CN115286529A - Stabilizer of hydroxy-alpha-sanshool and storage method - Google Patents
Stabilizer of hydroxy-alpha-sanshool and storage method Download PDFInfo
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- CN115286529A CN115286529A CN202210940131.2A CN202210940131A CN115286529A CN 115286529 A CN115286529 A CN 115286529A CN 202210940131 A CN202210940131 A CN 202210940131A CN 115286529 A CN115286529 A CN 115286529A
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- C07—ORGANIC CHEMISTRY
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- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention provides a stabilizing agent of hydroxy-alpha-sanshool: l-ascorbyl palmitate, tea polyphenol or tert-butyl-4-hydroxyanisole; the stabilizer has excellent protection effect on the hydroxy-alpha-sanshool, can effectively reduce the content loss of the hydroxy-alpha-sanshool in the storage process by combining nitrogen protection and low-temperature storage condition of-20 ℃, and has more excellent stabilizing effect in a liquid environment in which methanol exists. The invention provides an effective scheme for the stable storage of the hydroxy-alpha-sanshool and has popularization and application values.
Description
Technical Field
The invention belongs to the technical field of compound storage, and particularly relates to a stabilizing agent of hydroxy-alpha-sanshool and a storage method.
Background
Zanthoxylum bungeanum (Zanthoxylum L.), rutaceae (Rutaceae) Zanthoxylum, as a traditional condiment and Chinese medicinal materials in China, has a very long history. In the application of zanthoxylum, the most important is still its flavor, and unsaturated fatty amide compounds such as hydroxy- α -sanshool and hydroxy- β -sanshool are the main components of zanthoxylum. Wherein, the hydroxyl-alpha-sanshool (1) is the most main active component of pepper flavor substances and is a specific numb taste component contained in pepper plants.
The hydroxyl-alpha-sanshool is an amide substance with a long-chain structure. The appearance is colorless and viscous, has no volatility, has medium polarity, is easily soluble in organic solvents such as chloroform, methanol and the like, is insoluble in petroleum ether, and has poor water solubility. Hydroxy-alpha-sanshool has a variety of biological activities, such as: anesthesia, analgesia, gastrointestinal peristalsis power enhancement, antioxidation, anti-inflammation, antibiosis, tumor cell proliferation inhibition and the like.
In order to better utilize the pharmacological activity of the hydroxy-alpha-sanshool, researchers have searched for a preparation and purification process of the hydroxy-alpha-sanshool, and a preparation process report for improving the purity of the hydroxy-alpha-sanshool to more than 98% is provided at present (Chinese patent, application number 202011146305.5), but the hydroxy-alpha-sanshool is extremely unstable due to the C-6 cis double bond in the structure of the hydroxy-alpha-sanshool, the hydroxy-alpha-sanshool can quickly become yellow or light yellow syrupy substances under the conventional room temperature storage condition at present, even if the hydroxy-alpha-sanshool content in the product with the purity of up to 98% is also quickly reduced, so that the use of the hydroxy-alpha-sanshool standard product in various industries is seriously limited.
Therefore, the research on the effective and stable storage method of the hydroxy-alpha-sanshool is of great significance.
Disclosure of Invention
The invention aims to provide a stabilizing agent of hydroxy-alpha-sanshool and a storage method.
The present invention provides the use of an antioxidant or an alcoholic solution thereof as a stabilizer for hydroxy-alpha-sanshool; the antioxidant is L-ascorbyl palmitate, tea polyphenol or tert-butyl-4-hydroxyanisole.
The invention also provides a composition, which comprises the following components in parts by weight:
100 parts of hydroxy-alpha-sanshool and 0.02-1 part of antioxidant; the antioxidant is L-ascorbyl palmitate, tea polyphenol or tert-butyl-4-hydroxyanisole.
Further, the antioxidant was 0.02 part.
Further, the antioxidant is L-ascorbyl palmitate.
Further, the composition comprises hydroxy- α -sanshool and an antioxidant.
Further, the composition further comprises an alcohol, preferably methanol.
Further, the concentration of the hydroxy-alpha-sanshool is 0.5 to 1mg/mL.
