CN107935823A - The preparation method of cis-jasmone - Google Patents
The preparation method of cis-jasmone Download PDFInfo
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- CN107935823A CN107935823A CN201711030299.5A CN201711030299A CN107935823A CN 107935823 A CN107935823 A CN 107935823A CN 201711030299 A CN201711030299 A CN 201711030299A CN 107935823 A CN107935823 A CN 107935823A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/32—Preparation of ethers by isomerisation
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- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
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- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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Abstract
The present invention relates to a kind of preparation method of cis-jasmone, include the following steps：First pre- alkaline is mixed with 3 alkoxy, 1 pentyne, 3 alkoxy, 1,2 pentadiene is obtained after the first preset time is reacted under the first preset temperature；After 3 alkoxy, 1,2 pentadiene, 3 methyl rings, penta 2 ketenes and the first catalyst are mixed, the second preset time is reacted under the second preset temperature and obtains 3 methyl 2 (2 pentynyl) rings, penta 2 ketenes；The second catalyst is added after 3 methyl 2 (2 pentynyl) rings, penta 2 ketenes and the first solvent are added to a hydrogenation bottle, ventilation processing is carried out to hydrogenation bottle, the 3rd preset time is reacted under the 3rd preset temperature so that cis-jasmone is made.The preparation method of cis-jasmone proposed by the present invention, preparation flow is relatively simple, and technology difficulty and preparation are low, are conducive to large-scale production and application.
Description
Technical field
The present invention relates to chemical raw material synthesis technical field, more particularly to a kind of preparation method of cis-jasmone.
Background technology
Cis-jasmone is a kind of widely used important spices, its fragrance is the important perfume (or spice) of jasmine oil like jasmin
One of composition, is mainly used in advanced jasmine serial cosmetics essence, its corresponding molecular formula is C11H16O。
At present, the existing more report of synthesis on cis-jasmone, but most laboratories that all only rest on synthesize rank
Section, can really be used for the few of industrialized production.Generally, in industrial production, current more common method bag both at home and abroad
Include the following steps：(1) 2- methylfurans and acrolein reaction obtain 3- (5- methyl -2- furyls) propionic aldehyde；(2) 1- bromines third
Alkane and triphenylphosphine react to obtain three phenyl-bromide phosphonium salt of n-propyl；(3) three phenyl-bromide phosphonium salt of n-propyl and sodium hydride or uncle
Butanol potassium or Sodamide react to obtain n-propyl triphenylphosphine ylide；(4) n-propyl triphenylphosphine ylide and 3- (5- first
Base -2- furyls) propionic aldehyde reaction, obtain it is cis based on 5- methyl -2- (3- hexenyls) furans；(5) cis -5- methyl -2-
Open loop obtains cis 11 carbon -8- alkene -2,5- diketone to (3- hexenyls) furans in acid condition；(6) cis 11 carbon -8-
Alkene -2,5- diketone is condensed cyclization and obtains cis-jasmone-amyl- 2- of cis 3- methyl -2- (2- pentenyls) rings in alkaline conditions
Ketenes (as shown in Figure 1).
However, the existing industrial general method for preparing cis-jasmone, its operating process is complex, improves preparation
Technology difficulty and manufacturing cost, limit and prepare production on a large scale.
The content of the invention
Based on this, the purpose of the present invention is to solve cis-jasmone is industrially prepared now, operating process is more multiple
It is miscellaneous, the problem of technology difficulty of preparation is larger and manufacturing cost is higher.
The present invention proposes a kind of preparation method of cis-jasmone, wherein, include the following steps：
First pre- alkaline is mixed with 3- alkoxy -1- pentynes according to the first molar ratio, under the first preset temperature
Isomerization reaction is carried out, 3- alkoxy -1,2- pentadienes are obtained after reacting the first preset time；
By obtained 3- alkoxies -1,2- pentadiene, the amyl- 2- ketenes of 3- methyl rings and the first catalyst according to
After two molar ratios are mixed, it is stirred under the second preset temperature, 3- methyl -2- is obtained after reacting the second preset time
The amyl- 2- ketenes of (valerylene base)-ring；
It is anti-that the amyl- 2- ketenes of obtained 3- methyl -2- (valerylene the base)-ring and the first solvent are added to a hydrogenation
After answering bottle, the second catalyst is continuously added, the hydrogenation bottle is carried out at ventilation using first gas, second gas successively
Reason, reacts the 3rd preset time so that the cis-jasmone is finally made under the 3rd preset temperature.
