CN105037121B - A kind of method extracting separation bis-methyl naphthalene alkene-1,5-diketone of 4,8-from Exocarpium Juglandis Immaturus - Google Patents
A kind of method extracting separation bis-methyl naphthalene alkene-1,5-diketone of 4,8-from Exocarpium Juglandis Immaturus Download PDFInfo
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- CN105037121B CN105037121B CN201510372437.2A CN201510372437A CN105037121B CN 105037121 B CN105037121 B CN 105037121B CN 201510372437 A CN201510372437 A CN 201510372437A CN 105037121 B CN105037121 B CN 105037121B
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- diketone
- methyl naphthalene
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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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- 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
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/84—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by azeotropic distillation
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- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention provides a kind of method extracting 4,8 two methyl naphthalene alkene 1,5 diketone of separation from Exocarpium Juglandis Immaturus, and step is as follows: Exocarpium Juglandis Immaturus is put in water by (1), soak extraction；Or extract with ultrasound wave or microwave soaking；(2) by the aqueous phase decompression distillation after extraction, controlling bath temperature is 50 DEG C 70 DEG C, and vacuum is 0.06 0.08MPa, obtains containing 4, the aqueous solution of 8 two methyl naphthalene alkene 1,5 diketone；Wherein, the chemical structural formula of described 4,8 two methyl naphthalene alkene 1,5 diketone is:
Description
Technical field
The present invention relates to a kind of method extracted from Exocarpium Juglandis Immaturus and separate bis-methyl naphthalene alkene-1,5-diketone of 4,8-.
Background technology
Semen Juglandis also known as Semen Juglandis, Juglandales (Juglandales), Juglandaceae (Juglandaceae), Juglans (Juglans L.),
Semen Juglandis (Juglans regia L.).Originate in North China, northwest, southwest, Central China, south China and East China.It is distributed in the Central Asia, west
Asia, South Asia and Europe.It is born in hillside and the hilly country of height above sea level 400-1800 rice, the common cultivation in China Plain and knob
Training, likes fertile moistening sandy loam, is common in the place that both sides, river valley, mountain area soil layer is deep.Kernel oil content is high, contains
Abundant nutrient substance, can eat raw, be a kind of nut useful to human body, have the effects such as strong brain；Also can extract oil edible；
Timber is solid, is good hardwood material.
Exocarpium Juglandis Immaturus refers to the green-skinned of the fruit of Semen Juglandis, i.e. peel, is a kind of Chinese medicine, is referred to as Exocarpium Juglandis Immaturum.Exist every year
The Semen Juglandis harvest season, substantial amounts of Exocarpium Juglandis Immaturus can be produced.Owing to Pericarpium Citri Reticulatae Viride alkalescence is stronger, it is impossible to edible, can not be directly as
Agro-farming fertilizer, can cause certain pollution if directly abandoning to environment.So using Exocarpium Juglandis Immaturus as research material, i.e. realizing
Twice laid, can expand new content in field of natural product chemistry the most again.
Summary of the invention
The invention provides a kind of method extracted from Exocarpium Juglandis Immaturus and separate bis-methyl naphthalene alkene-1,5-diketone of 4,8-.
The present invention provides a kind of and extracts separation 4 from Exocarpium Juglandis Immaturus, and bis-methyl naphthalene alkene-1 of 8-, the method for 5-diketone, step is such as
Under:
(1) Exocarpium Juglandis Immaturus is put in water, soak extraction；Or extract with ultrasound wave or microwave soaking；
(2) by the aqueous phase decompression distillation after extraction, controlling bath temperature is 50 DEG C-70 DEG C, and vacuum is 0.06-0.08MPa,
Obtain the aqueous solution containing bis-methyl naphthalene alkene-1,5-diketone of 4,8-；Wherein, bis-methyl naphthalene alkene-1 of described 4,8-, 5-bis-
The chemical structural formula of ketone is:
Preferably, Exocarpium Juglandis Immaturus described in step (1) is 1:2-1:10 with the weight ratio of water.
