 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 2
- 239000000047 product Substances 0.000 description 49
- 235000005979 Citrus limon Nutrition 0.000 description 27
- 244000131522 Citrus pyriformis Species 0.000 description 27
- 230000000052 comparative effect Effects 0.000 description 27
- 239000000843 powder Substances 0.000 description 21
- 239000000796 flavoring agent Substances 0.000 description 15
- 235000019634 flavors Nutrition 0.000 description 15
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- 230000007423 decrease Effects 0.000 description 11
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- 229920001864 tannin Polymers 0.000 description 8
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- 238000011156 evaluation Methods 0.000 description 7
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- 229940087603 grape seed extract Drugs 0.000 description 5
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- 239000007787 solid Substances 0.000 description 5
- 239000001717 vitis vinifera seed extract Substances 0.000 description 5
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- 238000004945 emulsification Methods 0.000 description 4
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- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
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- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 240000004784 Cymbopogon citratus Species 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 241000196324 Embryophyta Species 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
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- 241001562081 Ikeda Species 0.000 description 2
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- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 description 2
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
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- 229940074391 gallic acid Drugs 0.000 description 2
- 235000004515 gallic acid Nutrition 0.000 description 2
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- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 1
- JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical compound C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-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
- 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 1
- PFPQMWRASYNLMZ-LGIMBNBCSA-N 2-(3,4-dihydroxyphenyl)-3-[(2s,3r,4r,5s,6r)-3,4-dihydroxy-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxychromen-4-one Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 PFPQMWRASYNLMZ-LGIMBNBCSA-N 0.000 description 1
- 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 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-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)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- NFLLKCVHYJRNRH-UHFFFAOYSA-N 8-chloro-1,3-dimethyl-7H-purine-2,6-dione 2-(diphenylmethyl)oxy-N,N-dimethylethanamine Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Cl)=N2.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 NFLLKCVHYJRNRH-UHFFFAOYSA-N 0.000 description 1
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 244000055850 Diospyros virginiana Species 0.000 description 1
- 241000792913 Ebenaceae Species 0.000 description 1
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- 235000015489 Emblica officinalis Nutrition 0.000 description 1
- 241000134874 Geraniales Species 0.000 description 1
- 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 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical 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 1
- 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 1
- 229920001991 Proanthocyanidin Polymers 0.000 description 1
- 241001092459 Rubus Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
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- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 229930014669 anthocyanidin Natural products 0.000 description 1
- 235000008758 anthocyanidins Nutrition 0.000 description 1
- 108010054251 arabinogalactan proteins Proteins 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229940102480 bilberry extract Drugs 0.000 description 1
- 235000019209 bilberry extract Nutrition 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229920002770 condensed tannin Polymers 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 235000020237 cranberry extract Nutrition 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 1
- NWKFECICNXDNOQ-UHFFFAOYSA-N flavylium Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 NWKFECICNXDNOQ-UHFFFAOYSA-N 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 235000015094 jam Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
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- 230000007774 longterm Effects 0.000 description 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 1
- 235000016046 other dairy product Nutrition 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 1
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- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
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Landscapes
- Non-Alcoholic Beverages (AREA)
- Fats And Perfumes (AREA)
- General Preparation And Processing Of Foods (AREA)
- Seasonings (AREA)
Abstract
Description
本発明は、シトラール残存率を向上させたシトラール含有組成物及びその製造方法等に関する。 The present invention relates to a citral-containing composition having an improved citral residual ratio, a method for producing the same, and the like.
シトラールは、レモンやオレンジ等の果実、レモングラスやレモンバーム等のハーブ、ショウガ等の香辛料に含まれる香気成分であり、爽快なレモン様の香味を呈し、様々な飲食品の嗜好性を高める目的で使用されている。しかしながら、シトラールは、比較的安定性が低く、熱や光等の影響によって経時的に減少するため、シトラールの安定性を向上させることを目的として種々の検討がなされている。 Citral is an aroma component contained in fruits such as lemon and orange, herbs such as lemongrass and lemon balm, and spices such as ginger. It has a refreshing lemon-like flavor and is intended to enhance the palatability of various foods and drinks. in use. However, since citral has relatively low stability and decreases with time due to the influence of heat, light, etc., various studies have been conducted for the purpose of improving the stability of citral.
特許文献１には、カキノキ科カキノキ属植物の果実又は未熟果由来のタンニン又は該タンニン精製物を含有することを特徴とする食品の香味劣化抑制剤が記載されており、特許文献２には、茶ポリフェノールを香味劣化抑制剤として含有することを特徴とする柑橘系フレーバー組成物が記載されている。また、特許文献３には、シトラールと、ブドウ種子抽出物、ビルベリー抽出物、アムラ抽出物、ルブス抽出物、赤ワインもろみ抽出物及びクランベリー抽出物から選択される一種又は二種以上の混合物であるシトラール分解抑制剤とを含んでなる柑橘類果実様香味組成物が記載されているが、依然としてシトラールの経時的な減少を、より効果的に抑制する方法が求められている。 Patent Document 1 describes a tannin derived from a fruit of a plant belonging to the genus Persimmon of the family Ebenaceae or an immature fruit, or an agent for suppressing flavor deterioration of foods, which is characterized by containing a purified product of the tannin. A tannin-based flavor composition characterized by containing tea polyphenol as a flavor deterioration inhibitor is described. Further, Patent Document 3 describes citral and citral which is one or a mixture of two or more kinds selected from grape seed extract, bilberry extract, amla extract, rubus extract, red wine syrup extract and cranberry extract. Although a citrus fruit-like flavor composition comprising a decomposition inhibitor has been described, there is still a need for a method for more effectively suppressing the decrease in citral over time.
