Ethane-1,1-dithiol

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Ethane-1,1-dithiol
Ethane-1,1-dithiol 1,1-ethanedithiol.svg
Ethane-1,1-dithiol
Ball-and-stick model of ethane-1,1-dithiol Ethane11dithiol-balls.png
Ball-and-stick model of ethane-1,1-dithiol
Names
Preferred IUPAC name
Ethane-1,1-dithiol
Other names
Methyldisulfanyl methane
1,1-Ethanedithiol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.166.839 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 248-103-1
PubChem CID
UNII
  • InChI=1S/C2H6S2/c1-2(3)4/h2-4H,1H3
    Key: DHBXNPKRAUYBTH-UHFFFAOYSA-N
  • SC(S)C
Properties
C2H6S2
Molar mass 94.19 g·mol−1
AppearanceColorless liquid
Density 0.83 g/cm3
Boiling point 71 °C (160 °F; 344 K)
12.97 g/L
Solubility in waterGood solubility in
most organic solvents
1.37
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H312, H332
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
Related compounds
Related thiols
Ethanethiol; Methanedithiol; 1,2-Ethanedithiol; 1,1,1-Ethanetrithiol; 1-hydroxy-ethanethiol; propane-1,1-dithiol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethane-1,1-dithiol is an organosulfur compound with formula CH3CH(SH)2. It is a colourless smelly liquid that is added to or found in some foods. The compound is an example of a geminal dithiol.

Contents

Use

Flavouring uses of ethane-1,1-dithiol may include drinks, oil, gravy, soup, meat, fruit, seasonings, and snacks. Maximum concentrations in use that are generally recognised as safe (GRAS) is five parts per million (ppm) but typical uses are around 0.2 ppm. [1] It is supplied as a 1% solution in ethanol, due to its strong offensive smell. [2] In the diluted form with 4% ethyl acetate and ethanol the CAS number is 69382-62-3. [3] Toxicity may be due to metabolism products hydrogen sulfide and acetaldehyde, however as used it has a margin of safety of over 10,000,000. [2] Other ways that it is modified in the body apart from hydrolysis is methylation to 1-methylsulfanyl-ethanethiol, oxidation of the sulfur to an ethyl sulfonate, glucuronidation of the sulfur, or combination with cysteine by way of a disulfide bridge. [2]

Identifiers

Since it is used in the food industry there are codes issued by various authorities. It is identified as JECFA number 1660. [4] The Flavor and Extract Manufacturers Association (FEMA) id is 4111. [1] The European designation for the flavouring is Fl 12.293. [5]

Natural occurrence

It can be produced during fermentation of grapes. [6] It is used as a food flavouring. [4]

It is found naturally in the scent of durian. [7] [8]

Properties

The nuclear magnetic resonance spectrum shows three environments for protons, in the ratio of 3:2:1 corresponding to CH3 SH and CH. [9]

Reactions

Ethane-1,1-dithiol has several reactions known that are important in white wine flavours. In the presence of oxygen, ethane-1,1-dithiol is converted to cis/trans-3,6-dimethyl-1,2,4,5-tetrathiane which has a rubbery aroma. This molecule has a ring with four sulfur atoms and two carbons, two ethane-1,1-dithiol molecules become linked at their sulfur atoms with the loss of hydrogen. [10] This can further oxidise to cis/trans-3,5-dimethyl-1,2,4-trithiolane which has a meat-like odour. [10]

Ethane-1,1-dithiol reacts with hydrogen sulfide to form cis/trans-4,7-dimethyl-1,2,3,5,6-pentathiepane, a ring containing five sulfur atoms and two carbons. This has a meaty smell. [10]

Formation

Ethane-1,1-dithiol can be formed in the reaction of acetaldehyde with hydrogen sulfide. 1-Hydroxyethanethiol is formed as an intermediary. [10]

See also

Related Research Articles

Ethanol Organic chemical compound

Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic chemical compound. It is a simple alcohol with the chemical formula C2H6O. Its formula can be also written as CH
3
CH
2
OH or C
2
H
5
OH (an ethyl group linked to a hydroxyl group), and is often abbreviated as EtOH. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive drug, recreational drug, and the active ingredient in alcoholic drinks.

