CN116559216A - Method for determining esterification degree of primary alcohol in sucrose laurate - Google Patents
Method for determining esterification degree of primary alcohol in sucrose laurate Download PDFInfo
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- CN116559216A CN116559216A CN202310500434.7A CN202310500434A CN116559216A CN 116559216 A CN116559216 A CN 116559216A CN 202310500434 A CN202310500434 A CN 202310500434A CN 116559216 A CN116559216 A CN 116559216A
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- 238000005886 esterification reaction Methods 0.000 title claims abstract description 76
- 230000032050 esterification Effects 0.000 title claims abstract description 68
- GCSPRLPXTPMSTL-IBDNADADSA-N [(2s,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[C@@]1([C@]2(CO)[C@H]([C@H](O)[C@@H](CO)O2)O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GCSPRLPXTPMSTL-IBDNADADSA-N 0.000 title claims abstract description 56
- 150000003138 primary alcohols Chemical class 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 32
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- 238000001228 spectrum Methods 0.000 claims abstract description 53
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- 238000004458 analytical method Methods 0.000 claims abstract description 23
- 239000005639 Lauric acid Substances 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
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- 239000012488 sample solution Substances 0.000 claims abstract description 7
- 239000000523 sample Substances 0.000 claims description 49
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- 239000000126 substance Substances 0.000 claims description 16
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 12
- 238000005570 heteronuclear single quantum coherence Methods 0.000 claims description 11
- 238000000990 heteronuclear single quantum coherence spectrum Methods 0.000 claims description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 11
- 230000003595 spectral effect Effects 0.000 claims description 11
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 claims description 9
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000005313 fatty acid group Chemical group 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
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- 230000008520 organization Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
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- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003084 food emulsifier Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
- G01N24/08—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects by using nuclear magnetic resonance
- G01N24/087—Structure determination of a chemical compound, e.g. of a biomolecule such as a protein
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/38—Diluting, dispersing or mixing samples
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A90/00—Technologies having an indirect contribution to adaptation to climate change
- Y02A90/30—Assessment of water resources
Abstract
The invention relates to a method for determining the esterification degree of primary alcohol in sucrose laurate, and belongs to the technical field of medicine analysis. Specifically discloses a nuclear magnetic resonance spectrum method for rapidly determining the esterification degree of primary alcohol in sucrose laurate, which comprises the steps of taking a proper amount of sucrose laurate, dissolving the sucrose laurate by using a deuterated solvent to prepare a sample solution, adding the sample solution into a nuclear magnetic tube, and collecting nuclear magnetic resonance hydrogen spectrum; analyzing the 1-position hydrogen resonance signal of the sucrose, the esterified primary alcohol methylene resonance signal and the lauric acid terminal methyl resonance signal, and respectively calculating the total esterification degree of the sucrose and the esterification degree of the primary alcohol methylene position. The invention does not need to use a large amount of organic solvents in the detection process, is environment-friendly, quick and efficient, and has high sensitivity and good reproducibility of detection results.
Description
Technical Field
The invention belongs to the technical field of medicine analysis, and relates to a nuclear magnetic resonance spectrum method for rapidly determining the esterification degree of primary alcohol in sucrose laurate. The analysis method is applied to quality control of preparing sucrose laurate by a chemical synthesis method.
Background
Sucrose laurate is colorless to yellowish thick gel, soft solid or white to yellowish brown powder. As a nonionic surfactant, the nonionic surfactant is widely applied to food, medicines, cosmetics, detergents and textile industries, is a food additive recommended by the United nations grain and agricultural organization and health organization (WHO/HAO), is approved as a pharmaceutical adjuvant and a food additive in both European and American countries, and is approved for use in the 80 th century in China. Sucrose esters have become the fourth largest food emulsifier category worldwide next to sorbitol esters, monoglycerides and propylene glycol esters; can replace the traditional microcrystalline cellulose, talcum powder, monoglyceride and the like to be used as candy tabletting lubricants.
