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Dimethyl sulfide
 
 
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Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur
Organosulfur compounds

Organosulfur compounds are organic compounds that contain sulfur . They are often associated with foul odours, but ironically many of the sweetest compounds known are organosulfur derivatives....
 compound with the formula (CH3)2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37°C and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably corn, cabbage, beetroot and seafoods. It is also an indication of bacteria
Bacteria

The Bacteria are a large group of unicellular microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals....
l infection in malt
Malt

Malting is a process applied to cereal grains, in which the grains are made to germinate by soaking in water and are then quickly halted from germinating further by drying/heating with hot air....
 production and brewing
Brewing

Brewing is the production of alcoholic beverages and alcohol fuel through fermentation . The term is used for the production of beer, although the word "brewing" is also used to describe the fermentation process used to create wine and mead....
.






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Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur
Organosulfur compounds

Organosulfur compounds are organic compounds that contain sulfur . They are often associated with foul odours, but ironically many of the sweetest compounds known are organosulfur derivatives....
 compound with the formula (CH3)2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37°C and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably corn, cabbage, beetroot and seafoods. It is also an indication of bacteria
Bacteria

The Bacteria are a large group of unicellular microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals....
l infection in malt
Malt

Malting is a process applied to cereal grains, in which the grains are made to germinate by soaking in water and are then quickly halted from germinating further by drying/heating with hot air....
 production and brewing
Brewing

Brewing is the production of alcoholic beverages and alcohol fuel through fermentation . The term is used for the production of beer, although the word "brewing" is also used to describe the fermentation process used to create wine and mead....
. It is a breakdown product of dimethylsulfoniopropionate
Dimethylsulfoniopropionate

Dimethylsulfoniopropionate , is a metabolite found in marine phytoplankton, seaweeds and some species of terrestrial and aquatic vascular plants....
 (DMSP), and is also produced by the bacterial metabolism of methanethiol
Methanethiol

Methanethiol is a colorless gas with a smell like rotten cabbage. It is a natural substance found in the blood, brain, and other animal as well as plant tissues....
.

Natural sources and link with climate

DMS originates from S-methylmethionine(SMM). DMS is the most abundant biological sulfur compound emitted to the atmosphere
Earth's atmosphere

The Earth's atmosphere is a layer of gases surrounding the planet Earth that is retained by the Earth's gravity. Dry air contains roughly 78.08% nitrogen, 20.95% oxygen, 0.93% argon, 0.038% Carbon dioxide in the Earth's atmosphere, and trace amounts of other gases....
. Emission occurs over the ocean
Ocean

An ocean is a major body of Seawater, and a principal component of the hydrosphere. Approximately 71% of the Earth's surface is covered by ocean, a World Ocean that is customarily divided into several principal oceans and smaller seas....
s by phytoplankton
Phytoplankton

Phytoplankton are the autotrophic component of the plankton community. The name comes from the Greek language words phyton, or "plant", and p?a??t?? , meaning "wanderer" or "drifter"....
. DMS is also produced naturally by bacterial transformation of dimethyl sulfoxide
Dimethyl sulfoxide

Dimethyl sulfoxide is the chemical compound with the chemical formula 2SO. It was first synthesized in 1866 by the Russian scientist Alexander Saytzeff, who reported his findings in a German chemistry journal in 1867....
 (DMSO) waste that is disposed of into sewers, where it can cause environmental odor problems..

DMS is oxidized in the marine atmosphere to various sulfur-containing compounds, such as sulfur dioxide
Sulfur dioxide

Sulfur dioxide is the chemical compound with the formula SO2. It is produced by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide....
, dimethyl sulfoxide
Dimethyl sulfoxide

Dimethyl sulfoxide is the chemical compound with the chemical formula 2SO. It was first synthesized in 1866 by the Russian scientist Alexander Saytzeff, who reported his findings in a German chemistry journal in 1867....
 (DMSO), dimethyl sulfone, methane sulfonic acid
Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
 and sulfuric acid
Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
.

