2,4-dithiapentane
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2,4-Dithiapentane is an
organosulfur compound Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
, and is the simplest alkyl dithioether. It is a colorless liquid with a strong odor, reminiscent of freshly prepared
mustard Mustard may refer to: Food and plants * Mustard (condiment), a paste or sauce made from mustard seeds used as a condiment * Mustard plant, one of several plants, having seeds that are used for the condiment ** Mustard seed, small, round seeds of ...
in the pure form. 2,4-Dithiapentane is the dimethyl
dithioacetal In organosulfur chemistry, thioacetals are the sulfur ('' thio-'') analogues of acetals (). There are two classes: the less-common monothioacetals, with the formula , and the dithioacetals, with the formula (symmetric dithioacetals) or (asy ...
of
formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
. Its synthesis was first reported in 1941. It is industrially prepared by the acid-catalyzed condensation of
methyl mercaptan Methanethiol (also known as methyl mercaptan) is an organosulfur compound with the chemical formula . It is a colorless gas with a distinctive putrid smell. In small amounts, it is pervasive in nature and found in certain foods, such as some n ...
, the main aromatic compound in both
halitosis Bad breath, also known as halitosis, is a symptom in which a noticeably unpleasant breath odour is present. It can result in anxiety among those affected. It is also associated with depression and symptoms of obsessive compulsive disorder. Th ...
and
foot odor Foot odor (also spelled foot odour) or bromodosis is a type of body odor that affects the feet of humans. Causes The main cause is foot sweat (also see focal hyperhidrosis). Sweat itself is odorless; however, it creates a beneficial environme ...
and a secondary compound in
flatulence Flatulence is the expulsion of gas from the Gastrointestinal tract, intestines via the anus, commonly referred to as farting. "Flatus" is the medical word for gas generated in the stomach or bowels. A proportion of intestinal gas may be swal ...
, with
formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
. :2 CH3SH + H2C=O → CH3SCH2SCH3 + H2O 2,4-Dithiapentane is found as an aromatic component in some
truffle A truffle is the Sporocarp (fungi), fruiting body of a subterranean ascomycete fungus, one of the species of the genus ''Tuber (fungus), Tuber''. More than one hundred other genera of fungi are classified as truffles including ''Geopora'', ''P ...
varieties. A synthetic version is used as the primary aromatic additive in commercial "truffle" products, such as
truffle oil Truffle oil is a modern culinary ingredient used to impart the flavor and aroma of truffles to a dish. The ingredient is commonly used as a finishing oil in a variety of dishes, including truffle fries, pasta dishes, pizzas, and puréed foods such ...
,
truffle butter "Truffle Butter" is a song by rapper Nicki Minaj featuring Drake and Lil Wayne. It is included as an exclusive bonus track on the iTunes edition of Minaj's third studio album ''The Pinkprint'' (2014). Produced by Young Money Entertainment with he ...
, truffle salt and truffle pastes, many of which contain no truffle content at all, and have elevated levels of 2,4-dithiapentane compared to levels in natural truffle products. It has also been found to occur naturally in rotting wood of some species in the genus ''
Lecythis ''Lecythis'' ( ) is a genus of woody plants in the Lecythidaceae family first described as a genus in 1758. It is native to Central America and South America. Several species produce edible seeds and referred to by a variety of common names inclu ...
''.


Notes and references

{{DEFAULTSORT:Dithiapentane, 2, 4- Thioethers