CN104387307B - The minimizing technology of ethoxyquinoline in a kind of lutein extract - Google Patents
The minimizing technology of ethoxyquinoline in a kind of lutein extract Download PDFInfo
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- CN104387307B CN104387307B CN201410656647.XA CN201410656647A CN104387307B CN 104387307 B CN104387307 B CN 104387307B CN 201410656647 A CN201410656647 A CN 201410656647A CN 104387307 B CN104387307 B CN 104387307B
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- ethoxyquinoline
- normal hexane
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- lutein extract
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- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 title claims abstract description 40
- 229960005375 lutein Drugs 0.000 title claims abstract description 40
- 239000001656 lutein Substances 0.000 title claims abstract description 40
- 235000012680 lutein Nutrition 0.000 title claims abstract description 39
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 title claims abstract description 39
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 title claims abstract description 39
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 title claims abstract description 39
- AZJQQNWSSLCLJN-UHFFFAOYSA-N 2-ethoxyquinoline Chemical compound C1=CC=CC2=NC(OCC)=CC=C21 AZJQQNWSSLCLJN-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000000243 solution Substances 0.000 claims abstract description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000011259 mixed solution Substances 0.000 claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 235000005881 Calendula officinalis Nutrition 0.000 claims abstract description 8
- 238000000605 extraction Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000002245 particle Substances 0.000 claims abstract description 8
- 240000000785 Tagetes erecta Species 0.000 claims abstract description 3
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 3
- 239000012141 concentrate Substances 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- 238000013517 stratification Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 235000020245 plant milk Nutrition 0.000 abstract description 2
- 241000736851 Tagetes Species 0.000 description 6
- 238000009413 insulation Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 241000628997 Flos Species 0.000 description 1
- 235000012311 Tagetes erecta Nutrition 0.000 description 1
- 235000003595 Tagetes minuta Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019261 food antioxidant Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention relates to the minimizing technology of ethoxyquinoline in a kind of lutein extract, belong to plant milk extract technical field, comprise the following steps: (1) marigold flower particle, through normal hexane extraction, filtration, concentrating under reduced pressure, obtains xenthophylls extracting solution; (2) in xenthophylls extracting solution, add alcohol solution, stir in 35-55 DEG C of water bath with thermostatic control and obtain mixed solution; (3) layering: mixed solution, at temperature 35-55 DEG C, through centrifugal layering or stratification, is released lower floor's alcoholic solution layer, obtained upper strata normal hexane layer; (4) wash: normal hexane layer clear water washing in upper strata is neutral to water layer pH; (5) concentrated: normal hexane layer concentrates and namely obtains not containing the lutein extract of ethoxyquinoline.The inventive method is simple to operate, and without the need to special equipment, special chemical reagent, treatment capacity is large, and product yield is high, can obtain not containing the lutein extract of ethoxyquinoline, and realize suitability for industrialized production.
Description
Technical field
The invention belongs to plant milk extract technical field, be specifically related to the minimizing technology of ethoxyquinoline in a kind of lutein extract.
Background technology
Fresh Flos Tagetis Erectae is through gathering-enzymolysis-dehydration-oven dry-granulation-leaching-lutein extract.Lutein extract can obtain the serial xenthophylls products such as lutein crystal, lutein ester, Xanthin micro-capsule through further deep processing.
Ethoxyquinoline, chemical name is 6-oxyethyl group-2,2,4-trimethylammonium-1,2-dihydroquinoline, is one of feed antioxidant of excellent property, and has certain mildew-resistant and freshening effect; Separately can be used as food antioxidant, fruit antistaling agent, rubber antioxidant, be widely adopted in the world at present.
Along with the continuous progress of society and the raising day by day of living standards of the people, while day by day the increasing of xenthophylls market demand, the requirement of people to Product Safety is more and more higher.Found by long-term research, in the xenthophylls product of domestic and international production, some can detect the ethoxyquinoline of trace or trace, present stage, mechanism was still not clear, and potential food safety risk is also uncertain, but under the severe situation of food safety, be necessary to develop a kind of method removing ethoxyquinoline.
Publication number is in the patent of CN101486671, adds sorbent material in Flower of Aztec Marigold extracting solution, stirs after 0.5 ~ 5 hour and filter at 20 ~ 70 DEG C, obtains not containing the product of ethoxyquinoline after mother liquor concentrations.Because adsorbent amount is large, and direct extracting solution does and adsorbs, and there will be product yield low, the shortcoming that treatment capacity is little, is difficult to suitability for industrialized production.
