JPH03163168A - Red dye, its production, and food and drink or cosmetic - Google Patents
Red dye, its production, and food and drink or cosmeticInfo
- Publication number
- JPH03163168A JPH03163168A JP2169081A JP16908190A JPH03163168A JP H03163168 A JPH03163168 A JP H03163168A JP 2169081 A JP2169081 A JP 2169081A JP 16908190 A JP16908190 A JP 16908190A JP H03163168 A JPH03163168 A JP H03163168A
- Authority
- JP
- Japan
- Prior art keywords
- yeast
- pigment
- food
- solvent
- dye
- 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
- 235000013305 food Nutrition 0.000 title claims abstract description 14
- 239000002537 cosmetic Substances 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000001044 red dye Substances 0.000 title abstract 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 19
- 241001542817 Phaffia Species 0.000 claims abstract description 12
- 239000012530 fluid Substances 0.000 claims abstract description 8
- 238000000199 molecular distillation Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 238000007127 saponification reaction Methods 0.000 claims abstract description 5
- 238000001256 steam distillation Methods 0.000 claims abstract description 5
- 238000000622 liquid--liquid extraction Methods 0.000 claims abstract description 4
- 239000000049 pigment Substances 0.000 claims description 35
- 238000000746 purification Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000001054 red pigment Substances 0.000 claims description 11
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 235000013970 phaffia yeast Nutrition 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 12
- 238000011282 treatment Methods 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- 238000011161 development Methods 0.000 abstract description 7
- 235000019441 ethanol Nutrition 0.000 abstract description 3
- 239000003240 coconut oil Substances 0.000 abstract description 2
- 235000019864 coconut oil Nutrition 0.000 abstract description 2
- 239000003549 soybean oil Substances 0.000 abstract description 2
- 235000012424 soybean oil Nutrition 0.000 abstract description 2
- 239000003760 tallow Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 21
- 235000019645 odor Nutrition 0.000 description 15
- 238000000605 extraction Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 description 7
- 235000013793 astaxanthin Nutrition 0.000 description 7
- 239000001168 astaxanthin Substances 0.000 description 7
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 description 7
- 229940022405 astaxanthin Drugs 0.000 description 7
- 238000004040 coloring Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 235000013361 beverage Nutrition 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 230000005070 ripening Effects 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 1
- CSTRPYAGFNTOEQ-MGMRMFRLSA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;octadecanoic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O.CCCCCCCCCCCCCCCCCC(O)=O CSTRPYAGFNTOEQ-MGMRMFRLSA-N 0.000 description 1
- RQFCJASXJCIDSX-UHFFFAOYSA-N 14C-Guanosin-5'-monophosphat Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(COP(O)(O)=O)C(O)C1O RQFCJASXJCIDSX-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 241000257465 Echinoidea Species 0.000 description 1
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 1
- 244000111489 Gardenia augusta Species 0.000 description 1
- GRSZFWQUAKGDAV-KQYNXXCUSA-N IMP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-KQYNXXCUSA-N 0.000 description 1
- GRSZFWQUAKGDAV-UHFFFAOYSA-N Inosinic acid Natural products OC1C(O)C(COP(O)(O)=O)OC1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 101100242191 Tetraodon nigroviridis rho gene Proteins 0.000 description 1
- 241000962283 Turdus iliacus Species 0.000 description 1
- 229930003451 Vitamin B1 Natural products 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 1
- 235000013928 guanylic acid Nutrition 0.000 description 1
- 238000003621 hammer milling Methods 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 235000013902 inosinic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 235000019685 rice crackers Nutrition 0.000 description 1
- 238000013077 scoring method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
この発明は、色素とその製造方法、および飲食品または
化粧料に関するものである.さらに詳しくは、この発明
は、ファフィア属酵母から抽出した発色性、耐光性、着
色性に優れ、しかも低臭性の赤色色素とその製造法、さ
らにこの色素を配合した飲食品および化粧料に関ずるも
のである.(従来の技術とその課U)
従来より、飲食品、化粧料には様々な着色剤が使用され
てきており、たとえば食用赤色2号、食用黄色3号など
のタール色素や酸化鉄、二酸化チタンなどの無faM料
が用いられてきている.しかしながら、通常使用されて
いるこれらの化学合成色素は飲食品や化粧料等の製品を
所要の色に簡便に着色することができ、製品の嗜好性を
高めることが容易であるという特徴を有しているものの
、安全性の面からは必ずしも好ましい色素とは言い難い
.身体の健康や安全性への関心の高まりにともなって、
化学合成色素に代わり得るものとしての天然色素への要
請が高まってきてもいる.このような天然色素はこれま
でにもすでに使用されてきており、たとえば、天然赤色
色素としては、パプリカ色素、紅翅色素、ベニバナ色素
、ぶどう果皮色素、クチナシ色素、ビートレッド、赤キ
ャベツ色素などが知られている.しかしながら、天然色
素の利用については、これまでの状況では発色性、耐光
性、耐熟性、着色性、臭い、価格などの点で満足できる
ものでなく、また、天然物であるため、その収量が天候
等の自然性に左右される場合が多いという欠点があった
.
