UPLC-MS/MS法测定油基类化妆品中39种性激素

doi:10.3969/j.issn.1001-1803.2022.03.015

Abstract

Abstract:

An ultra-performance liquid chromatography-tandem mass spectrometry （UPLC-MS/MS） method was developed for the determination of 39 sex hormones in oil-based cosmetics. The sample was dispersed with n-hexane, then extracted with 70% acetonitrile, and separated on a CORTECS C₁₈（2.1 mm×150 mm, 2.7 μm） column by gradient elution using acetonitrile-water as mobile phase. The analysis was performed under multiple reaction monitoring （MRM） mode. The results showed that the matrix effects of 39 sex hormones were 0.78-1.26. The limits of detection （LODs） and limits of quantitation （LOQs） for 39 sex hormones were in the range of 0.6-2.3 μg/L and 1.9~6.8 μg/L, respectively. There was good linear relationship for 39 sex hormones in the mass concentration range of 1.87-67.41 μg/L with their correlation coefficients （r） all above 0.995. The average recoveries at three spiked levels of 0.25, 0.50 and 1.00 μg/g were in the range of 81.7%-110.6%, with relative standard deviations （RSDs, n=6） of 1.2%-14.1%. The simplicity and accuracy of this method make it suitable for the analysis of sex hormones in oil-based cosmetics.

Key words: UPLC-MS/MS, cosmetics, sex hormone, determination

CLC Number:

TQ658

Hu Bei,Li Lixia,Liu Hong,Huang Wei,Ding Xiaoping. Determination of 39 sex hormones in oil-based cosmetics by ultra-performance liquid chromatography-tandem mass spectrometry[J].China Surfactant Detergent & Cosmetics, 2022, 52(3): 328-336.

Figures/Tables 5

Tab. 1

CAS number, retention time and MS parameters of 39 sex hormones"

序号	化合物	CAS号	保留时间/min	母离子（m/z）	子离子（m/z）	锥孔电压/V	碰撞能/eV	电离模式
1	雌三醇	50-27-1	3.42	287.2	171.2^*,143.2	20	37,43	ESI^-
2	肾上腺甾酮	382-45-6	6.69	301.3	121.2^*,257.3	40	26,21	ESI⁺
3	群勃龙	10161-33-8	6.74	271.2	199.1^*,253.2	44	22,19	ESI⁺
4	勃地酮	846-48-0	7.26	287.2	135.2^*,269.1	35	18,12	ESI⁺
5	诺龙	434-22-0	7.62	275.2	109.1^*,257.2	30	27,14	ESI⁺
6	双酚A	80-05-7	7.70	227.2	212.2^*,133.1	11	19,24	ESI^-
7	17-β-雌二醇	50-28-2	8.12	271.2	145.2^*,183.0	48	38,38	ESI^-
8	美雄酮	72-63-9	8.16	301.2	121.2^*,149.2	30	25,13	ESI⁺
9	氧甲氢龙	53-39-4	8.23	307.2	289.2^*,271.2	22	9,12	ESI⁺
10	睾酮	58-22-0	8.78	289.2	97.2^*,109.3	12	21,22	ESI⁺
11	17-α-雌二醇	57-91-0	9.00	271.3	145.1^*,183.0	10	42,44	ESI^-
12	炔诺酮	68-22-4	9.10	299.1	109.1^*, 91.1	40	25,38	ESI⁺
13	21-羟基孕酮	64-85-7	9.52	331.2	97.0^*,108.8	45	30,25	ESI⁺
14	炔雌醇	57-63-6	9.65	295.2	145.0^*,159.0	57	39,35	ESI^-
15	孕三烯酮	16320-04-0	9.89	309.1	241.2^*,199.2	9	22,33	ESI⁺
16	雌酮	53-16-7	10.07	269.1	145.2^*,183.1	30	36,36	ESI^-
17	甲睾酮	58-18-4	10.26	303.4	109.2^*, 97.2	21	26,27	ESI⁺
18	雄烯二酮	63-05-8	10.37	287.2	97.1^*,109.2	35	21,24	ESI⁺
19	孕二烯酮	60282-87-3	10.37	311.4	109.2^*, 81.2	35	26,27	ESI⁺
20	17-α-羟基孕酮	68-96-2	10.81	331.5	97.1^*,109.2	30	24,26	ESI⁺
21	表睾酮	481-30-1	10.83	289.1	97.1^*,109.1	48	20,26	ESI⁺
22	司坦唑醇	10418-03-8	11.50	329.2	81.2^*, 95.1	82	42,38	ESI⁺
23	己烯雌酚	56-53-1	12.16	267.1	251.2^*,222.2	20	24,33	ESI^-
24	炔诺孕酮	6533-00-2	12.42	313.2	109.3^*,245.3	16	24,18	ESI⁺
25	双烯雌酚	84-17-3	12.81	265.2	93.0^*,249.0	50	25,24	ESI^-
26	氯司替勃	1093-58-9	12.83	323.3	143.1^*,131.1	38	25,25	ESI⁺
27	己烷雌酚	84-16-2	13.08	269.2	119.0^*,133.0	37	37,15	ESI^-
28	甲羟孕酮	520-85-4	14.24	345.2	123.2^*, 97.0	30	24,25	ESI⁺
29	醋酸甲地孕酮	595-33-5	18.21	385.2	325.3^*, 267.3	9	24,16	ESI⁺
30	孕酮	57-83-0	18.24	315.2	109.2^*, 97.3	7	24,18	ESI⁺
31	达那唑	17230-88-5	18.51	338.4	148.2^*,120.3	30	23,30	ESI⁺
32	醋酸氯地孕酮	302-22-7	18.66	405.1	309.1^*,267.2	31	13,20	ESI⁺
33	醋酸美伦孕酮	2919-66-6	18.71	397.3	337.2^*,187.3	34	13,28	ESI⁺
34	醋酸甲羟孕酮	71-58-9	18.76	387.2	327.4^*,123.2	35	15,33	ESI⁺
35	17-乙酸睾酮激素	1045-69-8	20.13	331.5	97.1^*, 109.1	20	21,27	ESI⁺
36	醋酸氯睾酮	855-19-6	22.04	365.2	143.1^*,305.2	42	25,11	ESI⁺
37	丙酸睾酮	57-85-2	22.44	345.2	97.0^*,109.2	38	22,25	ESI⁺
38	己酸羟孕酮	630-56-8	23.34	429.2	313.2^*,271.3	25	13,18	ESI⁺
39	苯丙酸诺龙	62-90-8	24.91	407.2	105.2^*,257.1	35	26,16	ESI⁺