Further, the composition is an alcoholic solution of hydroxy- α -sanshool and an antioxidant, preferably a methanolic solution.
Further, the purity of the hydroxy-alpha-sanshool is not less than 98%.
The invention also provides a storage method of the hydroxyl-alpha-sanshool, which comprises the following steps:
(1) Preparing the composition;
(2) The composition was sealed with nitrogen and stored at-20 ℃.
The invention has the beneficial effects that: the L-ascorbyl palmitate, the tea polyphenol or the tert-butyl-4-hydroxyanisole is used as the stabilizer of the hydroxy-alpha-sanshool, the protective effect on the hydroxy-alpha-sanshool is excellent, the content loss of the hydroxy-alpha-sanshool in the storage process can be effectively reduced by combining the nitrogen protection and the low-temperature storage condition of-20 ℃, and the stabilizing effect is more excellent in the liquid environment with methanol. The invention provides an effective scheme for the stable storage of the hydroxy-alpha-sanshool and has popularization and application values.
Obviously, many modifications, substitutions, and variations are possible in light of the above teachings of the invention, without departing from the basic technical spirit of the invention, as defined by the following claims.
The present invention will be described in further detail with reference to the following examples. This should not be understood as limiting the scope of the above-described subject matter of the present invention to the following examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
Detailed Description
The raw materials and equipment used in the invention are known products and are obtained by purchasing commercial products.
The hydroxy-alpha-sanshool used in the invention is prepared according to the method disclosed by Chinese patent (application number: 202011146305.5), and the purity is higher than 98 percent;
example 1 composition of the invention containing hydroxy-alpha-sanshool and a stabilizer
Precisely weighing a proper amount of hydroxy-alpha-sanshool, dissolving the hydroxy-alpha-sanshool in methanol to prepare a 1.00mg/mL solution, placing the solution in 5 sample bottles (1 mL per bottle), precisely weighing 5mg of L-ascorbyl palmitate, adding 5mL of methanol to prepare a 1.00mg/mL mother solution I, diluting the solution to 0.01mg/mL solution A, respectively adding 20 mu L of solution A,100 mu L of solution A,200 mu L of solution A,500 mu L of solution A and 1000 mu L of solution A into the 5 sample bottles, preparing a hydroxy-alpha-sanshool solution containing 0.02, 0.10, 0.20, 0.50 and 1.00 mass percent of L-ascorbyl palmitate, and carrying out reduced pressure spin-drying to obtain a solid.
Example 2 composition of the invention containing hydroxy-alpha-sanshool and a stabilizer
Precisely weighing a proper amount of hydroxy-alpha-sanshool, dissolving the hydroxy-alpha-sanshool in methanol to prepare 1.00mg/mL solution, placing the solution into 5 sample bottles (1 mL per bottle), precisely weighing 5mg of L-ascorbyl palmitate, adding 5mL of methanol to prepare 1.00mg/mL mother solution I, diluting the solution to 0.01mg/mL solution A, respectively adding 20 mu L of solution A,100 mu L of solution A,200 mu L of solution A,500 mu L of solution A and 1000 mu L of solution A into the 5 sample bottles, preparing 0.02, 0.10, 0.20, 0.50 and 1.00 percent of hydroxy-alpha-sanshool solution by mass fraction of L-ascorbyl palmitate, adding methanol to quantify to 2mL, and preparing 0.50mg/mL hydroxy-alpha-sanshool solution.
Example 3 composition of the invention containing hydroxy-alpha-sanshool and stabilizer
Precisely weighing a proper amount of hydroxy-alpha-sanshool, dissolving the hydroxy-alpha-sanshool in methanol to prepare a solution of 1.00mg/mL, adding tea polyphenol with the mass fraction of 0.50 percent relative to the hydroxy-alpha-sanshool, and uniformly mixing to form the solution.
Example 4 composition of the invention containing hydroxy-alpha-sanshool and a stabilizer
Precisely weighing a proper amount of hydroxy-alpha-sanshool, dissolving the hydroxy-alpha-sanshool in methanol to prepare a solution of 1.00mg/mL, adding tea polyphenol with the mass fraction of 0.20 percent relative to the hydroxy-alpha-sanshool, and uniformly mixing to form the solution.
