Dimethyl sulfide
Encyclopedia
Dimethyl sulfide or methylthiomethane is an organosulfur
compound with the formula (CH3)2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37 °C (98.6 °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 bacteria
l infection in malt
production and brewing
. It is a breakdown product of dimethylsulfoniopropionate
(DMSP), and is also produced by the bacterial metabolism of methanethiol
.
. Emission occurs over the ocean
s by phytoplankton
. DMS is also produced naturally by bacterial transformation of dimethyl sulfoxide
(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
, dimethyl sulfoxide
(DMSO), dimethyl sulfone
, methanesulfonic acid
and sulfuric acid
. Among these compounds, sulfuric acid has the potential to create new aerosols which act as cloud condensation nuclei
. Through this interaction with cloud
formation, the massive production of atmospheric DMS over the oceans may have a significant impact on the Earth's climate
. The CLAW hypothesis
suggests that in this manner DMS may play a role in planetary homeostasis
.
-like smell that becomes highly disagreeable 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
, 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
s of algae called dictyopterene
s.
Dimethyl sulfide is also an odorant emitted by kraft pulping mills, and a byproduct of Swern oxidation
.
refining and in petrochemical
production processes to control the formation of coke
and carbon monoxide
. In addition it is used to control dusting in steel mills. It is also used in a range of organic syntheses
, including as a reducing agent in ozonolysis
reactions. It also has a use as a food flavoring component. It can also be oxidized by natural or artificial means to dimethyl sulfoxide
, (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
.
and other coordination compounds.
to eyes and skin. It is harmful if swallowed and has an unpleasant odor at even extremely low concentrations. Its ignition temperature is 205 °C.
Organosulfur compounds
Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odours, but many of the sweetest compounds known are organosulfur derivatives. Nature abounds with organosulfur compounds—sulfur is essential for life. Two of the 20 common amino acids are...
compound with the formula (CH3)2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37 °C (98.6 °F) and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize, cabbage, beetroot
Beetroot
The beetroot, also known as the table beet, garden beet, red beet or informally simply as beet, is one of the many cultivated varieties of beets and arguably the most commonly encountered variety in North America, Central America and Britain.-Consumption:The usually deep-red roots of beetroot are...
and seafoods. It is also an indication of bacteria
Bacteria
Bacteria are a large domain of prokaryotic 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
Malt is germinated cereal grains that have been dried in a process known as "malting". The grains are made to germinate by soaking in water, and are then halted from germinating further by drying with hot air...
production and brewing
Brewing
Brewing is the production of beer through steeping a starch source in water and then fermenting with yeast. Brewing has taken place since around the 6th millennium BCE, and archeological evidence suggests that this technique was used in ancient Egypt...
. It is a breakdown product of dimethylsulfoniopropionate
Dimethylsulfoniopropionate
Dimethylsulfoniopropionate , is an organosulfur compound with the formula 2S+CH2CH2COO−. This zwitterionic 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 and brain of humans and other animal as well as plant tissues. It is disposed of through animal feces. It occurs naturally in certain foods, such as some nuts and cheese...
.
Natural occurrence
DMS originates primarily from DMSP, a major secondary metabolite in some marine algae. DMS is the most abundant biological sulfur compound emitted to the atmosphereEarth's atmosphere
The atmosphere of Earth is a layer of gases surrounding the planet Earth that is retained by Earth's gravity. The atmosphere protects life on Earth by absorbing ultraviolet solar radiation, warming the surface through heat retention , and reducing temperature extremes between day and night...
. Emission occurs over the ocean
Ocean
An ocean is a major body of saline water, and a principal component of the hydrosphere. Approximately 71% of the Earth's surface is covered by ocean, a continuous body of water that is customarily divided into several principal oceans and smaller seas.More than half of this area is over 3,000...
s by phytoplankton
Phytoplankton
Phytoplankton are the autotrophic component of the plankton community. The name comes from the Greek words φυτόν , meaning "plant", and πλαγκτός , meaning "wanderer" or "drifter". Most phytoplankton are too small to be individually seen with the unaided eye...
. DMS is also produced naturally by bacterial transformation of dimethyl sulfoxide
Dimethyl sulfoxide
Dimethyl sulfoxide is an organosulfur compound with the formula 2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water...
(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 . It is released by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide unless the sulfur compounds are removed before burning the fuel...
, dimethyl sulfoxide
Dimethyl sulfoxide
Dimethyl sulfoxide is an organosulfur compound with the formula 2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water...
(DMSO), dimethyl sulfone
Methylsulfonylmethane
Methylsulfonylmethane is an organosulfur compound with the formula 2SO2. It is also known by several other names including DMSO2, methyl sulfone, and dimethyl sulfone. This colorless solid features the sulfonyl functional group and is considered relatively inert chemically...
, methanesulfonic acid
Methanesulfonic acid
Methanesulfonic acid is a colorless liquid with the chemical formula CH3SO3H. It is the simplest of the alkylsulfonic acids. Salts and esters of methanesulfonic acid are known as mesylates. Methanesulfonic acid is used as an acid catalyst in organic reactions because it is non-volatile, strong acid...
and sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
. 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 typically 0.2 µm, or 1/100 th the size of a cloud droplet ) about which cloud droplets coalesce. Water requires a non-gaseous surface to make the transition from a vapour to a liquid. In the atmosphere, this surface presents itself as tiny...