Preferably, further comprising the steps of: containing 4, bis-methyl naphthalene alkene-1 of 8-, the aqueous solution of 5-diketone adds oil
It is colourless that ether carries out being extracted to aqueous phase, takes petroleum ether and carries out decompression distillation mutually, obtains yellow crude extract；Yellow crude extract dress post is washed
De-, eluent is petroleum ether and chloroform, obtains 4 after purification, bis-methyl naphthalene alkene-1 of 8-, 5-diketone.
Preferably, described in take petroleum ether mutually carry out decompression distillation time, bath temperature be less than 35 DEG C.
Preferably, the volume ratio of described petroleum ether and chloroform is 2:1-1:2.When this volume ratio, eluted product purity is high.
Preferably, during dress post eluting, adsorbent is silica gel, aluminium oxide or magnesium oxide.
Steam distillation is only applicable to have volatile, can not be destroyed with vapor distillation, not react with water,
And indissoluble or the extraction of water-fast composition.The boiling point of specific examples of such components is many more than 100 DEG C, the most miscible with water or the most micro-
Molten, and have certain vapour pressure at about 100 DEG C.When heating together with water, the vapour pressure summation of its vapour pressure and water
When being an atmospheric pressure, liquid begins to boiling, and volatile material is taken out of by steam in the lump.Vapor distillation can not be applied
Bis-methyl naphthalene alkene-1,5-dione compounds of 4,8-in the present invention.And tradition Separation of Natural Products method-column chromatography methods,
Time-consuming long, and typically at least need the column chromatography of more than twice to separate, production efficiency is relatively low.The applicant is for 4,8-
Secondary methyl naphthalene alkene-1, the high symmetric feature of 5-diketone, use azeotropic to prepare method and carry out extracting separation, low cost, growth
Cycle is short.
Accompanying drawing explanation
Accompanying drawing is for providing a further understanding of the present invention, and constitutes a part for description, with embodiments of the invention
It is used for together explaining the present invention, is not intended that limitation of the present invention.In the accompanying drawings:
Fig. 1 is the infrared spectrogram of the compound of the present invention；
Fig. 2 is the mass spectrum of the compound of the present invention；
Fig. 3 is the ultraviolet-visible light spectrogram of the compound of the present invention；
Fig. 4 is the compound of the present invention1H-NMR schemes；
Fig. 5 is the compound of the present invention13CNMR schemes；
Fig. 6 is the HMBC figure of the compound of the present invention；
Fig. 7 is the HMQC figure of the compound of the present invention；
Fig. 8 is yellow needle-like crystals compound monocrystal diffraction patterns；
Fig. 9 is Gaussian quantum calculation model；
Figure 10 is the compound of present invention ultraviolet-visible light spectrogram in different pH value.
Detailed description of the invention
Below example facilitates a better understanding of the present invention, but does not limit the present invention.Experimental technique in following embodiment,
If no special instructions, it is conventional method.Test material used in following embodiment, if no special instructions, is from often
Rule biochemical reagents shop is commercially available.
Instrument and reagent are as follows:
Germany's Heidolph Rotary Evaporators；Germany's Greiffenberger Antriebstechnik vacuum pump；Shanghai
EYELA cooling water circulating device, model C A-1111；Column chromatography silica gel (200-300mesh) and tlc silica gel
(GF254) it is Haiyang Chemical Plant, Qingdao to produce；Petroleum ether, chloroform, ethyl acetate are industry and heavily steam；Thin plate detects
Using 254nm uviol lamp, sulphuric acid-ethanol (5%) submergence is heated.
The preparation method of the compounds of this invention is as follows:
(1) weighing 1kg Exocarpium Juglandis Immaturus, put in water, Exocarpium Juglandis Immaturus is 1:2-1:10 with the weight ratio of water；
(2) soak extraction 20-50 minute under room temperature environment；Immersion can be soaked, so by ultrasound wave or microwave-assisted
Soak time can more common soak time short.
(3) aqueous phase after extraction is moved in round-bottomed flask, be placed on Rotary Evaporators, be evaporated under reduced pressure to water in round-bottomed flask
Solution is almost colourless；During decompression distillation, controlling bath temperature is 50 DEG C-70 DEG C, and vacuum is 0.06-0.08MPa.Now,
Yellow transparent aqueous solution in receiving bottle, is the aqueous solution containing the compounds of this invention.
