CN109633064A - A method of using 2,4- diene aldehyde compound in GC-MS measurement daily essence - Google Patents
A method of using 2,4- diene aldehyde compound in GC-MS measurement daily essence Download PDFInfo
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Abstract
The present invention relates to a kind of methods using 2,4- diene aldehyde compound in GC-MS measurement daily essence, comprising: (1) weighs sample and diluted with solvent, through filtering, filtrate is as the sample solution to be tested;(2) the sample solution to be tested is measured using GC-MS, is analyzed with quantified by external standard method;By comparing the test result of the sample solution to be tested and standard solution, qualitative analysis is carried out.The present invention has the advantages that easy to operate, quick, high sensitivity, reproducible, qualitative, quantitative is accurate, European Union, Japan and other countries are able to satisfy to the technical requirements of corresponding daily essence safety detection, provide strong technical support to ensure that China's daily essence safety and export abroad trade develop in a healthy way.
Description
Technical field
It is the invention belongs to essence risk substance determination of residual amount field, in particular to a kind of daily using GC-MS measurement
The method of 2,4- diene aldehyde compound in essence.
Background technique
Essence is the aromatics mixture as made of a variety of perfume materials, solvent or carrier and the allotment of other auxiliary materials.Essence
It is matched in the works such as food, beverage, drinks, cigarette, articles for washing, cosmetics, toothpaste, medicine, feed, weaving and leather extensively
Industry.Also higher and higher to the quality requirements of food, daily necessities with the raising of people's level of consumption, this promotes fragrance
The rapid growth of essence industry.And today so flourishing in spices and essence industry, essence also attract people's attention safely.
Aldehydes, very important family in fragrance have very important fragrance to contribute daily essence.Earliest for perfume
One group of aldehydes of water is octanal, capraldehyde, aldehyde C-9.In the twenties in last century, people have found 2,4- diene aldehydes from vegetable oil
Compound.Their presence is then had found in fruit, milk, peanut, tealeaves and cold cuts food again.Wherein 2,4- hexadiene
Aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, trans- -2,4- decadienal and 2,4- undecadienal are 2,4-
Several aldehydes in two olefine aldehydrs (one group of substance), and they are all that there are two the unsaturated aldehydes of double bond for tool.
2,4- sorbic aldehydes, CAS accession number are 142-83-6, molecular formula: C6H8O, molecular weight: 96.127, boiling point: 69 DEG C.
The structural formula of 2,4- sorbic aldehyde is as follows:
Instead, trans- 2,4- heptadienal also known as trans- -2,4- heptadienal, CAS accession number be 4313-03-5, molecular formula:
C7H10O, molecular weight: 110.154, boiling point: 84 DEG C.Instead, the structural formula of trans- 2,4- heptadienal is as follows:
2,4- nonadienals, CAS accession number are 6750-03-4, molecular formula: C9H14O, molecular weight: 138.207, boiling point 97-
98℃.The structural formula of 2,4- nonadienal is as follows:
Trans- -2,4- decadienal, CAS accession number are 25152-84-5, molecular formula: C10H16O, molecular weight: 138.207,
114-116 DEG C of boiling point.The structural formula of trans- -2,4- decadienal is as follows:
2,4- undecadienals, CAS accession number are 30361-29-6, molecular formula: C11H18O, molecular weight: 166.260,
128-129 DEG C of boiling point.The structural formula of 2,4- undecadienal is as follows:
By 2,4- sorbic aldehyde, anti-in GB/T 22731-2017, trans- 2,4- heptadienal, 2,4- nonadienal, it is trans--
2,4- decadienal and 2,4- undecadienal are included in banned substance list.Wherein, 2,4- sorbic aldehyde is that a kind of yellow is saturating
Prescribed liquid, odor characteristics can be described as: green, fruity, aldehyde is fragrant, citrus, is suitable for preparing floral type, Fruity type product.Its
Acute toxicity shows themselves in that the median lethal dose (LD of rat oral50) it is 300mg/kg, the percutaneous LD of rabbit50It is right for 270 μ L/kg
Skin and eyes are irritant.Instead, trans- 2,4- heptadienal is also a kind of yellow transparent liquid, it has the smell of fatty taste
Type, be mainly used for prepare meat products, flavouring, baked goods type essence.Its acute toxicity shows themselves in that rat oral
Median lethal dose (LD50) it is 1150mg/kg, the percutaneous LD of rabbit50For 313mg/kg.When exposure reaches a certain level, can make
At skin irritatin.Cause serious Eye irritation.2,4- nonadienal is a kind of colourless to light yellow clear liquid.Its odor characteristics can
With description are as follows: when concentration is 0.10% in dipropylene glycol, there is the smell of fat, green cucumber, mainly to prepare meat and family
Fowl type essence.Trans- -2,4- decadienal is that one kind is light yellow to yellow transparent liquid, and odor characteristics can be described as:
When content is 1% in dipropylene glycol, the smell with citrus, pumpkin fruit.2,4- undecadienal is a kind of colourless to yellow
Color transparency liquid, odor characteristics can be described as: when content is 1% in dipropylene glycol, have oiliness, caramel, pungent, mandarin orange
Tangerine, butter, baking smell.