. Through this interaction with cloud
Cloud
A cloud is a visible mass of liquid droplets or frozen crystals made of water and/or various chemicals suspended in the atmosphere above the surface of a planetary body. They are also known as aerosols. Clouds in Earth's atmosphere are studied in the cloud physics branch of meteorology...
formation, the massive production of atmospheric DMS over the oceans may have a significant impact on the Earth's climate
Climate
Climate encompasses the statistics of temperature, humidity, atmospheric pressure, wind, rainfall, atmospheric particle count and other meteorological elemental measurements in a given region over long periods...
. The CLAW hypothesis
CLAW hypothesis
The CLAW hypothesis proposes a feedback loop 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...
suggests that in this manner DMS may play a role in planetary homeostasis
Homeostasis
Homeostasis is the property of a system that regulates its internal environment and tends to maintain a stable, constant condition of properties like temperature or pH...
.
Smell
Dimethyl sulfide has a characteristic cabbageCabbage
Cabbage is a popular cultivar of the species Brassica oleracea Linne of the Family Brassicaceae and is a leafy green vegetable...
-like smell that becomes highly disagreeable 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 research university based in Norwich, United Kingdom. It was established in 1963, and is a founder-member of the 1994 Group of research-intensive universities.-History:...
, 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 secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...
s of algae called dictyopterene
Dictyopterene
Dictyopterenes are a group of chemical compounds that are naturally present in freshwater environments. They are sexual attractants, or pheromones, found with several species of brown algae . The chemical formula of dictyopterene A is trans-1--2-vinylcyclopropane. The chemical formula of...
s.
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 oxidized 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 petroleumPetroleum
Petroleum or crude oil is a naturally occurring, flammable liquid consisting of a complex mixture of hydrocarbons of various molecular weights and other liquid organic compounds, that are found in geologic formations beneath the Earth's surface. Petroleum is recovered mostly through oil drilling...
refining and in petrochemical
Petrochemical
Petrochemicals are chemical products derived from petroleum. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as corn or sugar cane....
production processes to control the formation of coke
Coke (fuel)
Coke is the solid carbonaceous material derived from destructive distillation of low-ash, low-sulfur bituminous coal. Cokes from coal are grey, hard, and porous. While coke can be formed naturally, the commonly used form is man-made.- History :...
and carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
. 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 to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...
, including as a reducing agent in ozonolysis
Ozonolysis
Ozonolysis is the cleavage of an alkene or alkyne with ozone to form organic compounds in which the multiple carbon–carbon bond has been replaced by a double bond to oxygen...
reactions. 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 an organosulfur compound with the formula 2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water...
, (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, United States. The population was 13,365 at the 2000 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–Metairie–Bogalusa...
.
Other uses
Dimethyl sulfide finds a niche use as a displaceable ligand in chloro(dimethyl sulfide)gold(I)Chloro(dimethyl sulfide)gold(I)
Chlorogold is an coordination complex of gold. It is a white solid. This compound is a common entry point into gold chemistry.-Structure:...
and other coordination compounds.
Safety
Dimethyl sulfide is highly flammable and irritantIrritation
Irritation or exacerbation, in biology and physiology, is a state of inflammation or painful reaction to allergy or cell-lining damage. A stimulus or agent which induces the state of irritation is an irritant...
to eyes and skin. It is harmful if swallowed and has an unpleasant odor at even extremely low concentrations. Its ignition temperature is 205 °C.
See also
- CoccolithophoreCoccolithophoreCoccolithophores are single-celled algae, protists, and phytoplankton belonging to the division of haptophytes. They are distinguished by special calcium carbonate plates of uncertain function called coccoliths , which are important microfossils...
, a marine unicellular planktonic photosynthetic algae, producer of DMS - DimethylsulfoniopropionateDimethylsulfoniopropionateDimethylsulfoniopropionate , is an organosulfur compound with the formula 2S+CH2CH2COO−. This zwitterionic metabolite found in marine phytoplankton, seaweeds, and some species of terrestrial and aquatic vascular plants...
, a parent molecule of DMS and methanethiolMethanethiolMethanethiol is a colorless gas with a smell like rotten cabbage. It is a natural substance found in the blood and brain of humans and other animal as well as plant tissues. It is disposed of through animal feces. It occurs naturally in certain foods, such as some nuts and cheese...
in the oceans - Dimethyl selenide, a selenium analogue of DMS produced by bacteria and phytoplankton
- Dimethyl telluride, a tellurium analogue of DMS
- Emiliania huxleyiEmiliania huxleyiEmiliania huxleyi, often abbreviated "EHUX", is a species of coccolithophore with a global distribution from the tropics to subarctic waters. It is one of thousands of different photosynthetic plankton that freely drift in the euphotic zone of the ocean, forming the basis of virtually all marine...
, a coccolithophorid producing DMS - Swern oxidationSwern oxidationThe Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine...
- Gaia hypothesisGaia hypothesisThe Gaia hypothesis, also known as Gaia theory or Gaia principle, proposes that all organisms and their inorganic surroundings on Earth are closely integrated to form a single and self-regulating complex system, maintaining the conditions for life on the planet.The scientific investigation of the...