(4) aqueous solution in receiving bottle is taken out, add petroleum ether, be repeated that to be extracted to aqueous phase colourless, take petroleum ether phase, abandon
Remove aqueous phase.
(5) by the petroleum ether phase of extraction gained, it is placed on Rotary Evaporators, under conditions of bath temperature is less than 35 DEG C,
Decompression distillation, obtains yellow crude extract, weighs about 500mg.
(6) mix with 0.5g silica gel (200-300 mesh) after crude extract being dissolved with a small amount of solvent, then with the identical silicon of 50g
Glue carries out filling post, with petroleum ether: chloroform (v:v) 2:1-1:2 carries out eluting, obtains the component of yellow substance, and decompression is steamed
Evaporate the compound of the present invention i.e. obtaining extraction after removing solvent.Silica gel can also substitute with magnesium oxide or aluminium oxide.
Below in conjunction with embodiment, the extracting method of the compounds of this invention is described in detail.
Embodiment 1
(1) fresh for 1kg Exocarpium Juglandis Immaturus is put in the water of 2L；
(2) under room temperature environment, 30min is soaked；
(3) aqueous phase after extraction is moved in round-bottomed flask, be placed on Rotary Evaporators decompression distillation to water in round-bottomed flask
Solution is almost colourless, used time 30min；During decompression distillation, controlling bath temperature is 60 DEG C, and vacuum is 0.07MPa.This
Time, the yellow transparent aqueous solution in receiving bottle, it is the aqueous solution containing the compounds of this invention.
(4) aqueous solution in receiving bottle is taken out, add 1L petroleum ether in three times and extract, take petroleum ether phase, discard water
Phase.
(5) by the petroleum ether phase of extraction gained, it is placed on Rotary Evaporators, under conditions of bath temperature is less than 30 DEG C,
Decompression distillation, obtains yellow crude extract, weighs about 500mg；Vacuum does not has specific requirement herein, as long as can distilling off solvent
?；
(6) crude extract (as long as the solvent of this compound can be dissolved, can be used with a small amount of solvent；Such as
Solvent is petroleum ether) dissolve after mix with 0.5g silica gel (200-300 mesh), then with the identical silica gel of 50g carry out fill post, use stone
Oil ether: chloroform (v:v) 1:1 carries out eluting, obtains yellow substance, and decompression i.e. obtains the present invention extracted after solvent is distilled off
Compound, crystal weighs about 20mg；Distillation condition is: bath temperature is less than 30 DEG C, and vacuum does not has specific requirement,
As long as can distilling off solvent.
Embodiment 2
(1) fresh for 200g Exocarpium Juglandis Immaturus is added in the water of 1L；
(2) under room temperature environment, 20min is soaked；
(3) aqueous phase after extraction is moved in round-bottomed flask, be placed on Rotary Evaporators, 20min is evaporated under reduced pressure, now
In round-bottomed flask, aqueous solution is almost colourless；During decompression distillation, controlling bath temperature is 70 DEG C, and vacuum is 0.065MPa.
Now, the yellow transparent aqueous solution in receiving bottle, it is the aqueous solution containing the compounds of this invention.
(4) aqueous solution in receiving bottle is taken out, add 0.5L petroleum ether in three times and extract, take petroleum ether phase, discard
Aqueous phase.
(5) by the petroleum ether phase of extraction gained, it is placed on Rotary Evaporators, under conditions of bath temperature is less than 25 DEG C,
Decompression distillation, obtains yellow crude extract, weighs about 110mg；Vacuum does not has specific requirement herein, as long as can distilling off solvent
?；
(6) crude extract (as long as the solvent of this compound can be dissolved, can be used with a small amount of solvent；Such as
Solvent is petroleum ether) dissolve after mix with 0.1g silica gel (200-300 mesh), then with the identical silica gel of 20g carry out fill post, use stone
Oil ether: chloroform (v:v) 1:2 carries out eluting, obtains yellow substance, and decompression i.e. obtains the present invention extracted after solvent is distilled off
Compound, crystal weighs about 8mg；Distillation condition is: bath temperature is less than 30 DEG C, and vacuum does not has specific requirement, only
Can distilling off solvent.