Example 5 composition of the invention containing hydroxy-alpha-sanshool and a stabilizer
Precisely weighing a proper amount of hydroxy-alpha-sanshool, dissolving the hydroxy-alpha-sanshool in methanol to prepare a solution of 1.00mg/mL, adding tert-butyl-4-hydroxyanisole with the mass fraction of 0.50 percent relative to the hydroxy-alpha-sanshool, and uniformly mixing to form the solution.
Example 6 composition of the invention containing hydroxy-alpha-sanshool and stabilizer
Precisely weighing a proper amount of hydroxy-alpha-sanshool, dissolving the hydroxy-alpha-sanshool in methanol to prepare a solution of 1.00mg/mL, adding tert-butyl-4-hydroxyanisole accounting for 0.20% of the mass fraction of the hydroxy-alpha-sanshool, and uniformly mixing to form the solution.
Example 7 storage of a composition of the invention containing hydroxy-alpha-sanshool and a stabilizer
The composition prepared in example 1 was sealed, evacuated using a vacuum pump and syringe, then charged with nitrogen, protected from light and stored in a refrigerator at-20 ℃.
Example 8 storage of a composition containing hydroxy-alpha-sanshool and a stabilizer according to the invention
The composition prepared in example 2 was sealed, evacuated using a vacuum pump and syringe, then charged with nitrogen, protected from light and stored in a refrigerator at-20 ℃.
The beneficial effects of the present invention are demonstrated by the following experimental examples.
Experimental example 1 storage conditions and selection of antioxidant
1. Experimental method
Precisely weighing a proper amount of hydroxy-alpha-sanshool, adding methanol to dilute the hydroxy-alpha-sanshool to a concentration of 1.00mg/mL, placing 1.00mL of the diluted solution in a sample bottle, dividing the solution into 9 parts, one part of the diluted solution into a blank control group, one part of the diluted solution into a low-temperature group, one part of the diluted solution into a nitrogen group, and the other 7 parts of the diluted solution into sample groups, wherein each part of the sample groups is added with different types of antioxidants which account for 0.50% of the weight of the hydroxy-alpha-sanshool, including L-ascorbyl palmitate (L-AP), tea polyphenol (TPP), tert-butyl-4-hydroxyanisole (BHA), tert-butyl hydroquinone (TBHQ), rosmarinic acid (RosA), vitamin E (VE) and Vitamin C (VC), placing the groups at normal temperature (the low-temperature group is maintained by a low-temperature cooling system) and in an open place (the nitrogen group is sealed) under ultraviolet irradiation for 24h (accelerated test), and then analyzing the content of the hydroxy-alpha-sanshool in each group, and comparing the protective effects of the antioxidants on the hydroxy-alpha-sanshool.
2. Results of the experiment
As shown in table 1, in the accelerated test, the content of hydroxy- α -sanshool in the blank group was significantly reduced, and almost completely oxidized into other substances; the reduction of the purity of the hydroxy-alpha-sanshool can be delayed by filling nitrogen gas to isolate oxygen or adding an antioxidant at low temperature, wherein the L-ascorbyl palmitate (L-AP), tea polyphenol (TPP), tert-butyl-4-hydroxyanisole (BHA) and tert-butyl hydroquinone (TBHQ) have the strongest stabilizing effect on the hydroxy-alpha-sanshool, the content of the hydroxy-alpha-sanshool can still reach over 75 percent, and the effect is obviously superior to that of other antioxidants. Wherein, the L-ascorbyl palmitate has the optimal stabilizing effect on the hydroxy-alpha-sanshool, and the content of the hydroxy-alpha-sanshool is still over 85 percent.
Table 1 content of hydroxy- α -sanshool in accelerated test
* The purity of the hydroxy-alpha-sanshool used in the experiment is 98.52%.