At present, the industrial production of sucrose laurate mainly adopts a chemical method. The esterification reaction of sucrose and laurate is complex, the variety of products is varied, and chemical synthesis is accompanied by the formation of monoesters, diesters, triesters and a large number of isomers. The ether bond and the plurality of hydroxyl groups contained in the sucrose ester are hydrophilic groups, and the fatty acid group shows a certain lipophilicity. In general, sucrose monoesters are best in water solubility and hydrophilicity, and the more fatty acid chains the sucrose esters bind to, the weaker the hydrophilicity of the sucrose esters. The sucrose fatty acid ester with high degree of monoesterification has higher lipophilic-hydrophilic balance (HLB) and better emulsifying property, and is widely used compared with sucrose fatty acid monoester. The sucrose structure is shown in the following figure, and when the hydroxyl hydrogen atoms in the sucrose structure are further substituted, diesters, triesters, or even polyesters can be obtained.
Chromatography is one of the important analytical methods for quantitative analysis of various ester contents, which can completely separate and detect monoesters, diesters and triesters in the products. For sucrose laurate with monoester as main component, 8 hydroxyl sites can be subjected to esterification reaction, and sucrose laurate monoesters at different esterification positions show different properties due to the structural difference. It is reported in the literature that three primary alcohol methylene monoesters have similar solubility and HLB values, similar surface tension and higher thermal stability. However, the primary and secondary alcohol methylene monoesters differ greatly in their properties.
The inventors have found through many experiments that the esterification site of the monoester fatty acid cannot be determined without a control using a conventional chromatographic analysis method. To solve this problem, the inventors have attempted to use nuclear magnetic resonance spectroscopy, and have unexpectedly found that nuclear magnetic resonance spectroscopy can rapidly and efficiently determine the degree of primary alcohol esterification of sucrose laurate.
Disclosure of Invention
The invention adopts nuclear magnetic resonance spectroscopy to collect hydrogen spectrum and H-C HSQC spectrum in specific deuterated solvent, can rapidly and effectively analyze the esterification degree of primary alcohol and find out the difference between batches.
The rapid and efficient analysis of the content of various sucrose laurates (such as monoesters, diesters, triesters and the like) is a major issue in the later stages of the experiment. For the present invention, it is important to analyze the degree of esterification of sucrose laurate monoester primary alcohol.
The invention is realized by the following technical scheme:
a method for determining the degree of esterification of a primary alcohol in sucrose laurate comprising the steps of:
1) Weighing sucrose laurate sample with certain mass, and placing into a centrifuge tube; adding deuterated solvent to dissolve the sample to prepare a solution with the concentration of 10mg/mL-20 mg/mL; transferring the dissolved sample solution into a nuclear magnetic tube,
2) Placing the nuclear magnetic resonance tube in a nuclear magnetic resonance spectrometer, and detecting to obtain a nuclear magnetic resonance hydrogen spectrum, wherein the analysis conditions of the nuclear magnetic resonance hydrogen spectrum are as follows: the pulse sequence is as follows: zg or zg30,
3) Analyzing the collected nuclear magnetic resonance hydrogen spectrum, identifying the resonance signal of lauric acid end methyl in the hydrogen spectrum and the resonance signal of sucrose 1-position hydrogen in the hydrogen spectrum, confirming that the characteristic peak of the sucrose laurate sample is not interfered by active hydrogen, then collecting the H-C HSQC spectrum with phase editing,
4) Analyzing the collected H-C HSQC spectrum, identifying the resonance signal of the methylene of the primary alcohol after esterification,
5) And 4) respectively integrating one or more resonance signals of the esterified primary alcohol methylene in the hydrogen spectrum, which are obtained in the step 4), and the resonance signals of the lauric acid end methyl in the hydrogen spectrum, which are obtained in the step 3), and comparing the relative integral values to calculate the esterification degree of the primary alcohol.
In some preferred embodiments, the deuterated solvent in step 1) is selected from one of deuterated methanol, deuterated dimethyl sulfoxide, heavy water, deuterated chloroform, or any mixture thereof.
In a preferred embodiment, the deuterated solvent in step 1) is selected from deuterated methanol.
In another preferred embodiment, the deuterated solvent in step 1) is selected from deuterated dimethyl sulfoxide and heavy water in a volume ratio of 10: 1.
In some preferred embodiments, the concentration of the sucrose laurate sample solution configured in step 1) is 10mg/ml.
The method for determining the optimal concentration comprises the following steps: and 3) when analyzing the acquired nuclear magnetic resonance hydrogen spectrum, respectively carrying out hydrogen spectrum acquisition on samples with different concentrations and comparing peak shapes, and finding that when the concentration of the sucrose laurate sample is 10mg/ml, the sucrose laurate sample is not influenced by active hydrogen, the integral is most accurate, the result error is minimum, and the spectrum resolution is high, so that the sucrose laurate sample is determined to be the optimal concentration.
