Disulfide, methyl (methylthio)methyl

Formula: C₃H₈S₃
Molecular weight: 140.291
IUPAC Standard InChI: InChI=1S/C3H8S3/c1-4-3-6-5-2/h3H2,1-2H3
IUPAC Standard InChIKey: MYIOBINSHMEDEY-UHFFFAOYSA-N
CAS Registry Number: 42474-44-2
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: Methyl methylthiomethyl disulfide; 2,4,5-Trithiahexane; 2,3,5-Trithiahexane; Methane, (methyldithio)(methylthio)-; Methyl (methylthio)methyl disulphide; 1-Methyl-2-((methylthio)methyl)disulfane; (Methyldisulfanyl)(methylsulfanyl)methane; 1-(methylthio)dimethyl disulfide
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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
Packed	Apiezon M	130.	1143.	Garbuzov, Misharina, et al., 1985	He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m

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

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Column type	Active phase	I	Reference	Comment
Capillary	BPX-5	1144.	Dickschat J.S., Wagner-Dobler I., et al., 2005	25. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min; T_end: 300. C
Capillary	BPX-5	1154.	Mandin, Duckham, et al., 1999	50. m/0.32 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min, 250. C @ 5. min

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	1134.1	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)

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1650.	Cha, Kim, et al., 1998	30. m/0.32 mm/0.25 μm, He, 40. C @ 5. min, 6. K/min, 200. C @ 30. min
Capillary	DB-Wax	1662.	Cha, Kim, et al., 1998	60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 3. K/min, 200. C @ 60. min

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1705.5	Yang, Chyau, et al., 1998	He; Column length: 50. m; Column diameter: 0.32 mm; Program: 50C => 2.5C/min => 150C => 1.5C/min => 210C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	AT-5	1130.	Diaz, Vera, et al., 2011	60. m/0.25 mm/0.25 μm, Helium, 4. K/min, 260. C @ 20. min; T_start: 60. C
Capillary	SPB-1	1106.	Frerot, Velluz, et al., 2008	30. m/0.25 mm/1.0 μm, Helium, 60. C @ 5. min, 5. K/min; T_end: 250. C
Capillary	HP-1	1097.	Bendimerad and Bendiab, 2005	50. m/0.2 mm/0.5 μm, He, 2. K/min, 250. C @ 60. min; T_start: 60. C
Capillary	BPX-5	1146.	Dickschat, Martens, et al., 2005	25. m/0.22 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min; T_end: 320. C
Capillary	HP-1	1094.	Valette, Fernandez, et al., 2003	50. m/0.2 mm/0.5 μm, He, 2. K/min, 220. C @ 40. min; T_start: 60. C
Capillary	RSL-200	1099.	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-1	1139.	Rapior, Breheret, et al., 1997	30. m/0.2 mm/0.25 μm, He, 50. C @ 2. min, 4. K/min; T_end: 200. C
Capillary	DB-1	1110.	Rapior, Breheret, et al., 1997	30. m/0.2 mm/0.25 μm, He, 50. C @ 2. min, 4. K/min; 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	DB-5 MS	1147.	Cajka, Hajslova, et al., 2007	30. m/0.25 mm/0.25 μm, Helium; Program: 45 0C (0.75 min) 10 0C/min -> 200 0C 30 0C/min -> 245 0C (1.25 min)
Capillary	SPB-5	1139.	Begnaud, Pérès, et al., 2003	60. m/0.32 mm/1. μm; Program: not specified
Capillary	CP Sil 5 CB	1104.	Lermusieau, Bulens, et al., 2001	50. m/0.32 mm/1.2 μm; Program: 36C => 20C/min => 120C(20min) => 2C/min => 250C(30min)
Capillary	CP Sil 5 CB	1109.	Gijs, Piraprez, et al., 2000	50. m/0.32 mm/1.2 μm, He; Program: 33C (16.5min) => 2C/min => 160C => 20C/min => 200C (9min)

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1630.	Spadone, Matthey-Doret, et al., 2006	60. m/0.25 mm/0.25 μm, Helium, 35. C @ 3. min, 6. K/min, 240. C @ 10. min
Capillary	Innowax	1632.	Bendimerad and Bendiab, 2005	50. m/0.2 mm/0.5 μm, He, 2. K/min, 250. C @ 60. min; T_start: 60. C
Capillary	HP-Innowax	1666.	Kubec, Drhová, et al., 1998	30. m/0.25 mm/0.25 μm, N2, 40. C @ 3. min, 4. K/min, 190. C @ 10. min

References

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Garbuzov, Misharina, et al., 1985
Garbuzov, V.G.; Misharina, T.A.; Aerov, A.F.; Golovnya, R.V., Gas chromatographic retention indices for sulphur(II)-containing organic substances, J. Anal. Chem. USSR (Engl. Transl.), 1985, 40, 4, 576-586. [all data]

Dickschat J.S., Wagner-Dobler I., et al., 2005
Dickschat J.S.; Wagner-Dobler I.; Schulz S., The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria, J. Chem. Ecol., 2005, 31, 4, 925-947, https://doi.org/10.1007/s10886-005-3553-9 . [all data]

