Trisulfide, methyl 2-propenyl

Formula: C₄H₈S₃
Molecular weight: 152.301
IUPAC Standard InChI: InChI=1S/C4H8S3/c1-3-4-6-7-5-2/h3H,1,4H2,2H3
IUPAC Standard InChIKey: JGMPRNFEEAJLAJ-UHFFFAOYSA-N
CAS Registry Number: 34135-85-8
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: 1-Allyl-3-methyltrisulfane; Allyl methyl trisulfide; Allyl methyl trisulphide; Methyl 2-propenyl trisulfide; Methyl allyl trisulfide; Methyl allyl trisulphide
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Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	OV-101	130.	1132.	Misharina and Golovnya, 1989	He; Column length: 50. m; Column diameter: 0.32 mm

Kovats' RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	SE-54	1123.	Zoghbi, Ramos, et al., 1984	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 230. C

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1142.	Mahattanatawee K., Perez-Cacho P.R., et al., 2007	30. m/0.32 mm/0.5 μm, He, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	DB-1	1112.	Pino, Fuentes, et al., 2001	He, 60. C @ 4. min, 4. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_end: 250. C
Capillary	DB-5	1149.	Kim, Wu, et al., 1995	He, 40. C @ 10. min, 4. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 200. C
Capillary	DB-1	1130.	Yu, Lin, et al., 1994	60. m/0.25 mm/1.0 μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 60. min
Capillary	OV-101	1120.	Misharina and Golovnya, 1989	He, 4. K/min; Column length: 50. m; Column diameter: 0.32 mm; T_start: 50. C; T_end: 250. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1143.8	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)
Capillary	SPB-1	1116.	Mochizuki, Yamamoto, et al., 1998	30. m/0.32 mm/4.0 μm, N2; Program: 40 0C (10 min), 2 0C/min to 180 0C, 25 0C/min to 250 0C (5 min)

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1592.	Mahattanatawee K., Perez-Cacho P.R., et al., 2007	30. m/0.32 mm/0.5 μm, He, 7. K/min, 240. C @ 5. min; T_start: 40. C
Capillary	FFAP	1605.	Calvo-Gómez, Morales-López, et al., 2004	30. m/0.25 mm/0.25 μm, He, 40. C @ 3. min, 5. K/min; T_end: 220. C
Capillary	Carbowax	1591.	Edris and Fadel, 2002	He, 2. K/min; Column length: 60. m; Column diameter: 0.32 mm; T_start: 50. C; T_end: 200. C
Capillary	CP-Wax 52CB	1588.	Kim, Wu, et al., 1995, 2	N2, 60. C @ 4. min, 2. K/min, 200. C @ 30. min; Column length: 50. m; Column diameter: 0.25 mm
Capillary	CP-Wax 52CB	1587.	Kim, Wu, et al., 1995, 2	N2, 60. C @ 4. min, 2. K/min, 200. C @ 30. min; Column length: 50. m; Column diameter: 0.25 mm
Capillary	CP-Wax 52CB	1593.	Yu, Wu, et al., 1989	N2, 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; T_start: 50. C; T_end: 200. C
Capillary	CP-Wax 52CB	1593.	Yu, Wu, et al., 1989, 2	N2, 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; T_start: 50. C; T_end: 200. C
Capillary	CP-Wax 52CB	1593.	Yu and Wu, 1989	N2, 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; T_start: 50. C; T_end: 200. C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-1	1110.	Rao, Nagender, et al., 2007	30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 2. K/min; T_end: 220. C
Capillary	RSL-200	1124.	Jirovetz, Ngassoum, et al., 2002	30. m/0.32 mm/0.25 μm, H2, 50. C @ 5. min, 6. K/min, 280. C @ 5. min
Capillary	DB-5MS	1135.	Zoghbi, Andrade, et al., 2002	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 270. C
Capillary	HP-1	1100.	Lopes, Godoy, et al., 1997	25. m/0.32 mm/0.17 μm, H2, 5. K/min; T_start: 40. C; T_end: 200. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1148.	Rotsatschakul, Visesanguan, et al., 2009	60. m/0.25 mm/0.25 μm, Helium; Program: 30 0C (2 min) 2 0Cmin -> 60 0C 10 0C/min -> 100 0C 20 0C/min -> 140 0C 10 0C/min -> 200 0C (10 min)
Capillary	SPB-1	1126.	Rao, Nagender, et al., 2007	30. m/0.32 mm/0.25 μm, Helium; Program: not specified
Capillary	HP-5 MS	1130.	Pyun and Shin, 2006	30. m/0.25 mm/0.25 μm; Program: 40 0C (3 min) 2 0C/min -> 150 0C 20 0C/min -> 220 0C (5 min)
Capillary	SE-30	1120.	Vinogradov, 2004	Program: not specified
Capillary	HP-5MS	1133.	Ansorena, Gimeno, et al., 2001	30. m/0.25 mm/0.25 μm, He; Program: 40C (10min) => 3C/min => 120C => 10C/min => 250C (5min)
Capillary	DB-5	1165.	Mateo and Zumalacárregui, 1996	50. m/0.32 mm/0.25 μm, He; Program: 40C (10min) => 3C/min => 95C => 10C/min => 270C (10min)
Capillary	DB-5	1164.	Mateo and Zumalacárregui, 1996	50. m/0.32 mm/0.25 μm, He; Program: 40C (10min) => 3C/min => 95C => 10C/min => 270C (10min)
Capillary	DB-5	1162.	Mateo and Zumalacárregui, 1996	50. m/0.32 mm/0.25 μm, He; Program: 40C (10min) => 3C/min => 95C => 10C/min => 270C (10min)