Wherein in step 2), in some preferred embodiments, the analysis conditions of the nuclear magnetic resonance hydrogen spectrum are: a BBO probe is adopted; probe temperature: room temperature is 20-25 ℃; ambient humidity: 30-65%; the observation frequency is 400MHz; the pulse sequence is as follows: zg or zg30; spectral width: 8196Hz;90 degree pulse width: p1=10μs; pulse delay time: d1 =1s or 2s; and a transmitting center: o1=8.0 ppm; accumulating times: 8 or 16 or 32.
Wherein in step 3), in some preferred embodiments, the acquisition conditions for acquiring the phase-edited H-CHSQC map are: a BBO probe is adopted; probe temperature: room temperature is 20-25 ℃; ambient humidity: 30-65%; the observation frequency is 400MHz; the pulse sequence is as follows: hsqcdedtgpsisp2.3; sampling points: TD (F1) =256, TD (F2) =2048; spectral width: f1 dimension=21130 Hz, f2 dimension=2778 Hz; accumulating times: 64 or 80; number of empty sweeps: 16; hydrocarbon direct coupling constant: cnst2=145 Hz.
According to the method for determining the esterification degree of primary alcohol in sucrose laurate, when the deuterated solvent in the step 1) is selected from deuterated methanol, the chemical shift is confirmed to be methylene at two resonance signals of delta 4.50-4.30 ppm and delta 4.25-4.15 ppm by analyzing the acquired H-C HSQC spectrum in the step 4), and the two methylene are identified to be primary alcohol methylene CH2 resonance signals of esterification reaction with lauric acid; confirming that the resonance signal at the chemical shift delta 5.50-5.30 ppm in the hydrogen spectrum is the lowest field resonance signal and is regarded as the 1-position hydrogen resonance signal of the sucrose; the resonance signal at δ1.00 to 0.80ppm in the hydrogen spectrum was confirmed to be the t-peak, and was identified as the lauric acid terminal methyl resonance signal.
The method for determining the esterification degree of primary alcohol in sucrose laurate, disclosed by the invention, comprises the following steps of:
degree of esterification of primary alcohol= (3×a2)/(2×a3); wherein the method comprises the steps of
A2: the sum of the relative integral values of the resonance signals of the primary alcohol methylene after esterification in the hydrogen spectrum,
a3: relative integration value of lauric acid terminal methyl resonance signal in hydrogen spectrum.
In some preferred embodiments of the present invention, the step 5) may further integrate the resonance signal of the 1-hydrogen of sucrose in the hydrogen spectrum and the resonance signal of the lauric acid end methyl in the hydrogen spectrum, compare the integrated values, calculate the total esterification degree of sucrose, and confirm whether the main existing form of sucrose laurate exists in the form of monoester according to the calculated result of the total esterification degree of sucrose, thereby confirming the accuracy of the result of the esterification degree of primary alcohol. Wherein the formula for calculating the total esterification degree of the sucrose is as follows:
total degree of esterification of sucrose= (3 x a 1)/A3;
wherein the method comprises the steps of
A1: the relative integral value of the hydrogen resonance signal at the 1-position of sucrose in the hydrogen spectrum,
a3: relative integration value of lauric acid terminal methyl resonance signal in hydrogen spectrum.
The beneficial effects of the invention are as follows:
1. in the analysis method, during the first analysis, an H-C HSQC spectrogram is acquired and analyzed, and the resonance signal of the esterified primary alcohol methylene is identified; when the sucrose esterification degree and the primary alcohol esterification degree are analyzed later, only the hydrogen spectrum is needed to be collected, HSQC experiments are not needed, and the analysis time is short.
2. According to the analysis method, a reference substance or a standard substance is not needed; deuterated methanol is adopted as a solvent; only the hydrogen spectrum needs to be collected, and the analysis time is short; and the qualitative and quantitative synchronous completion.
3. The invention does not need to use a large amount of organic solvents in the detection process, is environment-friendly, quick and efficient, and has high sensitivity and good reproducibility of detection results.
