Determination of Organosulfides from Onion Oil
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Materials
2.2. Sample Preparation
2.3. GC-MS Method & Compound Identification
2.4. Statistical Analysis
3. Results and Discussion
3.1. Organosulfide Determination and Quantitation in Steam Distilled Onion Oil
3.2. Solvent Extraction Efficiency
3.2.1. Dichloromethane Extraction
3.2.2. Diethyl Ether Extraction
3.2.3. n-Pentane Extraction
3.2.4. Hexanes Extraction
3.3. Solvent Extraction
3.4. Organosulfide Profile of Steam Distilled Onion Oil
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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No a | r.t. (min) | Compound Name, Formula | Structure | Probability Score b | m/z (%) c | Identification d |
---|---|---|---|---|---|---|
1 | 7.02 | 3,4-Dimethylthiophene, C6H8S | | 10.76 | 111(100),112(66),97 (56),50(29), 77(27),59(26), 106(25),113(11) | MS, [4,6,24,25] |
2 | 7.87 | 2,4-Dimethyl Thiophene, C6H8S | | 21.13 | 111(100),112(61),97 (41),74(39), 116(34),50(21), 77(21),113(9) | MS, [4,6] |
3 | 9.65 | (E)-1-(Methyldisulfanyl)prop-1-ene, C6H8S2 | | 32.84 | 72(100),120(74), 72(42),103(27),91 (22),71(21), 104(12),121(4) | MS, [6,26] |
4 | 15.73 | (E)-Propenyl Propyl Disulfide, C6H12S2 | | 46.78 | 106(100),148(52),63 (21),73(20), 72(18),77(16), 59(15),149(5) | MS, [4,6,27] |
5 | 16.40 | Dipropyl Disulfide, C6H14S2 | | 52.04 | 150(100),108(54),65 (17),74(15), 148(14),117(10), 75(10),151(8) | MS, [4,6,28] |
6 | 16.95 | Allyl Isobutyl Disulfide, C7H12S2 | | 49.47 | 73(100),105(42), 148(39),83(15), 71(9),72(6),74(5), 149(3) | MS, [27] |
7 | 17.55 | 2-Ethyl-1,3-Dithiane, C6H12S2 | | 32.08 | 119(100),85(22), 148(21),58(12), 73(10),121(9), 75(6) | MS, [29,30] |
8 | 18.31 | 4-Methyl-1,2,3-Trithiolane, C3H3S6 | | 86.36 | 137(100),73(55), 63(14),139(14), 59(13),154(12), 74(12),95(9) * | MS, [12,13] |
9 | 19.97 | 3,4-Dimethyl-2,3-Dihydro-2-Thiophenethiol, C6H10S2 | | 80.51 | 144(100),111(77),117(49),146(28), 143(18),77(16), 99(16),129(12) | MS |
10 | 20.30 | 4H-1,2,3-Trithiin, C3H4S3 | | 14.51 | 70(100),135(68), 103(59),72(15), 143(14),63(13), 144(12),137(4) | MS, [14,31] |
11 | 20.53 | 2-Ethylidene-1,3-Dithiane, C6H10S2 | | 59.44 | 146(100),71(33), 104(33),103(31), 75(22),113(20), 85(14),147(10) | MS, [15,32] |
12 | 21.03 | 1-(Methylthiopropyl) Methyl Disulfide, C5H12S3 | | 24.54 | 89(100),61(53), 73(19),88(17), 146(14),71(13), 103(13),161(10) * | MS, [5,16,24,25] |