Tab. 1

Tab. 2

Extraction efficiencies of different extraction times （n=3）"

化合物	回收率/% （RSD/%,n=3）			化合物	回收率/% （RSD/%,n=3）
化合物	提取1次	提取2次	提取3次	化合物	提取1次	提取2次	提取3次
雌三醇	103.1（5.3）	104.5（1.3）	102.5（1.8）	表睾酮	104.7（0.8）	103.4（6.7）	102.8（3.1）
肾上腺甾酮	99.8（0.9）	99.8（2.3）	102.1（5.2）	司坦唑醇	106.1（0.8）	106.2（2.0）	105.7（2.1）
群勃龙	104.3（1.7）	105.6（1.8）	105.5（2.7）	己烯雌酚	102.0（4.0）	107.2（4.0）	97.8（2.6）
勃地酮	102.5（3.6）	104.2（0.5）	103.8（0.9）	炔诺孕酮	104.9（1.9）	110.9（6.1）	111.5（5.1）
诺龙	110.2（2.2）	113.6（3.6）	111.8（3.1）	双烯雌酚	97.5（3.0）	98.0（3.1）	101.1（2.1）
双酚A	98.8（1.3）	96.9（2.4）	91.3（6.6）	氯司替勃	100.4（4.9）	106.6（3.5）	111.7（3.1）
17-β-雌二醇	113.4（6.0）	112.1（8.1）	101.4（7.0）	己烷雌酚	99.9（3.5）	102.7（4.8）	95.8（8.4）
美雄酮	106.6（1.8）	108.2（0.6）	108.9（2.2）	甲羟孕酮	104.9（2.0）	108.7（3.2）	106.7（2.9）
氧甲氢龙	114.7（2.0）	109.5（3.2）	112.6（4.6）	醋酸甲地孕酮	104.3（1.5）	108.1（2.6）	106.3（3.4）
睾酮	107.2（3.4）	110.0（1.6）	111.3（1.3）	孕酮	96.1（1.5）	108.9（2.3）	108.2（3.2）
17-α-雌二醇	112.3（1.7）	102.5（7.4）	101.5（4.0）	达那唑	105.5（0.8）	110.5（3.3）	110.2（0.7）
炔诺酮	107.7（0.9）	108.9（2.2）	112.3（1.3）	醋酸氯地孕酮	105.0（1.9）	112.4（1.2）	110.5（2.4）
21-羟基孕酮	105.8（7.2）	107.7（2.0）	110.3（1.9）	醋酸美伦孕酮	105.6（3.4）	113.1（2.2）	109.3（3.2）
炔雌醇	115.2（6.0）	102.6（7.4）	112.5（6.9）	醋酸甲羟孕酮	103.1（2.1）	111.9（2.7）	111.5（2.1）
孕三烯酮	107.2（4.0）	107.8（2.6）	107.3（1.2）	17-乙酸睾酮激素	94.0（2.9）	107.2（1.8）	107.0（1.0）
雌酮	95.9（6.9）	99.2（4.1）	100.9（5.2）	醋酸氯睾酮	89.8（2.1）	100.3（5.8）	99.0（5.7）
甲睾酮	106.2（0.9）	110.4（4.9）	110.3（1.3）	丙酸睾酮	81.2（1.1）	100.9（1.3）	105.7（1.9）
雄烯二酮	99.8（4.2）	109.3（3.4）	107.5（3.0）	己酸羟孕酮	93.3（1.2）	106.0（2.4）	105.9（5.1）
孕二烯酮	105.6（4.6）	112.2（1.5）	114.8（2.8）	苯丙酸诺龙	86.2（3.2）	105.8（3.2）	104.3（4.1）
17-α-羟基孕酮	104.8（3.9）	109.5（3.3）	101.6（2.6）