この発明は、以上の通りの事情に鑑みてなされたもので
あり、天然色素の特徴を生かし、しかもこれまでの天然
色素の利用上の欠点を解消して、発色性、耐熱性、着色
性等に優れ、しかも低臭性の新しい色素を提供すること
を目的としている,さらに詳しくは、この発明は、この
新しい色素として赤色色素を提供し、さらにそのための
製造法と、これを添加配合してなる飲食品および化粧料
を提供することを目的としてもいる.(課題を解決する
ための手段)
この発明は、上記の課題を解決するものとして、ファフ
ィア属il}Il!より溶剤抽出してなることを特徴と
する赤色色素を提供する.すなわち、この発明の発明者
は微生物分類学上、不完全菌類に属する赤色醇母である
ファフィア属酵母、たとえばPhaffia rhod
oz laは発色性、耐光性、耐熟性、着色性に優れた
アスタキサンチン類を含み、大量に培養することができ
、色素原料として産業的に利用しうろこと、さらにまた
、低コストでの量産性に優れたその抽出精製方法を見出
してこの発明を完成した。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) This invention relates to a pigment, a method for producing the same, and food/beverage products or cosmetics. More specifically, this invention relates to a red pigment extracted from yeast of the genus Phaffia that has excellent color development, light fastness, and coloring properties and low odor, and a method for producing the same, as well as food and drink products and cosmetics containing this pigment. It's a cheat. (Conventional technology and its sections U) Various coloring agents have been used in food, drink, and cosmetics. For example, tar pigments such as Food Red No. 2 and Food Yellow No. 3, iron oxide, titanium dioxide, etc. Non-FAM fees such as However, these chemically synthesized pigments that are commonly used can easily color products such as food and beverages and cosmetics to desired colors, and have the characteristic that they can easily enhance the palatability of products. However, it is not necessarily a desirable dye from a safety perspective. With increasing interest in physical health and safety,
There is also an increasing demand for natural pigments as an alternative to chemically synthesized pigments. Such natural pigments have already been used in the past. For example, natural red pigments include paprika pigment, red-wing pigment, safflower pigment, grape skin pigment, gardenia pigment, beet red, and red cabbage pigment. Are known. However, the current situation with regard to the use of natural pigments has not been satisfactory in terms of color development, light resistance, ripening resistance, coloring properties, odor, price, etc. Also, since they are natural products, their yield is low. The disadvantage is that the weather is often influenced by natural factors such as the weather. This invention was made in view of the above-mentioned circumstances, and utilizes the characteristics of natural pigments and eliminates the drawbacks of conventional natural pigments, such as coloring properties, heat resistance, coloring properties, etc. The purpose of the present invention is to provide a new pigment that is excellent in color and has low odor.More specifically, the present invention provides a red pigment as this new pigment, and furthermore, a method for producing it and a method for adding and blending it. The aim is to provide food, drink, and cosmetics that are unique to the industry. (Means for Solving the Problems) The present invention solves the above problems by providing Phaffia genus il}Il! To provide a red pigment characterized by being extracted with a solvent. That is, the inventor of the present invention has discovered yeasts of the genus Phaffia, which are red yeasts belonging to Deuteromycetes in terms of microbial taxonomy, such as Phaffia rhod.
oz la contains astaxanthin, which has excellent color development, light resistance, ripening resistance, and coloring properties, and can be cultivated in large quantities, making it possible to use scales industrially as a raw material for pigments, as well as mass production at low cost. This invention was completed by discovering a highly efficient extraction and purification method.
