WO2021003792A1 - Procédé de chromatographie en phase gazeuse pour la détection et la séparation simultanées de multiples acides gras - Google Patents

Procédé de chromatographie en phase gazeuse pour la détection et la séparation simultanées de multiples acides gras Download PDF

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WO2021003792A1
WO2021003792A1 PCT/CN2019/099735 CN2019099735W WO2021003792A1 WO 2021003792 A1 WO2021003792 A1 WO 2021003792A1 CN 2019099735 W CN2019099735 W CN 2019099735W WO 2021003792 A1 WO2021003792 A1 WO 2021003792A1
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fatty acids
gas chromatography
keep
detector
separation
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PCT/CN2019/099735
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Chinese (zh)
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王强
郭芹
李甜
屈阳
石爱民
刘红芝
刘丽
胡晖
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中国农业科学院农产品加工研究所
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography

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  • the invention relates to the technical field of food detection. More specifically, the present invention relates to a gas chromatography method for simultaneous detection and separation of multiple fatty acids.
  • Fatty acids are a class of compounds composed of three elements: carbon, hydrogen, and oxygen. They are also one of the main energy sources of the human body; including short-chain fatty acids (C3-C5), medium-chain fatty acids (C6-C12) and long-chain fatty acids (C13- C24).
  • short-chain fatty acids are mainly derived from milk, oligosaccharides, malted barley food, oat bran and corn starch;
  • medium-chain fatty acids are mainly derived from edible oil (especially coconut oil and palm kernel oil), milk and milk
  • the main sources of long-chain fatty acids are meat foods, edible oils and hydrogenated foods.
  • the methods for detecting fatty acids in food mainly include gas chromatography, liquid chromatography, silver ion thin layer chromatography, infrared spectroscopy, mass spectrometry, capillary electrophoresis, etc.
  • gas chromatography is widely used due to its high separation efficiency and low detection limit.
  • detection technology there is an urgent need to establish a high-throughput, accurate identification and rapid detection technology for fatty acids, and the existing high-efficiency separation and detection methods of gas chromatography need to be further improved. Therefore, based on the existing fatty acid gas chromatography analysis method, a new detection method is established to achieve high-throughput, accurate qualitative and quantitative analysis of fatty acids in food, which has good promotion and application value.
  • An object of the present invention is to solve at least the above-mentioned problems and provide at least the advantages described later.
  • Another object of the present invention is to provide a gas chromatography method for simultaneous detection and separation of multiple fatty acids, which can achieve high-efficiency separation and qualitative and quantitative analysis of 72 fatty acids, and has the advantages of high throughput, high sensitivity, and low detection limit. .
  • a gas chromatography method for simultaneous detection and separation of multiple fatty acids including: using a cyanopropyl siloxane strong polar stationary phase CP Sil 88 gas chromatography column for gas chromatography
  • the specification is 80-200m ⁇ 0.25mm ⁇ 0.20 ⁇ m
  • the chromatographic conditions are:
  • the temperature of the injection port is 200-230°C; the injection volume is 1 ⁇ L; the split ratio is 8-12:1; the nitrogen flow rate is 10-12cm/s; the constant linear velocity mode;
  • the initial temperature of the chromatographic column is 60-80°C, keep it for 4-6min, increase to 150-180°C at a heating rate of 20-30°C/min, keep it for 3-5min, and increase it to 200-225°C at 1-5°C/min , Keep for 40-60min, then increase to 200-230°C at 0.5-2°C/min, keep it for 4-6min;
  • Detector hydrogen flame ionization detector FID; detector temperature 200-230°C; makeup flow rate 2-5mL/min.
  • the chromatographic column specification is 100m ⁇ 0.25mm ⁇ 0.20 ⁇ m.
  • the chromatographic conditions are:
  • Injection port temperature 230°C; injection volume 1 ⁇ L; split ratio 10:1; nitrogen flow rate 10.6cm/s; constant linear velocity mode;
  • the initial temperature of the chromatographic column is 60°C, keep it for 5min, raise it to 160°C at a heating rate of 25°C/min, keep it for 4min, raise it to 225°C at 2°C/min, keep it for 50min, then raise it to 230°C at 1°C/min , Keep for 5min;
  • Detector hydrogen flame ionization detector FID; detector temperature 230°C; makeup flow rate 3mL/min.
