JP5826674B2 - Gardenia yellowish liquid formulation - Google Patents
Gardenia yellowish liquid formulation Download PDFInfo
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- JP5826674B2 JP5826674B2 JP2012047441A JP2012047441A JP5826674B2 JP 5826674 B2 JP5826674 B2 JP 5826674B2 JP 2012047441 A JP2012047441 A JP 2012047441A JP 2012047441 A JP2012047441 A JP 2012047441A JP 5826674 B2 JP5826674 B2 JP 5826674B2
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- 239000012669 liquid formulation Substances 0.000 title claims description 10
- 240000001972 Gardenia jasminoides Species 0.000 title description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- SEBIKDIMAPSUBY-ARYZWOCPSA-N Crocin Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)OC(=O)C(C)=CC=CC(C)=C\C=C\C=C(/C)\C=C\C=C(C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1)O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SEBIKDIMAPSUBY-ARYZWOCPSA-N 0.000 claims description 26
- 239000009627 gardenia yellow Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 20
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims description 18
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims description 18
- 235000002949 phytic acid Nutrition 0.000 claims description 18
- 229940068041 phytic acid Drugs 0.000 claims description 18
- 239000000467 phytic acid Substances 0.000 claims description 18
- 229920000858 Cyclodextrin Polymers 0.000 claims description 16
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 13
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 13
- 241000394567 Viola pubescens Species 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 description 19
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 239000000284 extract Substances 0.000 description 15
- 239000013522 chelant Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000001179 sorption measurement Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 235000013305 food Nutrition 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
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- 239000000126 substance Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229930002875 chlorophyll Natural products 0.000 description 3
- 235000019804 chlorophyll Nutrition 0.000 description 3
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000013402 health food Nutrition 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 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
- 235000018958 Gardenia augusta Nutrition 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000011869 dried fruits Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 235000001727 glucose Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 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
- 241000257465 Echinoidea Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- IBFYXTRXDNAPMM-BVTMAQQCSA-N Geniposide Chemical compound O([C@@H]1OC=C([C@@H]2[C@H]1C(=CC2)CO)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O IBFYXTRXDNAPMM-BVTMAQQCSA-N 0.000 description 1
- IBFYXTRXDNAPMM-FZEIBHLUSA-N Geniposide Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@H]2[C@@H]1CC=C2CO IBFYXTRXDNAPMM-FZEIBHLUSA-N 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
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- FYGDTMLNYKFZSV-DZOUCCHMSA-N alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp 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]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-DZOUCCHMSA-N 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- VGLLGNISLBPZNL-RBUKDIBWSA-N arborescoside Natural products O=C(OC)C=1[C@@H]2C([C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)OC=1)=C(CO)CC2 VGLLGNISLBPZNL-RBUKDIBWSA-N 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- 150000001720 carbohydrates Chemical class 0.000 description 1
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- 235000013339 cereals Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
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- 239000000796 flavoring agent Substances 0.000 description 1
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- 239000000576 food coloring agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
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- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
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- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
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- Coloring Foods And Improving Nutritive Qualities (AREA)
Description
本発明は、クチナシ黄色素の液体製剤に関する。 The present invention relates to a liquid formulation of gardenia yellow.
クチナシ黄色素は、アカネ科クチナシ（Ｇａｒｄｅｎｉａ ａｕｇｕｓｔａ ＭＥＲＲＩＬ 、Ｇａｒｄｅｎｉａ ｊａｓｍｉｎｏｉｄｅｓ ＥＬＬＩＳ）の果実に含まれる色素であり、わが国においては古くから食用の着色料として利用されてきた。 Gardenia yellow is a pigment contained in the fruits of the gardenia gardenia (Gardenia augusta MERRIL, Gardenia jasminoides ELLIS), and has long been used as a food coloring in Japan.