The preparation method of cis-jasmone proposed by the present invention, first by the first pre- alkaline and 3- alkoxy -1- pentynes into
Row reaction obtains 3- alkoxy -1,2- pentadienes, then adds the amyl- 2- ketenes of 3- methyl rings and the first catalyst, reaction system
The amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring, then by the amyl- 2- ketenes of obtained 3- methyl -2- (valerylene base)-ring with
And first solvent be added in hydrogenation bottle, after continuously adding the second catalyst and carrying out ventilation processing, under preset temperature
Preset time is reacted, finally obtains cis-jasmone.The preparation method of the cis-jasmone proposed is invented, preparation flow is more simple
Single, technology difficulty and preparation are low, are conducive to large-scale production and application.
The preparation method of the cis-jasmone, wherein, the first pre- alkaline is potassium tert-butoxide or tertriary amylo alcohol potassium, described
First molar ratio is 0.001~0.1：1.0, first preset temperature is 40 DEG C~100 DEG C, and first preset time is 2
~10h.
The preparation method of the cis-jasmone, wherein, 3- alkoxies -1,2- pentadiene is 3- methoxyl groups -1,2-
Pentadiene, 3- ethyoxyls -1,2- pentadiene, 3- positive propoxies -1,2- pentadiene, 3- n-butoxies -1,2- pentadiene or 3- are different
At least one of butoxy -1,2- pentadiene.
The preparation method of the cis-jasmone, wherein, first catalyst is pungent for Isosorbide-5-Nitrae-diazabicylo [2.2.2]
Alkane or tri-n-butyl phosphine.
The preparation method of the cis-jasmone, wherein, second molar ratio is 1.0~1.3：1.0：0.001~
0.1, second preset temperature is 40 DEG C~140 DEG C, and second preset time is 2~10h.
The preparation method of the cis-jasmone, wherein, first solvent is water or ethanol, and second catalyst is
Diboride nickel catalyst.
The preparation method of the cis-jasmone, wherein, the first gas is nitrogen, and the second gas is hydrogen.
The preparation method of the cis-jasmone, wherein, the 3rd preset temperature is 0 DEG C~50 DEG C, and the described 3rd is pre-
If the time is 2~10h.
The preparation method of the cis-jasmone, wherein, it is described under the 3rd preset temperature react the 3rd preset time after,
Further included with being finally made the step of the cis-jasmone：
After reacting the 3rd preset time under the 3rd preset temperature, the intermediate product of generation is carried out successively
Filtering, precipitation and rectifying are with the obtained cis-jasmone.
The additional aspect and advantage of the present invention will be set forth in part in the description, and will partly become from the following description
Obtain substantially, or recognized by the practice of the present invention.
Brief description of the drawings
Fig. 1 is the flow chart for preparing cis-jasmone in the prior art；
Fig. 2 is the flow chart of the preparation method of cis-jasmone proposed by the present invention.
Embodiment
For the ease of understanding the present invention, the present invention is described more fully below with reference to relevant drawings.In attached drawing
Give the preferred embodiment of the present invention.But the present invention can realize in many different forms, however it is not limited to this paper institutes
The embodiment of description.On the contrary, the purpose for providing these embodiments is made to the disclosure more thorough and comprehensive.
Unless otherwise defined, all of technologies and scientific terms used here by the article is with belonging to technical field of the invention
The normally understood implication of technical staff is identical.Term used in the description of the invention herein is intended merely to description tool
The purpose of the embodiment of body, it is not intended that in the limitation present invention.Term as used herein " and/or " include one or more phases
The arbitrary and all combination of the Listed Items of pass.
Embodiment one
Referring to Fig. 2, a kind of preparation method of cis-jasmone, specific preparation flow are as follows：
(1) preparation of 3- alkoxies -1,2- pentadiene (connection alkene ether)：First pre- alkaline and 3- alkoxy -1- pentynes are pressed
According to 0.001~0.1：1.0 molar ratio is mixed, and carries out isomerization reaction at a temperature of 40 DEG C~100 DEG C, and reaction 2~
3- alkoxy -1,2- pentadienes are obtained after 10h.