本発明は、シトラールの経時的な減少を抑制したシトラール含有組成物及びその製造方法、並びに該組成物を使用した調味料又は飲食品を提供する。 The present invention provides a citral-containing composition in which the decrease of citral with time is suppressed, a method for producing the same, and a seasoning or food or drink using the composition.
発明者らは、シトラール含有物に、ポリフェノールを含むアカシアガムを含有させることによって、シトラールの経時的な減少を抑制できることを見出し、本発明を完成した。 The inventors have found that by adding acacia gum containing polyphenol to the citral-containing material, the decrease of citral over time can be suppressed, and the present invention has been completed.
すなわち、本発明は、以下の［１］〜［５］の態様に関する。
［１］シトラール及びポリフェノール含有アカシアガムを含む乳化物であって、シトラール１００重量部に対して、アカシアガム由来ポリフェノールを１５〜１００重量部含み、乳化物乾燥品の４０℃、２８日間保存後のシトラール残存率が保存前の７５％以上である、シトラール含有組成物。
［２］アカシアガムのポリフェノール含量が０．１重量％以上である、［１］記載のシトラール含有組成物。
［３］シトラール及びポリフェノール含有アカシアガムを含む乳化物であって、シトラール１００重量部に対して、アカシアガム由来ポリフェノールを１５〜１００重量部含み、乳化物乾燥品の４０℃、２８日間保存後のシトラール残存率が保存前の７５％以上である、シトラール含有組成物の製造方法。
［４］アカシアガムのポリフェノール含量が０．１重量％以上である、［３］記載のシトラール含有組成物の製造方法。
［５］［１］又は［２］記載のシトラール含有組成物を含む調味料又は飲食品。That is, the present invention relates to the following aspects [1] to [5].
[1] An emulsion containing citral and polyphenol-containing gum acacia, which contains 15 to 100 parts by weight of gum acacia-derived polyphenol with respect to 100 parts by weight of citral, and is a dried emulsion after storage at 40 ° C. for 28 days. A citral-containing composition having a citral residual ratio of 75% or more before storage.
[2] The citral-containing composition according to [1], wherein the polyphenol content of gum acacia is 0.1% by weight or more.
[3] An emulsion containing citral and polyphenol-containing gum acacia, which contains 15 to 100 parts by weight of gum acacia-derived polyphenol with respect to 100 parts by weight of citral, and is a dried emulsion after storage at 40 ° C. for 28 days. A method for producing a citral-containing composition, wherein the citral residual ratio is 75% or more before storage.
[4] The method for producing a citral-containing composition according to [3], wherein the polyphenol content of gum acacia is 0.1% by weight or more.
[5] A seasoning or food or drink containing the citral-containing composition according to [1] or [2].
本発明によって、シトラールの経時的な減少を強く抑制することができ、シトラールの香味を長期間保持することができるため、長期間保存においても、力価の高い爽快なレモン様の香味を有するシトラール含有組成物、並びに該組成物を使用した調味料又は飲食品を提供することができる。また、該シトラール含有組成物を製造できる製造方法を提供できる。 According to the present invention, the decrease of citral over time can be strongly suppressed, and the flavor of citral can be maintained for a long period of time. Therefore, citral having a refreshing lemon-like flavor with high potency even during long-term storage. The contained composition, and seasonings or foods and drinks using the composition can be provided. Further, it is possible to provide a production method capable of producing the citral-containing composition.
本発明のシトラール含有組成物は、シトラール及びポリフェノール含有アカシアガムを含む乳化物で、シトラール１００重量部に対して、アカシアガム由来ポリフェノールを１５〜１００重量部、好ましくは１７〜１００重量部、より好ましくは２０〜１００重量部含む。これによって、シトラールの経時的な減少を強く抑制することができ、シトラールの香味を長期間保持することができる。 The citral-containing composition of the present invention is a emulsion containing citral and polyphenol-containing acacia gum, and is more preferably 15 to 100 parts by weight, preferably 17 to 100 parts by weight, based on 100 parts by weight of citral. Includes 20-100 parts by weight. As a result, the decrease of citral over time can be strongly suppressed, and the flavor of citral can be maintained for a long period of time.
本発明のシトラール及びポリフェノール含有アカシアガムを含む乳化物は、シトラール、ポリフェノール含有アカシアガム及び水を乳化処理する工程を含む製造方法で得られ、液状品でもよく、乾燥品でもよいが、乾燥品の方がより強くシトラールの減少を抑制できる。乾燥は、本発明の組成物が得られれば特に限定されないが、噴霧乾燥、真空乾燥及び／又は凍結乾燥等が例示でき、噴霧乾燥が好ましい。 The emulsion containing citral and polyphenol-containing acacia gum of the present invention can be obtained by a production method including a step of emulsifying citral, polyphenol-containing acacia gum and water, and may be a liquid product, a dried product, or a dried product. It is possible to suppress the decrease of citral more strongly. The drying is not particularly limited as long as the composition of the present invention can be obtained, but spray drying, vacuum drying and / or freeze drying and the like can be exemplified, and spray drying is preferable.