Drawings
FIG. 1 is a heavy water dissolution nuclear magnetic pattern of sucrose laurate;
FIG. 2 is a deuterated chloroform-dissolved nuclear magnetic pattern of sucrose laurate;
FIG. 3 is a deuterated dimethyl sulfoxide dissolution nuclear magnetic pattern of sucrose laurate;
FIG. 4 is a deuterated methanol dissolution nuclear magnetic pattern of sucrose laurate;
FIG. 5 is a nuclear magnetic resonance spectrum of sucrose laurate dissolved in a mixed solvent of deuterated dimethyl sulfoxide and heavy water;
FIG. 6 is a deuterated methanol dissolution HSQC profile of sucrose laurate;
FIG. 7 is a graph of HSQC pattern of sucrose laurate dissolved in a mixed solvent of deuterated dimethyl sulfoxide and heavy water (10:1 volume ratio).
Detailed Description
The invention is further illustrated by the following sets of specific examples. It should be understood that: the examples of the present invention are intended to be illustrative of the invention and are not intended to be limiting. The technical scheme of the invention is that the invention is simply modified or the invention is obtained by adopting conventional means or active ingredients to be replaced equivalently on the basis of the technical scheme of the invention, and the technical scheme belongs to the protection scope of the invention.
Apparatus and device
The experimental facility includes: AVANCE NEO 400M nuclear magnetic resonance spectrometer (Bruce, switzerland), 9.4T superconducting magnet, 5mm binuclear z-gradient probe and Topspin 4.0.9 test control and data processing software; a 5mm nuclear magnetic resonance sample tube; KQ-250DB model digital control ultrasonic cleaner (Kunshan ultrasonic instruments Co., ltd.); MSA6.6S analytical balance (Sidoris, germany).
The experimental solvents included: deuterated water (deuterated degree 99.9%, also known as heavy water) was purchased from sigma; deuterated chloroform (99.8% deuterated) was purchased from sigma; deuterated dimethyl sulfoxide (99.9% deuterated) was purchased from sigma; deuterated methanol (99.8% deuterated) was purchased from sigma.
Example 1 screening of deuterated reagents
1.1 treatment of samples
Weighing a plurality of sucrose laurate samples respectively, and placing about 10mg of each sucrose laurate sample into a centrifuge tube; adding 0.6ml of mixed solvent of heavy water, deuterated chloroform, deuterated dimethyl sulfoxide and deuterated methyl alcohol respectively, shaking and ultrasonic to dissolve the sample; transferring the dissolved sample into a nuclear magnetic tube, and collecting a hydrogen spectrum.
1.2 establishment of Nuclear magnetic fingerprint database
Adjusting the nuclear magnetic resonance spectrometer, placing the nuclear magnetic tube in the nuclear magnetic resonance spectrometer, and performing hydrogen spectrum test to obtain nuclear magnetic resonance signals of the sample; a BBO probe is adopted; measurement temperature (probe temperature): room temperature is 20-25 ℃; ambient humidity: 30-65%; the observation frequency is 400MHz; the pulse sequence is as follows: zg or zg30; spectral width: 8196Hz;90 degree pulse width: p1=10μs; pulse delay time: d1 =1s or 2s; and a transmitting center: o1=8.0 ppm; accumulating times: 8 or 16 or 32.
1.3 spectrogram pretreatment
And carrying out Fourier transform on the obtained nuclear magnetic resonance signals by using data processing software of a nuclear magnetic resonance spectrometer, wherein the number of the transformation points is 65536, and the exponential linewidth factor is 0.3Hz, so as to obtain a nuclear magnetic hydrogen spectrogram of the sample.
The raw fingerprint obtained was pre-processed with topspin software (topspin software parameters set as follows: pulprog=zg30 or zg, aq_mod=dqd, td=64 k, ns=8×n, ds=2, td0=1, sw=8196hz, d1=1s, de=6.5 μs), including spectral peak alignment, baseline correction and phase adjustment. Spectral peak alignment was performed with chemical shift of deuterated reagent (4.70 ppm heavy water, 7.28ppm deuterated chloroform, 2.50ppm deuterated dimethyl sulfoxide heavy water (10:1 volume ratio) mixed solvent, 3.33ppm deuterated methanol); baseline correction selects bc_mod=quad fitting; the phase adjustment selection ph_mod=pk algorithm is automatically optimized. The nuclear magnetic hydrogen spectrograms of the obtained different deuterated reagent solvents are shown in figures 1-5.