At present about 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, trans- -2,4- decadinene
The detection method of aldehyde and 2,4- undecadienal there is no national standard to promulgate.It is detected in daily essence using GC-MS and limits use
Goods and materials have many advantages, such as quickly, simplicity, high sensitivity, selectivity is by force, it can be achieved that the detection and analysis of several hundred kinds of substances, but are so far
Only have no 2,4- sorbic aldehyde in daily essence, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, trans- -2,4- decadinene
Aldehyde and 2, the report of the GC-MS detection method of 4- undecadienal, therefore establish it is easy, quickly, it is accurate, can it is accurate qualitative and
2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, the trans- -2,4- last of the ten Heavenly stems two in quantitative analysis daily essence
The GC-MS detection method of olefine aldehydr and 2,4- undecadienal is of great significance.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of using 2,4- diene aldehydes in GC-MS measurement daily essence
The method of compound, this method have the advantages that easy to operate, quick, high sensitivity, reproducible, qualitative, quantitative is accurate.
The present invention provides a kind of methods using 2,4- diene aldehyde compound in GC-MS measurement daily essence, comprising:
(1) it weighs sample to be diluted with solvent, through filtering, filtrate is as the sample solution to be tested
(2) the sample solution to be tested is measured using GC-MS, is analyzed with quantified by external standard method;By comparing the sample solution to be tested and standard solution
Test result, carry out qualitative analysis;
Wherein, 2, the 4- diene aldehyde compound includes 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonyl
Two olefine aldehydrs, trans- -2,4- decadienal and 2,4- undecadienal.
Solvent in the step (1) is methanol;Extension rate is 100 times.
0.45 μm of filtering with microporous membrane is filtered into the step (1).
The determination condition of GC-MS in the step (2) is as follows:
Chromatographic column: HP-INNOWAX capillary column, 60m × 0.25mm (internal diameter) × 0.25 μm;
Carrier gas: helium, flow velocity: 0.8mL/min;
Temperature programming: 40 DEG C of holding 6min are warming up to 100 DEG C with the rate of 3 DEG C/min, 5min are kept, with 5 DEG C/min's
Rate
230 DEG C are warming up to, 10min is kept;
Transmission line temperature: 280 DEG C;
Injector temperature: 250 DEG C;
Input mode: automatic sampling;
Sample volume: 1 μ L;
Ionization mode: electron impact ionization EI;
Ionizing energy: 70eV;
Scanning mode: full scan and the scanning of SIM fragment.
While the present invention five kinds of 2,4- diene aldehyde compounds of realization in qualitative and quantitative detection process, temperature program
It plays an important role.
The method of the test result of comparison the sample solution to be tested and standard solution in the step (2) are as follows: the sample solution to be tested and mark
The selection ion chromatography peak of quasi- solution occurs at identical retention time, the mass-to-charge ratio and standard substance of corresponding mass spectrometric fragment ion
Unanimously, abundance ratio compared with standard solution within the specified scope.