一般に、酵母は大量培養が可能であり、古来より発IV
l醸造に広く用いられているほか、ビタミンB1やステ
ロイドの一種であるエルゴステロールなどの医薬品の原
料としても産業上利用されている。さらに食品添加物と
しては、天然調味料としての5′−イノシン酸、5′−
グアニル酸などが、核酸発酵を用いて酵母より産土され
ている。In general, yeast can be cultured in large quantities, and since ancient times yeast
In addition to being widely used in brewing, it is also used industrially as a raw material for pharmaceuticals such as vitamin B1 and ergosterol, a type of steroid. Furthermore, as food additives, 5'-inosinic acid as a natural seasoning, 5'-
Guanylic acid and other substances are produced from yeast using nucleic acid fermentation.
しかしながら、飲食品、化粧料に添加可能な醇母を原材
料とする色素はこれまでに存在していなかった.
この発明は、この従来の酵母利用技術の飛躍をも実現す
るものである。However, until now, there has been no pigment made from yambo that can be added to foods, drinks, and cosmetics. This invention also realizes a breakthrough in this conventional yeast utilization technology.
この発明においては、まず、ファフイア属酵母を溶剤抽
出し粗色素液を得る.次いで、さらに粗色素液を分子蒸
留、ウインタリング、カラムクロマトグラフ、水蒸気蒸
留、超臨界流体、液一液分配、けん化等の精製処理法を
組合わせて処理することにより該色素を濃縮精製し、発
色性、耐光性耐熟性、着色性に優れ、しかも赤色無臭の
色素を得ることができる.
ファフイア属酵母としては、より具体的にはPhaff
ia rhodoz laの乾燥物を原料酔母として例
示することができる.
このファフィア属酵母からのこの発明の色素の抽出は、
培養液から遠心分離、枦過等により回収した醇母を十分
に水洗した後に、そのまま、あるいは乾燥処理の上、抽
出原料として用いるが、ファフィア属酵母のml胞壁は
通常のパン酵母等に比ベて強固な組織であるため、ボー
ルミル、ハンマーミル、凍結粉砕、圧縮粉砕、超音波処
理等による物理的処理、あるいはセルラーゼ、ペクチタ
ーゼ等による酵素的処理を施して抽出率を向上させるの
が望ましい.
また、この発明に使用する抽出溶剤としては、たとえば
ヘキサン、アセトン、酢酸エチル、エタノール等の有機
溶剤、大豆白絞油、やし油、ひまし油、オリーブ油、豚
油、牛脂、魚油等の動植物油、セチルアルコール、ろう
、イソプロピルミリスチン酸エステル等の合成油溶性化
合物を単独または複数組合わせて使用し、抽出処理によ
り■色素油を得ることができる.
有機溶剤を用いて抽出した場合には、抽出後、有機溶剤
を留去し、粗色素油を得る。In this invention, first, yeast of the genus Faphia is extracted with a solvent to obtain a crude pigment solution. Next, the crude dye liquid is further concentrated and purified by treating the crude dye liquid with a combination of purification methods such as molecular distillation, wintering, column chromatography, steam distillation, supercritical fluid, liquid-liquid distribution, saponification, etc. It is possible to obtain a red odorless pigment that has excellent color development, light resistance, ripening resistance, and coloring properties. As Phaffia yeast, more specifically Phaff
An example of the raw material is the dried product of Ia rhodoz la. Extraction of the pigment of this invention from yeast of the genus Phaffia
After thoroughly washing the yeast collected from the culture solution by centrifugation, straining, etc., it is used as an extraction raw material either as it is or after drying. Because it has a very strong structure, it is desirable to improve the extraction rate by performing physical treatments such as ball milling, hammer milling, freeze-pulverization, compression crushing, ultrasonication, etc., or enzymatic treatment with cellulase, pectidase, etc. Examples of extraction solvents used in this invention include organic solvents such as hexane, acetone, ethyl acetate, and ethanol; animal and vegetable oils such as soybean oil, coconut oil, castor oil, olive oil, pork oil, beef tallow, and fish oil; (2) Pigment oil can be obtained by extraction using synthetic oil-soluble compounds such as cetyl alcohol, wax, and isopropyl myristate, either alone or in combination. In the case of extraction using an organic solvent, the organic solvent is distilled off after the extraction to obtain a crude pigment oil.
