CN104876989B - A kind of preparation method of natamycin acicular crystal - Google Patents
A kind of preparation method of natamycin acicular crystal Download PDFInfo
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- CN104876989B CN104876989B CN201510246444.8A CN201510246444A CN104876989B CN 104876989 B CN104876989 B CN 104876989B CN 201510246444 A CN201510246444 A CN 201510246444A CN 104876989 B CN104876989 B CN 104876989B
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- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 title claims abstract description 58
- 229960003255 natamycin Drugs 0.000 title claims abstract description 58
- 239000004311 natamycin Substances 0.000 title claims abstract description 56
- 235000010298 natamycin Nutrition 0.000 title claims abstract description 56
- 239000013078 crystal Substances 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000003756 stirring Methods 0.000 claims abstract description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- BQFCCCIRTOLPEF-UHFFFAOYSA-N chembl1976978 Chemical compound CC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 BQFCCCIRTOLPEF-UHFFFAOYSA-N 0.000 claims abstract description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 230000008025 crystallization Effects 0.000 claims abstract description 8
- 238000001694 spray drying Methods 0.000 claims abstract description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005119 centrifugation Methods 0.000 claims abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010583 slow cooling Methods 0.000 claims abstract description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Chemical group CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical group CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Chemical group CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940090181 propyl acetate Drugs 0.000 claims abstract description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical group CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 239000000725 suspension Substances 0.000 abstract description 9
- 239000007864 aqueous solution Substances 0.000 abstract description 5
- 239000002244 precipitate Substances 0.000 abstract description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 241000406668 Loxodonta cyclotis Species 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000010956 nickel silver Substances 0.000 description 3
- NCXMLFZGDNKEPB-UHFFFAOYSA-N Pimaricin Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCC(C)OC(=O)C=CC2OC2CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 NCXMLFZGDNKEPB-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019249 food preservative Nutrition 0.000 description 2
- 239000005452 food preservative Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229930195730 Aflatoxin Natural products 0.000 description 1
- XWIYFDMXXLINPU-UHFFFAOYSA-N Aflatoxin G Chemical compound O=C1OCCC2=C1C(=O)OC1=C2C(OC)=CC2=C1C1C=COC1O2 XWIYFDMXXLINPU-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000235342 Saccharomycetes Species 0.000 description 1
- 241000970906 Streptomyces natalensis Species 0.000 description 1
- 239000005409 aflatoxin Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a kind of new preparation process of high-quality natamycin acicular crystal：Natamycin is added in the aqueous solution, solvent orange 2 A is added, is heated to reflux, stirring makes it fully dissolve, uniform solution is formed；Then, add solvent B, stir and slow cooling is to 0~15 DEG C, crystallization process is completed in 18~24h and obtains acicular crystal, again through centrifugation, spray drying, natamycin acicular crystal is obtained, described solvent orange 2 A is ethanol, isopropanol, acetonitrile, pyridine or tetrahydrofuran, and solvent B is ethyl acetate, propyl acetate, butyl acetate, acetic acid or acetone.Using this inventive method, suspension stability is good in water or ethanol solution again for the sample of gained, does not precipitate for a long time, easy to use.The use of a large amount of soda acids is avoided in production process, organic solvent is recyclable to be used again, reduce production cost.
Description
(1) technical field
The present invention relates to a kind of preparation method of natamycin acicular crystal.
(2) background technology
Natamycin (Natamycin) also known as natamycin, pimaricin or pimaricin, belong to polyene macrolides
Material, it, by a kind of antibiotic of the fermented generations of Streptomyces natalensis, is a kind of odorless, tasteless, low dosage to be
And safe food preservative, can metastatic suppression saccharomycete and mould, the shape of prevention filamentous fungi aflatoxin
Into.Natamycin is to have a basic group and an acidic-group, pK in amphiprotic substance, moleculeaIt is worth for 4.6 and 8.35, etc.
Electricity point is 6.5.Solubility is very low in water and in polar solvent, insoluble in non-polar solven, and the solubility in water is at room temperature
30~50mg/L, at pH >=9 or≤3, solubility increases.Solubility just because of natamycin is low, can be with it to food table
Face is handled does not influence the local flavor and mouthfeel of food but with the shelf-life for increasing food.At present, natamycin is used as a kind of day
Right biological preservative has been approved in the production and preservation of the numerous food products such as some dairy products, meat, beverage, fruit.
At present, natamycin applies the formulation in food preservative to be mainly premixed type and suspension, but receives that he is mould
Solubility of the plain flat crystal in water or in ethanol is very low, easily forms floccule and settles, causes natamycin in water
Or distributing inhomogeneity in ethanol solution, so as to have influence on using effect.In addition, in industrial processes, natamycin sheet
Crystal suspensions are in spraying, and natamycin solid can also block shower nozzle regularly, cause production process extremely inconvenient.Although
The uniformity of natamycin in the solution can be increased by adding the assistant agents such as surfactant, but need to increase cost.