Ethane is an organic chemical compound with chemical formula C
2
H
6
. At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petrochemical by-product of petroleum refining. Its chief use is as feedstock for ethylene production.

Diethyl malonate Chemical compound

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Ethanethiol Chemical compound

Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH3CH2SH. is a colorless liquid with a distinct odor. It Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with sulfur in place of oxygen. The odor of EtSH is infamous. Ethanethiol is more volatile than ethanol due to a diminished ability to engage in hydrogen bonding. Ethanethiol is toxic in high concentrations. It occurs naturally as a minor component of petroleum, and may be added to otherwise odorless gaseous products such as liquefied petroleum gas (LPG) to help warn of gas leaks. At these concentrations, ethanethiol is not harmful.

Thiourea Chemical compound

Thiourea is an organosulfur compound with the formula SC(NH2)2. It is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom, but the properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. "Thioureas" refers to a broad class of compounds with the general structure (R1R2N)(R3R4N)C=S. Thioureas are related to thioamides, e.g. RC(S)NR2, where R is methyl, ethyl, etc.

Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur is essential for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.

Benzothiazole Chemical compound

Benzothiazole is an aromatic heterocyclic compound with the chemical formula C
7
H
5
NS
. It is colorless, slightly viscous liquid. Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature. Firefly luciferin can be considered a derivative of benzothiazole.

Sulfoxide

A sulfoxide is a chemical compound containing a sulfinyl (SO) functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are an oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.

Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH3)2S. Dimethyl sulfide is a flammable liquid that boils at 37 °C (99 °F) and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize, cabbage, beetroot, and seafoods. It is also an indication of bacterial contamination in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate (DMSP), and is also produced by the bacterial metabolism of methanethiol.

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Dimethyl dicarbonate Chemical compound

Dimethyl dicarbonate (DMDC) is a clear colorless liquid with a density of 1.25 g/mL and a pungent odor at high concentration at room temperature. It is primarily used as a beverage preservative, processing aid, or sterilant being highly active against typical beverage spoiling microorganisms like yeast, bacteria or mould. It acts by inhibiting enzymes involved in the microbial metabolism, e.g. acetate kinase and L-glutamic acid decarboxylase. It has also been proposed that DMDC inhibits the enzymes alcohol dehydrogenase and glyceraldehyde 3-phosphate dehydrogenase by causing the methoxycarbonylation of their histidine components.

In stereochemistry, topicity is the stereochemical relationship between substituents and the structure to which they are attached. Depending on the relationship, such groups can be heterotopic, homotopic, enantiotopic, or diastereotopic.

<i>tert</i>-Butylthiol Chemical compound

tert-Butylthiol, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol is used as an odorant for natural gas, which is otherwise odorless. It may also have been used as a flavoring agent.

Dimethyl trisulfide Chemical compound

Dimethyl trisulfide (DMTS) is an organic chemical compound and the simplest organic trisulfide, with the chemical formula CH3SSSCH3. It is a flammable liquid with a foul odor, which is detectable at levels as low as 1 part per trillion.

Yeast in winemaking Yeasts used for alcoholic fermentation of wine

The role of yeast in winemaking is the most important element that distinguishes wine from grape juice. In the absence of oxygen, yeast converts the sugars of wine grapes into alcohol and carbon dioxide through the process of fermentation. The more sugars in the grapes, the higher the potential alcohol level of the wine if the yeast are allowed to carry out fermentation to dryness. Sometimes winemakers will stop fermentation early in order to leave some residual sugars and sweetness in the wine such as with dessert wines. This can be achieved by dropping fermentation temperatures to the point where the yeast are inactive, sterile filtering the wine to remove the yeast or fortification with brandy or neutral spirits to kill off the yeast cells. If fermentation is unintentionally stopped, such as when the yeasts become exhausted of available nutrients and the wine has not yet reached dryness, this is considered a stuck fermentation.