本発明で行う乳化処理は、原料全体を１００重量％とした場合に、水を２０〜９０重量％含むのが好ましく、２５〜８０重量％含むのがより好ましく、３０〜７０重量％含むのがさらに好ましい。また、原料全体を１００重量％とした場合に、ポリフェノール含有アカシアガムを２〜７０重量％含むのが好ましく、５〜６０重量％含むのがより好ましく、１０〜５０重量％含むのがさらに好ましい。また、原料全体を１００重量％とした場合に、シトラールを０．０１〜２重量％含むのが好ましく、０．０２〜１重量％含むのがより好ましく、０．０５〜０．５重量％含むのがさらに好ましい。乳化処理は、前記成分を混合し、均質化すればよく、一般的な乳化方法で行うことができる。詳細には、乳化装置を用いて行うことができ、高圧ホモジナイザー、コロイドミル、超音波乳化機、ホモミキサー、ホモディスパー等を例示でき、二種類以上の装置を組み合わせてもよい。 The emulsification treatment performed in the present invention preferably contains 20 to 90% by weight, more preferably 25 to 80% by weight, and 30 to 70% by weight, when the whole raw material is 100% by weight. More preferred. Further, when the total amount of the raw material is 100% by weight, the polyphenol-containing acacia gum is preferably contained in an amount of 2 to 70% by weight, more preferably 5 to 60% by weight, and further preferably 10 to 50% by weight. Further, when the whole raw material is 100% by weight, it is preferable to contain 0.01 to 2% by weight of citral, more preferably 0.02 to 1% by weight, and 0.05 to 0.5% by weight. Is even more preferable. The emulsification treatment may be carried out by mixing and homogenizing the above components, and can be carried out by a general emulsification method. In detail, it can be carried out by using an emulsifying device, and examples thereof include a high-pressure homogenizer, a colloid mill, an ultrasonic emulsifying machine, a homomixer, and a homodisper, and two or more kinds of devices may be combined.
シトラールは、爽快なレモン様の香味を呈し、ゲラニアールとネラールとして存在しているが、本発明のシトラールは、特に限定されず、レモン、ライム、オレンジ等の果実、レモングラス、レモンバーム等のハーブ、ショウガ等の香辛料に含まれる香気成分が例示でき、該植物由来のシトラールを含む香料を用いることができる。 Citral has a refreshing lemon-like flavor and exists as geranial and neral, but the citral of the present invention is not particularly limited, and fruits such as lemon, lime and orange, herbs such as lemongrass and lemon balm, etc. The aroma component contained in a spice such as lemon can be exemplified, and a perfume containing the plant-derived citral can be used.
本発明に用いるポリフェノール含有アカシアガムは、ポリフェノールを含有するアカシアガムであれば特に限定されないが、好ましくは０．１０重量％以上、より好ましくは０．１２〜２重量％、さらに好ましくは０．１５〜１重量％のポリフェノールを含有するアカシアガムで、アカシアガム製品であるＦＩＢＲＥＧＵＭ（登録商標） Ｂ及びＦＩＢＲＥＧＵＭ ＴＡＮが例示できる。該製品は、一般的に安定剤として利用されるＩＮＳＴＡＮＴＧＵＭ ＡＡとは異なり、通常、食物繊維として利用されている。該ポリフェノールを含有するアカシアガムは、元々アカシアガムに含まれているポリフェノールを含有するものであって、アカシアガム由来ポリフェノール以外のポリフェノールをアカシアガム製品に含有させたものでは、本発明の効果は得られない。また、本発明のアカシアガムは、アラビノガラクタンタンパク質等のタンパク質を含んでおり、タンパク質含量は特に限定されないが、元々含まれる含量であって、一般的な約２重量％の含量が例示でき、１〜５重量％程度含むのが好ましい。 The polyphenol-containing gum acacia used in the present invention is not particularly limited as long as it is a polyphenol-containing gum acacia, but is preferably 0.10% by weight or more, more preferably 0.12 to 2% by weight, still more preferably 0.15. Examples of gums of acacia containing ~ 1% by weight of polyphenols include the gum products FIBREGUM (registered trademark) B and FIBREGUM TAN. The product is usually used as dietary fiber, unlike INSTANTGUM AA, which is generally used as a stabilizer. The acacia gum containing the polyphenol contains the polyphenol originally contained in the acacia gum, and the effect of the present invention is obtained when the acacia gum product contains a polyphenol other than the polyphenol derived from the acacia gum. I can't. Further, the acacia gum of the present invention contains a protein such as arabinogalactan protein, and the protein content is not particularly limited, but the content is originally contained, and a general content of about 2% by weight can be exemplified. It is preferably contained in an amount of about 1 to 5% by weight.
本発明のシトラール含有組成物は、シトラールにポリフェノール含有アカシアガムを含ませることで、シトラールの経時的な減少を強く抑制することができ、シトラールの香味を長期間保持できるが、乳化物を乾燥させた乳化物乾燥品について、４０℃、２８日間保存後のシトラール残存率が保存前の７５％以上であるのが好ましく、７７％以上であるのがより好ましく、８０％以上であるのがさらに好ましい。また、５０℃、１４日間保存後のシトラール残存率が保存前の８１％以上であるのが好ましく、８２％以上であるのがより好ましく、８３％以上であるのがさらに好ましい。 In the citral-containing composition of the present invention, by adding polyphenol-containing gum acacia gum to citral, the decrease of citral over time can be strongly suppressed, and the flavor of citral can be maintained for a long period of time, but the emulsion is dried. The citral residual ratio after storage at 40 ° C. for 28 days is preferably 75% or more, more preferably 77% or more, still more preferably 80% or more of the dried emulsion product. .. Further, the residual rate of citral after storage at 50 ° C. for 14 days is preferably 81% or more before storage, more preferably 82% or more, and further preferably 83% or more.