クチナシ黄色素の製剤化は、通常乾燥されたクチナシ果実を水またはアルコール及びそれらの混合液で抽出し、得られた抽出液をろ過して不純物を除いた後濃縮した濃縮物を、逆浸透膜或いは合成吸着樹脂等によりゲニポサイド等のイリドイド配糖体を除去し、液体、粉末或いは顆粒状に調製するなどの方法により行われている。 The formulation of gardenia yellow is usually obtained by extracting dried gardenia fruits with water or alcohol and a mixture thereof, filtering the obtained extract to remove impurities, and then concentrating the concentrated concentrate into a reverse osmosis membrane. Alternatively, iridoid glycosides such as geniposide are removed with a synthetic adsorption resin or the like, and the liquid is prepared in a liquid, powder or granular form.
この内、液体製剤は、保存中の腐敗を防止するため、エタノール、プロピレングリコール等のアルコール類、グリセリン、ソルビトール、還元糖等の糖アルコール類を含む水溶液が溶媒として用いられるが、中でもエタノールと水の混合液が好ましく使用される。 Among these liquid preparations, an aqueous solution containing alcohols such as ethanol and propylene glycol, and sugar alcohols such as glycerin, sorbitol, and reducing sugar is used as a solvent to prevent spoilage during storage. The liquid mixture of is preferably used.
しかし、エタノールと水の混合液を溶媒として使用したクチナシ黄色素の製剤を低温に保存すると不溶物が発生して沈殿し、製品価値を低下させるという問題があった。 However, there is a problem that when a gardenia yellow pigment preparation using a mixed solution of ethanol and water as a solvent is stored at a low temperature, an insoluble matter is generated and precipitates, thereby reducing the product value.
この問題を解決するため、上記製剤に特定のリン酸塩を添加する方法が提案されている（特許文献１）。しかし、リン酸塩を配合した色素製剤を食品に添加すると、リン酸塩が当該食品の物性に影響を及ぼすことが懸念される場合がある。 In order to solve this problem, a method of adding a specific phosphate to the above preparation has been proposed (Patent Document 1). However, when a pigment preparation containing a phosphate is added to food, there is a concern that the phosphate may affect the physical properties of the food.
一方、リン酸塩を使用せずに上記問題を解決する方法も提案されているが（特許文献２および３）、不溶物の発生を抑制可能な期間の点で必ずしも満足できるものではない。 On the other hand, although a method for solving the above problem without using a phosphate has been proposed (Patent Documents 2 and 3), it is not always satisfactory in terms of a period during which generation of insoluble matter can be suppressed.
本発明は、低温保存下での不溶物の発生がさらに長期間抑制されたクチナシ黄色素の液体製剤を提供することを課題とする。 It is an object of the present invention to provide a liquid preparation of gardenia yellow, in which the generation of insoluble substances under low temperature storage is further suppressed for a long period of time.
本発明者等は、上記課題を解決するために鋭意研究を重ねた結果、フィチン酸およびγ−シクロデキストリンを添加したクチナシ黄色素の液体製剤は、低温保存下での不溶物の発生が長期間抑制されることを見出し、本発明を完成した。
即ち、本発明は、
（１）フィチン酸およびγ−シクロデキストリンを含有することを特徴とするクチナシ黄色素の液体製剤、
（２）エタノールと水の混合液が溶媒として使用されていることを特徴とする前記（１）に記載のクチナシ黄色素の液体製剤、を提供するものである。
As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that the liquid preparation of gardenia chlorophyll added with phytic acid and γ-cyclodextrin has a long generation of insoluble matter under low-temperature storage. As a result, the present invention was completed.
That is, the present invention
(1) A liquid formulation of gardenia yellow, characterized by containing phytic acid and γ-cyclodextrin,
(2) The liquid preparation of gardenia yellow violet according to (1) above, wherein a mixed solution of ethanol and water is used as a solvent.
本発明のクチナシ黄色素の液体製剤は、５℃で６月保存しても不溶物が発生しない。 The liquid formulation of gardenia yellow violet according to the present invention does not generate insoluble matter even when stored at 5 ° C. for 6 months.