Among these compounds, sulfuric acid has the potential to create new aerosols which act as cloud condensation nuclei
Cloud condensation nuclei

Cloud condensation nuclei or CCNs are small particles about which cloud droplets coalescence . Water requires a non-gaseous surface to make the transition from a vapour to a liquid....
. Through this interaction with cloud
Cloud

A cloud is a visible mass of Drop or frozen crystals floating in the Celestial body atmosphere above the surface of the Earth or another planetary body....
 formation, the massive production of atmospheric DMS over the oceans may have a significant impact on the Earth's climate
Climate

Climate encompasses the temperatures, humidity, atmospheric pressure, winds, rainfall, atmospheric particle count and numerous other Meteorology elements in a given region over long periods of time, as opposed to the term weather, which refers to current activity of these same elements....
. The CLAW hypothesis
CLAW hypothesis

The CLAW hypothesis proposes a feedback that operates between ocean ecosystems and the Earth's climate. The hypothesis specifically proposes that particular phytoplankton that produce dimethyl sulfide are responsive to variations in climate forcing, and that these responses lead to a negative feedback that acts to stabilise the temperature o...
 suggests that in this manner DMS may play a role in planetary homeostasis
Homeostasis

Homeostasis is the property of a system, either open system or closed system, that regulates its internal environment and tends to maintain a stable, constant condition....
.

Smell

Dimethyl sulfide has a characteristic cabbage-like smell that becomes highly disagreeble at higher concentrations. DMS has a low olfactory threshold that varies from 0.02 to 0.1 ppm between different persons. However, it is also available as a food additive to impart a savory flavor; in such use, its concentration is low. Beetroot, asparagus, cabbage, corn and seafoods produce dimethyl sulfide when cooked.

Marine phytoplankton also produces dimethyl sulfide. Andrew Johnston, of the University of East Anglia
University of East Anglia

The University of East Anglia is a public university research university located in Norwich, England, and founded in 1963. The university is a member of the 1994 Group of research-intensive universities....
, has characterized DMS as being the "smell of the sea". It would be more accurate to say that DMS is a component of the "smell of the sea," another being pheromone
Pheromone

A pheromone is a chemical that triggers a natural behavioral response in another member of the opposite gender of the same species. There are alarm signal pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology....
s of algae called dictyopterenes.

Dimethyl sulfide is also an odorant emitted by kraft pulping mills, and a byproduct of Swern oxidation
Swern oxidation

The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is redox to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine....
.

Industrial uses

In industry it is used in petroleum
Petroleum

Petroleum or crude oil is a naturally occurring, flammable liquid found in rock formations in the Earth consisting of a complex mixture of hydrocarbons of various molecular weights, plus other organic compounds....
 refining and in petrochemical
Petrochemical

Petrochemicals are chemical products made from raw materials of petroleum or other hydrocarbon origin. Although some of the chemical compounds that originate from petroleum may also be derived from coal and natural gas, petroleum is the major source....
 production processes to control the formation of coke
Coke (fuel)

Cokes are the solid carbonaceous material derived from destructive distillation of low-ash, low-sulfur bituminous coal. Cokes from coal are grey, hard, and porous....
 and carbon monoxide
Carbon monoxide

Carbon monoxide, with the chemical formula CO, is a colorless and odorless, tasteless, yet highly toxic gas. Its molecules consist of one carbon atom covalent bond to one oxygen atom....
. In addition it is used to control dusting in steel mills. It is also used in a range of organic syntheses
Chemical synthesis

In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product , or several products. This happens by physics and chemical manipulations usually involving one or more reactions....
, also being a side product of Swern oxidation
Swern oxidation

The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is redox to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine....
. It also has a use as a food flavoring component. It can also be oxidized by natural or artificial means to dimethyl sulfoxide
Dimethyl sulfoxide

Dimethyl sulfoxide is the chemical compound with the chemical formula 2SO. It was first synthesized in 1866 by the Russian scientist Alexander Saytzeff, who reported his findings in a German chemistry journal in 1867....
, (DMSO), which has several important solvent properties.

The largest single commercial producer of DMS in the world is Gaylord Chemical Corporation, which is a significant economic component of the paper industry of Bogalusa, Louisiana
Bogalusa, Louisiana

Bogalusa is a city in Washington Parish, Louisiana, Louisiana, United States. The population was 13,365 at the 2000 United States Census. It is the principal city of the Bogalusa Micropolitan Statistical Area, which includes all of Washington Parish and is also part of the larger New Orleans, Louisiana–Metairie, Louisiana–Bogalusa...
.

Safety

Dimethyl sulfide is flammable and an irritant
Irritant

Irritant may refer to:* Something that causes irritation.* Irritant , a psychedelic trance album* Irritant , a United Kingdom rock musical group...
. Dimethyl sulfide has an unpleasant odor at even extremely low concentrations.

See also

  • Dimethyl telluride
  • Swern oxidation
    Swern oxidation

    The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is redox to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine....


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