本発明のシトラール含有組成物は、上記のとおり、ポリフェノール含有アカシアガムを適量用いて乳化物とすることで、力価の高い爽快なレモン様の香味を長期間保持しているシトラール含有組成物が得られ、該組成物を調味料や各飲食品に使用することにより該香味を長期間保持する調味料又は各飲食品を提供できる。調味料及び飲食品は特に限定されないが、ドレッシング、シーズニングパウダー、非アルコール飲料、アルコール飲料等の飲料、アイスクリーム等の冷菓、クッキー、ケーキ等の洋菓子、ヨーグルト等の乳製品、飴類、ジャム、フィリング、チップス、揚げ菓子等が例示できる。 As described above, the citral-containing composition of the present invention is a citral-containing composition that retains a high-potency and refreshing lemon-like flavor for a long period of time by using an appropriate amount of polyphenol-containing gum acacia to form an emulsion. By using the obtained composition in a seasoning or each food or drink, a seasoning or each food or drink that retains the flavor for a long period of time can be provided. Seasonings and foods and drinks are not particularly limited, but dressings, seasoning powders, non-alcoholic beverages, alcoholic beverages and other beverages, ice cream and other frozen desserts, cookies, cakes and other Western confectionery, yogurt and other dairy products, candy, jam, etc. Examples include fillings, chips, and fried confectionery.
以下、実施例を示して本発明を具体的に説明するが、本発明は以下の例によって限定されるものではない。尚、本発明において、残存率以外の％は別記がない限り全て重量％である。 Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited to the following examples. In the present invention,% other than the residual ratio is all weight% unless otherwise specified.
（１．アカシアガム中のポリフェノール含有量の測定）
本実施例に用いるアカシアガム製品３品（ＩＮＳＴＡＮＴＧＵＭ ＡＡ、ＦＩＢＲＥＧＵＭ Ｂ、ＦＩＢＲＥＧＵＭ ＴＡＮ、何れも炭水化物含有量：８０％以上、ネキシラ株式会社製）について、フォーリン・チオカルト法にて、ポリフェノール含有量（没食子酸換算）を測定した。結果を表１に示した。(1. Measurement of polyphenol content in gum acacia)
Three acacia gum products (INSTANTGUM AA, FIBREGUM B, FIBREGUM TAN, all of which have a carbohydrate content of 80% or more, manufactured by Nekishira Co., Ltd.) used in this example have a polyphenol content (gallic acid) by the Folin-Ciocalt method. Conversion) was measured. The results are shown in Table 1.
（２．シトラール含有パウダーの調製：各種抗酸化成分のシトラールへの影響）
アカシアガムとしてＩＮＳＴＡＮＴＧＵＭ ＡＡ １８８ｇとＦＩＢＲＥＧＵＭ Ｂ ９２ｇを水道水４９０ｇに溶解させた後、濃縮レモン果汁（固形分：４２％、雄山株式会社製）１９０ｇ、柑橘香料Ａ（シトラール含有量：３．０％、池田糖化工業株式会社製）４０ｇを加えて、高圧ホモジナイザーを用いて乳化処理（４０ＭＰａ）することにより、シトラール含有レモン乳化液９５０ｇを得た。次に、得られたシトラール含有レモン乳化液の一部を、スプレードライヤーを用いて噴霧乾燥することにより、シトラール含有レモンパウダー（実施品１）５０ｇを得た。パウダー中の配合比率、シトラール含有量、各アカシアガム由来ポリフェノール含有量、アカシアガム由来ポリフェノールの合計及びシトラールに対するアカシアガム由来ポリフェノールの比率を表２に示した。(2. Preparation of citral-containing powder: Effect of various antioxidant components on citral)
After dissolving 188 g of INSTANTGUM AA and 92 g of FIBREGUM B as acacia gum in 490 g of tap water, 190 g of concentrated lemon juice (solid content: 42%, manufactured by Oyama Co., Ltd.), citral flavor A (citral content: 3.0%, 40 g of (manufactured by Ikeda Saccharification Industry Co., Ltd.) was added and emulsified (40 MPa) using a high-pressure homogenizer to obtain 950 g of a citral-containing lemon emulsified solution. Next, a part of the obtained citral-containing lemon emulsion was spray-dried using a spray dryer to obtain 50 g of citral-containing lemon powder (Example product 1). Table 2 shows the blending ratio in the powder, the citral content, the content of each acacia gum-derived polyphenol, the total amount of acacia gum-derived polyphenols, and the ratio of acacia gum-derived polyphenols to citral.
ＦＩＢＲＥＧＵＭ Ｂ ９２ｇの代わりに、粉末還元麦芽糖（レシス（登録商標）、三菱商事フードテック株式会社製）９２ｇ（比較例１−１）、粉末還元麦芽糖８６ｇ及び抗酸化剤としてビタミンＥ（理研Ｅオイル（登録商標）６００Ｎ、理研ビタミン株式会社製）６ｇ（比較例１−２）、粉末還元麦芽糖８７ｇ及び抗酸化剤として酵素処理ルチン（αＧルチン、東洋精糖株式会社製）５ｇ（比較例１−３）、粉末還元麦芽糖９０ｇ及び抗酸化剤として酵素処理ヘスペリジン（αＧヘスペリジン、東洋精糖株式会社製）２ｇ（比較例１−４）、粉末還元麦芽糖８９ｇ及び抗酸化剤としてＬ−アスコルビン酸ナトリウム（渡辺ケミカル株式会社製）３ｇ（比較例１−５）、又は粉末還元麦芽糖８９ｇ及び抗酸化剤として茶カテキン（サンフェノン（登録商標）ＥＧＣＧ−ＯＰ、太陽化学株式会社製）３ｇ（比較例１−６）を使用し、それ以外は［００１９］と同様の工程で製造し、各シトラール含有レモンパウダー（比較品１−１〜１−６）５０ｇを得た。パウダー中の配合比率、シトラール含有量、各アカシアガム由来ポリフェノール含有量、アカシアガム由来ポリフェノールの合計及びシトラールに対するアカシアガム由来ポリフェノールの比率を表２に示した。 Instead of FIBREGUM B 92g, powder reduced malt sugar (Resis (registered trademark), manufactured by Mitsubishi Corporation Foodtech Co., Ltd.) 92g (Comparative Example 1-1), powder reduced malt sugar 86g and vitamin E (RIKEN E oil (RIKEN E oil)) as an antioxidant. Registered trademark) 600N, manufactured by RIKEN Vitamin Co., Ltd. 6 g (Comparative Example 1-2), powdered reduced malt sugar 87 g and enzyme-treated rutin (αG rutin, manufactured by Toyo Refinery Co., Ltd.) 5 g as an antioxidant (Comparative Example 1-3) , 90 g of powdered reduced malt sugar and 2 g of enzyme-treated hesperidin (αG hesperidin, manufactured by Toyo Seisaku Co., Ltd.) as an antioxidant (Comparative Example 1-4), 89 g of powdered reduced malt sugar and sodium L-ascorbate as an antioxidant (Watanabe Chemical Co., Ltd.) 3 g (Comparative Example 1-5) or 3 g (Comparative Example 1-6) of powdered reduced malt sugar and tea catechin (Sanphenon (registered trademark) EGCG-OP, manufactured by Taiyo Kagaku Co., Ltd.) as an antioxidant are used. However, other than that, the product was produced in the same process as in [0019] to obtain 50 g of each citral-containing lemon powder (comparative products 1-1 to 1-6). Table 2 shows the blending ratio in the powder, the citral content, the content of each acacia gum-derived polyphenol, the total amount of acacia gum-derived polyphenols, and the ratio of acacia gum-derived polyphenols to citral.
