CN104630315A - Reduced pressure enzyme process acylation method of black rice pigment - Google Patents
Reduced pressure enzyme process acylation method of black rice pigment Download PDFInfo
- Publication number
- CN104630315A CN104630315A CN201310547628.9A CN201310547628A CN104630315A CN 104630315 A CN104630315 A CN 104630315A CN 201310547628 A CN201310547628 A CN 201310547628A CN 104630315 A CN104630315 A CN 104630315A
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- CN
- China
- Prior art keywords
- black rice
- enzyme process
- rice pigments
- reaction
- acylations
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Links
- 239000000049 pigment Substances 0.000 title claims abstract description 35
- 241000371652 Curvularia clavata Species 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000010933 acylation Effects 0.000 title claims abstract description 17
- 238000005917 acylation reaction Methods 0.000 title claims abstract description 17
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 15
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 15
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 229940095102 methyl benzoate Drugs 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 102000004882 Lipase Human genes 0.000 claims abstract description 8
- 108090001060 Lipase Proteins 0.000 claims abstract description 8
- 239000004367 Lipase Substances 0.000 claims abstract description 8
- 235000019421 lipase Nutrition 0.000 claims abstract description 8
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 3
- 230000006837 decompression Effects 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 235000013305 food Nutrition 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 description 3
- VEVZSMAEJFVWIL-UHFFFAOYSA-O cyanidin cation Chemical compound [O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC=C(O)C(O)=C1 VEVZSMAEJFVWIL-UHFFFAOYSA-O 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000004976 Solanum vernei Nutrition 0.000 description 1
- 241000352057 Solanum vernei Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000002019 anti-mutation Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000007336 cyanidin Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 239000000989 food dye Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- -1 phenols acids Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention provides a reduced pressure enzyme process acylation method of a black rice pigment, and belongs to the technical filed of deep processing of agricultural products. The method comprises the following steps: dissolving the black rice in a small amount of pyridine, respectively adding methyl benzoate and Novozmy435 immobilized lipase, and carrying out a catalysis reaction under reduced pressure conditions for 48h; and adding water after the reaction to extract a product. The method has the advantages of cycle use of the above solvent and the above enzyme, low cost, suitableness for mass production, and good industrial prospect. The acylated black rice pigment obtained in the invention can be used in different fields as a natural food pigment.
Description
One, technical field
The present invention is a kind of decompression enzyme process acylations method of black rice pigments, belongs to deep-processing technical field of agricultural products.
Two, background technology
Black rice pigments is the water colo(u)r extracted from black rice and black rice seed coat, rice bran.Research about black rice pigments shows, black rice pigments belongs to anthocyani pigment, and main component is Cy-3-G.Black rice pigments has stronger hypotensive, reducing blood-fat, anti-mutation, physiologically active and the function such as anti-oxidant, antitumor.As a kind of abundant raw material; the natural food colour of easy extraction; in food, healthcare products, medicine, makeup etc., there is very large potentiality to be exploited; but because black rice pigments main component is non-acyl group anthocyanogen; so natural black rice pigment stability is poor, which limits it in the widespread use of processing and in storage.Acylations can improve anthocyanogen stability, improves colouring effect, improves oxidation-resistance.Lipase can catalysis transesterification reaction in organic phase, utilizes this principle the carboxyl groups in phenols acids can be transferred on the glucoside hydroxyl of Cyanidin, realizes the acylations to anthocyanogen, the natural pigment raw material of preparation high stability.Therefore, this method has important theory value and realistic meaning.
Three, summary of the invention
The main component Cy-3-G of technical problem black rice pigments is non-acyl group anthocyanogen, than acyl group anthocyanogen poor stabilities such as purple potatos, easily fades.Also black rice pigments is made to be restricted as the application of food dye.The present invention, mainly for the technical barrier of black rice pigments poor stability, by the black rice pigments of preliminary purification being carried out at reduced pressure conditions the enzyme process acylations in organic phase, obtains stability-enhanced black rice pigments.
Technical scheme the invention provides a kind of decompression enzyme process acylations method of black rice pigments, comprising:
1) preparation of reaction system: added by black rice pigments in round-bottomed flask, adds a small amount of pyridinium dissolution, then adds the methyl benzoate of certain volume, and Novozmy435 immobilized lipase, fully shakes up.
2) the lower enzymic catalytic reaction of decompression: round-bottomed flask is loaded on rotatory evaporator, control pressure 0.09MPa, slowly rotate, successive reaction 48 hours.Due to transesterification reaction generate methyl alcohol be distilled out of, react to generation benzoyl C-3-G direction carry out,
3) product separation: add certain volume water after reaction terminates and stir evenly, pour separating funnel into, leaves standstill and gets the filtration of upper water solution after 10 minutes.Filtrate reduced in volume is acylations black rice pigments, transformation efficiency about 30% after dry.The separating funnel lower floor molten thing of oil is the mixture of unreacted methyl benzoate and enzyme, reusable after drying.
Beneficial effect
1. obtain benzoylation black rice pigments, color stability is improved, and can be used as natural food pigment.
2. adopt immobilized lipase, repeatedly can use, reduce costs, be applicable to a large amount of production, industrial prospect is good.
3. using methyl benzoate to be both solvent, is also reaction substrate.Methyl benzoate is unfunctionalized olefins product, safe and reliable, can repeatedly utilize.
Four, embodiment
Added by black rice pigments in round-bottomed flask, add a small amount of pyridinium dissolution, then add the methyl benzoate of certain volume, Novozmy435 immobilized lipase, fully shakes up.Round-bottomed flask is loaded on rotatory evaporator, control pressure at 0.09MPa, successive reaction 48 hours.Add certain volume water after reaction terminates to stir evenly, pour separating funnel into, leave standstill and after 10 minutes, get the filtration of upper water solution.Filtrate reduced in volume is acylations black rice pigments after dry.The separating funnel lower floor molten thing of oil is the mixture of unreacted methyl benzoate and enzyme, reuses after drying.