Summary of the invention
In order to overcome the shortcoming of prior art, the invention provides the minimizing technology of ethoxyquinoline in a kind of lutein extract, the method treatment capacity is large, and yield is high, the ethoxyquinoline in lutein extract can be removed to below 5ppb.
The object of the present invention is to provide the minimizing technology of ethoxyquinoline in a kind of lutein extract, comprise the following steps:
(1) marigold flower particle is through normal hexane extraction, filtration, concentrating under reduced pressure, obtains xenthophylls extracting solution;
(2) in xenthophylls extracting solution, add alcohol solution, stir in 35-55 DEG C of water bath with thermostatic control and obtain mixed solution;
(3) layering: mixed solution, at temperature 35-55 DEG C, through centrifugal layering or stratification, is released lower floor's alcoholic solution layer, obtained upper strata normal hexane layer;
(4) wash: normal hexane layer clear water washing in upper strata is neutral to water layer pH;
(5) concentrated: normal hexane layer concentrates and namely obtains not containing the lutein extract of ethoxyquinoline.
In the present invention, the pH value of the alcohol solution added in described step (2) is 2-4, and preferably, described pH value is 2-3.
In the present invention, the alcohol solution added in described step (2) is volume fraction is 30-60% methyl alcohol or aqueous ethanolic solution, and preferably, described alcohol solution is volume fraction is 45-50% methyl alcohol or aqueous ethanolic solution.
In the present invention, be evaporated in described step (1) that lutein extract weight accounts for extracting liquid volume 30% ~ 70%.
In the present invention, the alcohol solution phosphoric acid in described step (2), hydrochloric acid, citric acid adjust ph.
In the present invention, in described step (2), the volume ratio of extracting solution and alcohol solution is 1:1-4.
In the present invention, the water bath with thermostatic control in described step (2) is 35-55 DEG C, and stir 30-60min, preferably described water bath with thermostatic control is 40-45 DEG C.
In the present invention, the normal hexane layer obtained in described step (3) repeats 3-6 time according to step (2), (3) again.
Ethoxyquinoline detection method reference " high performance liquid chromatography-tandem mass method measures ethoxyquinoline in fruit and remains " in the present invention, Ding Tao etc., mass spectrum journal, the 30th volume the 5th phase, 307-310 page, in September, 2009.Present method detects and is limited to 5ppb.
Mentality of designing of the present invention is: ethoxyquinoline solubleness in alcohol solution is comparatively large, and by regulating pH, heating up to increase its solubleness in alcohol solution, and then competes out from normal hexane by it.And lutein extract is almost insoluble in alcohol solution, product yield is high.
Beneficial effect of the present invention is: this technological operation is simple, and without the need to special equipment, special chemical reagent, treatment capacity is large, and product yield is high, can obtain not containing the lutein extract of ethoxyquinoline, and realize suitability for industrialized production.
Embodiment
Below in conjunction with embodiment, the present invention is further detailed explanation.
Embodiment 1
(1), 1000kg marigold flower particle through normal hexane extraction, filtration, concentrated after, obtain 200 liters of xenthophylls extracting solutions, detecting medicinal extract content through sampling is 50%, and total lutein content is 12000g, and in lutein extract, ethoxyquinoline content is 300ppb;
(2), in xenthophylls extracting solution, add the methanol solution (methanol solution phosphoric acid adjust pH to 2.5) of 400 liters of volume fractions 45%, stir 35 minutes in 40 DEG C, obtain mixed solution;
(3), mixed solution in the separator temperature 40 DEG C insulation leave standstill 1 hour, mixed solution is layered as normal hexane layer and methanol layer, is released by methanol layer;
(4), normal hexane layer washes 4 times by step (2), (3);
(5), upper strata normal hexane layer clear water washs to pH=7;
(6), normal hexane layer is concentrated obtains xenthophylls 100kg, total lutein content 11940g, content yield 99.50%; Use high performance liquid phase to detect ethoxyquinoline, do not detect (present method detects and is limited to 5ppb).
Embodiment 2
(1), 1500kg marigold flower particle through normal hexane extraction, filtration, concentrated after, obtain 250 liters of xenthophylls extracting solutions, detecting medicinal extract content through sampling is 45%, and total lutein content is 13400g, and in lutein extract, ethoxyquinoline content is 500ppb;
(2), in xenthophylls extracting solution, add the ethanolic soln (ethanolic soln hydrochloric acid adjust pH to 2.2) of 750 liters of volume fractions 48%, stir 50 minutes in 45 DEG C, obtain mixed solution;
(3), mixed solution in the separator temperature 45 C insulation leave standstill 1.5 hours, mixed solution is layered as normal hexane layer and alcohol layer, is released by alcohol layer;
(4), normal hexane layer washes 5 times by step (2), (3);
(5), upper strata normal hexane layer clear water washs to pH=7;
(6), normal hexane layer is concentrated obtains xenthophylls 112.5kg, total lutein content 13250g, content yield 98.88%; Use high performance liquid phase to detect ethoxyquinoline, do not detect.