［評価試験１］
実施品１、比較品１−１〜１−６について４０℃、２８日間の保存加速試験を実施し、シトラール含有量を指標として各シトラール含有レモンパウダーの経時変化を確認した。なお、シトラール含有量は、ＨＰＬＣを用いて、以下の方法で測定した。結果を表２に示した。
＜ＨＰＬＣ測定条件＞
・検出器：ＵＶ検出器（２４０ｎｍ）
・カラム：ＩｎｅｒｔＳｕｓｔａｉｎ Ｃ１８（内径４．６ｍｍ、長さ２５０ｍｍ）
・移動相：４０％メタノール水溶液から８０％メタノール水溶液へグラジエント
・流速：０．８ｍｌ／分
・カラム温度：４０℃
・標品：シトラール（純度＞９６％、東京化成工業株式会社製）をメタノールに溶解して検量線を作成した。
・検体：各試料をジメチルスルホキシドに溶解した後、適宜希釈したもの。[Evaluation test 1]
A storage acceleration test was carried out at 40 ° C. for 28 days for the product 1 and the comparative products 1-1 to 1-6, and the change over time of each citral-containing lemon powder was confirmed using the citral content as an index. The citral content was measured by the following method using HPLC. The results are shown in Table 2.
<HPLC measurement conditions>
-Detector: UV detector (240 nm)
-Column: InertStain C18 (inner diameter 4.6 mm, length 250 mm)
-Mobile phase: From 40% aqueous methanol solution to 80% aqueous methanol solution Gradient-Flow velocity: 0.8 ml / min-Column temperature: 40 ° C
-Standard: Citral (purity> 96%, manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in methanol to prepare a calibration curve.
-Sample: Each sample is dissolved in dimethyl sulfoxide and then diluted appropriately.
シトラールに対するアカシアガム由来ポリフェノールの比率が２４．０％である実施品１では、４０℃、２８日間の保存後もシトラール含有量が高く、保存前の９１．１％という高い残存率だった。一方で、シトラールに対するアカシアガム由来ポリフェノールの比率が１２．７％である比較品１−１、及び比較品１−１にさらに各種抗酸化剤を添加した比較品１−２〜１−６では、実施品１に比べ、保存後にシトラール含有量の低下がみられ、残存率も保存前の６７．６〜７３．１％と、実施品１より低かった。 In product 1 in which the ratio of acacia gum-derived polyphenol to citral was 24.0%, the citral content was high even after storage at 40 ° C. for 28 days, and the residual rate was as high as 91.1% before storage. On the other hand, in Comparative Products 1-1 in which the ratio of acacia gum-derived polyphenols to citral was 12.7%, and Comparative Products 1-2-1-6 in which various antioxidants were further added to Comparative Products 1-1. Compared with the product 1, the citral content was reduced after storage, and the residual rate was 67.6 to 73.1% before storage, which was lower than that of product 1.
よって、シトラールとアカシアガムとを含むシトラール含有レモンパウダーにおいて、アカシアガム由来ポリフェノールをシトラールに対して２４．０％含ませた方が、乾燥物中のシトラールをより安定に保つことができ、シトラールの減少を抑制できることが分かった。さらに、アカシアガムを使用してシトラール含有レモンパウダーを調製しても、シトラールに対するアカシアガム由来ポリフェノールの比率が低い場合や、アカシアガム以外のポリフェノールやその他抗酸化物質を含有させた場合は、効果は限定的であり、アカシアガム由来ポリフェノールを一定量含有させることが、シトラールの減少抑制に重要であることが分かった。 Therefore, in the citral-containing lemon powder containing citral and gum acacia, it is possible to keep the citral in the dried product more stable by adding 24.0% of the polyphenol derived from gum acacia to the citral, and the citral It was found that the decrease could be suppressed. Furthermore, even if citral-containing lemon powder is prepared using gum acacia, if the ratio of polyphenols derived from gum acacia to citral is low, or if polyphenols other than gum acacia and other antioxidants are contained, the effect is effective. It was found that it is important to contain a certain amount of gum acacia-derived polyphenols in order to suppress the decrease of citral.