Experimental example 2 optimization of storage conditions of Zanthoxylum piperitum
1. Experimental methods
To investigate the optimum storage conditions, a grouping experiment was performed under the following conditions:
(1) Blank group: preparing 1.00mg/mL hydroxyl-alpha-sanshool methanol solution, sealing and standing at normal temperature.
(2) And (3) low-temperature placing group: preparing 1.00mg/mL hydroxyl-alpha-sanshool methanol solution, sealing, keeping out of the sun, and storing in a refrigerator at-20 ℃.
(3) Nitrogen low-temperature group: preparing 1.00mg/mL hydroxyl-alpha-sanshool methanol solution, sealing, vacuumizing by using a vacuum pump and an injector, filling nitrogen, keeping out of the sun, and storing in a refrigerator at the temperature of-20 ℃.
(4) Low-temperature group: an appropriate amount of the solution of example 2 was taken, sealed, protected from light and stored in a refrigerator at-20 ℃.
(5) Nitrogen group: an appropriate amount of the solution of example 2 was taken, sealed, evacuated using a vacuum pump and syringe, charged with nitrogen, and stored at room temperature and 25 ℃ in the dark.
(6) Solution group: an appropriate amount of the solution of example 2 was taken, sealed, evacuated using a vacuum pump and syringe, then charged with nitrogen, and stored in a refrigerator at-20 ℃ in the dark.
(7) Solid group: an appropriate amount of the solid of example 1 was taken, sealed, evacuated using a vacuum pump and syringe, charged with nitrogen, and stored in a refrigerator at-20 ℃ in the dark.
Then, a proper amount of samples are taken out precisely at 10 days, 20 days, 30 days, 45 days and 60 days respectively, and the content of the hydroxy-alpha-sanshool is determined by an HPLC method.
2. Results of the experiment
As shown in table 2, it can be seen that the content of hydroxy- α -sanshool rapidly decreased significantly within 30 days for each group of samples to which no L-ascorbyl palmitate was added. The conditions of nitrogen protection and low-temperature storage are favorable for the stability of the hydroxy-alpha-sanshool, the L-ascorbyl palmitate is added, and the solution group and the solid group which are protected by nitrogen and stored at low temperature are adopted, so that the content of the hydroxy-alpha-sanshool is obviously higher within 60 days compared with the low-temperature group only under the low-temperature condition and the nitrogen group only under the nitrogen condition, and the stability advantage of the hydroxy-alpha-sanshool is more remarkable.
In addition, the solution group had better stability of hydroxy- α -sanshool than the solid group regardless of the length of time and the content of L-ascorbyl palmitate added. The stability of the hydroxy-alpha-sanshool is more favorably maintained under the condition of the common use of the methanol and the L-ascorbyl palmitate. And the effect is relatively best when the addition amount of the L-ascorbyl palmitate is 0.20%.
In general, the addition of 0.20 mass% L-ascorbyl palmitate with nitrogen aeration at-20 ℃ is the preferred storage method for hydroxy-alpha-sanshool, and the addition of methanol in solution is most preferred.
TABLE 2 variation of hydroxy-alpha-sanshool content under different storage conditions
Experimental example 3 evaluation of the Effect of different antioxidants in combination with optimum storage conditions
1. The experimental method comprises the following steps:
preparing 1.00mg/mL hydroxyl-alpha-sanshool methanol solution, respectively adding different antioxidants L-AP, TPP, BHA and TBHQ with the mass fraction of 0.20 percent relative to the mass fraction of the hydroxyl-alpha-sanshool, and filling inert gas nitrogen to test the purity of the hydroxyl-alpha-sanshool after 10, 20, 30 and 60 days in a dark condition at low temperature (-20 ℃).
TABLE 3 purity (%) of hydroxy-alpha-sanshool at-20 ℃ under conditions of exclusion of light, nitrogen, and different antioxidants
2. Results of the experiment
As can be seen from the data in Table 3, the addition of 0.20% by weight of an antioxidant under the conditions of nitrogen gas charging and storage at-20 ℃ can slow down the oxidation rate of the hydroxy-alpha-sanshool solution and prolong the storage time. Wherein, the effect of adding the antioxidants L-AP, TPP and BHA is better, the purity can be maintained to be more than 98 percent within 10 days, and the purity of HAS can be maintained to be more than 85 percent within 60 days. The low-temperature storage condition of-20 ℃ is easy to achieve; nitrogen is a common inert gas and is easy to obtain; the amount of the added antioxidant is 0.20 percent, which meets the requirement that the addition amount of the antioxidant in the food additive is not more than 0.20 percent; therefore, the method for storing the hydroxy-alpha-sanshool is stable and effective and has high feasibility.
