CN107162891A - A kind of naphthalene compounds extracted from lavender and its preparation method and application - Google Patents
A kind of naphthalene compounds extracted from lavender and its preparation method and application Download PDFInfo
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- CN107162891A CN107162891A CN201710516033.5A CN201710516033A CN107162891A CN 107162891 A CN107162891 A CN 107162891A CN 201710516033 A CN201710516033 A CN 201710516033A CN 107162891 A CN107162891 A CN 107162891A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/258—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/302—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by natural substances obtained from animals or plants
- A24B15/303—Plant extracts other than tobacco
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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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Abstract
The invention discloses a kind of naphthalene compounds extracted from lavender and its preparation method and application.The compound is named as：5 methoxyl group 2 methyl 7 (vinyl of 3 methyl, 2 oxo 3) 1 naphthaldehyde.The compound be using spice berry lavender as raw material, through organic solvent extract medicinal extract, silica gel column chromatography, high pressure liquid chromatography isolate and purify after obtain.The compound on animals is nontoxic, and using safety, with good antibacterial activity, more than 93.4% is reached to the bacteriostasis rate of Escherichia coli, staphylococcus aureus etc..The compounds of this invention is guaranteed the quality for tobacco tobacco sauce, can effectively suppress the microorganism growth in feed liquid, extend the shelf-life of tobacco sauce.
Description
Technical field
The invention belongs to field of natural product chemistry, it is specifically related to one kind and is carried first from traditional spice berry lavender
The naphthalene compounds obtained.Meanwhile, suppressing tobacco the invention further relates to the preparation method of the compound and the compound
Application during feed liquid is rotten.
Background technology
Lavender is Labiatae lavender platymiscium, is distributed widely in Atlantic Ocean Islands and Mediterranean Region to Somalia,
Pakistan and India；China only cultivates 2 kinds.Plant is fruticuli or undershrub, and dilute is draft.Cultivable kind is extensive
Cultivation is in plantation all over the world.Lavender is a kind of time-honored spice berry, just be used to take a shower from ancient times, smokes
Perfume, expelling parasite, except dirty.The essential oils fragrance distilled from lavender flower spike is strong fragrant, possesses multiple use.
Lavender herb contains volatile oil 1%~3%, and Lavender is many different types of aromatic compound compositions
Complex mixture, have 30 Multiple components, main component is that linalool, bergamio, cineole, B- Luo Qin alkene are (including suitable
Formula and trans) to, acetic acid lavender ester, lavender alcohol, terpene -4- alcohol and camphor etc..Additionally containing flavones, terpene, lactone etc.
Active involatile constituent.
Natural antiseptic agent is also referred to as natural organic anti-corrosive agent, is secreted or is existed in vivo by organism with bacteriostasis
Material, through it is artificial extract or processing and obtain.Such preservative be natural materials, the component for the inherently food having,
Therefore it is harmless to the human body, and the flavor quality of food can be promoted, thus be the promising food preservative of a class.With food
Product security is increasingly becoming focus of concern with healthcare function, and the selection of raw-food material or even food additives tends to day
So, health, the material with bioactivity, natural plants become the important sources of food antiseptic, antimicrobial component, available for resisting
Widely, structure type mainly has the natural substance resource that bacterium, preservative are developed：Flavones, tannin, anthraquinone, alkaloid, wooden ester
Element, terpenoid, sterol etc..
A kind of present invention new naphthalene compounds isolated first from lavender, the compound is safe and nontoxic, antibacterial
It is active notable, in the prior art there is not yet there is relevant report.
The content of the invention
It is an object of the invention to provide a kind of new naphthalene compounds.
It is a further object of the present invention to provide a kind of method for preparing the naphthalene compounds.
The present invention also aims to provide application of the described naphthalene compounds in suppression tobacco sauce is putrid and deteriorated.
The purpose of the present invention is achieved by the following technical programs.
Unless otherwise indicated, percentage of the present invention is percetage by weight.