13 | 21.33 | Methyl-trans-1-propenyl trisulfide | | 27.50 | 146(100),152(80),103(77),87(64), 117(58),71(43), 85(37),154(11) | MS, [6,16,28,33,34] |
14 | 21.89 | 3-Ethyl-5-methyl-1,2,4-trithiolane, C4H8S3 (isomer of 15) | | 13.50 | 166(100),101(68),59 (54),63(25), 69(22),168(14),137 (13),102(13) | MS, [17] |
15 | 22.22 | 3-Ethyl-5-methyl-1,2,4-trithiolane, C5H10S3 (isomer of 14) | | 92.55 | 166(100),101(63),58 (51),63(24), 69(21),168(14), 102(13),73(12) | MS |
16 | 23.66 | 2-Methyl-4-Methylsulfanyl-2,3-Dihydrothiophene, C6H10S2 | | 26.86 | 146(100),131(74),71 (41),73(24), 77(22),59(22), 55(21),79(19) | MS |
17 | 25.48 | 5-Methyl tetrathiane, C3H6S4 (isomer of 21) | | 94.32 | 169(100),106(78),63 (36),171(19), 59(14),127(14), 72(12),170(6) | MS, [10,29] |
18 | 26.22 | (E)-1-Propenyl Propyl Trisulfide, C6H12S3 (isomer of 19) | | 65.27 | 180(100),182(73),115(70),75(26), 106(18),58(18), 55(17),181(9) | MS, [6,24] |
19 | 26.55 | (Z)-1-Propenyl Propyl Trisulfide, C6H12S3 (isomer of 18) | | 81.35 | 180(100),115(68),81 (19),74(17), 58(16),106(16), 182(13),181(9) | MS, [6,24] |
20 | 26.84 | 3,5-Diethyl-1,2,4-Trithiolane, C6H12S3 | | 30.68 | 116(100),180(38),74 (32),73(22), 114(12),118(11), 182(6),181(3) | MS, [10] |
21 | 27.61 | 5-Methyltetrathiane, C3H6S4 (isomer of 17) | | 95.88 | 169(100),106(49),127(26),63(20), 171(18),59(9), 73(7),170(6) | MS, [10,25,33] |
22 | 29.28 | 1-(Methylthio)Propyl Propyl Disulfide, C7H16S3 (isomer of 23) | | 31.78 | 89(100),61(47),73 (35),194(14), 55(10),70(8), 88(7),59(6) | MS, [16,18,24,25] |
23 | 30.28 | 1-(Methylthio)Propyl Propyl Disulfide (isomer of 22), C7H16S3 | | 38.72 | 89(100),61(47), 73(35),194(14), 55(10),70(8), 88(7),59(6) | MS, [16, 18,24,25] |
24 | 31.72 | 2,3-Dimethyl-5,6-Dithiabicyclo [2.1.1]hexane 5,5-Dioxide, C6H10O2S2 | | 86.57 | 113(100),99(70), 177(34),79(23), 77(22),111(21), 97(16),65(16) | MS, [15,24] |
25 | 32.88 | Hexathiane, S6 | | 74.50 | 191(100),63(29), 193(28),127(26), 130(4),192(4), 96(4),65(3) | MS, [19,23] |
26 | 35.99 | Dipropyl Tetrasulfide, C6H14S4 | | 82.22 | 214(100),73(34), 108(27),216(17), 75(15),117(14), 171(13),69(11) | MS, [18,25,28] |
27 | 36.64 | 3,6-Diethyl-1,2,4,5-Tetrathiane, C6H12S4 (isomer of 28, 29) | | 35.67 | 73(100),115(91), 147(65),211(29), 74(17),138(14), 81(12),59(9) | MS, [23] |
28 | 37.84 | 3,6-Diethyl-1,2,4,5-Tetrathiane, C6H12S4 (isomer of 27, 29) | | 35.28 | 73(100),115(94), 147(60),211(22), 74(19),81(14), 137(13),180(10) | MS |