溶剤抽出後に行うことのできる分子蒸留精製は、5 n
m l g以下、好ましくは0.1ramHir以下の
真空下、90〜210℃、好ましくは140〜190’
Cの温度で行うことができ、この蒸留によって夾雑する
遊離脂肪酸などの不純物を除去し、赤色色素成分のアス
タキサンチン類を濃!i1精製する.この処理において
、大部分の低分子臭気成分も除去される.ウィンタリン
グ精製は、−60℃〜10℃、好ましくは−50℃〜−
10℃の温度で、ヘキサン、アセトン、エタノール等の
有機溶剤を用いて行うことができ、このウィンタリング
により、夾雑するトリグリセリドなどの不純物を除去し
、赤色色素戒分のアスタキサンチン類を濃1ta精製す
る.この処理において、一部の臭気或分も除去される.
なお、分子蒸留精製とウィンタリング¥n製は、どちら
か一方のみでもよく、両方を行う場合には、その順序は
いずれが先でもよい.
この発明で採用するクロマトグラフ法は通常の分離精製
法として知られているものとすることができ、シリカゲ
ル、活性アルミナ等を充填剤とし、ヘキサン、アセトン
等の有機溶剤を溶離液とすることにより、赤色色素成分
のアスタキサンチン類以外の或分の大部分を除去する.
また、水蒸気蒸留による精製としては、通常の方法とし
て知られている態様とすることができる.この処理にお
いて大部分の臭気成分を除去することができる.
さらに、液一液分配法についても、通常の方法として知
られている態様とすることができ、四分式、半連続式、
連続式、クロマト式、遠心クロマト式のいずれの方法で
もよい.
また、超臨界流体精製については、精製色素液に対し加
温したCO2等の超臨界流体を導入して実施することが
できる.導入時の温度及び圧力の調節により臭気戒分を
含む夾雑物を分離することにより、精製色素液を更に精
製:a縮ずる.以上の、猜製法の単独、または複数の組
合わせによる精製濃縮の過程の前または中間にけん化処
理を行うこともできる.
このけん化処理も、通常の方法による態様とすることが
できる.夾雑するトリグリゼドや遊離脂肪酸を効率よく
除去することができる.以上の溶剤抽出および精製法は
、現実的な用途に応じて、色素濃度、安定性、臭気等の
点についての要求度に対応ずべく適宜組合わせることが
望ましい.
この発明の赤色色素は、その優れた特性から、飲食品あ
るいは化粧科に配合することができ、天然色素配合の特
徴のある飲食品および化粧料が実現される.
また、この発明の赤色色素には、抗酸化剤、たとえばト
コフエロール、没食子酸プロビル、アスコルビン酸ステ
アレート等を添加することができる.さらには、乳化物
や包接化合物等に容易に製剤化することができる.
以下、この発明の実施例を示し、さらに詳しくこの発明
について説明する.
実施例1
添付した図面の第1図は、この発明の81製工程を例示
したものであり、この第l図を参照しつつ実施例を説明
する.