Embodiment 3
(1), 1000kg marigold flower particle through normal hexane extraction, filtration, concentrated after, obtain 750 liters of xenthophylls extracting solutions, detecting medicinal extract content through sampling is 30%, and total lutein content is 12000g, and in lutein extract, ethoxyquinoline content is 700ppb;
(2), in xenthophylls extracting solution, add the methanol solution (methanol solution phosphoric acid adjust pH to 4.0) of 750 liters of volume fractions 60%, stir 30 minutes in 35 DEG C, obtain mixed solution;
(3), mixed solution in the separator temperature 35 DEG C insulation leave standstill 1 hour, mixed solution is layered as normal hexane layer and methanol layer, is released by methanol layer;
(4), normal hexane layer washes 6 times by step (2), (3);
(5), upper strata normal hexane layer clear water washs to pH=7;
(6), normal hexane layer is concentrated obtains xenthophylls 100kg, total lutein content 11921g, content yield 99.34%; Use high performance liquid phase to detect ethoxyquinoline, do not detect.
Embodiment 4
(1), 1500kg marigold flower particle through normal hexane extraction, filtration, concentrated after, obtain 200 liters of xenthophylls extracting solutions, detecting medicinal extract content through sampling is 70%, and total lutein content is 13500g, and in lutein extract, ethoxyquinoline content is 400ppb;
(2), in xenthophylls extracting solution, add the ethanolic soln (ethanolic soln hydrochloric acid adjust pH to 3.0) of 800 liters of volume fractions 50%, stir 60 minutes in 55 DEG C, obtain mixed solution;
(3), mixed solution in the separator temperature 55 DEG C insulation leave standstill 1 hour, mixed solution is layered as normal hexane layer and alcohol layer, is released by alcohol layer;
(4), normal hexane layer washes 3 times by step (2), (3);
(5), upper strata normal hexane layer clear water washs to pH=7;
(6), normal hexane layer is concentrated obtains xenthophylls 100kg, total lutein content 13476g, content yield 99.82%; Use high performance liquid phase to detect ethoxyquinoline, do not detect.
Embodiment 5
(1), 1000kg marigold flower particle through normal hexane extraction, filtration, concentrated after, obtain 180 liters of xenthophylls extracting solutions, detecting medicinal extract content through sampling is 58%, and total lutein content is 12600g, and in lutein extract, ethoxyquinoline content is 350ppb;
(2), in xenthophylls extracting solution, add the methanol solution (methanol solution citric acid adjust pH to 2.0) of 450 liters of volume fractions 30%, stir 40 minutes in 42 DEG C, obtain mixed solution;
(3), mixed solution in the separator temperature 42 DEG C insulation leave standstill 1 hour, mixed solution is layered as normal hexane layer and methanol layer, is released by methanol layer;
(4), normal hexane layer washes 4 times by step (2), (3);
(5), upper strata normal hexane layer clear water washs to pH=7;
(6), normal hexane layer is concentrated obtains xenthophylls 100kg, total lutein content 12540g, content yield 99.52%; Use high performance liquid phase to detect ethoxyquinoline, do not detect.
Above by embodiment to invention has been detailed description; but described content is only preferred embodiment of the present invention; utilize technical solutions according to the invention; or those skilled in the art is under the inspiration of technical solution of the present invention; design similar technical scheme; and reach above-mentioned technique effect, be all fall into protection scope of the present invention.
Claims (7)
1. the minimizing technology of ethoxyquinoline in lutein extract, is characterized in that, comprise the following steps:
(1) marigold flower particle is through normal hexane extraction, filtration, concentrating under reduced pressure, obtains xenthophylls extracting solution;
(2) in xenthophylls extracting solution, add the alcohol solution that pH value is 2-4, stir in 35-55 DEG C of water bath with thermostatic control and obtain mixed solution;
(3) layering: mixed solution, at temperature 35-55 DEG C, through centrifugal layering or stratification, is released lower floor's alcoholic solution layer, obtained upper strata normal hexane layer;
(4) wash: normal hexane layer clear water washing in upper strata is neutral to water layer pH;
(5) concentrated: normal hexane layer concentrates and namely obtains not containing the lutein extract of ethoxyquinoline.