本発明のクチナシ黄色素の液体製剤は、フィチン酸およびγ−シクロデキストリンを含有することを特徴とする。 The liquid preparation of gardenia yellow pigment of the present invention is characterized by containing phytic acid and γ-cyclodextrin.
一般にフィチン酸（myo-イノシトールの六リン酸エステル）は、主に穀物或いは植物種子中にフィチン酸のカルシウム・マグネシウム混合塩として存在する。本発明に用いられるフィチン酸としては、この塩を抽出後、塩酸等の酸に溶解し、カチオン交換樹脂処理を行うことなどにより製造されるものであって、フィチン酸の濃厚水溶液（例えば、５０％程度）したものなどが好ましい。フィチン酸としては、例えばフィチン酸（５０％水溶液）（商品名；築野ライスファインケミカルズ社製）等が商業的に製造・販売されており、本発明ではこれらを用いることができる。 In general, phytic acid (hexophosphate ester of myo-inositol) exists mainly as a calcium / magnesium mixed salt of phytic acid in grains or plant seeds. The phytic acid used in the present invention is produced by extracting this salt, dissolving it in an acid such as hydrochloric acid, and treating it with a cation exchange resin. The phytic acid is a concentrated aqueous solution of phytic acid (for example, 50 %) Is preferred. As phytic acid, for example, phytic acid (50% aqueous solution) (trade name; manufactured by Tsukino Rice Fine Chemicals Co., Ltd.) is commercially produced and sold, and these can be used in the present invention.
一般にシクロデキストリンとは、ブドウ糖を構成単位とする環状無還元マルトオリゴ糖のことであり、澱粉類に酵素（サイクロデキストリングルカノトランスフェラーゼ）を作用させて得られるものである。シクロデキストリンとしては、ブドウ糖の数が６つのα−シクロデキストリン、７つのβ−シクロデキストリン、８つのγ−シクロデキストリンなどがあるが、本発明ではγ−シクロデキストリンが好ましく用いられる。γ−シクロデキストリンとしては、例えばＣＡＶＡＭＡＸ Ｗ８ Ｆｏｏｄ（商品名；シクロケム社製）等が商業的に製造・販売されており、本発明ではこれらを用いることができる。 In general, cyclodextrin is a cyclic non-reducing maltooligosaccharide having glucose as a structural unit, and is obtained by causing an enzyme (cyclodextrin glucanotransferase) to act on starches. Examples of the cyclodextrin include α-cyclodextrin having 6 glucoses, 7 β-cyclodextrin, 8 γ-cyclodextrin and the like. In the present invention, γ-cyclodextrin is preferably used. As γ-cyclodextrin, for example, CAVAMAX W8 Food (trade name; manufactured by Cyclochem) and the like are commercially produced and sold, and these can be used in the present invention.
本発明に用いられるクチナシ黄色素は、クチナシ抽出液を濃縮・精製することにより得られる。該クチナシ抽出液は、クチナシの乾燥果実を粉砕し、水またはアルコール及びそれらの混合液を用いて抽出されたものである。抽出溶媒として水が安全性の面からは好ましいが、抽出速度が遅い。そこで工業的にはアルコールと水の混合液が、通常用いられる。アルコールとしては、例えばエタノール、メタノール等が挙げられるが、エタノールが好ましく用いられる。アルコールと水の混合割合は、例えば５０ｖｏｌ％が好ましく用いられる。抽出条件は、例えば水・アルコール混合液を用いた場合、室温（約０〜５０℃）で約１〜１８時間が好ましく、約３０〜４０℃で約２〜４時間がより好ましい。抽出終了後、抽出液は一つに集められ、必要なら珪藻土等のろ過助剤を用いて、ろ紙或いはろ布を通してろ過される。ろ液はアルコールを回収するため濃縮され、クチナシ抽出液濃縮物が得られる。 Gardenia yellow used in the present invention can be obtained by concentrating and purifying gardenia extract. The gardenia extract is obtained by crushing dried fruits of gardenia and using water or alcohol and a mixture thereof. Water is preferable as the extraction solvent from the viewpoint of safety, but the extraction rate is slow. Therefore, industrially, a mixture of alcohol and water is usually used. Examples of the alcohol include ethanol and methanol, and ethanol is preferably used. The mixing ratio of alcohol and water is preferably 50 vol%, for example. For example, when a water / alcohol mixed solution is used, the extraction condition is preferably about 1 to 18 hours at room temperature (about 0 to 50 ° C.), more preferably about 2 to 4 hours at about 30 to 40 ° C. After completion of the extraction, the extracts are collected together and, if necessary, filtered through filter paper or filter cloth using a filter aid such as diatomaceous earth. The filtrate is concentrated to recover the alcohol and a gardenia extract concentrate is obtained.