すなわち、まず発酵により得られたPhaffiaΩ也
士■ヱl一の乾燥物を原料とし、まずこの原料酵母(A
o)10ksrをアセトン30jと攪拌混合し、APV
GAULIN(15MR)により圧縮粉砕と同時に
抽出を行った後に枦別して、抽出液を得る.次いでこの
溶液のアセトンを減圧下、40℃の温度で留去し、粗色
素液( A ) 1752gを得る.この粗色素液(A
)254gを、さらに0.01n+nl−[g、110
゜Cの条件で分子蒸留して精製色素液(B)182gを
得る.またこれとは別に、粗色素液(A)の724gを
0.001關}{.、160℃の条件で分子蒸留精製し
て得た精製色素液(C)348gのうちの120 .か
ら45゜C、160気圧条件下のC O 2流体30j
(25℃、1気圧)による超臨界流体精製によって色
素液( D ) 72.Ezrを得る.上記色素液(C
)についてはその114gをヘキサンーアセトン(3:
1)の混合溶液を溶離液とし、シリカゲルを充填剤とず
るカラムクロマト精製により赤色成分を含む両分を分取
し、溶剤を減圧下40℃で留去して色素油(E)8.2
gら得る.以下の方法により得られた色素i(A)〜(
E)についてそれぞれのアスタキサンチン濃度、臭い、
保存後の臭いと変退色について評価した.その結果を示
したものが表1である.なお、保存は試験管中に試験液
1 mlを入れ窓際に1ケ月間放置したなお、アスタキ
サンチン濃度は480nnの吸光度より算出し、また臭
い、変退色は、訓練された2名の評価者によって評価し
、点数法による評価点の平均値で表1に示した.数値が
大きいほど特性が良いことを示している.
比較例1
比較のために実施例1で得た粗色素液(A)の68.
1 gを15關}lg、120℃の条件で常法により水
蒸気蒸留を行い、処理色素液( F ) 54.5tを
得る.また粗色素液(A)の78.0,から、実施例1
に記栽したのと同様の超臨界流体精製により処理色素液
( G ) 52.2Kを得る.さらにまた、■色素液
(A>の48. 3.を実施例1に記栽したのと同様の
カラムクロマト精製法により処理して処理色素液(H)
12.3gを得る.
なお、■色素液(A)の遊離脂肪酸を除去するため、そ
の10gと2%水酸化ナトリウム水溶液100 mlを
混合攪拌後、その水層を除去することを試みたが、乳化
層が土或し、色素液を分離することは極めて困牝であっ
た。Molecular distillation purification that can be performed after solvent extraction is 5 n
Under a vacuum of m l g or less, preferably 0.1 ramHir or less, 90 to 210°C, preferably 140 to 190'
This distillation removes impurities such as free fatty acids and concentrates astaxanthin, a red pigment component. Purify i1. This treatment also removes most of the low-molecular-weight odor components. Wintering purification is carried out at -60°C to 10°C, preferably -50°C to -
This can be carried out at a temperature of 10°C using an organic solvent such as hexane, acetone, or ethanol. Through this wintering, impurities such as contaminating triglycerides are removed, and astaxanthin, which is a red pigment component, is purified to a high concentration. .. In this process, some odors are also removed. In addition, only one of molecular distillation purification and wintering may be performed, and if both are performed, either one may be performed first. The chromatographic method employed in this invention can be a known ordinary separation and purification method, and uses silica gel, activated alumina, etc. as a filler and an organic solvent such as hexane, acetone, etc. as an eluent. , removes most of the red pigment components other than astaxanthin. Furthermore, purification by steam distillation can be carried out in a manner known as a normal method. This treatment can remove most odor components. Furthermore, the liquid-liquid distribution method can also be in a manner known as a normal method, such as a four-part method, a semi-continuous method,
Any of the continuous, chromatographic, and centrifugal chromatographic methods may be used. Furthermore, supercritical fluid purification can be carried out by introducing a heated supercritical fluid such as CO2 into the purified dye solution. The purified dye liquid is further purified by separating impurities including odor components by adjusting the temperature and pressure at the time of introduction: a. Saponification treatment can also be carried out before or during the purification and concentration process using the above-mentioned method of making ajie, alone or in combination. This saponification treatment can also be carried out using a conventional method. Contaminant triglylides and free fatty acids can be efficiently removed. It is desirable to combine the above solvent extraction and purification methods as appropriate to meet the requirements for pigment concentration, stability, odor, etc., depending on the practical application. Due to its excellent properties, the red pigment of the present invention can be incorporated into foods and beverages or cosmetics, thereby realizing food and beverages and cosmetics containing characteristic natural pigments. Furthermore, antioxidants such as tocopherol, provil gallate, ascorbic acid stearate, etc. can be added to the red pigment of the present invention. Furthermore, it can be easily formulated into emulsions and clathrate compounds. Hereinafter, examples of the present invention will be shown and the present invention will be explained in more detail. Embodiment 1 FIG. 1 of the attached drawings illustrates the 81 manufacturing process of the present invention, and an embodiment will be described with reference to FIG. 1. That is, first, the dried product of Phaffia Oyaji obtained by fermentation is used as a raw material, and this raw material yeast (A
o) Stir and mix 10ksr with acetone 30j, APV
Extraction is performed simultaneously with compression and pulverization using GAULIN (15MR), followed by separation to obtain an extract. Then, the acetone in this solution was distilled off under reduced pressure at a temperature of 40°C to obtain 1752 g of crude dye solution (A). This crude dye solution (A
) 254g, further 0.01n+nl-[g, 110
Molecular distillation was carried out under the conditions of °C to obtain 182 g of purified pigment solution (B). Separately, 724 g of crude pigment liquid (A) was added by 0.001 cm. Of the 348 g of purified pigment liquid (C) obtained by molecular distillation purification at 160°C, 120. C O 2 fluid 30j under conditions of 45°C and 160 atm.