Wherein, which can be potassium tert-butoxide or tertriary amylo alcohol potassium, and 3- alkoxies -1,2- pentadiene can be 3-
Methoxyl group -1,2- pentadiene, 3- ethyoxyls -1,2- pentadiene, 3- positive propoxies -1,2- pentadiene, 3- n-butoxies -1,2- penta
Any one in diene or 3- isobutoxy -1,2- pentadienes.Herein it may also be noted that to the above-mentioned first default temperature
For degree, its preferred scope is 50 DEG C~80 DEG C；For the first above-mentioned preset time, its preferred scope is 4~8h.
(2) preparation of the amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring：By the obtained 3- alkoxies -1,2- penta
The amyl- 2- ketenes of diene, 3- methyl rings and the first catalyst are according to 1.0~1.3：1.0：0.001~0.1 molar ratio is mixed
After conjunction, it is stirred at a temperature of 40 DEG C~140 DEG C, it is amyl- to obtain 3- methyl -2- (valerylene base)-ring after 2~10h of reaction
2- ketenes.
Wherein, for above-mentioned second preset temperature, preferred scope is 60 DEG C~120 DEG C；To above-mentioned second preset time
For, preferred scope is 4~8h.In this step, selected solvent can be tetrahydrofuran, 2- methyltetrahydrofurans, second
Glycol dimethyl ether or tirethylene glycol dimethyl ether.Preferably tetrahydrofuran or tirethylene glycol dimethyl ether.
(3) preparation of cis-jasmone：By the amyl- 2- ketenes of obtained 3- methyl -2- (valerylene the base)-ring and water
Or after ethanol is added to a hydrogenation bottle, continuously add diboride nickel catalyst, first with after air in nitrogen displacement bottle 3 times,
Again with the nitrogen 3 times in hydrogen displacement bottle, 2~10h is reacted at a temperature of 0 DEG C~50 DEG C so that cis-jasmone is finally made.
Wherein, for above-mentioned 3rd preset temperature, its preferred scope is 10 DEG C~40 DEG C；To above-mentioned 3rd preset time
For, its preferred scope is 4~8h.In addition, diboride nickel catalyst, hydrogen and the amyl- 2- of 3- methyl -2- (valerylene base)-rings
The corresponding molar ratio of alkene -1- ketone is 0.001~0.1：1.0~1.3：1.0.
The preparation method of cis-jasmone proposed by the present invention, first by the first pre- alkaline and 3- alkoxy -1- pentynes into
Row reaction obtains 3- alkoxy -1,2- pentadienes, then adds the amyl- 2- ketenes of 3- methyl rings and the first catalyst, reaction system
The amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring, then by the amyl- 2- ketenes of obtained 3- methyl -2- (valerylene base)-ring with
And first solvent be added in hydrogenation bottle, after continuously adding the second catalyst and carrying out ventilation processing, under preset temperature
Preset time is reacted, finally obtains cis-jasmone.The preparation method of the cis-jasmone proposed is invented, preparation flow is more simple
Single, technology difficulty and preparation are low, are conducive to large-scale production and application.
Embodiment two
1st, the preparation of 3- methoxyl groups -1,2- pentadiene
In the three neck round bottom flask with thermometer and the 1000ml of reflux condensing tube, the 3- methoxyl groups -1- of 687g is added
The potassium tert-butoxide of pentyne and 7.9g, is heated to 80 DEG C, carries out air-distillation after stirring reaction 8h, 110 DEG C~112 DEG C of collection evaporates
Divide 666g, corresponding yield is 97%.
2nd, the preparation of the amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring
In the three neck round bottom flask with thermometer and the 2000ml of reflux condensing tube, the 3- methyl rings for adding 192g are amyl-
2- ketenes, 3- methoxyl groups -1,2- pentadiene of 255g, the tetrahydrofuran of 890g and Isosorbide-5-Nitrae-diazabicylo of 2.3g
[2.2.2] octane (DABCO), after heating reflux reaction 8h, is cooled to room temperature, the benzoic acid of 2.5g is added, after 1h is stirred at room temperature
Filtered, filtrate elder generation normal pressure recycling tetrahydrofuran, rear vacuum distillation, collects the cut of 107~110 DEG C/1mmHg, obtain
The amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring of 282.3g, corresponding yield are 87%.
3rd, the preparation of the cis amyl- 2- ketenes (cis-jasmone) of (2- pentenyls)-ring of 3- methyl -2-
(1) preparation of diboride nickel catalyst
2.2g bis- is added in the single port bottle of 50ml and is hydrated nickel acetate and 20ml ethanol, is stirred at ambient temperature
Mix, the sodium borohydride of 0.4g is then added portionwise, continue stirring and react 1h, it is stand-by.