29 | 37.84 | 3,6-Diethyl-1,2,4,5-Tetrathiane, C6H12S4 (isomer of 27, 28) | | 35.28 | 73(100),115(94), 147(60),211(22), 74(19),81(14), 137(13),180(10) | MS |
Organosulfide Content (mg/kg) in Each Solvent | ||||
---|---|---|---|---|
No α | DCM | DEE | n-Pentane | Hexanes |
1 | 3.03 ± 0.06 a | 2.94 ± 0.04 b | 2.90 ± 0.01 a | n.d. |
2 | 3.36 ± 0.17 a | n.d. | n.d. | n.d. |
3 | 3.98 ± 0.45 a | n.d. | 3.70 ± 0.29 b | n.d. |
I.S. | 5.29 ± 1.09 a | 5.08 ± 0.26 b | 5.13 ± 0.56 c | 4.96 ± 0.08 d |
4 | 3.27 ± 0.02 a | 3.71 ± 1.1 b | 3.22 ± 0.03 c | 3.16 ± 0.09 d |
5 | 3.32 ± 0.16 a | n.d. | 3.14 ± 0.09 b | 3.10 ± 0.13 c |
6 | 4.26 ± 0.62 a | 3.22 ± 0.16 b | 3.82 ± 0.31 c | 3.64 ± 0.49 d |
7 | 2.99 ± 0.05 a | n.d. | n.d. | n.d. |
8 | 4.30 ± 0.56 a | 3.21 ± 0.15 b | 3.93 ± 0.3 c | 3.55 ± 0.68 d |
9 | 3.40 ± 0.21 a | n.d. | 3.21 ± 0.11 b | 3.14 ± 0.17 c |
10 | 2.99 ± 0.02 a | 3.14 ± 0.31 b | 2.98 ± 0.02 c | 2.96 ± 0.01 d |
11 | 2.93 ± 0.01 a | n.d. | n.d. | n.d. |
12 | 3.16 ± 0.14 a | n.d. | n.d. | n.d. |
13 | 3.30 ± 0.08 a | n.d. | n.d. | 3.07 ± 0.15 b |
14 | 3.08 ± 0.09 a | n.d. | 3.00 ± 0.06 b | 2.96 ± 0.06 c |
15 | 3.23 ± 0.19 a | n.d. | 3.10 ± 0.11 b | 3.02 ± 0.09 c |
16 | 2.90 ± 0.02 a | n.d. | n.d. | n.d. |
17 | 3.06 ± 0.23 a | n.d. | 3.03 ± 0.07 b | 2.98 ± 0.06 c |
18 | 5.66 ± 1.35 a | 3.41 ± 0.22 b | 4.06 ± 1.09 b | 4.27 ± 0.84 c |
19 | 5.84 ± 1.30 a | 3.56 ± 0.30 a | 4.84 ± 0.74 b | 4.40 ± 0.76 c |
20 | 3.61 ± 0.30 a | n.d. | n.d. | 3.26 ± 0.26 |
21 | n.d. | 3.17 ± 0.28 a | 3.86 ± 0.14 b | 3.67 ± 0.32 a |
22 | 3.23 ± 0.09 a | n.d. | n.d. | 3.02 ± 0.13 b |
23 | 2.97 ± 0.05 a | n.d. | n.d. | n.d. |
24 | 3.20 ± 0.11 a | n.d. | 3.20 ± 0.10 b | 3.15 ± 0.13 c |
25 | n.d. | 3.21 ± 0.07 a | 3.28 ± 0.11 b | 3.24 ± 0.08 c |
26 | 3.19 ± 0.16 a | n.d. | 3.07 ± 0.07 b | n.d. |
27 | 4.50 ± 0.68 a | n.d. | n.d. | n.d. |
28 | 3.20 ± 0.11 a | n.d. | 4.20 ± 0.45 b | n.d. |
29 | 5.37 ± 1.14 a | 3.41 ± 0.26 a | 4.60 ± 0.68 b | n.d. |
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Cantrell, M.S.; Seale, J.T.; Arispe, S.A.; McDougal, O.M. Determination of Organosulfides from Onion Oil. Foods 2020, 9, 884. https://doi.org/10.3390/foods9070884
Cantrell MS, Seale JT, Arispe SA, McDougal OM. Determination of Organosulfides from Onion Oil. Foods. 2020; 9(7):884. https://doi.org/10.3390/foods9070884
Chicago/Turabian StyleCantrell, Maranda S., Jared T. Seale, Sergio A. Arispe, and Owen M. McDougal. 2020. "Determination of Organosulfides from Onion Oil" Foods 9, no. 7: 884. https://doi.org/10.3390/foods9070884