1.4 analysis of Nuclear magnetic resonance Spectrometry
By comparing and analyzing nuclear magnetism hydrogen spectrograms dissolved by different solvents, the sample spectrograms dissolved by heavy water, deuterated chloroform and deuterated dimethyl sulfoxide are found that the resolution ratio and the signal to noise ratio of the spectrograms do not meet the requirements and cannot be further analyzed; and the resolution and the signal to noise ratio of the sample spectrum dissolved by the deuterated methanol or deuterated dimethyl sulfoxide heavy water (10:1 volume ratio) mixed solvent can meet the analysis requirements.
And (3) taking deuterated methanol as a solvent, and performing two-dimensional nuclear magnetic resonance analysis on the sample to identify the esterified primary alcohol methylene CH2 resonance signal, so as to calculate the esterification degree of the primary alcohol.
Example 2 two-dimensional Nuclear magnetic resonance Studies with deuterated methanol as solvent
2.1 treatment of samples
About 20mg of sucrose laurate sample is weighed and placed in a centrifuge tube; adding 0.6ml of deuterated methanol, shaking and ultrasonic to dissolve the sample; transferring the dissolved sample into a nuclear magnetic resonance tube, and collecting an HSQC spectrum (hydrocarbon direct correlation spectrum).
2.2 establishment of Nuclear magnetic fingerprint database
Adjusting a nuclear magnetic resonance spectrometer, placing a nuclear magnetic tube in the nuclear magnetic resonance spectrometer, and performing HSQC test to obtain nuclear magnetic resonance signals of the sample; a BBO probe is adopted; measurement temperature (probe temperature): room temperature is 20-25 ℃; ambient humidity: 30-65%; the observation frequency is 400MHz; the pulse sequence is as follows: hsqcdedtgpsisp2.3; sampling points: TD (F1) =256, TD (F2) =2048; spectral width: f1 dimension=21130 Hz, f2 dimension=2778 Hz; accumulating times: 64 or 80; number of empty sweeps: 16; hydrocarbon direct coupling constant: cnst2=145 Hz.
2.3 spectrogram pretreatment
And carrying out Fourier transformation on the obtained nuclear magnetic resonance signals by using data processing software of a nuclear magnetic resonance spectrometer to obtain a nuclear magnetic HSQC spectrogram of the sample.
The obtained original spectra were pre-processed with topspin software (topspin software parameters set as follows: pulprog=hsqcecetgppsisp 2.3, aq_mod=dqd, TD (F1) =256, TD (F2) =2048, ns=16×n, ds=16, td0=1, d1=1.5 s, de=6.5 μs), including spectral peak alignment, baseline correction and phase adjustment. Baseline correction selects bc_mod=quad fitting; the phase adjustment selection ph_mod=pk algorithm is automatically optimized. The obtained H-C HSQC spectrum is shown in FIG. 6.
2.4 analysis of Nuclear magnetic resonance Spectrometry
By analyzing the HSQC spectrogram, the resonance signal phase of the chemical shift at delta 4.50-4.30 ppm and delta 4.25-4.15 ppm is negative, which shows that the resonance signals at the two positions are methylene; meanwhile, compared with other methylene resonance signals, the chemical shift of the two positions is obviously towards low field shift, which indicates that the hydroxyl connected with the two positions of methylene and lauric acid are subjected to esterification reaction, so that primary alcohol methylene CH2 resonance signals subjected to esterification reaction with lauric acid are identified; the resonance signal at the chemical shift delta 5.50-5.30 ppm in the hydrogen spectrum is the lowest field resonance signal and is identified as the 1-position hydrogen resonance signal of sucrose. The resonance signal at δ1.00 to 0.80ppm in the hydrogen spectrum is a t-peak, and is referred to as a lauric acid terminal methyl resonance signal.
