1,1-乙二硫醇

1,1-乙二硫醇
Ethane-1,1-dithiol	Ball-and-stick model of ethane-1,1-dithiol
別名	1,1-二巰基乙烷
識別
CAS號	69382-62-3
PubChem	33645
ChemSpider	31030
SMILES	SC(S)C;
EINECS	248-103-1
性質
化學式	C2H6S2
摩爾質量	94.2 g·mol−1
外觀	無色液體
密度	每立方厘米0.83克
沸點	71 °C（344 K）
溶解性（水）	每公升12.97克
溶解性（其它）	在多數有機溶劑溶解度良好
折光度n; D	1.37
危險性
	GHS危險性符號;
GHS提示詞	Warning
H-術語	H302, H312, H332
P-術語	P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501
相關物質
相關化合物	Ethanethiol; Methanedithiol; 1,2-Ethanedithiol; 1,1,1-Ethanetrithiol; 1-hydroxy-ethanethiol; propane-1,1-dithiol
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1,1-乙二硫醇（Ethane-1,1-dithiol）是有機硫化合物，分子式CH₃CH(SH)₂；是種添加到或出現在某些食物的無色有氣味液體；是偕（geminal）二硫醇。

用途

1,1-乙二硫醇可用於調味飲品、油、肉汁、湯、肉、水果、增味劑和零食。公認安全（GRAS）最高濃度為百萬分之五（ppm），但常用濃度約0.2 ppm。^[1]其氣味強烈難聞，故常用其1%乙醇溶液。^[2]其有4%乙酸乙酯和乙醇的溶液CAS編號為69382-62-3。^[3]毒性可能是代謝產物硫化氫和乙醛引起，但在使用時它的安全邊際（margin of safety）超過1000萬。^[2]除水解外，它在體內的其它反應方式包括加甲基為1-甲硫基乙硫醇、硫氧化為磺酸乙酯、硫葡糖醛酸化或與半胱氨酸以二硫鍵結合。^[2]

自然存在

它可在葡萄發酵時生成，^[4]可用作食品調味劑，^[5]亦是榴槤香味的成份。^[6]^[7]

性質

核磁共振譜顯示三種質子環境，CH₃、SH和CH的比例分別對應於3:2:1。^[8]

反應

1,1-乙二硫醇有幾種對白葡萄酒風味很重要的已知反應。有氧時轉化為有橡膠香氣的順／反-3,6-二甲基-1,2,4,5-四硫雜環己烷，這分子的環有四粒硫原子和兩粒碳原子，兩粒1,1-乙二硫醇分子脫氫並以其硫原子連接起來；^[9]繼續氧化則成順／反-3,5-二甲基-1,2,4-三硫雜環戊烷，氣味類似肉；^[9]1,1-乙二硫醇與硫化氫反應成有肉味的順／反-4,7-二甲基-1,2,3,5,6-五硫雜環庚烷，其環有五粒硫原子和兩粒碳原子。^[9]

生成

乙醛與硫化氫反應可生成1,1-乙二硫醇，中間體為1-羥基乙硫醇。^[9]