The preparation of standard solution in the step (2): with methanol by 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadiene
Aldehyde, 2,4- nonadienal, trans- -2,4- decadienal and 2,4- undecadienal standard reserving solution dilute obtain concentration step by step
For the mixing mark of 0.0005mg/mL, 0.001mg/mL, 0.005mg/mL, 0.010mg/mL, 0.050mg/mL, 0.100mg/mL
Quasi- working solution, according to same determination condition concentration, sample introduction is measured from low to high, is made with qualitative fragment ion peak area-concentration
Figure, obtains standard curve regression equation.
Beneficial effect
(1) pre-treating method of the present invention is generally applicable to the essence of clear, and behaviour need to be only diluted to sample
Make, it is simple to operation, quick, and meet the low analysis requirement of favorable reproducibility, detection limit, it avoids because sample pre-treatments mode is to analysis
As a result it has an impact;
(2) present invention is using 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadiene in GC-MS qualitative, quantitative measurement daily essence
Aldehyde, 2,4- nonadienal, trans- -2,4- decadienal and 2, the content of 4- undecadienal, the rate of recovery be 80%~
120%, selectivity is strong, and relative standard deviation (RSD) is 1%-8%, reproducible, effectively eliminates the interference of matrix;
(3) method of the invention, 2,4- sorbic aldehydes, anti-, the inspection of trans- 2,4- heptadienal, 2,4- nonadienal are used
Rising limit is 0.5mg/kg, is quantitatively limited to 1.6mg/kg, trans- -2,4- decadienal and 2, and the detection of 4- undecadienal is limited to
5.4mg/kg is quantitatively limited to 16.1mg/kg, meets trace analysis testing requirements;
(4) present invention can it is easy, quickly, 2,4- sorbic aldehyde, anti-, trans- 2,4- in qualitative, quantitative measurement daily essence
Heptadienal, 2,4- nonadienal, trans- -2,4- decadienal and 2,4- undecadienal, high sensitivity, it is reproducible,
Qualitative, quantitative is accurate, is able to satisfy European Union, Japan and other countries to the technical requirements of essence safety detection in corresponding cosmetics, to ensure
China's cosmetic essence safety and export abroad trade, which develop in a healthy way, provides strong technical support.
Detailed description of the invention
Fig. 1 is the mass spectral analysis figure of five kinds of 2,4- diene aldehyde compound standard items;
Fig. 2 is the fragment ion relative abundance value map of 2,4- sorbic aldehyde;
Fig. 3 is anti-, the fragment ion relative abundance value map of trans- 2,4- heptadienal;
Fig. 4 is the fragment ion relative abundance value map of 2,4- nonadienal;
Fig. 5 is the fragment ion relative abundance value map of trans- -2,4- decadienal;
Fig. 6 is the fragment ion relative abundance value map of 2,4- undecadienal.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Instrument used in embodiment:
Gas chromatography-mass spectrum (GC-MS) instrument (GC7890B-MS5977B, Anjelen Sci. & Tech. Inc, the U.S.): it is furnished with
Electron impact ionization ion source (EI).Vortex oscillator (VORTEX-5, its woods Bell's instrument manufacturing Co., Ltd, Haimen City);Point
Analyse balance (ME104E/02, Mettler-Toledo Instrument (Shanghai) Co., Ltd.) etc..
Standard items: 2,4- sorbic aldehyde (purity >=95%), anti-, trans- 2,4- heptadienal (purity >=90%), trans--
2,4- decadienal (purity >=90%), 2,4- nonadienal (purity >=90%) and 2,4- undecadienal (purity >=
90%) it is chromatographically pure, is purchased from Sigma company;Methanol and acetone are chromatographically pure, purchased from Town in Shanghai spectrum experiment high-tech stock
Part Co., Ltd.