Tab. 2

Fig. 1

Tab. 3

Linear range, linear equations, correlation coefficients, LODs and LOQs of 39 sex hormones"

序号	化合物	线性范围/（μg/L）	线性方程	相关系数（r）	检出限/（μg/L）	定量限/（μg/L）
1	雌三醇	2.21~55.24	y=406.0x-347.8	0.999 7	2.2	6.6
2	肾上腺甾酮	2.13~53.31	y=1 727.3x+1 637.0	0.996 7	0.6	2.1
3	群勃龙	1.88~47.09	y=25 732.1x+8 397.9	0.999 7	0.6	1.9
4	勃地酮	1.92~47.92	y=18 760.0x+10 111.4	0.999 6	0.6	1.9
5	诺龙	1.95~48.83	y=11 670.2x+6 989.9	0.998 9	0.6	2.0
6	双酚A	2.03~50.75	y=845.5x+152.7	0.998 3	2.0	6.1
7	17-β-雌二醇	2.24~55.95	y=276.0x-179.5	0.999 7	2.2	6.7
8	美雄酮	2.55~63.65	y=41 420.6x+25 689.8	0.999 8	0.8	2.5
9	氧甲氢龙	1.92~48.02	y=2 925.0x+366.1	0.997 4	1.9	5.8
10	睾酮	2.28~57.04	y=19 703.8x+3 002.4	0.999 8	0.7	2.3
11	17-α-雌二醇	2.15~53.87	y=511.8x-882.0	0.996 7	2.2	6.5
12	炔诺酮	2.30~57.40	y=12 564.9x+8 434.5	0.999 6	0.7	2.3
13	21-羟基孕酮	2.06~51.60	y=8 795.9x+6 406.4	0.996 8	0.6	2.1
14	炔雌醇	1.99~49.64	y=187.6x-228.6	0.997 7	2.0	6.0
15	孕三烯酮	2.00~49.90	y=35 732.8x+13 007.8	0.999 9	0.6	2.0
16	雌酮	2.27~56.87	y=1 229.5x-915.1	0.998 7	2.3	6.8
17	甲睾酮	2.29~57.30	y=18 565.1x+15 883.4	0.999 6	0.7	2.3
18	雄烯二酮	2.10~52.38	y=9 884.0x+8 752.2	0.997 8	0.6	2.1
19	孕二烯酮	2.05~51.24	y=6 181.0x+6 163.2	0.999 0	0.6	2.0
20	17-α-羟基孕酮	2.08~52.04	y=6 727.0x+4 125.1	0.998 9	0.6	2.1
21	表睾酮	2.00~50.00	y=12 645.7x-569.0	0.999 9	0.6	2.0
22	司坦唑醇	2.09~52.15	y=96 428.6x+11 241.5	0.999 9	0.6	2.1
23	己烯雌酚	2.11~52.64	y=1 235.5x-474.2	0.999 5	0.6	2.1
24	炔诺孕酮	2.00~50.05	y=6 484.3x-1 328.6	0.998 6	0.6	2.0
25	双烯雌酚	1.95~48.73	y=1 523.3x-370.1	0.999 8	0.6	1.9
26	氯司替勃	2.14~53.39	y=7 104.4x+567.6	0.998 7	0.6	2.1
27	己烷雌酚	2.13~53.29	y=904.4x-791.1	0.998 3	0.6	2.1
28	甲羟孕酮	2.07~51.73	y=16 346.5x-3 006.3	0.999 4	0.6	2.1
29	醋酸甲地孕酮	1.87~46.73	y=2 768.2x-175.7	0.999 9	0.6	1.9
30	孕酮	1.99~49.65	y=9 855.9x+5 871.7	0.999 7	0.6	2.0
31	达那唑	2.63~65.72	y=12 138.2x+13 068.7	0.998 8	0.8	2.6
32	醋酸氯地孕酮	2.30~57.60	y=4 578.3x+4 984.4	0.998 3	0.7	2.3
33	醋酸美伦孕酮	1.96~48.90	y=25 738.8x+37 445.0	0.998 2	0.6	2.0
34	醋酸甲羟孕酮	2.03~50.74	y=17 670.1x+18 941.3	0.998 6	0.6	2.0
35	17-乙酸睾酮激素	2.10~52.59	y=9 123.1x+274.5	0.998 8	0.6	2.1
36	醋酸氯睾酮	1.90~47.43	y=1 821.9x-1 055.9	0.997 9	0.6	1.9
37	丙酸睾酮	2.06~51.54	y=9 154.6x-2 343.3	0.999 7	0.6	2.1
38	己酸羟孕酮	2.70~67.41	y=14 468.4x+14 947.1	0.998 6	0.8	2.7
39	苯丙酸诺龙	2.29~57.18	y=22 143.2x-12 578.4	0.999 2	0.7	2.3