このクチナシ抽出液濃縮物を精製処理する方法に特に制限はないが、例えば、キレート樹脂などのイオン交換樹脂、合成吸着樹脂、逆浸透膜などにより処理する方法が挙げられ、好ましくはキレート樹脂および合成吸着樹脂により処理する方法である。 The method for purifying the gardenia extract concentrate is not particularly limited, and examples thereof include a method of treating with an ion exchange resin such as a chelate resin, a synthetic adsorption resin, a reverse osmosis membrane, etc., preferably a chelate resin and a synthetic resin. This is a method of treating with an adsorption resin.
ここで、キレート樹脂処理は、例えば下記の方法により行うことができる。 Here, the chelate resin treatment can be performed, for example, by the following method.
初めに、クチナシ抽出液濃縮物を適当な濃度に希釈し、さらにｐＨを中性付近に調整したものをキレート樹脂を充填したカラムに供給し、排出液を回収する。キレート樹脂としては、ダイヤイオンＣＲ１１、ダイヤイオンＣＲ２０、ダイヤイオンＣＲＢ０２（製品名；三菱化学社製）等が商業的に製造・販売されており、本発明ではこれらを用いることができる。 First, the gardenia extract concentrate is diluted to an appropriate concentration, and further adjusted to a neutral pH is supplied to a column packed with a chelate resin, and the effluent is recovered. As the chelating resin, Diaion CR11, Diaion CR20, Diaion CRB02 (product name; manufactured by Mitsubishi Chemical Corporation) and the like are commercially produced and sold, and these can be used in the present invention.
次に、キレート樹脂に吸着された一部の色素を回収するため、約５０〜７０ｖｏｌ％のアルコールによりカラム内の色素を脱着・溶出し、溶出液を得る。ここで、アルコールとしては、例えばメタノール、エタノール、プロパノール、イソプロパノール、ｎ−ブタノール、ｉ−ブタノール、ｓｅｃ−ブタノール、ｔｅｒｔ−ブタノール等の炭素数１〜４の低級アルコールが挙げられ、エタノールが好ましく用いられる。 Next, in order to collect a part of the dye adsorbed on the chelate resin, the dye in the column is desorbed and eluted with about 50 to 70 vol% of alcohol to obtain an eluate. Here, examples of the alcohol include lower alcohols having 1 to 4 carbon atoms such as methanol, ethanol, propanol, isopropanol, n-butanol, i-butanol, sec-butanol, tert-butanol, and ethanol is preferably used. .
更に、排出液と溶出液を合わせた色素液を濃縮し、クチナシ抽出液濃縮物のキレート樹脂精製物を得る。 Further, the dye solution obtained by combining the effluent and the eluate is concentrated to obtain a purified chelate resin product of the gardenia extract concentrate.
また、合成吸着樹脂処理は、例えば、下記の方法により行うことができる。 In addition, the synthetic adsorption resin treatment can be performed, for example, by the following method.