The preparation of mixed mark stock solution: 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, trans- -2,
4- decadienal and 2,4- undecadienal standard reserving solution: weighing 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,
4- nonadienal, trans- -2,4- decadienal and 2,4- undecadienal standard items 0.0100g are placed in 10mL volumetric flask,
Scale is dissolved and be settled to methanol, is shaken up, and is configured to the standard reserving solution that concentration is 1mg/mL, is kept in dark place, can make in 4 DEG C
With three months.
Embodiment 1
2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, the trans- -2,4- last of the ten Heavenly stems in DB-2008 essence
The GC-MS of two olefine aldehydrs and 2,4- undecadienal detection:
(1) sample treatment: weighing 1.0g essence sample, with 100 times of methanol dilution, through 0.45 μm of filtering with microporous membrane, filter
Liquid is as the sample solution to be tested.
(2) Gas Chromatography-Mass Spectrometry condition is as follows:
A) chromatographic column: HP-innowax capillary column, 60m × 0.25mm (internal diameter) × 0.25 μm.
B) carrier gas: helium, flow velocity: 0.8mL/min.
C) temperature programming: 40 DEG C of holding 6min are warming up to 100 DEG C with the rate of 3 DEG C/min, 5min are kept, with 5 DEG C/min
Rate be warming up to 230 DEG C, keep 10min.
D) transmission line temperature: 280 DEG C.
E) injector temperature: 250 DEG C.
F) input mode: automatic sampling.
G) sample volume: 1 μ L.
H) mode: electron impact ionization (EI) is ionized.
I) ionizing energy: 70eV.
J) scanning mode: full scan and the scanning of SIM fragment, feature selecting ion and abundance ratio are shown in Table 1.
1 feature selecting ion of table and abundance ratio
Fragrance title | Molecular formula | CAS | Feature selecting ion and abundance ratio |
2,4- sorbic aldehyde | C6H8O | 142-83-6 | 81(100)、67(38)、96(36) |
Instead, trans- 2,4- heptadienal | C7H10O | 4313-03-5 | 81(100)、53(28)、110(26) |
2,4- nonadienal | C9H14O | 6750-03-4 | 81(100)、67(22)、138(10) |
Trans- -2,4- decadienal | C10H16O | 25152-84-5 | 81(100)、67(20)、95(12) |
2,4- undecadienal | C11H18O | 30361-29-6 | 81(100)、67(22)、95(14) |
(3) preparation of standard working solution: with methanol by trans- -2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,
4- nonadienal, trans- -2,4- decadienal and 2,4- undecadienal standard reserving solution dilute step by step to be obtained concentration and is
The hybrid standard of 0.0005mg/mL, 0.001mg/mL, 0.005mg/mL, 0.010mg/mL, 0.050mg/mL, 0.100mg/mL
Working solution is obtained according to the determination condition concentration sample introduction measurement from low to high of (2) with qualitative fragment ion peak area-concentration mapping
To standard curve regression equation, it is shown in Table 2.
It is 2 2,4- sorbic aldehyde of table, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, trans- -2,4- decadienal and
The standard working curve of 2,4- undecadienal
(4) it quantitative determines:
Prepare liquid is measured according to the determination condition of step (2), uses quantified by external standard method.2,4- hexadiene in prepare liquid
Aldehyde, anti-, the response of trans- 2,4- heptadienal, 2,4- nonadienal, trans- -2,4- decadienal and 2,4- undecadienal
Value should be in the range of linearity of standard curve, and sample introduction is analyzed again after should then diluting more than the range of linearity.
(5) qualitatively judge: under instrument condition, the selection ion chromatography peak of sample determinand and standard solution is in identical guarantor
It stays at the time and occurs, and the mass-to-charge ratio of corresponding mass spectrometric fragment ion is consistent with standard substance, abundance ratio and standard solution phase
It, can qualitative confirmation target analytes than range as defined in table 3 should be met.
With respect to the maximum allowable offset of abundance of ions when 3 qualitative confirmation of table
Relative ion abundance/% | >50 | > 20~50 | > 10~20 | ≤10 |
Maximum deviation/% of permission | ±20 | ±20 | ±30 | ±50 |
(6) it blank assay: in addition to not weighing sample, is carried out by said determination condition and step.