(2) normal pressure hydrogenation reacts
The amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring, the second of 395g of 162g is added in the there-necked flask of 1000ml
Alcohol and the diboride nickel catalyst made before.First replace nitrogen three in bottle with air in nitrogen displacement bottle three times, then with hydrogen
It is secondary, 8h is hydrogenated with room temperature, filters off catalyst, and ethanol is removed in decompression rotation, and gained crude product is through being evaporated under reduced pressure to sterling cis-jasmone
156g, corresponding yield are 95%.
Embodiment three
1st, the preparation of 3- methoxyl groups -1,2- pentadiene
In the three neck round bottom flask with thermometer and the 1000ml of reflux condensing tube, the 3- methoxyl groups -1- of 687g is added
The potassium tert-butoxide of pentyne and 7.9g, is heated to 80 DEG C, 8h, air-distillation, the cut of 110~112 DEG C of collection are reacted in stirring
666g, corresponding yield are 97%.
2nd, the preparation of the amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring
In the three neck round bottom flask with thermometer and the 2000ml of reflux condensing tube, the 3- methyl rings for adding 192g are amyl-
3- methoxyl groups -1,2- pentadiene, the tetrahydrofuran of 890g and the tri-n-butyl phosphine of 4.0g of 2- ketenes, 255g, are put with nitrogen
Change in bottle air three times, heating reflux reaction 8h.First normal pressure recycles tetrahydrofuran, is then evaporated under reduced pressure, and collection 107~
The cut of 110 DEG C/1mmHg, obtains the amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring of 282.3g, yield 87%.
3rd, the preparation of the cis amyl- 2- ketenes (cis-jasmone) of (2- pentenyls)-ring of 3- methyl -2-
(1) preparation of diboride nickel catalyst
The two hydration nickel acetates of 2.2g and the ethanol of 20ml are added in the single port bottle of 50ml, is stirred at room temperature down and adds in batches
Enter the sodium borohydride of 0.4g, continue stirring and react 1h, it is stand-by.
(2) normal pressure hydrogenation reacts
In the there-necked flask of 1000ml, the amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring, the second of 395g of 162g are added
Alcohol and the diboride nickel catalyst made before.First replace nitrogen three in bottle with air in nitrogen displacement bottle three times, then with hydrogen
It is secondary, 8h is hydrogenated with room temperature, filters off catalyst, and ethanol is removed in decompression rotation, and gained crude product is through being evaporated under reduced pressure to sterling cis-jasmone
156g, corresponding yield are 95%.
Example IV
1st, the preparation of 3- methoxyl groups -1,2- pentadiene
In the three neck round bottom flask with thermometer and the 1000ml of reflux condensing tube, the 3- methoxyl groups -1- of 687g is added
The potassium tert-butoxide of pentyne and 7.9g, is heated to 80 DEG C of temperature, carries out air-distillation after stirring reaction 8h, collect 110~112 DEG C
Cut 666g, corresponding yield be 97%.
2nd, the preparation of the amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring
In the three neck round bottom flask with thermometer and the 2000ml of reflux condensing tube, the 3- methyl rings for adding 192g are amyl-
2- ketenes, 3- methoxyl groups -1,2- pentadiene of 255g, the diethylene glycol dimethyl ether of 943g and Isosorbide-5-Nitrae-diazabicylo of 2.3g
[2.2.2] octane (DABCO), reacts 8h after being heated to 120 DEG C.After being cooled to room temperature, the benzoic acid of 2.5g is added, 1h is stirred at room temperature
After filtered, filtrate is evaporated under reduced pressure, collect 107~110 DEG C/1mmHg cut, obtain the 3- methyl -2- of 304g
The amyl- 2- ketenes of (valerylene base)-ring, corresponding yield are 93.7%.
3rd, the preparation of the cis amyl- 2- ketenes (cis-jasmone) of (2- pentenyls)-ring of 3- methyl -2-
(1) preparation of diboride nickel catalyst
The two hydration nickel acetates of 2.2g and the ethanol of 20ml are added in the single port bottle of 50ml, is carried out at ambient temperature
Stirring, is added portionwise the sodium borohydride of 0.4g, continues stirring and reacts 1h, stand-by.