（３．シトラール含有乳化液の調製：シトラールに対するアカシアガム由来ポリフェノール比率の影響）
アカシアガムとしてＦＩＢＲＥＧＵＭ Ｂ ２３０ｇを水道水５７７ｇに溶解させた後、濃縮レモン果汁（固形分：４２％）１６０ｇ、柑橘香料Ｂ（シトラール含有量：４．５％、池田糖化工業株式会社製）３３ｇを加えて、高圧ホモジナイザーを用いて乳化処理（４０ＭＰａ）することにより、シトラール含有レモン乳化液（実施品２−１）９５０ｇを得た。乳化液中の固形物の配合比率、シトラール含有量、各アカシアガム由来ポリフェノール含有量、アカシアガム由来ポリフェノールの合計及びシトラールに対するアカシアガム由来ポリフェノールの比率を表３に示した。(3. Preparation of citral-containing emulsion: Effect of ratio of acacia gum-derived polyphenols to citral)
After dissolving 230 g of FIBREGUM B as acacia gum in 577 g of tap water, 160 g of concentrated lemon juice (solid content: 42%) and 33 g of citral flavor B (citral content: 4.5%, manufactured by Ikeda Saccharification Industry Co., Ltd.) are added. In addition, 950 g of a citral-containing lemon emulsified solution (Example product 2-1) was obtained by emulsification treatment (40 MPa) using a high-pressure homogenizer. Table 3 shows the mixing ratio of solids in the emulsion, the citral content, the content of each acacia gum-derived polyphenol, the total amount of acacia gum-derived polyphenols, and the ratio of acacia gum-derived polyphenols to citral.
ＦＩＢＲＥＧＵＭ Ｂ ２３０ｇの代わりに、ＦＩＢＲＥＧＵＭ ＴＡＮ ２３０ｇ（実施例２−２）、ＦＩＢＲＥＧＵＭ Ｂ １６４ｇ及びＩＮＳＴＡＮＴＧＵＭ ＡＡ ６６ｇ（実施例２−３）、ＦＩＢＲＥＧＵＭ Ｂ １１５ｇ及びＩＮＳＴＡＮＴＧＵＭ ＡＡ １１５ｇ（実施例２−４）、又はＩＮＳＴＡＮＴＧＵＭ ＡＡ ２３０ｇ（比較例２）を使用し、それ以外は［００２５］と同様の工程で製造し、各シトラール含有レモン乳化液（実施品２−２〜２−４及び比較品２）９５０ｇを得た。乳化液中の固形物の配合比率、シトラール含有量、各アカシアガム由来ポリフェノール含有量、アカシアガム由来ポリフェノールの合計及びシトラールに対するアカシアガム由来ポリフェノールの比率を表３に示した。 Instead of FIBREGUM B 230g, FIBREGUM TAN 230g (Example 2-2), FIBREGUM B 164g and INSTANTGUM AA 66g (Example 2-3), FIBERGUM B 115g and INSTANTGUM Example 2-2g, INSTANTGUM B 115g 230 g of AA (Comparative Example 2) was used, and 950 g of each citral-containing lemon emulsified solution (Example product 2-2-2-4 and Comparative product 2) was obtained by producing the product in the same process as in [0025] except for the above. .. Table 3 shows the mixing ratio of solids in the emulsion, the citral content, the content of each acacia gum-derived polyphenol, the total amount of acacia gum-derived polyphenols, and the ratio of acacia gum-derived polyphenols to citral.
［評価試験２］
実施品２−１〜２−４及び比較品２について８０℃、２時間の保存加速試験を実施し、シトラール含有量を指標として各シトラール含有レモン乳化液の経時変化を確認した。なお、シトラール含有量は、評価試験１と同様の方法で測定した。結果を表３に示した。[Evaluation test 2]
A storage acceleration test at 80 ° C. for 2 hours was carried out for the product 2-1 to 2-4 and the comparative product 2, and the time course of each citral-containing lemon emulsion was confirmed using the citral content as an index. The citral content was measured by the same method as in Evaluation Test 1. The results are shown in Table 3.
シトラールに対するアカシアガム由来ポリフェノールの比率が１７．９〜８４．０％である実施品２−１〜２−４の方が、該比率が１２．４％である比較品２に比べ、８０℃、２時間保存後の乳化液中のシトラール残存率が高かった。 The ratio of acacia gum-derived polyphenols to citral was 17.9 to 84.0%, and the product 2-1 to 2-4 was 80 ° C., compared to the comparative product 2, which had a ratio of 12.4%. The residual rate of citral in the emulsion after storage for 2 hours was high.
よって、シトラールとアカシアガムとを含むシトラール含有レモン乳化液において、アカシアガム由来ポリフェノールをシトラールに対して１５％以上含ませることで、乳化液中でもシトラールを安定に保つことができ、シトラールの減少を抑制できることが分かった。 Therefore, in the citral-containing lemon emulsion containing citral and gum acacia, by adding 15% or more of the polyphenol derived from gum acacia to the citral, the citral can be kept stable even in the emulsion and the decrease of citral is suppressed. I found that I could do it.
（４．シトラール含有パウダーの調製：シトラールに対するアカシアガム由来ポリフェノール比率の影響）
実施品２−１、２−３及び比較品２のシトラール含有レモン乳化液の一部を、スプレードライヤーを用いて噴霧乾燥することにより、シトラール含有レモンパウダー（実施品３−１、３−２及び比較品３）５０ｇを得た。アカシアガム由来ポリフェノールの合計及びシトラールに対するアカシアガム由来ポリフェノールの比率を表４に示した。(4. Preparation of citral-containing powder: Effect of ratio of acacia gum-derived polyphenols to citral)
By spray-drying a part of the citral-containing lemon emulsions of Examples 2-1 and 2-3 and Comparative Product 2 using a spray dryer, citral-containing lemon powder (Equipment 3-1 and 3-2 and) Comparative product 3) 50 g was obtained. Table 4 shows the total amount of acacia gum-derived polyphenols and the ratio of acacia gum-derived polyphenols to citral.