EXAMPLE 3 screening of sample concentrations
Three sucrose laurate samples are weighed respectively, dissolved by deuterated methanol to prepare sample solutions with the concentration of 5mg/ml, 10mg/ml and 20mg/ml, hydrogen spectra are collected, and peak shapes at the positions of chemical shifts delta 5.50-5.30 ppm are compared. According to the comparison analysis, when the concentration of the sample is 5mg/ml, the signal-to-noise ratio of the 1-position hydrogen resonance signal of the sucrose is reduced, and the relative integral value is smaller, so that the calculated esterification degree is influenced; when the concentration of the sample is 20mg/ml, the active hydrogen of the hydroxyl group of partial sucrose is not deuterated, and the active hydrogen near 5ppm can lead the 1-position hydrogen resonance signal of the sucrose to be larger than the integral value, so as to influence the calculated esterification degree. Thus, the final preferred sample concentration is determined to be 10mg/ml.
Example 4 actual sample detection with deuterated methanol as solvent
The method for rapidly determining the esterification degree of primary alcohol in sucrose laurate by using deuterated methanol as a solvent is used for detecting samples produced by different processes, and the samples are operated according to the steps of 1.1-1.3 to obtain nuclear magnetic resonance hydrogen spectrograms of the samples; peaks at chemical shifts of delta 5.50-5.30 ppm, delta 4.50-4.30 ppm, delta 4.25-4.15 ppm and delta 1.00-0.80 ppm in the hydrogen spectrum are respectively integrated, and calculated according to a calculation formula of the esterification degree. The results of the esterification degree and the primary alcohol esterification degree of different production processes/different batches of products are shown in Table 1.
The calculation formula of the esterification degree in the invention is as follows:
total degree of esterification of sucrose= (3 x a 1)/A3
Degree of esterification of primary alcohols= (3×a2)/(2×a3)
A1: relative integration value at delta 5.50-5.30 ppm;
a2: the sum of the relative integral values at δ4.50 to 4.30ppm and δ4.25 to 4.15 ppm;
a3: δ1.00 to 0.80 ppm.
TABLE 1
| Different batches of products | Total degree of esterification of sucrose | Degree of esterification of primary alcohols |
| Batch 1 | 1.09 | 0.75 |
| Batch 2 | 0.90 | 0.75 |
| Batch 3 | 0.91 | 0.82 |
| Batch 4 | 0.85 | 0.77 |
| Batch 5 | 1.01 | 0.75 |
| Batch 6 | 0.94 | 0.61 |
| Batch 7 | 0.95 | 0.58 |
The primary alcohols have different degrees of esterification and the sucrose laurate has different properties. The inventor can quickly find out the sucrose laurate product batch with the primary alcohol esterification degree meeting the requirement through the analysis method. The process optimization can be carried out on other batches of products according to the production process of the batch of products, so that the subsequent amplified production is carried out on the basis of the optimized process, and the sucrose laurate with high quality is obtained; the above analysis method of the present invention can also be used as a qualification standard for judging the quality of sucrose laurate of different batches, and the like.
Example 5 two-dimensional nuclear magnetic resonance study with deuterated dimethyl sulfoxide heavy Water (10:1 volume ratio) Mixed solvent
5.1 treatment of samples
About 20mg of sucrose laurate sample is weighed and placed in a centrifuge tube; 0.6ml of deuterated dimethyl sulfoxide heavy water (10:1 volume ratio) mixed solvent, and shaking and ultrasonic treatment to dissolve the sample; transferring the dissolved sample into a nuclear magnetic resonance tube, and collecting an HSQC spectrum (hydrocarbon direct correlation spectrum).
5.2 establishment of Nuclear magnetic fingerprint database
Adjusting a nuclear magnetic resonance spectrometer, placing a nuclear magnetic tube in the nuclear magnetic resonance spectrometer, and performing HSQC test to obtain nuclear magnetic resonance signals of the sample; a BBO probe is adopted; measurement temperature (probe temperature): room temperature is 20-25 ℃; ambient humidity: 30-65%; the observation frequency is 400MHz; the pulse sequence is as follows: hsqcdedtgpsisp2.3; sampling points: TD (F1) =256, TD (F2) =2048; spectral width: f1 dimension=21130 Hz, f2 dimension=2778 Hz; accumulating times: 64 or 80; number of empty sweeps: 16; hydrocarbon direct coupling constant: cnst2=145 Hz.
5.3 spectrogram pretreatment
And carrying out Fourier transformation on the obtained nuclear magnetic resonance signals by using data processing software of a nuclear magnetic resonance spectrometer to obtain a nuclear magnetic HSQC image of the sample.