Embodiment
Added in 250 milliliters of round-bottomed flasks by 20 milligrams of black rice pigments, add 1 milliliter of pyridinium dissolution, then add 10 milliliters of methyl benzoate, 50 milligrams of Novozmy435 immobilized lipases, fully shake up.Loaded by round-bottomed flask on rotatory evaporator, control pressure, at 0.09MPa, slowly rotates, successive reaction 48 hours.Add 20 ml waters after reaction terminates to stir evenly, pour separating funnel into, leave standstill and after 10 minutes, get the filtration of upper water solution.Filtrate reduced in volume is acylations black rice pigments after dry.
Claims (5)
1. a decompression enzyme process acylations method for black rice pigments, comprising:
1) reaction system prepares: added by black rice pigments in round-bottomed flask, add a small amount of pyridinium dissolution, then add the methyl benzoate of certain volume, Novozmy435 immobilized lipase, fully shakes up.
2) the lower enzymic catalytic reaction of decompression: round-bottomed flask is loaded on rotatory evaporator, control pressure at 0.09MPa, successive reaction 48 hours.Due to transesterification reaction generate methyl alcohol be distilled out of, react to generation benzoyl C-3-G direction carry out,
3) product separation: add certain volume water after reaction terminates and stir evenly, pour separating funnel into, leaves standstill and gets the filtration of upper water solution after 10 minutes.Filtrate reduced in volume is acylations black rice pigments, transformation efficiency about 30% after dry.The separating funnel lower floor molten thing of oil is the mixture of unreacted methyl benzoate and enzyme, reusable after drying.
2. the decompression enzyme process acylations method of a kind of black rice pigments according to claim 1, is characterized in that: immobilized lipase model used is Novozmy435, and letter company limited of Novi produces.
3. a kind of decompression enzyme process acylations method of black rice pigments according to claim 1 or 2, is characterized in that: use solvent and reaction substrate to be methyl benzoate.
4. a kind of decompression enzyme process acylations method of black rice pigments according to claim 1 or 2, is characterized in that: use water to carry out extraction product.
5. the product that obtains of the decompression enzyme process acylations method of the described a kind of black rice pigments of one of claim 1-5.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310547628.9A CN104630315B (en) | 2013-11-06 | 2013-11-06 | A kind of decompression enzyme process acylation method of black rice pigments |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310547628.9A CN104630315B (en) | 2013-11-06 | 2013-11-06 | A kind of decompression enzyme process acylation method of black rice pigments |
Publications (2)
| Publication Number | Publication Date |
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| CN104630315A true CN104630315A (en) | 2015-05-20 |
| CN104630315B CN104630315B (en) | 2018-08-14 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114403224A (en) * | 2021-12-20 | 2022-04-29 | 蚌埠市和平乳业有限责任公司 | High-stability modified milk and preparation method thereof |
| CN116253708A (en) * | 2023-03-07 | 2023-06-13 | 陕西嘉禾生物科技股份有限公司 | Method for extracting anthocyanin from black rice |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1876824A (en) * | 2006-04-21 | 2006-12-13 | 华南理工大学 | Method for preparing cytosine arabinoside ester by enzyme catalysis |
| CN100999749A (en) * | 2007-01-05 | 2007-07-18 | 华南理工大学 | Process of preparing 5-fluorouradine ester by enzyme catalyzing |
-
2013
- 2013-11-06 CN CN201310547628.9A patent/CN104630315B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1876824A (en) * | 2006-04-21 | 2006-12-13 | 华南理工大学 | Method for preparing cytosine arabinoside ester by enzyme catalysis |
| CN100999749A (en) * | 2007-01-05 | 2007-07-18 | 华南理工大学 | Process of preparing 5-fluorouradine ester by enzyme catalyzing |
Non-Patent Citations (9)
| Title |
|---|
| DAVID E. STEVENSON等: "Direct acylation of flavonoid glycosides with phenolic acids catalysed by Candida antarctica lipase B(Novozym 435®)", 《ENZYME AND MICROBIAL TECHNOLOGY》 * |
| E.ENAUD等: "Enzymatic synthesis of new aromatic esters of phloridzin", 《JOURNAL OF MOLECULAR CATALYSIS B: ENZYMATIC》 * |
| JAMILA HADJ SALEM等: "Biological activities of flavonoids from Nitraria retusa (Forssk.) Asch.and their acylated derivatives", 《FOOD CHEMISTRY》 * |
| XIAOLING LU等: "Acylation of Anthocyanins From Black Rice and Their Stability Properties", 《ADVANCED MATERIALS RESEARCH》 * |
| 审查员: "《化合物结构检索》", 10 July 2017 * |
| 曹清丽等: "有机相中脂肪酶催化合成黄酮酯类研究进展", 《化学世界》 * |
| 王运吉、张苓花: "《酶化工》", 30 September 1997 * |
| 田小燕等: "花色苷有机酸酰化及黄酮辅色研究进展", 《农产品加工(学刊)》 * |
| 马祥等: "脂肪酶催化竹叶抗氧化物中异荭草苷和异牡荆苷酰化", 《食品科学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114403224A (en) * | 2021-12-20 | 2022-04-29 | 蚌埠市和平乳业有限责任公司 | High-stability modified milk and preparation method thereof |
| CN116253708A (en) * | 2023-03-07 | 2023-06-13 | 陕西嘉禾生物科技股份有限公司 | Method for extracting anthocyanin from black rice |
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| CN104630315B (en) | 2018-08-14 |
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