(2) normal pressure hydrogenation reacts
The amyl- 2- ketenes of 3- methyl -2- (valerylene base)-ring, the second of 395g of 162g is added in the there-necked flask of 1000ml
Alcohol and the diboride nickel catalyst made before.First replace nitrogen three in bottle with air in nitrogen displacement bottle three times, then with hydrogen
It is secondary, catalyst is filtered off after being hydrogenated with 8h at room temperature, ethanol is removed in decompression rotation, and gained crude product is through being evaporated under reduced pressure to sterling cis-jasmone
156g, corresponding yield are 95%.
Embodiment described above only expresses the several embodiments of the present invention, its description is more specific and detailed, but simultaneously
Therefore the limitation to the scope of the claims of the present invention cannot be interpreted as.It should be pointed out that for those of ordinary skill in the art
For, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to the guarantor of the present invention
Protect scope.Therefore, the protection domain of patent of the present invention should be determined by the appended claims.
Claims (9)
1. a kind of preparation method of cis-jasmone, it is characterised in that include the following steps：
First pre- alkaline is mixed with 3- alkoxy -1- pentynes according to the first molar ratio, is carried out under the first preset temperature
Isomerization reaction, 3- alkoxy -1,2- pentadienes are obtained after reacting the first preset time；
Obtained 3- alkoxies -1,2- pentadiene, the amyl- 2- ketenes of 3- methyl rings and the first catalyst are rubbed according to second
After you are than being mixed, it is stirred under the second preset temperature, 3- methyl -2- (2- penta is obtained after reacting the second preset time
Alkynyl) the amyl- 2- ketenes of-ring；
The amyl- 2- ketenes of obtained 3- methyl -2- (valerylene the base)-ring and the first solvent are added to a hydrogenation bottle
Afterwards, the second catalyst is continuously added, ventilation processing is carried out to the hydrogenation bottle using first gas, second gas successively,
After reacting the 3rd preset time under the 3rd preset temperature, the cis-jasmone is finally made.
2. the preparation method of cis-jasmone according to claim 1, it is characterised in that the first pre- alkaline is tertiary fourth
Potassium alcoholate or tertriary amylo alcohol potassium, first molar ratio are 0.001~0.1：1.0, first preset temperature is 40 DEG C~100 DEG C,
First preset time is 2~10h.
3. the preparation method of cis-jasmone according to claim 1, it is characterised in that the 3- alkoxies -1,2- penta
Diene is 3- methoxyl groups -1,2- pentadiene, 3- ethyoxyls -1,2- pentadiene, 3- positive propoxies -1,2- pentadiene, the positive fourth oxygen of 3-
At least one of base -1,2- pentadiene or 3- isobutoxy -1,2- pentadienes.
4. the preparation method of cis-jasmone according to claim 1, it is characterised in that first catalyst for Isosorbide-5-Nitrae-
Diazabicylo [2.2.2] octane or tri-n-butyl phosphine.
5. the preparation method of cis-jasmone according to claim 1, it is characterised in that second molar ratio is 1.0
~1.3：1.0：0.001~0.1, second preset temperature is 40 DEG C~140 DEG C, and second preset time is 2~10h.
6. the preparation method of cis-jasmone according to claim 1, it is characterised in that first solvent is water or second
Alcohol, second catalyst are diboride nickel catalyst.
7. the preparation method of cis-jasmone according to claim 1, it is characterised in that the first gas is nitrogen,
The second gas is hydrogen.
8. the preparation method of cis-jasmone according to claim 1, it is characterised in that the 3rd preset temperature is 0
DEG C~50 DEG C, the 3rd preset time is 2~10h.
9. the preparation method of the cis-jasmone according to claim 1 to 8 any one, it is characterised in that described
After reacting the 3rd preset time under three preset temperatures, further included with being finally made the step of the cis-jasmone：
After reacting the 3rd preset time under the 3rd preset temperature, the intermediate product of generation was carried out successively
Filter, precipitation and rectifying are with the obtained cis-jasmone.
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| CN111574347A (en) * | 2020-05-27 | 2020-08-25 | 广西大学 | A molecular imprinting method for extracting jasmonone and jasmonolide from jasmine slag |
| CN111777500A (en) * | 2020-07-06 | 2020-10-16 | 昆山亚香香料股份有限公司 | Process for synthesizing cis-jasmone |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574347A (en) * | 2020-05-27 | 2020-08-25 | 广西大学 | A molecular imprinting method for extracting jasmonone and jasmonolide from jasmine slag |
| CN111777500A (en) * | 2020-07-06 | 2020-10-16 | 昆山亚香香料股份有限公司 | Process for synthesizing cis-jasmone |
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