  • the various fatty acids include C3-C5 short-chain fatty acids, C6-C12 medium-chain fatty acids, and C13-C24 long-chain fatty acids.
  • multiple fatty acids include C3:0, C4:0, C5:0, C6:0, C7:0, C8:0, C9:0, C10:0, C11:0, C12:0, C11: 1-10c, C13:0, C12:1-11c, C14:0, C13:1-12c, C14:1-9t, C14:1-9c, C15:0, C15:1-10t, C15:1- 10c, C16:0, C15:1-14c, C16:1-9t, C16:1-9c, C17:0, C17:1-10t, C17:1-10c, C18:0, C18:1-6t, C18:1-9t, C18:1-11t, C18:1-6c, C18:1-9c, C18:1-11c, C19:0, C18:2-9t, 12t, C19:1-7t, C19: 1-10t, C19:1-7c, C19:1-10
  • the detection limit is between 0.000084-0.001276g/100g
  • the quantification limit is between 0.000289-0.004263g/100g.
  • the RSD value of intraday precision is controlled between 0.57-9.81%, and the RSD value of intraday precision is controlled between 0.47-9.87%.
  • the present invention uses the cyanopropyl siloxane strong polar stationary phase CP Sil 88 gas chromatography column to establish a method that can simultaneously detect 72 C3-C24 series fatty acids with high throughput, including 36 unsaturated fatty acids, 22 There are three types of saturated fatty acids, 12 types of trans fatty acids and 2 types of conjugated fatty acids. Compared with the national standard GB5009.168-2016 "Determination of Fatty Acids in Food" testing method, 35 types of fatty acids are detected, including 18 types of unsaturated fatty acids and 5 types. Saturated fatty acids, 10 trans fatty acids and 2 conjugated fatty acids;
  • the RSD value of the intraday precision of the 72 fatty acid detection methods established by the present invention is controlled within 0.57-9.81%, and the RSD value of the intraday precision is controlled within 0.47-9.87%, which is lower than the national standard GB 5009.168-2016. 10%, far lower than the 15% required in the national standard GB 5009.257-2016, with good stability and meeting the requirements of accurate quantitative analysis;
  • the detection limit of the 72 fatty acid detection methods established in the present invention is between 0.000084-0.001276g/100g, which shows that under the conditions of existing equipment and the parameters used, each fatty acid methyl ester of 0.0013g/100g can be qualitatively
  • the detection is two tenths of the detection limit of the national standard GB 5009.168-2016 (0.0013-0.0066g/100g), and one tenth of the detection limit of the national standard GB 5009.257-2016 (0.012g/100g); the present invention
  • the limit of quantification is between 0.000289-0.004263g/100g, indicating that under the conditions of existing instruments and the parameters used, all fatty acid methyl esters of 0.0043g/100g can be quantitatively analyzed, which is the limit of quantification (0.024) of the national standard GB 5009.257-2016 g/100g), which significantly reduces the detection limit and quantification limit of fatty acids, with good accuracy and accurate identification of fatty acids;
  • the linear relationship of the 72 fatty acid detection methods established by the present invention the instrument response value of each fatty acid is well linearly related to the concentration, and the linear relationship is basically higher than 0.999, which fully meets the requirements of quantitative analysis, and the method has wide adaptability ;
  • the present invention can also realize the high-efficiency separation of 21 trans fatty acids, 3 cis-trans conjugated linoleic acids, and 2 anti-trans conjugated linoleic acids.
  • the national standard GB5009.257-2016 "Trans Fatty Acids in Food Determination ⁇ Detection method, detecting 12 kinds of fatty acids, including 7 kinds of trans fatty acids, 3 kinds of cis-trans conjugated linoleic acid and 2 kinds of anti-trans conjugated linoleic acid.
  • Figure 1 is a diagram of the gas chromatograph temperature rising program of the present invention
  • Figure 2 is one of the gas chromatograms of 72 fatty acid methyl esters of the present invention.
  • Figure 3 is the second gas chromatogram of 72 kinds of fatty acid methyl esters of the present invention.
  • Figure 4 is the third gas chromatogram of 72 fatty acid methyl esters of the present invention.
  • Figure 5 is a gas chromatogram of 26 fatty acid isomers of the present invention.
  • Figure 6 is a gas chromatogram of peanut oil in Example 1 of the present invention.