［評価試験３］
実施品３−１、３−２及び比較品３について５０℃、１４日間の保存加速試験を実施し、シトラール含有量を指標として各シトラール含有レモンパウダーの経時変化を確認した。なお、シトラール含有量は、評価試験１と同様の方法で測定した。結果を表４に示した。[Evaluation test 3]
A storage acceleration test was carried out at 50 ° C. for 14 days for the products 3-1 and 3-2 and the comparative product 3, and the time course of each citral-containing lemon powder was confirmed using the citral content as an index. The citral content was measured by the same method as in Evaluation Test 1. The results are shown in Table 4.
シトラールに対するアカシアガム由来ポリフェノールの比率が２３．３又は２０．２％である実施品３−１又は３−２では、５０℃、１４日間の保存後もシトラール含有量が高く、保存前の９０．５％又は８３．８という高い残存率だった。一方で、シトラールに対するアカシアガム由来ポリフェノールの比率が１２．４％である比較品３では、実施品３−１又は３−２に比べ、保存後にシトラール含有量の低下がみられ、残存率も保存前の７３．０％と、実施品３−１又は３−２より低かった。 In the product 3-1 or 3-2 in which the ratio of the acacia gum-derived polyphenol to citral was 23.3 or 20.2%, the citral content was high even after storage at 50 ° C. for 14 days, and 90. It had a high survival rate of 5% or 83.8. On the other hand, in Comparative Product 3 in which the ratio of acacia gum-derived polyphenol to citral was 12.4%, the citral content was reduced after storage and the residual rate was also preserved as compared with the product 3-1 or 3-2. It was 73.0% of the previous one, which was lower than that of the product 3-1 or 3-2.
よって、シトラールとアカシアガムとを含むシトラール含有レモンパウダーにおいて、アカシアガム由来ポリフェノールをシトラールに対して２０％以上含ませることで、乾燥物中のシトラールをより安定に保つことができ、シトラールの減少を抑制できることが分かった。 Therefore, in the citral-containing lemon powder containing citral and gum acacia, by adding 20% or more of the polyphenol derived from gum acacia gum to the citral, the citral in the dried product can be kept more stable and the citral can be reduced. It turned out that it can be suppressed.
（５．アカシアタンニン中のポリフェノール含有量の測定）
アカシア由来のポリフェノールとしてアカシアタンニン（川村通商株式会社製）について、フォーリン・チオカルト法にて、ポリフェノール含有量（没食子酸換算）を測定した。結果を表５に示した。(5. Measurement of polyphenol content in acacia tannin)
The polyphenol content (gallic acid equivalent) of acacia tannin (manufactured by Kawamura Tsusho Co., Ltd.) as a polyphenol derived from acacia was measured by the Folin-Ciocalt method. The results are shown in Table 5.
（６．シトラール含有パウダーの調製：各ポリフェノール成分のシトラールへの影響）
アカシアガムとしてＦＩＢＲＥＧＵＭ Ｂ ２３０ｇを水道水５７７ｇに溶解させた後、濃縮レモン果汁（固形分：４２％）１６０ｇ、柑橘香料Ｂ（シトラール含有量：４．５％）３３ｇを加えて、高圧ホモジナイザーを用いて乳化処理（４０ＭＰａ）することにより、シトラール含有レモン乳化液９５０ｇを得た。次に、得られたシトラール含有レモン乳化液の一部を、スプレードライヤーを用いて噴霧乾燥することにより、シトラール含有レモンパウダー（実施品４）５０ｇを得た。パウダー中の配合比率、シトラール含有量、各アカシアガム由来ポリフェノール含有量、アカシアガム由来ポリフェノールの合計、シトラールに対するアカシアガム由来ポリフェノールの比率、アカシアガム由来ポリフェノールとその他ポリフェノールとの合計及びシトラールに対するアカシアガム由来ポリフェノールとその他ポリフェノールとの合計の比率を表６に示した。(6. Preparation of citral-containing powder: Effect of each polyphenol component on citral)
After dissolving 230 g of FIBREGUM B as acacia gum in 577 g of tap water, 160 g of concentrated lemon juice (solid content: 42%) and 33 g of citral flavor B (citral content: 4.5%) are added, and a high-pressure homogenizer is used. By emulsifying (40 MPa), 950 g of a citral-containing lemon emulsion was obtained. Next, a part of the obtained citral-containing lemon emulsion was spray-dried using a spray dryer to obtain 50 g of citral-containing lemon powder (Example product 4). Blending ratio in powder, citral content, content of each acacia gum-derived polyphenol, total of acacia gum-derived polyphenols, ratio of acacia gum-derived polyphenols to citral, total of acacia gum-derived polyphenols and other polyphenols, and acacia gum-derived to citral Table 6 shows the total ratio of polyphenols and other polyphenols.