Dye solution (D) by supercritical fluid purification (25 °C, 1 atm) 72. Get Ezr. The above dye solution (C
), 114g of it was mixed with hexane-acetone (3:
Using the mixed solution of 1) as the eluent and column chromatography using silica gel as the packing material, both fractions containing the red component were separated, and the solvent was distilled off at 40°C under reduced pressure to obtain pigment oil (E) 8.2
g et al. Dye i(A) ~(
Regarding E), each astaxanthin concentration, odor,
The odor and discoloration after storage were evaluated. Table 1 shows the results. For storage, 1 ml of the test solution was placed in a test tube and left by a window for 1 month.The astaxanthin concentration was calculated from the absorbance at 480 nn, and odor, discoloration, and fading were evaluated by two trained evaluators. Table 1 shows the average value of the evaluation score using the scoring method. The larger the number, the better the characteristics. Comparative Example 1 For comparison, 68.
1 g is subjected to steam distillation using a conventional method at 15 lg at 120°C to obtain 54.5 tons of treated dye liquid (F). In addition, from 78.0 of the crude dye solution (A), Example 1
A treated dye solution (G) 52.2K was obtained by supercritical fluid purification similar to that described in . Furthermore, the treated dye solution (H) was obtained by treating the dye solution (48. 3. of A> with the same column chromatography purification method as described in Example 1).
Obtain 12.3g. In order to remove free fatty acids from the dye solution (A), we tried to mix and stir 10 g of the dye solution (A) with 100 ml of a 2% aqueous sodium hydroxide solution and then remove the aqueous layer, but the emulsified layer was soil or However, it was extremely difficult to separate the dye solution.
上記(F)〜(H)の処理色素液についても実施例1と
同様にしてアスタキサンチン濃度、臭い、および変退色
を評価した。その特性は、表1に示したように実施例1
のものに比べて劣っていた。The treated dye solutions (F) to (H) above were also evaluated for astaxanthin concentration, odor, and discoloration in the same manner as in Example 1. The characteristics of Example 1 are as shown in Table 1.
It was inferior to that of
実施例2
実施例1で得た色素液(B),(C),(D)および(
E)をそれぞれ飴、かまぼこ、せんべい、チューインガ
ム、人エイクラ、ウニ、ドレッシングに1%添加して着
色した。非常に鮮明な橙色に着色でき、異味異臭は感じ
られず、40゜Cで1ヶ月間放置した後も変退色は認め
られなかった。Example 2 Dye solutions (B), (C), (D) and (
1% of E) was added to candy, kamaboko, rice crackers, chewing gum, human eikura, sea urchin, and dressing to color them. It was colored a very clear orange color, had no strange taste, and no discoloration or fading was observed even after being left at 40°C for one month.