  • Figure 7 is a gas chromatogram of milk in Example 2 of the present invention.
  • Figure 8 is a gas chromatogram of linseed oil in Example 3 of the present invention.
  • Figure 9 is a gas chromatogram of the milk of Comparative Example 1 of the present invention.
  • Figure 10 is a gas chromatogram of linseed oil in Comparative Example 2 of the present invention.
  • the temperature of the injection port is 200-230°C; the injection volume is 1 ⁇ L; the split ratio is 8-12:1; the nitrogen flow rate is 10-12cm/s; the constant linear velocity mode;
  • the initial temperature of the chromatographic column is 60-80°C, keep it for 4-6min, raise it to 150-180°C at a heating rate of 20-30°C/min, keep it for 3-5min, raise it to 200-225°C at 1-5°C/min , Keep for 40-60min, then increase to 200-230°C at 0.5-2°C/min, keep it for 4-6min;
  • Detector hydrogen flame ionization detector FID; detector temperature 200-230°C; makeup flow rate 2-5mL/min.
  • the specification of the chromatographic column is 100m ⁇ 0.25mm ⁇ 0.20 ⁇ m, and the commonly purchased chromatographic column has this specification.
  • the chromatographic conditions are:
  • Injection port temperature 230°C; injection volume 1 ⁇ L; split ratio 10:1; nitrogen flow rate 10.6cm/s; constant linear velocity mode;
  • the initial temperature of the chromatographic column is 60°C, keep it for 5 minutes, raise it to 160°C at a heating rate of 25°C/min, hold it for 4 minutes, raise it to 225°C at 2°C/min, hold it for 50 minutes, and then increase it at 1°C. /min to 230°C, keep it for 5min;
  • Detector hydrogen flame ionization detector FID; detector temperature 230°C; makeup flow rate 3mL/min.
  • multiple fatty acids include C3-C5 short-chain fatty acids, C6-C12 medium-chain fatty acids, and C13-C24 long-chain fatty acids.
  • the reference retention time of 72 kinds of fatty acid methyl esters is shown in Table 1.
  • a variety of fatty acids include C3:0, C4:0, C5:0, C6:0, C7:0, C8:0, C9:0, C10:0, C11:0, C12:0, C11:1-10c, C13:0, C12:1-11c, C14:0, C13:1-12c, C14:1-9t, C14: 1-9c, C15:0, C15:1-10t, C15:1-10c, C16:0, C15:1-14c, C16:1-9t, C16:1-9c, C17:0, C17:1- 10t, C17:1-10c, C18:0, C18:1-6t, C18:1-9t, C18:1-11t, C18:1-6c, C18:1-9c, C18:1-11c, C19: 0, C18:2-9t,12t, C19:1
  • the present invention adopts cyanopropyl siloxane strong polar stationary phase CP Sil 88 gas chromatography column to establish a method that can simultaneously detect 72 C3-C24 series fatty acids with high throughput, including 36 unsaturated fatty acids and 22 saturated fatty acids , 12 kinds of trans fatty acids and 2 kinds of conjugated fatty acids, as shown in Figure 2-4, the peaks are numbered in Arabic numerals, and the numbers in Table 1 correspond to the names of fatty acids.
  • the precision of the instrument is expressed by the relative standard deviation (RSD), which is used to evaluate the reproducibility of the reproducibility of the measurement result of the same sample by the gas chromatography method.
  • RSD relative standard deviation
  • the same gas chromatography analysis method was used to investigate the intra-day (7 determinations in a day) and intra-day (7 consecutive days of determination) precision of 72 fatty acid mixed standard solutions.
  • the intra-day and inter-day precisions of 72 fatty acids were as follows As shown in Table 2, the RSD value of the intraday precision of each fatty acid methyl ester is controlled at 0.57-9.81%, and the daytime precision is controlled at 0.47-9.87%, which is lower than the 10% required in the national standard GB 5009.168-2016, and far lower than the national standard 15% of the requirements in GB5009.257-2016, good stability, and meet the requirements of accurate quantitative analysis.