(7) result calculates
As a result it is calculated by formula (1), calculated result retains two-decimal.
In formula:
X: 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, trans- -2,4- decadinene in sample
Aldehyde and 2, the content of 4- undecadienal, unit are milligrams per kilogram (mg/kg);
ρ: 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2 from the sample solution found on standard working curve,
4- nonadienal, trans- -2,4- decadienal and 2, the mass concentration of 4- undecadienal, unit are every milliliter of milligram (mg/
mL);
V: sample constant volume, unit are milliliter (mL);
M: sample quality, unit are gram (g);
1000: conversion coefficient.
It is not detected 2,4- sorbic aldehyde, anti-in DB-2008 essence, it is trans- 2,4- heptadienal, 2,4- nonadienal, anti-
Formula -2,4- decadienal and 2,4- undecadienal.2,4- sorbic aldehyde, anti-, trans- 2,4- are added in DB-2008 essence
Heptadienal, 2,4- nonadienal, trans- -2,4- decadienal and 2,4- undecadienal standard items are prepared into sample 1, and
Quantitative analysis is carried out, the content of five kinds of banned substances is shown in Table 4.
2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonadienal, the trans- -2,4- last of the ten Heavenly stems two in 4 sample 1 of table
The residual content of olefine aldehydr and 2,4- undecadienal
The 2,4- sorbic aldehyde of the present embodiment, anti-, the detection of trans- 2,4- heptadienal, 2,4- nonadienal is limited to
0.5mg/kg, trans- -2,4- decadienal and 2, the detection of 4- undecadienal are limited to 5.4mg/kg.2,4- sorbic aldehyde,
Instead, trans- 2,4- heptadienal, 2,4- nonadienal, trans- -2,4- decadienal and the 2,4- undecadienal rate of recovery exist
Between 90%~120%.
Claims (5)
1. a kind of method using 2,4- diene aldehyde compound in GC-MS measurement daily essence, comprising:
(1) it weighs sample to be diluted with solvent, through filtering, filtrate is as the sample solution to be tested;
(2) the sample solution to be tested is measured using GC-MS, is analyzed with quantified by external standard method;By comparing the survey of the sample solution to be tested and standard solution
Test result carries out qualitative analysis;
Wherein, 2, the 4- diene aldehyde compound includes 2,4- sorbic aldehyde, anti-, trans- 2,4- heptadienal, 2,4- nonadiene
Aldehyde, trans- -2,4- decadienal and 2,4- undecadienal.
2. according to the method described in claim 1, it is characterized by: the solvent in the step (1) is methanol;Extension rate is
100 times.
3. according to the method described in claim 1, it is characterized by: being filtered into 0.45 μm of miillpore filter in the step (1)
Filtering.
4. according to the method described in claim 1, it is characterized by: the determination condition of the GC-MS in the step (2) is as follows:
Chromatographic column: HP-INNOWAX capillary column, 60m × 0.25mm × 0.25 μm;
Carrier gas: helium, flow velocity: 0.8mL/min;
Temperature programming: 40 DEG C of holding 6min are warming up to 100 DEG C with the rate of 3 DEG C/min, 5min are kept, with the rate of 5 DEG C/min
230 DEG C are warming up to, 10min is kept;
Transmission line temperature: 280 DEG C;
Injector temperature: 250 DEG C;
Input mode: automatic sampling;
Sample volume: 1 μ L;
Ionization mode: electron impact ionization EI;
Ionizing energy: 70eV;
Scanning mode: full scan and the scanning of SIM fragment.
5. according to the method described in claim 1, it is characterized by: comparison the sample solution to be tested and standard in the step (2) are molten
The method of the test result of liquid are as follows: the sample solution to be tested occurs at identical retention time with the selection ion chromatography peak of standard solution,
The mass-to-charge ratio of corresponding mass spectrometric fragment ion is consistent with standard substance, abundance ratio compared with standard solution within the specified scope.
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