A kind of naphthalene compounds, are to extract isolated from lavender, with following structural formula：
The compound is named as：5- methoxyl group -2- methyl -7- (3- methyl -2- oxo -3- vinyl) -1- naphthaldehydes；
English is entitled：
5-methoxy-2-methyl-7-(3-methyl-2-oxobut-3-enyl)-1-naphthaldehyde。
A kind of method for preparing the naphthalene compounds, comprises the following steps：
(1) medicinal extract is extracted：Lavender powder is broken to 30~50 mesh, with the methanol of concentration expressed in percentage by weight 80%~100% or
Ethanol, or concentration expressed in percentage by weight 60%~90% acetone as Extraction solvent, the volume of Extraction solvent for lavender weight 2~
5 times, extract 3~5 times, merge extract solution, filtering and concentrating into flowable thick medicinal extract；
(2) silica gel column chromatography：160~300 mesh silica gel dry column-packings of the medicinal extract with weight than 2~4 times of amounts carry out silicagel column
Chromatography；Gradient elution is carried out with chloroform-acetone solution, the volume proportion of chloroform-acetone solution is respectively 1:0、20:1、9:1、8:
2、7:3、6:4、1:1 and 1:2, merge identical part, collect each several part eluent and concentrate；
(3) high pressure liquid chromatography is isolated and purified：By 8:The eluent that 2 chloroform-acetone is afforded be concentrated to it is dry, with pure
Methanol dissolves, and is further isolated and purified with high pressure liquid chromatography, and UV-detector Detection wavelength is 346nm, collects 31.6min
Chromatographic peak, it is repeatedly cumulative after be evaporated, produce described naphthalene compounds.
Further, in step (1), lavender is crushed to 30 mesh；The weight ratio of Extraction solvent and lavender for (3~
4)：Extracted after 1, immersion 24h~72h.
In step (2), pure methanol or pure second that medicinal extract is first measured before through silica gel column chromatography rough segmentation with weight than 1.5~3 times
Alcohol or pure acetone dissolving, then with 80~100 mesh silica gel mixed samples of 0.8~1.2 times of medicinal extract weight, then with 1-10 times of 160 mesh
Silica gel dress post carries out silica gel column chromatography.
In step (3), it is to use 21.2mm × 250mm, 5 μm of C that described high pressure liquid chromatography, which is isolated and purified,18Chromatogram
Post, flow velocity is 20mL/min, and mobile phase is 66% methanol, and UV-detector Detection wavelength is 346nm, each μ L of sample introduction 200,
31.6min chromatographic peak is collected, is evaporated after repeatedly adding up.
In step (3), the compound obtained after being isolated and purified through high pressure liquid chromatography is first dissolved with pure methanol, then with pure
Methanol is mobile phase, is separated with gel filtration chromatography, further to isolate and purify.
Described naphthalene compounds have suppression tobacco sauce putrid and deteriorated, extend the purposes of tobacco sauce shelf-life.
Compared with prior art, the present invention has advantage following prominent：
The compounds of this invention is isolated from traditional spice berry lavender, nontoxic to animal, uses safety, compound
Good antibacterial activity is shown, more than 93.4% is reached to the bacteriostasis rate of Escherichia coli, staphylococcus aureus etc.；As
Tobacco sauce bacteriostatic agent, can significantly extend the shelf-life of tobacco sauce.And the compound structure is simple, if using artificial conjunction
Into technique is also easily realized, and production cost is low.
Brief description of the drawings
Fig. 1 is the carbon-13 nmr spectra of naphthalene compounds of the present invention；
Fig. 2 is the proton nmr spectra of naphthalene compounds of the present invention；
Fig. 3 schemes for the main HMBC correlations of naphthalene compounds of the present invention.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, below in conjunction with drawings and Examples pair
The present invention is described in further detail.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, and
It is not used in the restriction present invention.In the examples where no specific technique or condition is specified, according to the skill described by document in the art
Art or condition are carried out according to product description.Agents useful for same or the unreceipted production firm person of instrument, being can be by purchase
Buy the conventional products of acquisition.
Lavender raw material used of the invention is not limited by area and kind, can realize the present invention.
The preparation of embodiment 1 --- compound
Lavender sample source is in Kunming, Yunnan.The lavender for being crushed to 30 mesh is sampled into 2.0kg, carried with 95% methanol
Take 5 times, 24h is extracted every time, extract solution merges, filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 105g.Medicinal extract is with weight than 2.0 times
The 120g thick silica gel mixed sample of 100 mesh is used after the pure methanol dissolving of amount, 0.6kg 160 mesh silica gel dress post carries out silica gel column chromatography, used
Volume proportion is 1:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge identical
Part, obtain 8 parts, wherein volume proportion is 8:2 chloroform-acetone elution fraction is prepared efficient with the prompt logical sequence 1,100 half of peace
Liquid chromatogram is separated, using 66% methanol as mobile phase, and it is fixation that Zorbax SB-C18 (21.2 × 250mm, 5 μm), which prepare post,
Phase, flow velocity is 20ml/min, and UV-detector Detection wavelength is 346nm, each μ L of sample introduction 200, collects 31.6min chromatogram
Peak, is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, uses Sephadex LH-
20 gel filtration chromatographies are separated, and produce described naphthalene compounds.