実施例3
実施例1で得た色素液(D)および(E)をそれぞれ、
表2に示すような口紅基剤に1%配合して口紅を製造し
た。非常に鮮明な橙色に着色でき、異昧異臭は感じられ
ず、また35゜Cで1ケ月間放置しても戻り臭や変退色
は認められなかった。Example 3 The dye solutions (D) and (E) obtained in Example 1 were each
A lipstick was manufactured by adding 1% of the composition to a lipstick base as shown in Table 2. It was colored in a very clear orange color, with no strange odor, and even after being left at 35°C for one month, no returning odor or discoloration was observed.
表
2
比較例2
比較例1で得た処理色素液(F)、(G)および(F【
)を実施例3と同様にして口紅基剤に1%配合して口紅
をyI!遺した.色濃度が薄く、40℃で放置すると1
ケ月で戻り奥が発生し、使用に耐え得なかった.
(発明の効果)
この発明により、安全性が高く、発色性、耐光性2着色
性に潰れ、しかも低臭性の天然赤色色素を低コストで大
量に製造することが可能になる.またこの発明の製造法
によって得られた色素を配合することによって優れた赤
色を有する飲食品および化粧料を実現することができる
.Table 2 Comparative Example 2 Processed dye solutions (F), (G) and (F[
) was added to the lipstick base at 1% in the same manner as in Example 3 to make a lipstick! I left it behind. The color density is low, and if left at 40℃, it will change to 1
After a few months, it started to go back, making it unusable. (Effects of the Invention) This invention makes it possible to produce a natural red pigment in large quantities at low cost, which is highly safe, has excellent color development, light fastness, and two coloring properties, and has low odor. Furthermore, by blending the pigment obtained by the production method of the present invention, food/beverage products and cosmetics having an excellent red color can be realized.
第1図は、この発明の粗色素液およびfIII製色素液
の製造法の一例を処理色素液!!!造の比較例とともに
示した工程ブロック図である.FIG. 1 shows an example of the method for producing the crude dye liquid and fIII dye liquid of the present invention. ! ! This is a process block diagram shown together with a comparative example of construction.
Claims (4)
徴とする赤色色素。(1) A red pigment characterized by being obtained by solvent extraction from yeast of the genus Phaffia.
留、ウィンタリング、カラムクロマトグラフ、水蒸気蒸
留、超臨界流体、液−液分配、けん化等の精製処理法を
組合わせて処理することにより濃縮精製することを特徴
とする色素の製造方法。(2) Phaffia yeast is extracted with a solvent, and then concentrated by a combination of purification methods such as molecular distillation, wintering, column chromatography, steam distillation, supercritical fluid, liquid-liquid distribution, and saponification. A method for producing a pigment, characterized by purification.
色素を配合してなる飲食品。(3) A food or drink product containing the solvent-extracted pigment of yeast of the genus Phaffia according to claim (1).
色素を配合してなる化粧料。(4) A cosmetic containing the solvent-extracted pigment of yeast of the genus Phaffia according to claim (1).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2169081A JPH03163168A (en) | 1989-08-18 | 1990-06-26 | Red dye, its production, and food and drink or cosmetic |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21262889 | 1989-08-18 | ||
JP1-212628 | 1989-08-18 | ||
JP2169081A JPH03163168A (en) | 1989-08-18 | 1990-06-26 | Red dye, its production, and food and drink or cosmetic |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03163168A true JPH03163168A (en) | 1991-07-15 |
Family
ID=26492543
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2169081A Pending JPH03163168A (en) | 1989-08-18 | 1990-06-26 | Red dye, its production, and food and drink or cosmetic |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03163168A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2716802A1 (en) * | 1994-03-04 | 1995-09-08 | Pacific Corp | Cosmetic make-up compsns. contg. powdered Phaffia yeast |
JP2010514423A (en) * | 2006-12-22 | 2010-05-06 | ケミン、インダストリーズ、インコーポレーテッド | Carotenoid-based colorants |
-
1990
- 1990-06-26 JP JP2169081A patent/JPH03163168A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2716802A1 (en) * | 1994-03-04 | 1995-09-08 | Pacific Corp | Cosmetic make-up compsns. contg. powdered Phaffia yeast |
JP2010514423A (en) * | 2006-12-22 | 2010-05-06 | ケミン、インダストリーズ、インコーポレーテッド | Carotenoid-based colorants |
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