Mandin, Duckham, et al., 1999
Mandin, O.; Duckham, S.C.; Ames, J.M., Volatile compounds from potato-like model systems, J. Agric. Food Chem., 1999, 47, 6, 2355-2359, https://doi.org/10.1021/jf981277+ . [all data]

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

Cha, Kim, et al., 1998
Cha, Y.J.; Kim, H.; Cadwallader, K.R., Aroma-active compounds in Kimchi during fermentation, J. Agric. Food Chem., 1998, 46, 5, 1944-1953, https://doi.org/10.1021/jf9706991 . [all data]

Yang, Chyau, et al., 1998
Yang, M.-S.; Chyau, C.-C.; Horng, D.-T.; Yang, J.-S., Effects of Irradiation and Drying on Volatile Components of Fresh Shiitake edodes (Lentinus Sing), J. Sci. Food Agric., 1998, 76, 1, 72-76, https://doi.org/10.1002/(SICI)1097-0010(199801)76:1<72::AID-JSFA921>3.0.CO;2-0 . [all data]

Diaz, Vera, et al., 2011
Diaz, A.B.; Vera, J.R.; Fermin, L.R.; Mendez, A.M.; Zambrano, R.A.; Contreras L.R., Composition of the essential oil of leaves and roots of Allium schoenoprasum L. (Alliaceae), Boletin LAtinoamericano y del Caribe de Plantas Medicinales y Aromaticas, 2011, 10, 3, 218-221. [all data]

Frerot, Velluz, et al., 2008
Frerot, E.; Velluz, A.; Bagnoud, A.; Delort, E., Analysis of the volatile constituents of cooked petai beans (Parkia speciosa) using high-resolution GC/TOF-MS, Flav. Fragr. J., 2008, 23, 6, 434-440, https://doi.org/10.1002/ffj.1902 . [all data]

Bendimerad and Bendiab, 2005
Bendimerad, N.; Bendiab, S.A.T., Composition and antibacterial activity of Pseudocytisus integrifolius (Salisb.) essential oil from Algeria, J. Agric. Food Chem., 2005, 53, 8, 2947-2952, https://doi.org/10.1021/jf047937u . [all data]

Dickschat, Martens, et al., 2005
Dickschat, J.S.; Martens, T.; Brinkhoff, T.; Simon, M.; Schulz, S., Volatiles released by a Streptomyces species isolated from the North Sea, Chemistry and Biodiversity, 2005, 2, 7, 837-865, https://doi.org/10.1002/cbdv.200590062 . [all data]

Valette, Fernandez, et al., 2003
Valette, L.; Fernandez, X.; Poulain, S.; Loiseau, A.-M.; Lizzani-Cuvelier, L.; Levieil, R.; Restier, L., Volatile constituents from Romanesco cauliflower, Food Chem., 2003, 80, 3, 353-358, https://doi.org/10.1016/S0308-8146(02)00272-8 . [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]

Rapior, Breheret, et al., 1997
Rapior, S.; Breheret, S.; Talou, T.; Bessiére, J.-M., Volatile flavor constituents of fresh Marasmius alliaceus (garlic Marasmius), J. Agric. Food Chem., 1997, 45, 3, 820-825, https://doi.org/10.1021/jf960511y . [all data]

Cajka, Hajslova, et al., 2007
Cajka, T.; Hajslova, J.; Cochran, J.; Holadova, K.; Klimankova, E., Solid phase microextraction - comprehensive two dimensional gas chromatography - time-of-flight mass spectrometry for the analysis of honey volatiles, J. Sep. Sci., 2007, 30, 4, 534-546, https://doi.org/10.1002/jssc.200600413 . [all data]

Begnaud, Pérès, et al., 2003
Begnaud, F.; Pérès, C.; Berdagué, J.-L., Characterization of volatile effluents of livestock buildings by solid-phase microextraction, Int. J. Environ. Anal. Chem., 2003, 83, 10, 837-849, https://doi.org/10.1080/03067310310001603349 . [all data]

Lermusieau, Bulens, et al., 2001
Lermusieau, G.; Bulens, M.; Collin, S., Use of GC-olfactometry to identify the hop aromatic compounds in beer, J. Agric. Food Chem., 2001, 49, 8, 3867-3874, https://doi.org/10.1021/jf0101509 . [all data]

Gijs, Piraprez, et al., 2000
Gijs, L.; Piraprez, G.; Perpète, P.; Spinnler, E.; Collin, S., Retention of sulfur flavours by food matrix and determination of sensorial data independent of the medium composition, Food Chem., 2000, 69, 3, 319-330, https://doi.org/10.1016/S0956-7135(99)00111-5 . [all data]

Spadone, Matthey-Doret, et al., 2006
Spadone, J.-C.; Matthey-Doret, W.; Blank, I., Formation of methyl(methylthio)methyl disulfide in broccoli (Brassica oleracea (L.) var. italica) in Flavour Science: Recent Advances and Trends, Bredie, W.L.P.; Petersen, M.A., ed(s)., Elsevier, Amsterdam, 2006, 309-314. [all data]

Kubec, Drhová, et al., 1998
Kubec, R.; Drhová, V.; Velísek, J., Thermal degradation of S-methylcysteine and its sulfoxide-important flavor precursors of Bassica and Allium vegetables, J. Agric. Food Chem., 1998, 46, 10, 4334-4340, https://doi.org/10.1021/jf980379x . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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