  • the detection limit and quantification limit of 72 fatty acids are shown in Table 3. It can be seen that the detection limit of the present invention is between 0.000084-0.001276g/100g, indicating that under the conditions of existing equipment and the parameters used, 0.0013g/100g All fatty acid methyl esters can be qualitatively detected, which is two-tenths of the detection limit of the national standard GB 5009.168-2016 (0.0013-0.0066g/100g), and the detection limit of the national standard GB 5009.257-2016 (0.012g/100g)
  • the quantification limit of the present invention is between 0.000289-0.004263g/100g, indicating that under the conditions of existing instruments and the parameters used, each fatty acid methyl ester of 0.0043g/100g can be quantitatively analyzed, which is the national standard GB Two-tenths of the limit of quantification (0.024g/100g) of 5009.257-2016.
  • the invention significantly reduces the detection limit and the determination limit of fatty acids, has good accuracy,
  • the 72 kinds of fatty acid standard curves, correlation coefficients and concentration ranges are shown in Table 4.
  • the 72 kinds of fatty acid methyl ester standard solutions are gradually diluted, and the diluted mixed standard solutions of each concentration are analyzed by gas chromatography according to the established method. Linear fitting was performed within the concentration range, and the linear equation and correlation coefficient of each fatty acid methyl ester were obtained. The linear relationship was basically higher than 0.999, which fully met the requirements of quantitative analysis.
  • the present invention can also realize the high-efficiency separation of 21 trans fatty acids, 3 cis-trans conjugated linoleic acids, and 2 kinds of anti-anti-conjugated linoleic acids.
  • each wave peak is numbered in Arabic numerals, as shown in Table 5.
  • the serial number corresponds to the name of the fatty acid.
  • the unmarked peak between No. 11 and No. 12 is C18:2-9c, 12c (same as No. 41 in Table 1), and the unmarked peak between No. 17 and No. 18 is C18:3- 9c, 12c, 15c (same as No. 49 in Table 1), in order not to affect the display of 26 fatty acid isomers, these two substances are not numbered in Figure 5.
  • Step: Weigh 100mg of peanut oil, place it in a 10mL centrifuge tube, add 2mL of C11:0 internal standard solution, and then add 0.1mL 2mol/L of potassium hydroxide methanol solution, vortex and mix for 30s. Centrifuge at 4000 rpm for 10 min.
  • the gas chromatography column is CP Sil 88 (100m ⁇ 0.25mm ⁇ 0.20 ⁇ m), chromatographic condition position: Inlet temperature: 200°C ;Injection volume: 1 ⁇ L; split ratio: 8:1; flow rate: 10cm/s (nitrogen); constant linear velocity mode; oven heating program: 60°C for 5 min, 21°C/min to 150°C, hold for 5 minutes, Raise to 200°C at 1°C/min, hold for 60min, then rise to 200°C at 0.5°C/min, hold for 6min; Detector: hydrogen flame ionization detector (FID); detector temperature: 200°C; makeup flow : 2.0mL/min.
  • FID hydrogen flame ionization detector
  • milk may have 10 fatty acids after detection by this method, including C4:0, C6:0, C8:0, C10:0, C12:0, C14:0, palmitic acid (C16:0), Stearic acid (C18:0), oleic acid (C18:1-9c) and linoleic acid (C18:2-9c, 12c).
  • Step: Weigh 100mg of linseed oil, place it in a 10mL centrifuge tube, add 2mL of C11:0 internal standard solution, and then add 0.1mL 2mol/L of methanol solution of potassium hydroxide, vortex and mix for 30s. Centrifuge at 4000 rpm for 10 min.
  • the gas chromatography column is CP Sil 88 (100m ⁇ 0.25mm ⁇ 0.20 ⁇ m), chromatographic condition position: inlet temperature: 230°C ;Sample volume: 1 ⁇ L; Split ratio: 10:1; Flow rate: 10.6cm/s (nitrogen); Constant linear velocity mode; Oven heating program: 60°C for 5min, 25°C/min to 160°C, and hold for 4min , Rise to 225°C at 2°C/min, hold for 50 minutes, then rise to 230°C at 1°C/min, hold for 5 minutes; detector: hydrogen flame ionization detector (FID); detector temperature: 230°C; makeup Flow rate: 3.0mL/min.