參見

1,2-乙二硫醇

參考資料

^ Smith, R. L.; Cohen, S. M.; Doull, J.; Feron, V. J.; Goodman, J. I.; Marnett, L. J.; Portoghese, P. S.; Waddell, W. J.; Wagner, B. M.; Adams, T. B. GRAS Flavoring Substances 22 (PDF). Food Technology. Institute of Food Technologists: 47. August 2005 [1 December 2012]. （原始內容存檔 (PDF)於2013-09-09）.
^ ^2.0 ^2.1 ^2.2 Meeting, Joint FAO/WHO Expert Committee on Food Additives.; Organization, World Health. Evaluation of Certain Food Additives and Contaminants: Sixty-eighth Report of the Joint FAO/WHO Expert Committee on Food Additives Geneva from 19 to 28 June 2007 (PDF). World Health Organization. 2007: 108, 214–218 [1 December 2012]. ISBN 9789241209472. （原始內容存檔 (PDF)於2014-03-03）.
^ 1,1-ethane dithiol 1% in ethanol 94.5% / ethyl acetate 4% fragrance 69382-62-3. 2018-04-15 [1 December 2012]. （原始內容存檔於2022-11-16）.
^ Fedrizzi, Bruno; Giuseppe Versini; Roberto Ferrarini; Fabio Finato; Giorgio Nicolini; Franco Magno. Volatile Sulfur Compounds in Food. ACS Symposium Series 1068. 2011: 215–228. ISBN 978-0-8412-2616-6. ISSN 0097-6156. doi:10.1021/bk-2011-1068.ch010.
^ Joint FAO/WHO Expert Committee on Food Additives. List of Codex Specification for Food Additives (PDF). CAC/MISC 6: 90. 2012 [1 December 2012]. （原始內容 (PDF)存檔於2013-01-02）.
^ American Chemical Society. Scientists sniff out the substances behind the aroma in the 'king of fruits'. 28 November 2012 [1 December 2012]. （原始內容存檔於2022-11-16）.
^ Li, Jia-Xiao; Peter Schieberle; Martin Steinhaus. Characterization of the Major Odor-Active Compounds in Thai Durian (Durio zibethinus L. 'Monthong') by Aroma Extract Dilution Analysis and Headspace Gas Chromatography–Olfactometry. Journal of Agricultural and Food Chemistry. 2012, 60 (45): 11253–11262. ISSN 0021-8561. PMID 23088286. doi:10.1021/jf303881k.
^ No 1660 Ethane-1,1-dithiol HNMR. [2 December 2012]. ^{[失效連結]}
^ ^9.0 ^9.1 ^9.2 ^9.3 Moreno-Arribas, M. Victoria; Polo, Carmen. Wine Chemistry and Biochemistry. Springer. 2008-11-14: 604– [2 December 2012]. ISBN 9780387741161.

[Smith-1] Smith, R. L.; Cohen, S. M.; Doull, J.; Feron, V. J.; Goodman, J. I.; Marnett, L. J.; Portoghese, P. S.; Waddell, W. J.; Wagner, B. M.; Adams, T. B. GRAS Flavoring Substances 22 (PDF). Food Technology. Institute of Food Technologists: 47. August 2005 [1 December 2012]. （原始內容存檔 (PDF)於2013-09-09）.

[MeetingOrganization2007-2] 2.0 ^2.1 ^2.2 Meeting, Joint FAO/WHO Expert Committee on Food Additives.; Organization, World Health. Evaluation of Certain Food Additives and Contaminants: Sixty-eighth Report of the Joint FAO/WHO Expert Committee on Food Additives Geneva from 19 to 28 June 2007 (PDF). World Health Organization. 2007: 108, 214–218 [1 December 2012]. ISBN 9789241209472. （原始內容存檔 (PDF)於2014-03-03）.

[3] 1,1-ethane dithiol 1% in ethanol 94.5% / ethyl acetate 4% fragrance 69382-62-3. 2018-04-15 [1 December 2012]. （原始內容存檔於2022-11-16）.

[4] Fedrizzi, Bruno; Giuseppe Versini; Roberto Ferrarini; Fabio Finato; Giorgio Nicolini; Franco Magno. Volatile Sulfur Compounds in Food. ACS Symposium Series 1068. 2011: 215–228. ISBN 978-0-8412-2616-6. ISSN 0097-6156. doi:10.1021/bk-2011-1068.ch010.

[faowho-5] Joint FAO/WHO Expert Committee on Food Additives. List of Codex Specification for Food Additives (PDF). CAC/MISC 6: 90. 2012 [1 December 2012]. （原始內容 (PDF)存檔於2013-01-02）.

[6] American Chemical Society. Scientists sniff out the substances behind the aroma in the 'king of fruits'. 28 November 2012 [1 December 2012]. （原始內容存檔於2022-11-16）.

[7] Li, Jia-Xiao; Peter Schieberle; Martin Steinhaus. Characterization of the Major Odor-Active Compounds in Thai Durian (Durio zibethinus L. 'Monthong') by Aroma Extract Dilution Analysis and Headspace Gas Chromatography–Olfactometry. Journal of Agricultural and Food Chemistry. 2012, 60 (45): 11253–11262. ISSN 0021-8561. PMID 23088286. doi:10.1021/jf303881k.

[8] No 1660 Ethane-1,1-dithiol HNMR. [2 December 2012]. ^{[失效連結]}

[Moreno-ArribasPolo2008-9] 9.0 ^9.1 ^9.2 ^9.3 Moreno-Arribas, M. Victoria; Polo, Carmen. Wine Chemistry and Biochemistry. Springer. 2008-11-14: 604– [2 December 2012]. ISBN 9780387741161.

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