The preparation of embodiment 2 --- compound
Lavender sample source will be crushed to the lavender sample 3.5kg of 40 mesh, with 95% second in Kashi
Alcohol extracting 4 times, extracts 48h every time, and extract solution merges, and filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 250g.Medicinal extract weight ratio
The 250g thick silica gel mixed sample of 80 mesh is used after the pure methanol dissolving of 2.0 times of amounts, 1.2kg 200 mesh silica gel dress post carries out silica gel column layer
Analysis, is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings are closed
And identical part, 8 parts are obtained, wherein volume proportion is 8:2 chloroform-acetone elution fraction is made with the prompt logical sequence 1,100 half of peace
Standby high performance liquid chromatography separation, using 66% methanol as mobile phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) prepare post
For stationary phase, flow velocity is 20ml/min, and UV-detector Detection wavelength is 346nm, each μ L of sample introduction 200, collects 31.6min's
Chromatographic peak, is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, uses Sephadex
LH-20 gel filtration chromatographies are separated, and produce described naphthalene compounds.
The preparation of embodiment 3 --- compound
Lavender sample source will be crushed to the lavender sample 5kg of 50 mesh, with 75% acetone in Xichang Sichuan
With ultrasonic extraction 3 times, 72h is extracted every time, extract solution merges, filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 380g.Medicinal extract weight
The thick silica gel mixed sample of 90 mesh that 400g is used after the pure methanol dissolving than 1.6 times of amounts is measured, 2.4kg 180 mesh silica gel dress post carries out silica gel
Column chromatography, is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC prisons
Survey and merge identical part, obtain 8 parts, wherein volume proportion is 8:2 chloroform-acetone elution fraction prompt logical sequence 1100 of peace
Half preparative high-performance liquid chromatographic is separated, using 66% methanol as mobile phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) systems
Standby post is stationary phase, and flow velocity is 20ml/min, and UV-detector Detection wavelength is 346nm, each μ L of sample introduction 200, is collected
31.6min chromatographic peak, is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, is used
Sephadex LH-20 gel filtration chromatographies are separated, and produce described naphthalene compounds.
The identification of embodiment 4 --- compound structure
Compound prepared by Example 1, determines its structure by the following method；Its high resolution mass spectrum HRESIMS (just from
Son collection) display quasi-molecular ion peak be m/z 305.1147 [M+Na]+, (calculated value 305.1154).As shown in Figure 1-2, tie
Close1H and13C H NMR spectroscopies determine that compound molecule formula is C18H18O3, degree of unsaturation is 10.Carbonyl (1695 is shown in infrared spectrum
And 1680cm-1) and aromatic ring (1585,1530 and 1422cm-1) resonance absorbing peak.Ultraviolet spectra has most in 205,238,346nm
Big absorb confirms there is aromatic ring structure in compound.Compound1H、13C NMR and DEPT data (table -1) are shown in compound
In the presence of 18 carbon and 18 hydrogen, including 11,2,5,7- quaternary naphthalene parent nucleus (C-1~C-10；H-3, H-4, H-6 and H-8),
One aldehyde radical (δC191.1d；δH9.98s), 1 methoxyl group (δC56.4q；δH3.81), 1 methyl (δC20.8；δH
, and 1 3- methyl -2- oxo butyl -3- vinyl structure fragments (C-3'~C-7' 2.08)；H2- 3', H2- 6' and H3-
7').1,2,5,7- quaternary naphthalene parent nucleus can further by H-3 and C-1, C-2, C-4 and C-10, H-4 and C-2, C-3, C-5,
C-9 and C-10, H-6 and C-5, C-7, C-8 and C10, and H-8 is related to C-10 HMBC to C-1, C-6, C-7, C-9 obtains
Confirm.Its HMBC Correlated Spectroscopy is further analyzed, according to methoxyl group hydrogen (δH3.81) with C-5 (δC155.3) HMBC correlations can be pushed away
Methoxy substitution is surveyed in the C-5 positions of naphthalene parent nucleus.The C-1 positions that carboxaldehyde radicals is substituted in naphthalene parent nucleus can be by H-1 ' (δH9.98) with C-1 (δC
125.7)、C-2(δC 149.1)、C-9(δC131.3) HMBC correlations are confirmed.According to H3-2′(δH2.49) with C-1 (δC
125.7)、C-2(δC 149.1)、C-3(δC, and H-3 (δ 124.1)H7.55) with C-2 ' (δC20.8) HMBC can speculate
Methyl is substituted in the C-2 positions of naphthalene parent nucleus.3- methyl -2- oxo butyl -3- vinyl structure fragments are substituted in the C-7 positions of naphthalene parent nucleus
Can be by H2-3′(δH4.51) with C-6 (δC 108.5)、C-7(δC 138.4)、C-8(δC116.3), H-6 (δHAnd C- 6.89)
3′(δC, and H-8 (δ 43.7)H8.50) with C-3 ' (δC43.7) HMBC correlations are confirmed.Typical proton on phenyl ring
Signal H-3 (δH7.55, d, J=8.2), H-4 (δH8.39, d, J=8.2), H-6 (δH6.89, d, J=1.6) and H-8 (δH
8.50, d, J=1.6) also support naphthalene parent nucleus on above-mentioned substituent pattern.So far, the structure of compound is determined, and is named
It is for Compound nomenclature：5- methoxyl group -2- methyl -7- (3- methyl -2- oxo -3- vinyl) -1- naphthaldehydes；English is entitled：
5-methoxy-2-methyl-7- (3-methyl-2-oxobut-3-enyl) -1-naphthaldehyde, is red gluey
Thing, as shown in Figure 3.