In summary, the present invention provides a method for stabilizing hydroxy- α -sanshool, comprising: the antioxidant L-ascorbyl palmitate (L-AP), tea polyphenol (TPP) or tert-butyl-4-hydroxyanisole (BHA) is added to have excellent protection effect on hydroxy-alpha-sanshool, the content loss of the hydroxy-alpha-sanshool in the storage process can be effectively reduced by combining nitrogen protection and low-temperature storage condition of-20 ℃, and the stabilizing effect is more excellent in a liquid environment with methanol. The invention provides an effective scheme for the stable storage of the hydroxy-alpha-sanshool and has popularization and application values.
Claims (10)
1. Use of an antioxidant or an alcoholic solution thereof as a stabilizer for hydroxy-alpha-sanshool; the antioxidant is L-ascorbyl palmitate, tea polyphenol or tert-butyl-4-hydroxyanisole.
2. The composition is characterized by comprising the following components in parts by weight:
100 parts of hydroxyl-alpha-sanshool and 0.02-1 part of antioxidant; the antioxidant is L-ascorbyl palmitate, tea polyphenol or tert-butyl-4-hydroxyanisole.
3. The composition of claim 2, wherein the antioxidant is 0.02 parts.
4. The composition of claim 2 or 3, wherein the antioxidant is L-ascorbyl palmitate.
5. A composition according to claim 2 or 3, characterized in that it consists of hydroxy- α -sanshool and an antioxidant.
6. The composition of claim 2 or 3, further comprising an alcohol, preferably methanol.
7. The composition of claim 6, wherein the concentration of the hydroxy- α -sanshool is 0.5 to 1mg/mL.
8. The composition of claim 6, which is an alcoholic solution of hydroxy- α -sanshool and an antioxidant.
9. The composition of claim 2 or 3, wherein the hydroxy- α -sanshool is not less than 98% pure.
10. A method for storing hydroxy-alpha-sanshool is characterized by comprising the following steps:
(1) Formulating the composition of any one of claims 2 to 9;
(2) The composition was sealed with nitrogen and stored at-20 ℃.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481711A (en) * | 2015-11-26 | 2016-04-13 | 西南交通大学 | Hydroxy-beta-sanshool monomer preparation method |
| CN107966514A (en) * | 2017-11-28 | 2018-04-27 | 晨光生物科技集团股份有限公司 | The detection method of numb-taste component of zanthoxylum content in a kind of pepper extract |
| CN113777190A (en) * | 2021-08-27 | 2021-12-10 | 重庆市日用化学工业研究所 | Method for separating and measuring sanshool content in pepper extract and pepper extract product and application of sanshool content |
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- 2022-08-05 CN CN202210940131.2A patent/CN115286529A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481711A (en) * | 2015-11-26 | 2016-04-13 | 西南交通大学 | Hydroxy-beta-sanshool monomer preparation method |
| CN107966514A (en) * | 2017-11-28 | 2018-04-27 | 晨光生物科技集团股份有限公司 | The detection method of numb-taste component of zanthoxylum content in a kind of pepper extract |
| CN113777190A (en) * | 2021-08-27 | 2021-12-10 | 重庆市日用化学工业研究所 | Method for separating and measuring sanshool content in pepper extract and pepper extract product and application of sanshool content |
Non-Patent Citations (2)
| Title |
|---|
| 宋莹莹: "花椒贮藏过程中麻味物质含量降低机理的初步研究", 中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑, no. 10, pages 1 - 2 * |
| 王盼盼;: "肉制品加工中使用的辅料――抗氧化剂", 肉类研究, vol. 25, no. 03, pages 25 - 31 * |
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