上記キレート樹脂精製物を適当な濃度に希釈し、合成吸着樹脂を充填したカラムに希釈液を供給する。合成吸着樹脂としては、アンバーライトＸＡＤ−４、アンバーライトＸＡＤ−７（製品名；オルガノ社製）、ダイヤイオンＨＰ−２０、ダイヤイオンＨＰ−２１、ダイヤイオンＨＰ−４０（製品名；三菱化学社製）等が商業的に製造・販売されており、本発明ではこれらを用いることができる。 The chelate resin purified product is diluted to an appropriate concentration, and the diluted solution is supplied to a column packed with a synthetic adsorption resin. As synthetic adsorption resin, Amberlite XAD-4, Amberlite XAD-7 (product name: manufactured by Organo), Diaion HP-20, Diaion HP-21, Diaion HP-40 (Product name: Mitsubishi Chemical Corporation) Are manufactured and sold commercially, and these can be used in the present invention.
次に、水または低濃度のアルコールと水の混合液でカラム内の不純物を洗い流した後、約５０〜７０ｖｏｌ％のアルコールによりカラム内の色素を脱着・溶出する。ここで、アルコールとしては、例えばメタノール、エタノール、プロパノール、イソプロパノール、ｎ−ブタノール、ｉ−ブタノール、ｓｅｃ−ブタノール、ｔｅｒｔ−ブタノール等の炭素数１〜４の低級アルコールが挙げられ、エタノールが好ましく用いられる。 Next, the impurities in the column are washed away with water or a mixed solution of low-concentration alcohol and water, and then the dye in the column is desorbed and eluted with about 50 to 70 vol% alcohol. Here, examples of the alcohol include lower alcohols having 1 to 4 carbon atoms such as methanol, ethanol, propanol, isopropanol, n-butanol, i-butanol, sec-butanol, tert-butanol, and ethanol is preferably used. .
次に、カラムからの溶出液は、濃縮釜を用いて常法により濃縮され、クチナシ抽出液濃縮物のキレート／合成吸着樹脂精製物が得られる。 Next, the eluate from the column is concentrated by a conventional method using a concentration kettle, and a chelate / synthetic adsorption resin purified product of gardenia extract concentrate is obtained.
更に、上記キレート／合成吸着樹脂精製物は、好ましくは乾燥・粉末化され、色価（Ｅ10% 1cm）が３０００〜７０００のクチナシ黄色素が得られる。乾燥方法としては、例えば、噴霧乾燥、真空乾燥、通風乾燥および凍結乾燥などが挙げられる。色価は、「第８版 食品添加物公定書」（日本食品添加物協会）の「クチナシ黄色素」に記載の方法に準じて測定される。 Further, the purified chelate / synthetic adsorption resin product is preferably dried and powdered to obtain gardenia yellow having a color value (E 10% 1 cm ) of 3000 to 7000. Examples of the drying method include spray drying, vacuum drying, ventilation drying, freeze drying, and the like. The color value is measured in accordance with the method described in “Kuchinashi Ajimoto” in “8th Edition Food Additives Official Document” (Japan Food Additives Association).
本発明のクチナシ黄色素の液体製剤は、上述のフィチン酸、γ−シクロデキストリンおよびクチナシ黄色素を溶解槽の中で溶媒に溶解させることにより得ることができる。また、該製剤は、水酸化ナトリウム水溶液などを用いてｐＨが５．５〜７．５に調整されていることが好ましい。 The liquid formulation of gardenia yellow violet according to the present invention can be obtained by dissolving the above-described phytic acid, γ-cyclodextrin and gardenia chlorophyll in a solvent in a dissolution tank. Moreover, it is preferable that pH of this formulation is adjusted to 5.5-7.5 using sodium hydroxide aqueous solution etc.
