二甲基三硫
二甲基三硫 | |
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IUPAC名 (methyltrisulfanyl)methane | |
识别 | |
CAS号 | 3658-80-8 ![]() |
PubChem | 19310 |
ChemSpider | 18219 |
SMILES |
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InChI |
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InChIKey | YWHLKYXPLRWGSE-UHFFFAOYAF |
性质 | |
化学式 | C2H6S3 |
摩尔质量 | 126.26 g·mol⁻¹ |
外观 | 液体 |
密度 | 1.1978 g/cm3 |
熔点 | -68.05 °C(205 K) |
沸点 | 170 °C(443 K) |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
二甲基三硫(缩写:DMTS)是一种有机化合物,化学式为CH3S3CH3,它是最简单的有机三硫化物。[1][2]它是具有恶臭气味的可燃液体,其含量在万亿分之一时便可以被检测到。[3]
自然存在
二甲基三硫存在于洋葱、韭菜和其他葱属物种中,以及西兰花和卷心菜释放的挥发物,还有林堡芝士也会产生它。[4]它甚至是陈年的啤酒和陈年的日本酒的香气的成分之一。[5]它是细菌分解的分解产物,包括人类尸体分解的早期阶段,[6]是麗蠅寻找宿主的主要引诱剂。二甲基三硫,以及二甲基硫醚和二甲基二硫,已经被确认为是一种名为死马海芋百合(Helicodiceros muscivorus)的吸引苍蝇的植物所释放的挥发性化合物。这些苍蝇被吸引到肉类的气味,以帮助这种植物授粉。[7]二甲基三硫是鬼笔属真菌白鬼笔发出的恶臭的成分之一,也是真菌病变的特征性恶臭,例如癌症伤口。[3]它还是人类粪便的气味成分之一。[8]
制备
二甲基三硫有多种方法[2]可以制备,如可以由甲硫醇和硫化氢在铜(II)的存在下[9]与二氯化硫[10]反应得到:
- 2 CH3SH + SCl2 → CH3SSSCH3 + 2 HCl
化学性质
二甲基三硫加热至80 °C(353 K),缓慢分解,得到二甲基二硫、二甲基三硫和二甲基四硫的混合物。[10]它的反应性主要体现在它的弱S-S键上(约188.3 kJ/mol)。[1]而二甲基四硫更加活泼,也包含着弱的S-S键(约150.6 kJ/mol,中心)。[10]间氯过氧苯甲酸(mCPBA)和二甲基三硫反应,得到对应的S-氧化物CH3S(O)SSCH3。[11]
应用
诱饵中添加二甲基三硫可以用于捕捉斑颧丽蝇和其它丽蝇。[12]
参考文献
- ^ 1.0 1.1 Edward L. Clennan; Kristina L. Stensaas. Recent progress in the synthesis, properties and reactions of trisulfanes and their oxides. Organic Preparations and Procedures International. 1998, 30 (5): 551–600. doi:10.1080/00304949809355321.
- ^ 2.0 2.1 Ralf Steudel. The Chemistry of Organic Polysulfanes R−Sn−R (n > 2). Chemical Reviews. 2002, 102 (11): 3905–3945. doi:10.1021/cr010127m.
- ^ 3.0 3.1 Shirasu, Mika; Nagai, Shunji; Hayashi, Ryuichi; Ochiai, Atsushi; Touhara, Kazushige. Dimethyl trisulfide as a characteristic odor associated with fungating cancer wounds. Bioscience, Biotechnology, and Biochemistry. 2009, 73 (9): 2117–20. PMID 19734656. doi:10.1271/bbb.90229.
- ^ Thomas H. Parliament; Michael G. Kolor; Donald J. Rizzo. Volatile components of Limburger cheese. J. Agric. Food Chem. 1982, 30 (6): 1006–1008. doi:10.1021/jf00114a001.
- ^ Atsuko Isogai; Ryoko Kanda; Yoshikazu Hiraga; Toshihide Nishimura; Hiroshi Iwata; Nami Goto-Yamamoto. Screening and Identification of Precursor Compounds of Dimethyl Trisulfide (DMTS) in Japanese Sake. J. Agric. Food Chem. 2009, 57 (1): 189–195. PMID 19090758. doi:10.1021/jf802582p.
- ^ M. Statheropoulosa; A. Agapioua; C. Spiliopoulou; G.C. Pallis; E. Sianos. Environmental aspects of VOCs evolved in the early stages of human decomposition.. Science of The Total Environment. 2007, 385 (1-3): 221–227. doi:10.1016/j.scitotenv.2007.07.003.
- ^ Marcus C. Stensmyr; Isabella Urru; Ignazio Collu; Malin Celander; Bill S. Hansson; Anna-Maria Angioy. Rotting smell of dead-horse arum florets. Nature. 2002, 420: 625–626. PMID 12478279. doi:10.1038/420625a.
- ^ J.G. Moore; L.D. Jessop; D.N. Osborne DN. Gas-chromatographic and mass-spectrometric analysis of the odor of human feces.. Gastroenterology. 1987, 93 (6): 1321–1329. PMID 3678751.
- ^ Mustapha Nedjma; Norbert Hoffmann. Hydrogen Sulfide Reactivity with Thiols in the Presence of Copper(II) in Hydroalcoholic Solutions or Cognac Brandies: Formation of Symmetrical and Unsymmetrical Dialkyl Trisulfides.. J. Agric. Food Chem. 1996, 44 (12): 3935–3938. doi:10.1021/jf9602582.
- ^ 10.0 10.1 10.2 Timothy L. Pickering; K. J. Saunders; Arthur V. Tobolsky. Disproportionation of organic polysulfides. J. Am. Chem. Soc. 1967, 89 (10): 2364–2367. doi:10.1021/ja00986a021.
- ^ J. Auger; Y. Koussourakos; E. Thibout. Monooxidation of organic trisulfides. Chimika Chronika. 1985, 14 (4): 263–264.
- ^ Nilssen Arne C.; Åge Tǿmmerås Bjǿrn; Schmid Rudolf; Barli Evensen Sissel. Dimethyl trisulphide is a strong attractant for some calliphorids and a muscid but not for the reindeer oestrids Hypoderma tarandi and Cephenemyia trompe (PDF). Entomologia Experimentalis et Applicata. 1996, 79 (2): 211–218 [2017-07-04]. doi:10.1111/j.1570-7458.1996.tb00828.x. (原始内容 (PDF)存档于2012-12-17).