References

Go To: Top, Gas Chromatography, Notes

Misharina and Golovnya, 1989
Misharina, T.A.; Golovnya, R.V., Regularities of retention of a pseudohomologous series of dialkylpolysulfides in capillary gas chromatography, Zh. Anal. Khim., 1989, 44, 514-519. [all data]

Zoghbi, Ramos, et al., 1984
Zoghbi, M.G.B.; Ramos, L.S.; Maia, J.G.S.; da Silva, M.L.; Luz, A.I.R., Volatile sulfides of the Amazonian garlic bush, J. Agric. Food Chem., 1984, 32, 5, 1009-1010, https://doi.org/10.1021/jf00125a014 . [all data]

Mahattanatawee K., Perez-Cacho P.R., et al., 2007
Mahattanatawee K.; Perez-Cacho P.R.; Davenport T.; Rouseff R., Comparison of three lychee cultivar odor profiles using gas chromatography-olfactometry and gas chromatography-sulfur detection, J. Agric. Food Chem., 2007, 55, 5, 1939-1944, https://doi.org/10.1021/jf062925p . [all data]

Pino, Fuentes, et al., 2001
Pino, J.A.; Fuentes, V.; Correa, M.T., Volatile constituents of Chinese chive (Allium tuberosum Rottl. ex Sprengel) and Rakkyo (Allium chinense G. Don), J. Agric. Food Chem., 2001, 49, 3, 1328-1330, https://doi.org/10.1021/jf9907034 . [all data]

Kim, Wu, et al., 1995
Kim, S.M.; Wu, C.M.; Kobayashi, A.; Kubota, K.; Okumura, J., Volatile compounds in stir-fried garlic, J. Agric. Food Chem., 1995, 43, 11, 2951-2955, https://doi.org/10.1021/jf00059a033 . [all data]

Yu, Lin, et al., 1994
Yu, T.-H.; Lin, L.-Y.; Ho, C.-T., Volatile compounds of blanched, fried blanched, and baked blanched garlic slices, J. Agric. Food Chem., 1994, 42, 6, 1342-1347, https://doi.org/10.1021/jf00042a018 . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Mochizuki, Yamamoto, et al., 1998
Mochizuki, E.; Yamamoto, T.; Komiyama, Y.; Nakazawa, H., Identification of allium products using flame photometric detection gas chromatography and distribution patterns of volatile sulfur compounds, J. Agric. Food Chem., 1998, 46, 12, 5170-5176, https://doi.org/10.1021/jf9803076 . [all data]

Calvo-Gómez, Morales-López, et al., 2004
Calvo-Gómez, O.; Morales-López, J.; López, M.G., Solid-phase microextraction-gas chromatographic-mass spectrometric analysis of garlic oil obtained by hydrodistillation, J. Chromatogr. A, 2004, 1036, 1, 91-93, https://doi.org/10.1016/j.chroma.2004.02.072 . [all data]