At present, researcher has found that suspension stability of the natamycin acicular crystal in water and ethanol solution is higher than
In natamycin flat crystal, but traditional natamycin acicular crystal production technology, a large amount of soda acids are used, and cause follow-up production
Raw high-salt wastewater, and during regulation pH, pH whard to control during big production or crosses alkali at easy local overacidification, and destruction receives him
Mycin chemical constitution, and cause final natamycin purity relative reduction, increase production cost.
(3) content of the invention
It is an object of the invention to provide a kind of preparation method of natamycin acicular crystal.
The technical solution adopted by the present invention is：
A kind of preparation method of natamycin acicular crystal, methods described is as follows：Natamycin is added in the aqueous solution,
Solvent orange 2 A is added, is heated to reflux, stirring makes it fully dissolve, uniform solution is formed；Then, solvent B is added, stirs and slowly drops
Temperature is to 0~15 DEG C, and the interior crystallization process that completes of 18~24h obtains acicular crystal, then through centrifugation, spray drying, obtains natamycin pin
Shape crystal, the addition of the described aqueous solution is calculated as 50~500ml/g with natamycin quality, described solvent orange 2 A, solvent B with
The ratio between volume of water is 10~40：5~20：100, described solvent orange 2 A is ethanol, isopropanol, acetonitrile, pyridine or tetrahydrofuran,
Solvent B is ethyl acetate, propyl acetate, butyl acetate or acetone.The ratio between volume of more preferably described solvent orange 2 A, solvent B and water
For 25：12.5：100.
The preferred described crystallization process of the inventive method is completed in the case where applying 0.5~15T magnetic field, and quickening forms crystal
Speed.
Further, the addition of the described aqueous solution is calculated as 50~300ml/g with natamycin quality.
Further, described solvent orange 2 A is one of pyridine, tetrahydrofuran or acetonitrile, described solvent B is ethyl acetate,
One of acetone or acetic acid.
Further, acicular crystal is suspended in water or 75% ethanol in described method, then through centrifugation, spray drying,
Obtain natamycin acicular crystal.
The main of the present invention has the beneficial effect that：Using this inventive method, the sample of gained is again in water or ethanol solution
Suspension stability is good, does not precipitate for a long time, easy to use.The use of a large amount of soda acids, You Jirong are avoided in production process
Agent is recyclable to be used again, reduces production cost.
(4) illustrate
Fig. 1 is the natamycin of raw material Zhejiang Silver Elephant Bioengineering Co., Ltd. production used herein under microscope
Flat crystal photo (40 × 10).
Fig. 2 is the natamycin flat crystal that raw material Zhejiang Silver Elephant Bioengineering Co., Ltd. used herein produces
Electron-microscope scanning figure.
Fig. 3 is the photo (40 × 10) of natamycin acicular crystal made from embodiment 1 under microscope.
Fig. 4 is the electron-microscope scanning figure of natamycin acicular crystal made from embodiment 1.
Fig. 5 natamycin sheet standard items HPLC chromatograms.
The HPLC chromatogram of aciculiform natamycin product made from Fig. 6 examples 1
(5) embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This:
Embodiment 1：Take the natamycin product (content 93.5%) produced by Zhejiang Silver Elephant Bioengineering Co., Ltd.
10g is added in 1L beakers, adds water 800mL, is added 200mL acetonitrile, is heated to reflux, and stirring makes it fully dissolve, shape
Into uniform solution, then, add 100mL acetone, stir and slow cooling is to 10 DEG C, 18h completes crystallization process, then through from
The heart, spray drying, obtain crystal 9.5g.By electron-microscope scanning, it is that crystal formation is aciculiform to find the crystal, cylindrical.Utilize height
Effect liquid phase chromatogram method (HPLC) determines natamycin content, first accurately takes standard items 0.2g into 100mL volumetric flasks, adds 5mL
Tetrahydrofuran, ultrasonic 10min adds methanol 60mL, and rotation is finally settled to scale to dissolving with water, to be analyzed, with same
Method configuration sample solution, detection to be analyzed.Analysis process is completed by GB 25532-2010, and gained spectrogram is shown in Fig. 5 and figure
6, sample is consistent with standard items appearance time, it is seen that the crystal is really natamycin, and its content is 95.7%.
Embodiment 2：Take the natamycin product (content 93.5%) produced by Zhejiang Silver Elephant Bioengineering Co., Ltd.
10g is added in 1L beakers, adds water 800mL, is added 200mL pyridine, is heated to reflux, and stirring makes it fully dissolve, shape
Into uniform solution, then, 100mL ethyl acetate is added, stir and slow cooling is to 10 DEG C, 18h completes crystallization process, then passes through
Centrifugation, spray drying, are obtained crystal 9.3g, are analyzed using HPLC, and analysis method is with example 1, and gained crystal is natamycin, its
Content is 95.2%, by electron-microscope scanning, and it is aciculiform to find the crystal habit.