(solvent is CDCl to the nuclear magnetic resonance data of the compound of table -1 (1)3)
Infrared, the ultraviolet and mass spectrometric data of compound：UV (methanol), λmax(logε)346(3.72)、238(3.28)、205
(4.02)nm；IR (pressing potassium bromide troche)：νmax3074、2938、2752、1695、1680、1585、1530、1422、1179、1068、
854、748cm-1；1H and13C NMR datas (500 and 125MHz, (CDCl3), it is shown in Table -1；Positive ion mode ESIMS m/z 305
[M+Na]+；Positive ion mode HRESIMS m/z 305.1147 [M+Na]+(calculated value C18H18NaO3, 305.1154).
The identification of embodiment 5 --- compound structure
Compound prepared by Example 2, is red gum.Assay method is same as Example 4, confirms embodiment 2
The compound of preparation is identical naphthalene compounds -5- methoxyl group -2- methyl -7- (3- methyl -2- oxo -3- vinyl) -1-
Naphthaldehyde.
The identification of embodiment 6 --- compound structure
Compound prepared by Example 3, is red gum.Assay method is same as Example 4, confirms embodiment 3
The compound of preparation is identical 5- methoxyl group -2- methyl -7- (3- methyl -2- oxo -3- vinyl) -1- naphthaldehydes.
Embodiment 7 --- antifungal activity is tested
Any naphthalene compounds prepared by Example 1-3 carry out antibacterial activity experiment, and process of the test is as follows：
Antimicrobial test is carried out with agar diffusion method, and tested bacterium is equably coated in into plain agar culture medium (ox first
Meat extract, peptone, sodium chloride, serum, agar) flat board on, then by testing compound (the compounds of this invention 10mL DMSO
Dissolving, is diluted with water into 50 μ g/mL solution) soaked tablet (diameter 5mm) is placed on the culture medium carried disease germs, is put into constant temperature
In case, it is incubated in 25 DEG C after 24-72h and observes inhibition zone size.As a result show：The compounds of this invention to staphylococcus aureus,
Escherichia coli, angstrom uncommon bacterium, hay bacillus, proteus etc. have very strong activity；Inhibiting rate is up to more than 93.4%.To the present invention
Compound has carried out safety evaluatio, is tested by Micronuclei In The Mouse Bone Marrow, Ames experiments and TK gene mutations are tested, it was demonstrated that this hair
Bright compound on animals is nontoxic, uses safety.
Embodiment 8 --- compound application
The embodiment 1-3 any naphthalene compounds prepared are added in tobacco sauce, addition is 10 μ g/mL, 20 μ g/
ML and 50 μ g/mL, and to be not added with the feed liquid of compound as control, the microbiology turbidity after placing two weeks in observation sample.
As a result show：Compared with control, after the compounds of this invention for adding 10 μ g/mL, 20 μ g/mL and 50 μ g/mL, three addition concentration
To the inhibiting rate difference of total number of bacteria, coliform, staphylococcus aureus, Pseudomonas aeruginosa, hemolytic streptococcus, total number of fungi
Reach：61.4%th, 72.3% and 83.2%.Because the growth of microorganism has obtained effective suppression, the quality guarantee period of tobacco sauce is significantly
It is extended.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
Any modifications, equivalent substitutions and improvements made within refreshing and principle etc., should be included in the scope of the protection.