Embodiment 3
(1) fresh for 1kg Exocarpium Juglandis Immaturus is put in the water of 10L；
(2) under room temperature environment, 50min is soaked；
(3) aqueous phase after extraction is moved in round-bottomed flask, be placed on Rotary Evaporators decompression distillation to water in round-bottomed flask
Solution is almost colourless, used time 30min；During decompression distillation, controlling bath temperature is 50 DEG C, and vacuum is 0.08MPa.This
Time, the yellow transparent aqueous solution in receiving bottle, it is the aqueous solution containing the compounds of this invention.
(4) aqueous solution in receiving bottle is taken out, add 1L petroleum ether in three times and extract, take petroleum ether phase, discard water
Phase.
(5) by the petroleum ether phase of extraction gained, it is placed on Rotary Evaporators, under conditions of bath temperature is less than 30 DEG C,
Decompression distillation, obtains yellow crude extract, weighs about 1150mg；Vacuum does not has specific requirement herein, as long as can distill out molten
Agent；
(6) crude extract (as long as the solvent of this compound can be dissolved, can be used with a small amount of solvent；Such as
Solvent is petroleum ether) dissolve after mix with 0.5g magnesium oxide, then with the identical magnesium oxide of 50g carry out fill post, with petroleum ether: chloroform
(v:v) 2:1 carries out eluting, obtains yellow substance, and decompression i.e. obtains the compound of the present invention extracted after solvent is distilled off,
Crystal weighs about 50mg；Distillation condition is: bath temperature is less than 30 DEG C, and vacuum does not has specific requirement, as long as can distill
Go out solvent.
Embodiment 4
1, Spectrum Analysis result
Embodiment 1 and 2 is extracted the compound obtained and is identified by the applicant, is 4,8-dimethylenenaphth
Alene-1,5 (4H, 8H)-dione, Chinese is: 4,8-bis-methyl naphthalene alkene-1, and 5-diketone (is called for short NEO-Z).
Its structure is as follows.
Concrete qualification process is as follows:
(1) this compound is yellow needle-like crystals, under the uviol lamp of 254nm wavelength, fluorescence detected, sulphuric acid-
Ethanol (5%, v:v) colour developing is yellow.
(2) the applicant combine Modern spectroscopy means (IR, MS,1H-NMR,13C-NMR, HMBC, HMQC, ultraviolet-can
Seeing spectrum, X-ray single crystal diffraction is analyzed) determine its structure.Its nuclear magnetic resonance, NMR, infrared, ultraviolet and mass spectrogram
It is analyzed as follows:
1H-NMR spectrum shows this compound, at displacement δH=11.9 unimodal identical with the result of Gaussian quantum calculation,
It is the peak of the hydrogen of hydrogen bond.
13C-NMR spectrum shows this compound, has 10 C, wherein 5 quaternary carbons.
Can analyze from HMBC spectrogram and HMQC spectrogram, this compound is at CDCl3In may have tautomer.
Infrared spectrum shows, the broad peak of wave number 3435 is intramolecular hydrogen bond, and 3076 are probably intermolecular hydrogen bond, and 1643 are
Carbonyl peak, 1290 is the peak of the tertiary alcohol.Molecule can be deduced and there is the phenomenon that carbonyl converts to enol form.
Ultraviolet-visible spectrum shows, this compound has absworption peak at 230nm-280nm and 360nm-500nm.
Determine that compound is Fig. 7 structure according to single crystal diffraction.
2, the explanation of Gaussian quantum calculation result
By said structure, Gaussian 09 quantum chemistry software is used to calculate.Result of calculation shows,1H-NMR
In spectrum, the chemical shift δ of these No. 20 and No. 21 hydrogen atoms of compoundH=10.77, this explains at the 20 of methylene
Number between hydrogen atom and No. 12 oxygen atoms, there is hydrogen bond；In like manner, there is also hydrogen between No. 21 hydrogen atoms and No. 14 oxygen atoms
Key.Fig. 8 is Gaussian quantum calculation model.