Embodiment 3：Take the natamycin product (content 93.5%) produced by Zhejiang Silver Elephant Bioengineering Co., Ltd.
10g is added in 1L beakers, adds water 800mL, is added 200mL acetonitrile, is heated to reflux, and stirring makes it fully dissolve, shape
Into uniform solution, then, 100mL acetone is added, stir and slow cooling is to 15 DEG C.In the lab, produced using electromagnet
Raw constant magnetic field, control electric current intensity makes magnetic field intensity be 0.8T, and beaker is placed in the middle of magnet spool, and 12h is completed
Crystallization process, then through centrifugation, spray drying, crystal 9.3g is obtained, determine that the crystal habit is aciculiform through electron-microscope scanning, utilize
HPLC is analyzed, and analysis method is with example 1, and it is 95.9% to measure natamycin content.
Embodiment 4：Natamycin needle-shaped crystals that embodiment 1, embodiment 2, example 3 and example 4 are obtained and new silver as
Natamycin flat crystal carries out suspension stability experiment, takes 0.1g natamycin samples, adds 100mL 75% ethanol water
In solution, placed after stirring, experimental result is as shown in table 1.In addition, by the natamycin acicular crystal sample of the gained of example 1
Product are analyzed with new silver as sheet natamycin sample carries out microexamination, electron-microscope scanning and HPLC, gained spectrogram see respectively Fig. 1~
6。
The embodiment 1 of table one, embodiment 2, acicular crystal described in example 3 and flat crystal are steady in 75% ethanol solution
Qualitative test
As seen from the above table, the natamycin acicular crystal obtained by the present invention, has fine in 75% ethanol solution
Suspension stability, compared with flat crystal, for a long time do not precipitate, convenient use.
Embodiment 5：The natamycin needle-shaped crystals that embodiment 1, embodiment 2, example 3 are obtained are with new silver as natamycin
Flat crystal carries out suspension stability experiment, takes 0.1g natamycin samples, in the water for adding 100mL, is placed after stirring,
Experimental result is as shown in table 2.The part is mainly experimental phenomena, no data analysis
The aqueous solution stability test of the embodiment 1 of table two, embodiment 2, acicular crystal and flat crystal described in example 3
As seen from the above table, the natamycin acicular crystal obtained by the present invention, has good suspension stability in water,
Compared with flat crystal, do not precipitate for a long time, convenient use.
Claims (4)
1. a kind of preparation method of natamycin acicular crystal, methods described is as follows：Natamycin is added to the water, added molten
Agent A, is heated to reflux, and stirring makes it fully dissolve, and forms uniform solution；Then, add solvent B, stir and slow cooling to 0~
15 DEG C, the interior crystallization process that completes of 18~24h obtains acicular crystal, then through centrifugation, spray drying, obtains natamycin acicular crystal,
The addition of described water is calculated as 50~500ml/g with natamycin quality, the ratio between volume of described solvent orange 2 A, solvent B and water
For 10~40：5~20：100, described solvent orange 2 A is ethanol, isopropanol, acetonitrile, pyridine or tetrahydrofuran, and solvent B is acetic acid second
Ester, propyl acetate, butyl acetate or acetone.
2. the method as described in claim 1, it is characterised in that described crystallization process is complete in the case where applying 0.5~15T magnetic field
Into quickening forms the speed of crystal.
3. the method as described in claim 1, it is characterised in that the addition of described water is calculated as 50 with natamycin quality~
300ml/g。
4. the method as described in claim 1, it is characterised in that described solvent orange 2 A is one of pyridine, tetrahydrofuran or acetonitrile, institute
The solvent B stated is ethyl acetate or acetone.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101048510A (en) * | 2004-10-28 | 2007-10-03 | 帝斯曼知识产权资产管理有限公司 | Stable needle-shaped crystals of natamycin |
| CN102286044A (en) * | 2011-08-22 | 2011-12-21 | 浦城绿康生化有限公司 | Preparation method of natamycin laminar crystal |
| AU2011253811B2 (en) * | 2004-10-28 | 2014-02-20 | Dsm Ip Assets B.V. | Stable needle-shaped crystals of natamycin |
-
2015
- 2015-05-14 CN CN201510246444.8A patent/CN104876989B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101048510A (en) * | 2004-10-28 | 2007-10-03 | 帝斯曼知识产权资产管理有限公司 | Stable needle-shaped crystals of natamycin |
| AU2011253811B2 (en) * | 2004-10-28 | 2014-02-20 | Dsm Ip Assets B.V. | Stable needle-shaped crystals of natamycin |
| CN102286044A (en) * | 2011-08-22 | 2011-12-21 | 浦城绿康生化有限公司 | Preparation method of natamycin laminar crystal |
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