The obtained original spectra were pre-processed with topspin software (topspin software parameters set as follows: pulprog=hsqcecetgppsisp 2.3, aq_mod=dqd, TD (F1) =256, TD (F2) =2048, ns=16×n, ds=16, td0=1, d1=1.5 s, de=6.5 μs), including spectral peak alignment, baseline correction and phase adjustment. Baseline correction selects bc_mod=quad fitting; the phase adjustment selection ph_mod=pk algorithm is automatically optimized. The obtained H-C HSQC spectrum is shown in FIG. 7.
5.4 analysis of Nuclear magnetic resonance Spectrometry
By analyzing the HSQC spectrogram, the resonance signal phase of the chemical shift at delta 4.35-3.95 ppm is found to be negative, which indicates that the resonance signal is methylene; meanwhile, compared with other methylene peaks, the chemical shift at the position is obviously shifted to a low field, which indicates that the hydroxyl connected with the methylene at the position is subjected to esterification reaction with lauric acid, so that a primary alcohol methylene CH2 resonance signal subjected to esterification reaction with lauric acid is identified; the resonance signal at the chemical shift delta 5.25-5.05 ppm in the hydrogen spectrum is the lowest field resonance signal and is identified as the 1-position hydrogen resonance signal of sucrose. The resonance signal at δ1.00 to 0.80ppm in the hydrogen spectrum is a t-peak, and is referred to as a lauric acid terminal methyl resonance signal.
Example 6 actual sample detection with deuterated heavy water in dimethyl sulfoxide (10:1 volume ratio) mixture as solvent
Detecting samples produced by different processes by using an established method for rapidly determining the esterification degree of primary alcohol in sucrose laurate, and operating the samples according to the steps of 1.1-1.3 to obtain nuclear magnetic resonance hydrogen spectrograms of the samples; peaks at chemical shifts delta 5.25-5.05 ppm, delta 4.35-3.95 ppm and delta 1.00-0.80 ppm in the hydrogen spectrum are respectively integrated, and calculated according to a calculation formula of the esterification degree. The results of the degree of esterification and the degree of esterification of primary alcohols were shown in Table 2, as analyzed by using deuterated methanol as solvent and deuterated dimethylsulfoxide heavy water (10:1 volume ratio) as solvent.
The calculation formula of the esterification degree in the invention is as follows:
total degree of esterification of sucrose= (3 x a 1)/A3
Degree of esterification of primary alcohols= (3×a2)/(2×a3)
A1: relative integral value at delta 5.25-5.05 ppm
A2: the sum of the relative integral values at delta 4.35-3.95 ppm
A3: relative integral value at δ1.00 to 0.80ppm
TABLE 2
The results obtained by comparing different deuterated solvents show that the total esterification degree and the primary alcohol esterification data obtained by using the different deuterated solvents selected by the invention are basically consistent, namely: the analysis method provided by the invention has better durability for different deuterated solvents, and the results are consistent.
Claims (10)
1. A method for determining the degree of esterification of a primary alcohol in sucrose laurate comprising the steps of:
1) Weighing sucrose laurate sample with certain mass, and placing into a centrifuge tube; adding deuterated solvent to dissolve the sample to prepare a solution with the concentration of 10mg/mL-20 mg/mL; transferring the dissolved sample solution into a nuclear magnetic tube,
2) Placing the nuclear magnetic resonance tube in a nuclear magnetic resonance spectrometer, and detecting to obtain a nuclear magnetic resonance hydrogen spectrum, wherein the analysis conditions of the nuclear magnetic resonance hydrogen spectrum are as follows: the pulse sequence is as follows: zg or zg30,
3) Analyzing the collected nuclear magnetic resonance hydrogen spectrum, identifying the resonance signal of lauric acid end methyl in the hydrogen spectrum and the resonance signal of sucrose 1-position hydrogen in the hydrogen spectrum, confirming that the characteristic peak of the sucrose laurate sample is not interfered by active hydrogen, then collecting the H-C HSQC spectrum with phase editing,
4) Analyzing the collected H-C HSQC spectrum, identifying the resonance signal of the methylene of the primary alcohol after esterification,
5) And 4) respectively integrating one or more resonance signals of the esterified primary alcohol methylene in the hydrogen spectrum, which are identified in the step 4), and the resonance signals of the lauric acid end methyl in the hydrogen spectrum, which are identified in the step 3), and comparing the relative integral values to calculate the esterification degree of the primary alcohol.