The character of embodiment 5 the compounds of this invention and application
Because the compound of the present invention is to be in the news out for the first time, the parameter relevant in order to improve its physicochemical property, the most also
In order to probe into the character of this compound further, its physicochemical property is further studied by the applicant.
The molecular weight of the compounds of this invention is 184, [M+H]+Molecular weight be 185.059, can be dissolved in chloroform, petroleum ether,
Acetone, methanol and water equal solvent；The compound of the present invention, in aqueous in yellow transparent solution, shows faintly acid；?
During pH value 8-9, the secondary colour for yellow and pink colour is interval；In the aqueous solution of pH >=9, it is transparent molten that solution becomes pink colour
Liquid；The highest color of pH value is the deepest, to aubergine clear solution.This compound i.e. can refer to as the pH of instruction soda acid change
Show agent.
The common method measuring acid-base indicator pK value, has spectrophotometry method and potentiometric titration.The application adopts
With the acid dissociation constant pKa of spectrophotometry compound, result obtains the theoretical color transition point of the compound of the present invention and is
PH=8.87.8.87 refer to yellow becomes the color transition point of pink colour, and pink colour causes to aubergine due to color burn, not
It it is second time variable color.
By experiment, find that the concentration at this compound is 1 × 10-5During mol/L, close to the limit of human eye observation；The present invention
Compound does not reacts with the water in air, oxygen and carbon dioxide, good stability.
Finally it is noted that the foregoing is only the preferred embodiments of the present invention, it is not limited to the present invention, to the greatest extent
The present invention has been described in detail by pipe with reference to previous embodiment, and for a person skilled in the art, it is the most permissible
Technical scheme described in foregoing embodiments is modified, or wherein portion of techniques feature is carried out equivalent.All
Within the spirit and principles in the present invention, any modification, equivalent substitution and improvement etc. made, should be included in the present invention's
Within protection domain.
Claims (5)
1. one kind is extracted separation 4, bis-methyl naphthalene alkene-1 of 8-, the method for 5-diketone from Exocarpium Juglandis Immaturus, it is characterised in that: step is as follows:
(1) Exocarpium Juglandis Immaturus is put in water, soak extraction；Or extract with ultrasound wave or microwave soaking；
(2) by the aqueous phase decompression distillation after extraction, controlling bath temperature is 50 DEG C-70 DEG C, and vacuum is 0.06-0.08MPa, obtains containing 4, bis-methyl naphthalene alkene-1 of 8-, the aqueous solution of 5-diketone；Wherein, bis-methyl naphthalene alkene-1 of described 4,8-, the chemical structural formula of 5-diketone is:
(3) containing 4, bis-methyl naphthalene alkene-1 of 8-, adding petroleum ether in the aqueous solution of 5-diketone, to carry out being extracted to aqueous phase colourless, takes petroleum ether and carries out decompression distillation mutually, obtains yellow crude extract；Yellow crude extract is filled post eluting, and eluent is petroleum ether and chloroform, obtains 4 after purification, bis-methyl naphthalene alkene-1 of 8-, 5-diketone.
Method the most according to claim 1, it is characterised in that: Exocarpium Juglandis Immaturus described in step (1) is 1:2-1:10 with the weight ratio of water.
Method the most according to claim 1, it is characterised in that take described in: petroleum ether mutually carry out decompression distillation time, bath temperature be less than 35 DEG C.
Method the most according to claim 1, it is characterised in that: the volume ratio of described petroleum ether and chloroform is 2:1-1:2.
Method the most according to claim 1, it is characterised in that: during dress post eluting, adsorbent is silica gel, aluminium oxide or magnesium oxide.
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| CN201510372437.2A CN105037121B (en) | 2015-06-30 | 2015-06-30 | A kind of method extracting separation bis-methyl naphthalene alkene-1,5-diketone of 4,8-from Exocarpium Juglandis Immaturus |
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| CN103319321B (en) * | 2013-06-09 | 2014-12-17 | 吕梁学院 | Extraction method of juglone and derivative in walnut green tangerine peel |
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