  • FID hydrogen flame ionization detector
  • Gas chromatography column is CP Sil 88 (100m ⁇ 0.25mm ⁇ 0.20 ⁇ m), chromatographic condition position: inlet temperature: 270°C ;Sample volume: 1 ⁇ L; Split ratio: 100:1; Flow rate: 10.6cm/s (nitrogen); Constant linear velocity mode; Oven heating program: 100°C for 13min, 10°C/min to 180°C, for 6min , Rise to 200°C at 1°C/min, hold for 20min, then rise to 230°C at 4°C/min, hold for 10.5min; detector: hydrogen flame ionization detector (FID); detector temperature: 280°C; tail Blowing flow: 3.0mL/min.
  • FID hydrogen flame ionization detector
  • milk may have 7 fatty acids after detection by this method, including C4:0, C6:0, C8:0, C10:0, C12:0, C14:0, and palmitic acid (C16:0). It can be seen that compared to Example 2, stearic acid (C18:0), oleic acid (C18:1-9c) and linoleic acid (C18:2-9c, 12c) were not detected.
  • Step: Weigh 100mg of linseed oil, place it in a 10mL centrifuge tube, add 0.1mL of 2mol/L potassium hydroxide methanol solution, vortex and mix for 30s. Centrifuge at 4000 rpm for 10 min. Take 20 ⁇ L of supernatant to a 1mL volumetric flask and use Shimadzu GC-2010 gas chromatography for determination.
  • the gas chromatography column is CP Sil 88 (100m ⁇ 0.25mm ⁇ 0.20m), and the chromatographic condition position: inlet temperature: 270°C ;Sample volume: 1 ⁇ L; Split ratio: 100:1; Flow rate: 10.6cm/s (nitrogen); Constant linear velocity mode; Oven heating program: 100°C for 13min, 10°C/min to 180°C, for 6min , Rise to 200°C at 1°C/min, hold for 20min, then rise to 230°C at 4°C/min, hold for 10.5min; detector: hydrogen flame ionization detector (FID); detector temperature: 280°C; tail Blowing flow: 3.0mL/min.
  • FID hydrogen flame ionization detector
  • linseed oil may have 7 fatty acids after being tested by this method, including linolenic acid (C18:3-9c, 12c, 15c), oleic acid (C18:1-9c), and linoleic acid (C18: 2-9c, 12c), stearic acid (C18:0) and palmitic acid (C16:0) are higher in content, in addition to C18: 3-6c, 9c, 12c, C20: 1-5c, It can be seen that relative to examples 3C16:1-9c, C17:0, C18:1-11c, C20:0, C18:3-9t, 12t, 15c, C18:3-9c, 12t, 15t, C19:2 -10c, 13c, C18: 3-9t, 12c, 15c, C20: 2-11c, 14c, C22:0, C20: 3-8c, 11c, 14c, C21: 2-12c, 15c and C24:
  • this method is suitable for detecting substances containing C3-C24 fatty acids.
  • peanut oil, linseed oil and milk in the above cases, it can also detect various fatty acid-rich edible oils, meat foods, vegetables, and milk. And dairy products and other fatty acid-rich substances, due to the limited length of the instructions, they will not be detailed one by one.

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Abstract

L'invention concerne un procédé de chromatographie en phase gazeuse pour la détection et la séparation simultanées de multiples acides gras, consistant à : exécuter une détection de chromatographie en phase gazeuse à l'aide d'une colonne chromatographique en phase gazeuse stationnaire fortement polaire de cyanopropyl siloxane CP Sil 88 ayant la spécification de 80-100 m*0,25 mm*0,20 µm. Les conditions chromatographiques sont telles que : la température de l'orifice d'injection d'échantillon est comprise entre 200 et 230 °C, la quantité d'injection d'échantillon est de 1 µl, le rapport de division est de 8-12:1, la vitesse d'écoulement d'azote est de 10 à 12 cm/s, un mode de vitesse linéaire constante est adopté, un détecteur est un détecteur d'ionisation de flamme (FID), la température du détecteur s'inscrit dans la plage de 200 à 230 °C, et le débit d'appoint est de 2 à 5 ml/min. Le procédé permet une séparation efficace et une analyse qualitative et quantitative de 72 acides gras, et présente les avantages d'un haut rendement, d'une haute sensibilité et d'une faible limite de détection.
PCT/CN2019/099735 2019-07-10 2019-08-08 Procédé de chromatographie en phase gazeuse pour la détection et la séparation simultanées de multiples acides gras WO2021003792A1 (fr)

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