Tab. 3

Tab. 4

Recoveries and relative standard deviations （RSD, n=6）"

序号	化合物	平均加标回收率/%			相对标准偏差RSD/%
序号	化合物	低水平	中水平	高水平	低水平	中水平	高水平
1	雌三醇	89.1	98.6	100.9	5.2	4.0	4.9
2	肾上腺甾酮	92.4	95.5	105.1	6.3	6.4	4.1
3	群勃龙	96.7	99.8	101.6	3.2	3.7	2.5
4	勃地酮	93.7	97.7	103.2	2.5	2.3	1.5
5	诺龙	96.6	98.2	102.3	5.9	4.8	4.1
6	双酚A	91.2	99.1	105.2	10.4	6.0	4.9
7	17-β-雌二醇	96.0	104.2	110.0	12.8	11.8	8.2
8	美雄酮	95.9	99.1	101.0	5.7	4.2	2.3
9	氧甲氢龙	95.4	98.9	99.3	10.2	3.7	1.9
10	睾酮	101.6	103.6	104.1	7.9	1.2	3.8
11	17-α-雌二醇	110.6	100.6	98.1	7.1	11.0	8.7
12	炔诺酮	93.9	102.4	103.4	9.7	5.5	4.3
13	21-羟基孕酮	95.3	101.9	102.1	5.8	4.6	4.8
14	炔雌醇	84.4	90.8	97.8	14.1	11.4	8.3
15	孕三烯酮	94.5	99.3	100.7	5.0	4.8	1.6
16	雌酮	100.0	97.8	102.4	8.7	6.0	2.4
17	甲睾酮	88.4	98.0	102.8	4.7	5.0	3.4
18	雄烯二酮	90.0	97.4	101.3	3.7	8.6	5.0
19	孕二烯酮	85.8	100.4	101.4	5.5	4.4	2.0
20	17-α-羟基孕酮	90.7	100.1	101.4	5.8	5.0	3.8
21	表睾酮	98.8	102.4	100.9	5.5	2.7	3.6
22	司坦唑醇	91.2	96.1	101.5	3.5	4.2	3.4
23	己烯雌酚	93.3	96.1	104.9	5.1	5.0	7.3
24	炔诺孕酮	103.1	101.6	100.7	3.9	2.3	4.5
25	双烯雌酚	96.8	99.5	101.7	4.8	3.3	4.1
26	氯司替勃	100.3	99.4	101.5	7.5	3.2	6.1
27	己烷雌酚	99.0	101.8	101.9	4.2	8.0	4.8
28	甲羟孕酮	99.0	102.5	99.6	6.2	3.8	3.5
29	醋酸甲地孕酮	97.3	104.1	103.0	4.8	2.8	2.5
30	孕酮	101.3	101.2	103.2	4.9	1.9	3.2
31	达那唑	95.4	104.6	105.1	8.8	4.3	2.5
32	醋酸氯地孕酮	96.2	103.9	106.7	8.5	4.7	4.9
33	醋酸美伦孕酮	87.4	100.3	103.8	8.0	3.6	4.1
34	醋酸甲羟孕酮	90.8	101.9	101.5	7.6	3.8	4.4
35	17-乙酸睾酮激素	81.7	91.6	95.2	8.0	5.3	6.1
36	醋酸氯睾酮	107.3	99.8	99.8	6.0	2.8	3.1
37	丙酸睾酮	97.4	96.8	96.3	4.2	2.9	3.7
38	己酸羟孕酮	89.4	94.0	102.4	9.9	5.2	4.6
39	苯丙酸诺龙	106.9	106.7	102.4	5.3	1.7	3.6

Tab. 4

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Determination of 39 sex hormones in oil-based cosmetics by ultra-performance liquid chromatography-tandem mass spectrometry

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