ＦＩＢＲＥＧＵＭ Ｂ ２３０ｇの代わりに、ＩＮＳＴＡＮＴＧＵＭ ＡＡ ２３０ｇ及びアカシアタンニン０．２３ｇ（比較例４−１）、ＩＮＳＴＡＮＴＧＵＭ ＡＡ ２３０ｇ及びアカシアタンニン１ｇ（比較例４−２）、又はＩＮＳＴＡＮＴＧＵＭ ＡＡ ２２２ｇ及びポリフェノールの一種であるプロトアントシアニジンを高含有するブドウ種子抽出物（プロトアントシアニジン８３％以上、グラヴィノール（登録商標）、キッコーマンバイオケミファ株式会社製）８ｇ（比較例４−３）を使用し、それ以外は［００３８］と同様の工程で製造し、各シトラール含有レモン乳化液（比較品４−１〜４−３）５０ｇを得た。パウダー中の配合比率、シトラール含有量、各アカシアガム由来ポリフェノール含有量、アカシアガム由来ポリフェノールの合計、シトラールに対するアカシアガム由来ポリフェノールの比率、アカシアガム由来ポリフェノールとその他ポリフェノールとの合計及びシトラールに対するアカシアガム由来ポリフェノールとその他ポリフェノールとの合計の比率を表６に示した。 Instead of FIBREGUM B 230g, INSTANTGUM AA 230g and acacia tannin 0.23g (Comparative Example 4-1), INSTANTGUM AA 230g and acacia tannin 1g (Comparative Example 4-2), or INSTANTGUM AA 222g and a type of polyphenol. 8 g (Comparative Example 4-3) of a grape seed extract containing a high amount of anthocyanidins (proanthocyanidin 83% or more, Gravinol (registered trademark), manufactured by Kikkoman Biochemifa Co., Ltd.) was used, and other than that, the same as in [0038]. 50 g of each citral-containing lemon emulsion (comparative products 4-1 to 4-3) was obtained. Blending ratio in powder, citral content, content of each acacia gum-derived polyphenol, total of acacia gum-derived polyphenols, ratio of acacia gum-derived polyphenols to citral, total of acacia gum-derived polyphenols and other polyphenols, and acacia gum-derived to citral Table 6 shows the total ratio of polyphenols and other polyphenols.
［評価試験４］
実施品４及び比較品４−１〜４−３について５０℃、１４日間の保存加速試験を実施し、シトラール含有量を指標として各シトラール含有レモンパウダーの経時変化を確認した。なお、シトラール含有量は、評価試験１と同様の方法で測定した。結果を表６に示した。[Evaluation test 4]
An accelerated storage test was carried out at 50 ° C. for 14 days for the product 4 and the comparative products 4-1 to 4-3, and the change over time of each citral-containing lemon powder was confirmed using the citral content as an index. The citral content was measured by the same method as in Evaluation Test 1. The results are shown in Table 6.
シトラールに対するアカシアガム由来ポリフェノールの比率が２３．３％である実施品４では、５０℃、１４日間の保存後もシトラール含有量が高く、保存前の９０．５％という高い残存率だった。一方で、シトラールに対するアカシアガム由来ポリフェノールの比率１２．４％に、さらにアカシアタンニンを添加して、シトラールに対するポリフェノールの合計が２４．４％である比較品４−１、６３．８％である比較品４−２では、実施品４に比べ、保存後にシトラール含有量の低下がみられ、残存率も保存前の７２．２〜７７．６％と、実施品４より低かった。また、シトラールに対するアカシアガム由来ポリフェノールの比率１２．０％に、さらにプロトアントシアニジンを高含有するブドウ種子抽出物を添加して、シトラールに対するポリフェノールの合計が４５５％以上である比較品４−３でも、実施品４に比べ、保存後にシトラール含有量の低下がみられ、残存率も保存前の８０．２％と、実施品４より低かった。また、比較品４−３は、ブドウ種子抽出物の色の影響で、シトラール含有レモンパウダーが淡褐色になり、色の点からも製品化は困難と思われた。 In the product 4 in which the ratio of the acacia gum-derived polyphenol to the citral was 23.3%, the citral content was high even after storage at 50 ° C. for 14 days, and the residual rate was as high as 90.5% before storage. On the other hand, the ratio of acacia gum-derived polyphenols to citral was 12.4%, and acacia tannin was further added, so that the total amount of polyphenols to citral was 24.4%. Comparative products 4-1 and 63.8%. In product 4-2, the citral content was reduced after storage as compared with product 4, and the residual rate was 72.2 to 77.6% before storage, which was lower than that of product 4. Further, in Comparative Product 4-3 in which the total amount of polyphenols to citral is 455% or more by adding a grape seed extract containing a high amount of proanthocyanidins to the ratio of acacia gum-derived polyphenols to citral of 12.0%. Compared with the product 4, the citral content was reduced after storage, and the residual rate was 80.2% before storage, which was lower than that of product 4. In addition, the comparative product 4-3 had a light brown color of the citral-containing lemon powder due to the influence of the color of the grape seed extract, and it was considered difficult to commercialize it in terms of color.
以上より、シトラールに対するアカシアガム由来ポリフェノールの比率が低いものに、最終的なポリフェノール比率が同等になるようアカシア由来のポリフェノールを別途添加しても、効果は限定的であり、また、シトラール分解抑制効果が知られているブドウ種子抽出物を、別途添加しても、アカシアガム由来ポリフェノールほどのシトラール減少抑制効果は見られず、アカシアガム由来ポリフェノールを一定量含有させることで、高いシトラール減少抑制効果が得られることが分かった。 From the above, even if acacia-derived polyphenols are separately added to those having a low ratio of gum-derived polyphenols to citral so that the final polyphenol ratio becomes the same, the effect is limited, and the effect of suppressing citral decomposition is also limited. Even if a grape seed extract known to be added is added separately, the effect of suppressing the reduction of citral is not as high as that of polyphenols derived from acacia gum. It turned out to be obtained.
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| JP2012255153A (en) * | 1999-11-18 | 2012-12-27 | Givaudan Nederland Services Bv | Stable spray dried composition in carbohydrate support and method for preparing the same |
| JP2014518091A (en) * | 2011-07-01 | 2014-07-28 | ペプシコ，インコーポレイテッド | Coacervate complex, method and food |
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| JP2008543831A (en) * | 2005-06-13 | 2008-12-04 | カーギル インコーポレイテッド | Cyclodextrin inclusion complex and method for producing the same |
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