上記溶媒としては、水または水とアルコールとの混合溶液等を挙げることができる。後者の場合、水との混合で用いるアルコールの種類としては、エタノールが好ましい。また、水に対するアルコールの混合割合としては、１〜５０ｖｏｌ％が好ましい。 Examples of the solvent include water or a mixed solution of water and alcohol. In the latter case, ethanol is preferred as the type of alcohol used for mixing with water. Moreover, as a mixing ratio of the alcohol with respect to water, 1-50 vol% is preferable.
本発明のクチナシ黄色素の液体製剤１００質量％中のフィチン酸、γ−シクロデキストリンおよびクチナシ黄色素の含有量に特に制限はないが、フィチン酸が通常０．１〜５．０％質量％、好ましくは０．２〜３．０質量％であり、γ−シクロデキストリンが通常０．０５〜３．０質量％、好ましくは０．１５〜１．５質量％であり、クチナシ黄色素（色価５０００として）が通常０．５〜２５．０質量％、好ましくは１．０〜１５．０質量％である。 There is no particular limitation on the content of phytic acid, γ-cyclodextrin and gardenia chlorophyll in 100% by mass of the liquid formulation of gardenia yellow of the present invention, but phytic acid is usually 0.1 to 5.0% by mass, Preferably, it is 0.2 to 3.0% by mass, and γ-cyclodextrin is usually 0.05 to 3.0% by mass, preferably 0.15 to 1.5% by mass. 5000) is usually 0.5 to 25.0 mass%, preferably 1.0 to 15.0 mass%.
また、本発明のクチナシ黄色素の液体製剤は、上記フィチン酸、γ−シクロデキストリンおよびクチナシ黄色素の他、本発明の目的を阻却しない範囲内において、賦型剤、崩壊剤、結合剤、界面活性剤、乳化剤、湿潤剤、滑沢剤、糖類、ｐH調整剤、防腐剤、香料もしくは着色料等を添加して製造できる。 Further, the liquid formulation of gardenia yellow violet according to the present invention includes, in addition to the above-mentioned phytic acid, γ-cyclodextrin and gardenia yellow violet, an excipient, a disintegrating agent, a binder, an interface within the range not obstructing the object of the present invention It can be produced by adding an activator, an emulsifier, a wetting agent, a lubricant, a saccharide, a pH adjusting agent, a preservative, a fragrance or a coloring agent.
本発明のクチナシ黄色素の液体製剤は、例えば、食品及び健康食品の分野で好適に利用することができる。本発明のクチナシ黄色素の液体製剤を添加した食品及び健康食品は、各種の栄養素、ビタミン類、香料、着色料、酸化防止剤、チーズやチョコレート等の風味物質もしくは合成甘味料等を当業者が適宜添加して製造できる。食品の形態は、菓子類、麺類、乳製品、練り製品或いはその他の漬物、酢の物、練り羊羹、水羊羹、ういろう、煮豆、練りウニ、ふりかけ等が挙げられる。また、健康食品の形態は、顆粒、錠菓、ガム、キャンディ、ゼリー、飲料等が挙げられる。 The liquid preparation of gardenia yellow violet according to the present invention can be suitably used, for example, in the fields of foods and health foods. Foods and health foods to which the liquid preparation of gardenia yellow pigment according to the present invention is added are various nutrients, vitamins, fragrances, coloring agents, antioxidants, flavor substances such as cheese and chocolate, or synthetic sweeteners by those skilled in the art. Appropriate additions can be made. Examples of the form of the food include confectionery, noodles, dairy products, kneaded products or other pickles, vinegared products, kneaded sheep crab, water sheep crab, seaweed, boiled beans, kneaded sea urchin, sprinkles and the like. Examples of health foods include granules, tablet candy, gum, candy, jelly, and beverages.
以下に本発明を実施例に基づいてより具体的に説明するが、本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be described more specifically based on examples, but the present invention is not limited thereto.
