CN106046850B - A kind of high-purity natural curcumin product preparation method - Google Patents
A kind of high-purity natural curcumin product preparation method Download PDFInfo
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- CN106046850B CN106046850B CN201610435647.6A CN201610435647A CN106046850B CN 106046850 B CN106046850 B CN 106046850B CN 201610435647 A CN201610435647 A CN 201610435647A CN 106046850 B CN106046850 B CN 106046850B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The present invention relates to a kind of natural pigment curcumin product and its production technology, belong to deep-processing technical field of agricultural products.Using turmeric rhizome as raw material, eutectic solvent prepared by natural component is extractant, and using the characteristic of natural eutectic solvent, curcumin is extracted highly selectively, by ultrasonically treated, improves extraction efficiency.After extraction, using water as solvent, using anti-solvent method selective precipitation curcumin, precipitation prepares the Natural Curcumin product of high-purity through centrifuging and being dried in vacuo.This method uses nontoxic natural eutectic solvent and water for extractant and precipitating reagent, production process is simple, efficiently, safety, green；Overcoming traditional curcumin production needs a large amount of toxic organic solvents and complicated column separation process.
Description
Technical field
The invention belongs to food processing field, it is related to a kind of high-purity natural pigment curcumin product and preparation method thereof.
Background technology
Curcumin is one of active ingredient of Chinese medicine turmeric (Curcuma longa L.), is that turmeric plays pharmacology work
Main component.Curcumin class mainly has curcumin (C21H20O6, account for 70%), Demethoxycurcumin (C20H18O5,
Account for 15%), Bisdemethoxycurcumin (C19H16O4, account for 10%), be rare diones coloring matter in the Nature.Ginger
Flavine is one of curcuma primary bioactive components, is used as a kind of natural pigment, curcumin strong coloring force, safe nothing
Poison, foodstuff product can be used extensively as colouring agent, be the safety in utilization of FAO, WHO and China's GB2760-2014 defineds
One of very high natural pigment.In addition, curcumin also has the pharmacological actions such as antitumor and anti-inflammatory.
Curcumin is water insoluble, and conventional extraction process is right frequently with organic solvent (such as methanol, ethanol, acetone, chloroform)
It is extracted.At present, 3 kinds of main components of curcumin are separated and the existing more research of purifying, but most of use thin layer
Chromatography and column chromatography, and TLC separation amount is small, pillar layer separation effect is undesirable, and curcumin composition can not be very
Separate well, the curcumin product purity of acquisition is not high；And curcumin can expend a large amount of organic solvents in extraction and elution,
Cost is very high.In addition, traditional organic solvent extraction take it is longer.
Natural eutectic solvent, is, by heating the eutectic liquid being prepared from, to be by two or more natural components
A kind of green liquid.It is typically that the eutectic combined by the hydrogen bond donor and hydrogen bond receptor of certain stoichiometric proportion is mixed
Thing.Further, since its preparing raw material is with low cost, preparation process is very atom economic reaction, and preparation process is not present
Three wastes problem, product easily biological-degradable, to environment non-hazardous and toxic and side effect, so it is a kind of novel green solvent.Naturally
Eutectic solvent has a wide range of applications in separation engineering is extracted.Using the difference of constituent property, it can prepare not
The natural eutectic solvent of same characteristic (such as polarity, dissolubility), and there is spy using the efficient high selectivity extraction of this characteristic
The active skull cap components of different property, this is the property that most organic solvents do not possess.Extracted for current domestic curcumin product
The defect of presence is isolated and purified, a kind of high-purity natural curcumin product preparation method is researched and developed, the product of acquisition will have preferably
Market prospects.
The content of the invention
Technical problem
Present invention aims at the defect existed for existing domestic curcumin product extraction separation and purification, there is provided a kind of high
Purity natural pigment product curcumin preparation method.