2. The method of determining the degree of esterification of a primary alcohol in sucrose laurate according to claim 1, wherein the deuterated solvent in step 1) is selected from one of deuterated methanol, deuterated dimethyl sulfoxide, heavy water, deuterated chloroform, or any mixture thereof.
3. The method of determining the degree of esterification of a primary alcohol in sucrose laurate according to claim 1, wherein the deuterated solvent in step 1) is selected from deuterated methanol.
4. The method of determining the degree of esterification of a primary alcohol in sucrose laurate according to claim 1, wherein the deuterated solvent in step 1) is selected from deuterated dimethyl sulfoxide and heavy water in a volume ratio of 10: 1.
5. The method for determining the degree of esterification of a primary alcohol in sucrose laurate according to claim 1, wherein the concentration of the sucrose laurate sample solution prepared in step 1) is 10mg/ml.
6. The method for determining the esterification degree of primary alcohols in sucrose laurate according to claim 1, wherein in said step 2), the analysis conditions of the nmr hydrogen spectrum are: a BBO probe is adopted; probe temperature: room temperature is 20-25 ℃; ambient humidity: 30-65%; the observation frequency is 400MHz; the pulse sequence is as follows: zg or zg30; spectral width: 8196Hz;90 degree pulse width: p1=10μs; pulse delay time: d1 =1s or 2s; and a transmitting center: o1=8.0 ppm; accumulating times: 8 or 16 or 32.
7. The method for determining the esterification degree of primary alcohol in sucrose laurate according to claim 1, wherein in the step 3), the acquisition conditions for acquiring the H-C HSQC spectrum with phase editing are as follows: a BBO probe is adopted; probe temperature: room temperature is 20-25 ℃; ambient humidity: 30-65%; the observation frequency is 400MHz; the pulse sequence is as follows:
hsqcdedtgpsisp2.3; sampling points: TD (F1) =256, TD (F2) =2048; spectral width: f1 dimension=21130 Hz, f2 dimension=2778 Hz; accumulating times: 64 or 80; number of empty sweeps: 16; hydrocarbon direct coupling constant: cnst2=145 Hz.
8. The method for determining the esterification degree of primary alcohol in sucrose laurate according to claim 3, wherein in the step 4), the chemical shift is confirmed to be methylene at two resonance signals of delta 4.50-4.30 ppm and delta 4.25-4.15 ppm by analyzing the collected H-C HSQC pattern, and the two resonance signals are confirmed to be primary alcohol methylene CH2 resonance signals of esterification reaction with lauric acid; confirming that the resonance signal at the chemical shift delta 5.50-5.30 ppm in the hydrogen spectrum is the lowest field resonance signal and is regarded as the 1-position hydrogen resonance signal of the sucrose; the resonance signal at δ1.00 to 0.80ppm in the hydrogen spectrum was confirmed to be the t-peak, and was identified as the lauric acid terminal methyl resonance signal.
9. The method for determining the degree of esterification of a primary alcohol in sucrose laurate according to any one of claims 1 to 8, wherein the formula calculated in step 5) is:
degree of esterification of primary alcohol= (3×a2)/(2×a3); wherein the method comprises the steps of
A2: the sum of the relative integral values of the resonance signals of the primary alcohol methylene after esterification in the hydrogen spectrum,
a3: relative integration value of lauric acid terminal methyl resonance signal in hydrogen spectrum.
10. The method for determining the degree of esterification of primary alcohol in sucrose laurate according to claim 1, wherein in step 5), the resonance signal of hydrogen at position 1 of sucrose in the hydrogen spectrum and the resonance signal of methyl at lauric acid end in the hydrogen spectrum are integrated respectively, the relative integration values are compared, the total degree of esterification of sucrose is calculated, and the result of calculation of the total degree of esterification of sucrose is used to determine whether the main existing form of sucrose laurate exists in the form of monoester, thereby determining the accuracy of the result of the degree of esterification of primary alcohol, wherein the formula of calculation of the total degree of esterification of sucrose is:
total degree of esterification of sucrose= (3 x a 1)/A3;
wherein the method comprises the steps of
A1: the relative integral value of the hydrogen resonance signal at the 1-position of sucrose in the hydrogen spectrum,
a3: relative integration value of lauric acid terminal methyl resonance signal in hydrogen spectrum.
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