［クチナシ黄色素の調製］
粉砕したクチナシの乾燥果実１２００ｇに５０ｖｏｌ％エタノール・水混合液２．４Ｌを加え、室温で３時間攪拌した後吸引ろ過した。さらに、抽出残に５０ｖｏｌ％エタノール・水混合液２．４Ｌを加え室温で３０分間攪拌した後吸引ろ過する操作を２回繰り返し、ろ液として計約７．０Ｌの抽出液を得た。この抽出液を、ロータリーエバポレーターを用いて、約６０℃及び約４ｋＰａの条件で濃縮し、クチナシ抽出液濃縮物約４２０ｇを得た。
[Preparation of gardenia yellow pigment]
2.4L of a 50 vol% ethanol / water mixture was added to 1200 g of pulverized dried fruit of gardenia, and the mixture was stirred at room temperature for 3 hours and filtered with suction. Further, 2.4 L of 50 vol% ethanol / water mixed solution was added to the extraction residue and stirred at room temperature for 30 minutes, followed by suction filtration twice to obtain about 7.0 L of extract as a filtrate. This extract was concentrated using a rotary evaporator under the conditions of about 60 ° C. and about 4 kPa to obtain about 420 g of gardenia extract concentrate.
次に、クチナシ抽出液濃縮物に精製水を加えて２．３Ｌとし（ｐＨ＝４．２）、水酸化ナトリウム１０ｗ／ｖ％水溶液を加えてｐＨ＝６．７に調整した後、水を加えて全量を２．５Ｌの溶液とした。得られた溶液を吸引ろ過し、ろ液をダイヤイオンＣＲ１１（三菱化学社製）１５０ｍＬを充填したカラムに流速ＳＶ＝５．０で通液し、排出液を回収した。さらに、７０ｖｏｌ％エタノール・水混合液２．０Ｌを流速ＳＶ＝５．０で通液し、溶出液を得た。排出液と溶出液を一つにした液を、ロータリーエバポレーターを用いて、約６０℃及び約４ｋＰａの条件で濃縮し、クチナシ抽出液濃縮物のキレート樹脂精製物４５０ｇを得た。 Next, purified water is added to the gardenia extract concentrate to 2.3 L (pH = 4.2), 10% aqueous sodium hydroxide solution is added to adjust the pH to 6.7, and then water is added. The total volume was 2.5 L. The obtained solution was subjected to suction filtration, and the filtrate was passed through a column packed with 150 mL of Diaion CR11 (manufactured by Mitsubishi Chemical Corporation) at a flow rate of SV = 5.0 to collect the discharged liquid. Furthermore, 2.0 L of 70 vol% ethanol / water mixture was passed at a flow rate SV = 5.0 to obtain an eluate. The liquid obtained by combining the discharged liquid and the eluate was concentrated using a rotary evaporator at about 60 ° C. and about 4 kPa, thereby obtaining 450 g of a chelate resin purified product of gardenia extract concentrate.
次に、このキレート樹脂精製物４５０ｇに精製水を加えて２．５Ｌとし、アンバーライトＸＡＤ−７（オルガノ社製）２Ｌを充填したカラムに流速ＳＶ＝０．５で通液した。続いて、精製水１６Ｌをカラムに流速ＳＶ＝０．５で通液し、排出液を廃棄した。最後に、７０ｖｏｌ％エタノール・水混合液４Ｌを流速ＳＶ＝０．５で通液し、色素を脱着・溶出し、クチナシ抽出液濃縮物のキレート／合成吸着樹脂精製物を得た。 Next, purified water was added to 450 g of this purified chelate resin product to make 2.5 L, and the solution was passed through a column packed with 2 L of Amberlite XAD-7 (manufactured by Organo) at a flow rate of SV = 0.5. Subsequently, 16 L of purified water was passed through the column at a flow rate SV = 0.5, and the discharged liquid was discarded. Finally, 4 L of a 70 vol% ethanol / water mixture was passed at a flow rate SV = 0.5 to desorb and elute the dye, and a chelate / synthetic adsorption resin purified product of gardenia extract was obtained.