Technical scheme
The object of the invention can be realized by following technical matters scheme：Using turmeric stem product as raw material, after crushed
The natural eutectic solvent of 1,2-PD/alanine is used for extractant, selective extraction curcumin, while by ultrasonically treated
To improve extraction efficiency；Extraction process parameter is：Solid-liquid ratio 1: 10~20,15~25 DEG C of temperature, ultrasonic power 75W, the time 1~
2h.Curcumin isolation and purification method is：Deionized water is added in the ratio of extraction mixture and deionized water quality ratio 1: 5~10
To extraction mixture in, at 4 DEG C place 1~2h, and after centrifuged through 5000rpm, remove supernatant, precipitate it is vacuum dried, obtain
Yield be 0.2~0.35% curcumin product, product purity through high performance liquid chromatography (HPLC) determine be more than 98.0% (see
Accompanying drawing).
The inventive method and product have the following advantages that compared with existing conventional method and the curcumin product of preparation：
1st, organic solvent is substituted using nontoxic natural eutectic solvent, process is more green；
2nd, precipitating reagent is adopted water as, the curcumin product of preparation can be widely used in food and medical industry；
3rd, extraction process is carried out at low ambient temperatures, it is to avoid curcumin ingredient degradation, and the time is short, efficiency high.
Brief description of the drawings
Accompanying drawing is that curcumin product purity HPLC detects spectrogram.
Embodiment
Curcumin product nuclear magnetic resonance (NMR) information is as follows：1H-NMR：δ 9.64 (2H, s, Ph-OH-4 ', 4 ") 7.53
(1H, d, J=15.7Hz, H-1,7), 7.30 (2H, s, H-2 ', 2 "), 7.14 (2H, d, J=8.2Hz, H-6 ', 6 "), 6.82
(1H, d, J=8.5Hz, H-5 ', 5 "), 6.75 (2H, d, J=15.7Hz, H-2,6), 3.81 (6H, s, OMe × 2)；13C-NMR：δ
183.2 (C-3,5), 149.2 (C-4 ', 4 "), 148.1 (C-3 ', 3 "), 140.7 (C-1,7), 126.4 (C-1 ', 1 "), 123.2
(C-6 ', 6 "), 121.2 (C-2,6), 115.8 (C-5 ', 5 "), 111.4 (C-2 ', 2 "), 109.9 (C-4), 55.6 (OMe).
Embodiment 1
Turmeric stem powder 100g, the natural eutectic solvent 1kg of 1,2-PD/alanine, are well mixed, are put into ultrasound
In container, feed temperature control is at 15 DEG C, and the ultrasonically treated 1h of 75W then add 5.5kg and add deionized water to extraction mixture
In, 2h is placed at 4 DEG C, supernatant is removed after being centrifuged through 5000rpm, precipitates vacuum dried, curcumin product 0.2g is obtained, it is pure
Degree 98.5%
Embodiment 2
Turmeric stem powder 100g, the natural eutectic solvent 1.5kg of 1,2-PD/alanine, are well mixed, are put into super
In acoustic capacitance device, feed temperature control is at 20 DEG C, and the ultrasonically treated 1.5h of 75W then add 12kg addition deionized waters mixed to extraction
In compound, 2h is placed at 4 DEG C, supernatant is removed after being centrifuged through 5000rpm, precipitates vacuum dried, obtains curcumin product
0.28g, purity 99.3%
Embodiment 3
Turmeric stem powder 100g, the natural eutectic solvent 2kg of 1,2-PD/alanine, are well mixed, are put into ultrasound
In container, feed temperature control is at 25 DEG C, and the ultrasonically treated 2h of 75W then add 21kg and add deionized water to extraction mixture
In, 2h is placed at 4 DEG C, supernatant is removed after being centrifuged through 5000rpm, precipitates vacuum dried, obtains curcumin product 0.35g,
Purity 99.5%.
Claims (4)
1. a kind of natural pigment curcumin preparation method, it is characterised in that using turmeric stem product as raw material, adopt after crushed
It is extractant with the natural eutectic solvent prepared by 1,2-PD/alanine, utilizes the solvent property, high selectivity extraction
Curcumin is taken, while by ultrasonically treated to improve extraction efficiency；After extraction, using water as solvent, using anti-solvent method selectivity
Curcumin is precipitated, supernatant is removed after centrifugation, vacuum dried rear acquisition yellow powder, as Natural Curcumin product is precipitated.