2. the minimizing technology of ethoxyquinoline in a kind of lutein extract according to claim 1, it is characterized in that, the alcohol solution added in described step (2) is volume fraction is 30-60% methyl alcohol or aqueous ethanolic solution.
3. the minimizing technology of ethoxyquinoline in a kind of lutein extract according to claim 1, is characterized in that, be evaporated in described step (1) that lutein extract weight accounts for extracting liquid volume 30% ~ 70%.
4. in a kind of lutein extract according to claim 1-3 any one, the minimizing technology of ethoxyquinoline, is characterized in that, the alcohol solution phosphoric acid in described step (2), hydrochloric acid, citric acid adjust ph.
5. in a kind of lutein extract according to claim 1-3 any one, the minimizing technology of ethoxyquinoline, is characterized in that, in described step (2), the volume ratio of extracting solution and alcohol solution is 1:1-4.
6. in a kind of lutein extract according to claim 1-3 any one, the minimizing technology of ethoxyquinoline, is characterized in that, the water bath with thermostatic control in described step (2) is 35-55 DEG C, stirs 30-60min.
7. in a kind of lutein extract according to claim 1-3 any one, the minimizing technology of ethoxyquinoline, is characterized in that, the normal hexane layer obtained in described step (3) repeats 3-6 time according to step (2), (3) again.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6191293B1 (en) * | 1998-04-20 | 2001-02-20 | Inexa, Industria Extractora C.A. | Trans-xanthophyll ester concentrates of enhanced purity and methods of making same |
| WO2003037833A1 (en) * | 2001-11-02 | 2003-05-08 | Sobhanadri, Jonnalagadda | Extraction of lutein from marigold meal |
| CN1436774A (en) * | 2002-02-05 | 2003-08-20 | 海宁凤鸣叶绿素有限公司 | Lutein crystal preparing process from marigold flower |
| EP1513804B1 (en) * | 2002-06-05 | 2009-01-14 | OmniActive Health Technologies Private Limited | Novel trans-lutein enriched xanthophyll ester concentrate and a process for its preparation |
| CN101486671A (en) * | 2009-02-27 | 2009-07-22 | 大连医诺生物有限公司 | Preparation and stabilization of high-purity xanthophyll ester and method for removing pollutant thereof |
| CN102174005A (en) * | 2011-01-25 | 2011-09-07 | 石河子大学医学院第一附属医院 | Method for extracting lutein from marigold dried flowers |
| CN104059007A (en) * | 2014-04-30 | 2014-09-24 | 西安岳达植物科技有限公司 | Method for extracting lutein ester from marigold flowers |
-
2014
- 2014-11-18 CN CN201410656647.XA patent/CN104387307B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6191293B1 (en) * | 1998-04-20 | 2001-02-20 | Inexa, Industria Extractora C.A. | Trans-xanthophyll ester concentrates of enhanced purity and methods of making same |
| WO2003037833A1 (en) * | 2001-11-02 | 2003-05-08 | Sobhanadri, Jonnalagadda | Extraction of lutein from marigold meal |
| CN1436774A (en) * | 2002-02-05 | 2003-08-20 | 海宁凤鸣叶绿素有限公司 | Lutein crystal preparing process from marigold flower |
| EP1513804B1 (en) * | 2002-06-05 | 2009-01-14 | OmniActive Health Technologies Private Limited | Novel trans-lutein enriched xanthophyll ester concentrate and a process for its preparation |
| CN101486671A (en) * | 2009-02-27 | 2009-07-22 | 大连医诺生物有限公司 | Preparation and stabilization of high-purity xanthophyll ester and method for removing pollutant thereof |
| CN102174005A (en) * | 2011-01-25 | 2011-09-07 | 石河子大学医学院第一附属医院 | Method for extracting lutein from marigold dried flowers |
| CN104059007A (en) * | 2014-04-30 | 2014-09-24 | 西安岳达植物科技有限公司 | Method for extracting lutein ester from marigold flowers |
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| Title |
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Effective date of registration: 20210106 Address after: 679100 shitoushan Industrial Park, Tengchong City, Baoshan City, Yunnan Province Patentee after: Chenguang biotechnology group Tengchong Co., Ltd Patentee after: Chenguang Biotech Group Co.,Ltd. Address before: 057250 Chenguang Road, Quzhou County, Handan City, Hebei Province Patentee before: Chenguang Biotech Group Co.,Ltd. |