Decenoic acid is any mono-carboxylic acid with an unbranched chain of ten carbons connected by eight single bonds and one double bond; that is, a chemical compound with formula HO(O=)C(CH
2
)
k
CH=CH(CH
2
)
7-k
–H, where k is between 0 and 7 inclusive.

Radical theory is an obsolete scientific theory in chemistry describing the structure of organic compounds. The theory was pioneered by Justus von Liebig, Friedrich Wöhler and Auguste Laurent around 1830 and is not related to the modern understanding of free radicals. In this theory, organic compounds were thought to exist as combinations of radicals that could be exchanged in chemical reactions just as chemical elements could be interchanged in inorganic compounds.

4-Methylcyclohexanemethanol Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

Cinnamyl acetate Chemical compound

Cinnamyl acetate is a chemical compound of the cinnamyl ester family, in which the variable R group is substituted by a methyl group. As a result of the non-aromatic carbon-carbon double bond, cinnamyl acetate can exist in a Z and an E configuration:

Trithioacetone Chemical compound

Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an organic chemical with formula C
9
H
18
S
3
. Its covalent structure is [–C(CH
3
)
2
–S–]
3
, that is, a six-membered ring of alternating carbon and sulfur atoms, with two methyl groups attached to each carbon. It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group substituents for all of the hydrogen atoms in that parent structure.

References

  1. 1 2 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. (August 2005). "GRAS Flavoring Substances 22" (PDF). Food Technology. Institute of Food Technologists. p. 47. Retrieved 1 December 2012.
  2. 1 2 3 Meeting, Joint FAO/WHO Expert Committee on Food Additives.; Organization, World Health (2007). 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. pp. 108, 214–218. ISBN   9789241209472 . Retrieved 1 December 2012.
  3. "1,1-ethane dithiol 1% in ethanol 94.5% / ethyl acetate 4% fragrance 69382-62-3". 2018-04-15. Retrieved 1 December 2012.
  4. 1 2 Joint FAO/WHO Expert Committee on Food Additives (2012). "List of Codex Specification for Food Additives" (PDF). CAC/MISC 6. p. 90. Retrieved 1 December 2012.
  5. European Food Safety Authority (2011). "Scientific Opinion on Flavouring Group Evaluation 91, Revision 1". EFSA Journal. 9 (12): 2459. doi: 10.2903/j.efsa.2011.2459 .
  6. Fedrizzi, Bruno; Giuseppe Versini; Roberto Ferrarini; Fabio Finato; Giorgio Nicolini; Franco Magno (2011). "Sulfur Compounds in Still and Sparkling Wines and in Grappa: Analytical and Technological Aspects". Volatile Sulfur Compounds in Food. ACS Symposium Series. Vol. 1068. pp. 215–228. doi:10.1021/bk-2011-1068.ch010. ISBN   978-0-8412-2616-6. ISSN   0097-6156.
  7. American Chemical Society (28 November 2012). "Scientists sniff out the substances behind the aroma in the 'king of fruits'" . Retrieved 1 December 2012.
  8. Li, Jia-Xiao; Peter Schieberle; Martin Steinhaus (2012). "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. 60 (45): 11253–11262. doi:10.1021/jf303881k. ISSN   0021-8561. PMID   23088286.
  9. "No 1660 Ethane-1,1-dithiol HNMR" . Retrieved 2 December 2012.
  10. 1 2 3 4 Moreno-Arribas, M. Victoria; Polo, Carmen (2008-11-14). Wine Chemistry and Biochemistry. Springer. pp. 604–. ISBN   9780387741161 . Retrieved 2 December 2012.