Edris and Fadel, 2002
Edris, A.E.; Fadel, H.M., Investigation of the volatile aroma components of garlic leaves essential oil. Possibility of utilization to enrich garlic bulb oil, Eur. Food Res. Technol., 2002, 214, 2, 105-107, https://doi.org/10.1007/s00217-001-0429-2 . [all data]

Kim, Wu, et al., 1995, 2
Kim, S.M.; Wu, C.M.; Kubota, K.; Kobayashi, A., Effect of soybean oil on garlic volatile compounds isoalted by distillation, J. Agric. Food Chem., 1995, 43, 2, 449-452, https://doi.org/10.1021/jf00050a036 . [all data]

Yu, Wu, et al., 1989
Yu, T.-H.; Wu, C.-M.; Liou, Y.-C., Volatile compounds from garlic, J. Agric. Food Chem., 1989, 37, 3, 725-730, https://doi.org/10.1021/jf00087a032 . [all data]

Yu, Wu, et al., 1989, 2
Yu, T.-H.; Wu, C.-M.; Chen, S.-Y., Effects of pH adjustment and heat treatment on the stability and the formation of volatile compounds of garlic, J. Agric. Food Chem., 1989, 37, 3, 730-734, https://doi.org/10.1021/jf00087a033 . [all data]

Yu and Wu, 1989
Yu, T.-H.; Wu, C.-M., Stability of Allicin in Garlic Juice, J. Food Sci., 1989, 54, 4, 977-981, https://doi.org/10.1111/j.1365-2621.1989.tb07926.x . [all data]

Rao, Nagender, et al., 2007
Rao, P.P.; Nagender, A.; Rao, L.J.; Rao, D.G., Studies on the effects of microwave drying and cabinet tray drying on the chemical composition of volatile oils of garlic powders, Eur. Food Res. Technol., 2007, 224, 6, 791-795, https://doi.org/10.1007/s00217-006-0364-3 . [all data]

Jirovetz, Ngassoum, et al., 2002
Jirovetz, L.; Ngassoum, M.B.; Geissler, M., Analysis of the headspace aroma compounds of the seeds of the Cameroonian garlic plant Hua gabonii using SPME/GC/FID, SPME/GC/MS and olfactometry, Eur. Food Res. Technol., 2002, 214, 3, 212-215, https://doi.org/10.1007/s00217-001-0481-y . [all data]

Zoghbi, Andrade, et al., 2002
Zoghbi, M.G.B.; Andrade, E.H.A.; Maia, J.G.S., Volatile constituents from Adenocalymma alliaceum Miers and Petiveria alliacea L., two medicinal herbs of the Amazon, Flavour Fragr. J., 2002, 17, 2, 133-135, https://doi.org/10.1002/ffj.1051 . [all data]

Lopes, Godoy, et al., 1997
Lopes, D.; Godoy, R.L.O.; Goncalves, S.L.; Koketsu, M.; Oliveira, A.M., Sulphur constituents of the essential oil of Nira (Allium tuberosum Rottl.) cultivated in Brazil, Flavour Fragr. J., 1997, 12, 4, 237-239, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<237::AID-FFJ644>3.0.CO;2-9 . [all data]

Rotsatschakul, Visesanguan, et al., 2009
Rotsatschakul, P.; Visesanguan, W.; Smitinont, T.; Chaiseri, S., Changes in volatile compounds during fermentation of nham (Thai fermented sausage), Int. Food Res. J., 2009, 16, 391-414. [all data]

Pyun and Shin, 2006
Pyun, M.-S.; Shin, S., Antifungal effects of the volatile oils from Allium plants against Trichophyton species and synergism of the oils with ketoconazole, Phytomedicine, 2006, 13, 6, 394-400, https://doi.org/10.1016/j.phymed.2005.03.011 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Ansorena, Gimeno, et al., 2001
Ansorena, D.; Gimeno, O.; Astiasarán, I.; Bello, J., Analysis of volatile compounds by GC-MS of a dry fermented sausage: chorizo de Pamplona, Food Res. Int., 2001, 34, 1, 67-75, https://doi.org/10.1016/S0963-9969(00)00133-2 . [all data]

Mateo and Zumalacárregui, 1996
Mateo, J.; Zumalacárregui, J.M., Volatile compounds in chorizo and their changes during ripening, Meat Sci., 1996, 44, 4, 255-273, https://doi.org/10.1016/S0309-1740(96)00028-9 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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