Claims (7)
1. a kind of naphthalene compounds, extract isolated, with following structural formula from lavender：
The compound is named as：5- methoxyl group -2- methyl -7- (3- methyl -2- oxo -3- vinyl) -1- naphthaldehydes；English
It is entitled：
5-methoxy-2-methyl-7-(3-methyl-2-oxobut-3-enyl)-1-naphthaldehyde。
2. a kind of method for preparing naphthalene compounds described in claim 1, comprises the following steps：
(1) medicinal extract is extracted：Lavender powder is broken to 30~50 mesh, with the methanol or ethanol of concentration expressed in percentage by weight 80%~100%,
Or the acetone of concentration expressed in percentage by weight 60%~90%, as Extraction solvent, the volume of Extraction solvent is 2~5 times of lavender weight,
Extract 3~5 times, merge extract solution, filtering and concentrating into flowable thick medicinal extract；
(2) silica gel column chromatography：160~300 mesh silica gel dry column-packings of the medicinal extract with weight than 2~4 times of amounts carry out silica gel column chromatography；
Gradient elution is carried out with chloroform-acetone solution, the volume proportion of chloroform-acetone solution is respectively 1:0、20:1、9:1、8:2、7:
3、6:4、1:1 and 1:2, merge identical part, collect each several part eluent and concentrate；
(3) high pressure liquid chromatography is isolated and purified：By 8:The eluent that 2 chloroform-acetone is afforded is concentrated to dry, uses pure methanol
Dissolving, and further isolated and purified with high pressure liquid chromatography, UV-detector Detection wavelength is 346nm, collects 31.6min color
Spectral peak, is evaporated after repeatedly adding up, and produces described naphthalene compounds.
3. preparation method according to claim 2, it is characterised in that：In step (1), lavender is crushed to 30 mesh；Carry
The weight ratio for taking solvent and lavender is (3~4)：Extracted after 1, immersion 24h~72h.
4. preparation method according to claim 2, it is characterised in that：In step (2), medicinal extract is first with weight than 1.5~3 times
Pure methanol or straight alcohol or the pure acetone dissolving of amount, then with 80~100 mesh silica gel mixed samples of 0.8~1.2 times of medicinal extract weight, then
Silica gel column chromatography is carried out with 1~10 times of 160 mesh silica gel dress post.
5. preparation method according to claim 2, it is characterised in that：In step (3), described high pressure liquid chromatography separation
Purifying is to use 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow velocity is 20mL/min, and mobile phase is 66% methanol, ultraviolet
Detector Detection wavelength is 346nm, each μ L of sample introduction 200, collects 31.6min chromatographic peak, is evaporated after repeatedly adding up.
6. preparation method according to claim 2, it is characterised in that：In step (3), isolated and purified through high pressure liquid chromatography
The compound obtained afterwards, is first dissolved with pure methanol, then using pure methanol as mobile phase, is separated with gel filtration chromatography, further to divide
From purifying.
7. the naphthalene compounds described in claim 1 are putrid and deteriorated in suppression tobacco sauce, in the extension tobacco sauce shelf-life
Using.
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| CN108017528A (en) * | 2017-11-03 | 2018-05-11 | 云南民族大学 | A kind of naphthalene compounds and preparation method and application |
| CN108911958A (en) * | 2018-08-07 | 2018-11-30 | 云南中烟工业有限责任公司 | A kind of naphthaldehyde class compound with antibacterial activity, preparation method and for purposes in cigarette paper |
| CN111018822A (en) * | 2019-12-11 | 2020-04-17 | 云南中烟工业有限责任公司 | Compound with bacteriostatic action, preparation method thereof and application thereof in cigarettes |
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| CN108017528A (en) * | 2017-11-03 | 2018-05-11 | 云南民族大学 | A kind of naphthalene compounds and preparation method and application |
| CN108017528B (en) * | 2017-11-03 | 2020-08-18 | 云南民族大学 | Naphthalene compound and preparation method and application thereof |
| CN108911958A (en) * | 2018-08-07 | 2018-11-30 | 云南中烟工业有限责任公司 | A kind of naphthaldehyde class compound with antibacterial activity, preparation method and for purposes in cigarette paper |
| CN108911958B (en) * | 2018-08-07 | 2021-05-07 | 云南中烟工业有限责任公司 | Naphthalene formaldehyde compound with antibacterial activity, preparation method thereof and application of compound in cigarette paper |
| CN111018822A (en) * | 2019-12-11 | 2020-04-17 | 云南中烟工业有限责任公司 | Compound with bacteriostatic action, preparation method thereof and application thereof in cigarettes |
| CN111018822B (en) * | 2019-12-11 | 2022-05-24 | 云南中烟工业有限责任公司 | Compound with bacteriostatic action, preparation method thereof and application thereof in cigarettes |
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