得られた精製物を、をスプレードライヤー（製品名：ミニスプレードライヤーＢ−２９０；日本ビュッヒ社製）を用い、熱風入口温度１１５℃、排気温度４０℃で乾燥し、粉末状のクチナシ黄色素（試作品Ａ；色価５０００）５０ｇを得た。 The obtained purified product was dried at a hot air inlet temperature of 115 ° C. and an exhaust temperature of 40 ° C. using a spray dryer (product name: Mini Spray Dryer B-290; manufactured by Nihon Büch). 50 g of prototype A (color value 5000) was obtained.
［クチナシ黄色素の液体製剤の調製］
（１）原材料
１）フィチン酸（商品名：フィチン酸（５０％水溶液）；築野ライスファインケミカルズ社製）
２）γ−シクロデキストリン（商品名：ＣＡＶＡＭＡＸ Ｗ８ Ｆｏｏｄ；シクロケム社製）
３）クチナシ黄色素（試作品Ａ）
４）イオン交換水
５）エタノール
[Preparation of Liquid Formulation of Gardenia Yellow]
(1) Raw materials 1) Phytic acid (trade name: Phytic acid (50% aqueous solution); manufactured by Tsukino Rice Fine Chemicals)
2) γ-cyclodextrin (trade name: CAVAMAX W8 Food; manufactured by Cyclochem)
3) Gardenia yellow (prototype A)
4) Ion exchange water 5) Ethanol
（２）液体製剤の配合
上記原材料を用いて調製した液体製剤１〜４の配合組成を表１に示した。この内、製剤１は本発明に係る実施例であり、製剤２〜４はそれらに対する比較例である。
(2) Formulation of liquid preparation Table 1 shows the composition of liquid preparations 1 to 4 prepared using the above raw materials. Of these, Formulation 1 is an example according to the present invention, and Formulations 2 to 4 are comparative examples for them.
（３）液体製剤の調製方法
表１に示した原材料の配合割合に基づいて、フィチン酸、γ−シクロデキストリンおよびクチナシ黄色素をイオン交換水およびエタノールの混合液に溶解し、水酸化ナトリウム４８ｗ／ｖ％水溶液でｐＨ＝６．５に調整し、全量１ｋｇのクチナシ黄色素の液体製剤（製剤１〜４）を調製した。
(3) Preparation method of liquid preparation Based on the mixing ratio of the raw materials shown in Table 1, phytic acid, γ-cyclodextrin and gardenia yellow are dissolved in a mixture of ion-exchanged water and ethanol, and sodium hydroxide 48 w / The pH was adjusted to 6.5 with a v% aqueous solution to prepare a liquid preparation (formulations 1 to 4) of 1 kg of gardenia yellow.
［評価試験］
クチナシ黄色素の液体製剤（製剤１〜４）を５℃の冷蔵庫内で保存し、不溶物が確認されるまでに要した時間を評価した。不溶物の確認は、保存開始から毎月行い、保存開始から６月を経過した時点で試験を終了した。結果を表２に示す。
[Evaluation test]
The liquid formulation (formulations 1 to 4) of gardenia yellow was stored in a refrigerator at 5 ° C., and the time required until insoluble matter was confirmed was evaluated. The insoluble matter was confirmed every month from the start of storage, and the test was terminated when 6 months passed from the start of storage. The results are shown in Table 2.
表２の結果から、本発明のクチナシ黄色素の液体製剤（製剤１）は５℃で６月保存しても不溶物が発生しないことが明らかである。これに対し、比較例の製剤（製剤２〜４）は、いずれも保存中に不溶物の発生が確認された。 From the results shown in Table 2, it is clear that the liquid preparation (formulation 1) of gardenia yellow violet according to the present invention does not generate insoluble matter even when stored at 5 ° C. for 6 months. In contrast, in the preparations of Comparative Examples (Formulations 2 to 4), it was confirmed that insoluble matters were generated during storage.
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