2. according to the method described in claim 1, it is characterised in that the extractant used is that 1,2-PD/alanine is naturally low
Congruent melting solvent, the eutectic solvent be by natural products 1,2-PD and alanine in molar ratio 1: 2 ratio at 85 DEG C
Heat congruent melting, the transparency liquid formed after cooling.
3. according to the method described in claim 1, it is characterised in that extraction process parameter is：Solid-liquid ratio 1: 10~20, temperature 15
~25 DEG C, ultrasonic power 75W, 1~2h of time.
4. according to the method described in claim 1, it is characterised in that curcumin isolation and purification method is：Mixture and gone by extraction
The ratio of ionized water mass ratio 1: 5~10 adds deionized water into extraction mixture, places 2h at 4 DEG C, and after through 5000rpm
Supernatant is removed after centrifugation, precipitates vacuum dried, the yellow powder that yield is 0.2~0.35% is obtained, through nuclear magnetic resonance skill
Art is accredited as curcumin, and product determines purity through high performance liquid chromatography and is more than 98.0%.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3520802A1 (en) * | 2018-02-06 | 2019-08-07 | EFESON - Chemical Research & Engineering Development | Process for extracting curcuminoids |
| WO2020254579A1 (en) * | 2019-06-20 | 2020-12-24 | Givaudan Sa | Eutectic extraction of solids |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106939043A (en) * | 2017-05-12 | 2017-07-11 | 甘肃凯源生物技术开发中心 | A kind of method of phycocyanin in eutectic solvent salt aqueous two-phase extraction spirulina |
| CN107271594B (en) * | 2017-07-14 | 2019-09-17 | 河南中大恒源生物科技股份有限公司 | A method of identifying Natural Curcumin and synthesis curcumin |
| CN107937009B (en) * | 2017-11-10 | 2020-08-04 | 中国五环工程有限公司 | Method for separating phenolic compounds from coal tar and direct coal liquefaction product |
| CN107805193B (en) * | 2017-11-27 | 2020-11-06 | 晨光生物科技集团股份有限公司 | Production method of low-solubility residual curcumin crystal |
| CN110240541A (en) * | 2019-07-08 | 2019-09-17 | 哈尔滨工业大学 | It is a kind of to use vacuum couplings ultrasonic wave-supercritical CO2The method of extraction extraction curcumin |
| CN110771892B (en) * | 2019-11-12 | 2023-05-16 | 晨光生物科技集团股份有限公司 | High-quality curcumin product, production method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104045541A (en) * | 2014-06-18 | 2014-09-17 | 大连大学 | Method for synthesizing aromatic ketone compound |
| CN104860797A (en) * | 2015-05-21 | 2015-08-26 | 济南大学 | Isopropyl ether-isopropyl alcohol azeotrope distillation separation method based on choline chloride deep eutectic solvent |
| CN104887723A (en) * | 2015-06-18 | 2015-09-09 | 天津理工大学 | Method for extracting flavonoids from ginkgo biloba leaves with deep eutectic solvent |
| CN105288634A (en) * | 2015-10-23 | 2016-02-03 | 南京农业大学 | Preparation method of glycerin-amino acid deep eutectic solvent |
-
2016
- 2016-06-14 CN CN201610435647.6A patent/CN106046850B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104045541A (en) * | 2014-06-18 | 2014-09-17 | 大连大学 | Method for synthesizing aromatic ketone compound |
| CN104860797A (en) * | 2015-05-21 | 2015-08-26 | 济南大学 | Isopropyl ether-isopropyl alcohol azeotrope distillation separation method based on choline chloride deep eutectic solvent |
| CN104887723A (en) * | 2015-06-18 | 2015-09-09 | 天津理工大学 | Method for extracting flavonoids from ginkgo biloba leaves with deep eutectic solvent |
| CN105288634A (en) * | 2015-10-23 | 2016-02-03 | 南京农业大学 | Preparation method of glycerin-amino acid deep eutectic solvent |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3520802A1 (en) * | 2018-02-06 | 2019-08-07 | EFESON - Chemical Research & Engineering Development | Process for extracting curcuminoids |
| WO2020254579A1 (en) * | 2019-06-20 | 2020-12-24 | Givaudan Sa | Eutectic extraction of solids |
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