Syn-Propanethial-S-oxide

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syn-Propanethial S-oxide
Syn-Propanethial S-oxide Structural Formula V1.svg
Syn-propanethial-S-oxide-3D-balls.png
Names
IUPAC name
(Z)-propylidene-λ4-sulfanone [1]
Other names
Thiopropanal S-oxide
1-Sulfinylpropane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3 Yes check.svgY
    Key: BAZSXBOAXJLRNH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3
    Key: BAZSXBOAXJLRNH-UHFFFAOYAF
  • O=S=C/CC
Properties
C3H6OS
Molar mass 90.14 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

syn-Propanethial S-oxide (or (Z)-propanethial S-oxide), a member of a class of organosulfur compounds known as thiocarbonyl S-oxides (formerly "sulfines"), [2] is a volatile liquid that acts as a lachrymatory agent (triggers tearing and stinging on contact with the eyes). The chemical is released from onions, Allium cepa, as they are sliced. The release is due to the breaking open of the onion cells and their releasing enzymes called alliinases, which then break down amino acid sulfoxides, generating sulfenic acids. A specific sulfenic acid, 1-propenesulfenic acid, formed when onions are cut, is rapidly rearranged by a second enzyme, called the lachrymatory factor synthase or LFS, giving syn-propanethial S-oxide. [3] The gas diffuses through the air and, on contact with the eye, it stimulates sensory neurons creating a stinging, painful sensation. Tears are released from the tear glands to dilute and flush out the irritant. [4] A structurally related lachrymatory compound, syn-butanethial S-oxide, C4H8OS, has been found in another genus Allium plant, Allium siculum . [5]

See also

Related Research Articles

Onion Bulbous vegetable, grown for food

The onion, also known as the bulb onion or common onion, is a vegetable that is the most widely cultivated species of the genus Allium. The shallot is a botanical variety of the onion which was classified as a separate species until 2010. Its close relatives include garlic, scallion, leek, and chive.

Acetyl group Chemical compound

In organic chemistry, acetyl is a moiety, the acyl with chemical formula CH3CO. It is sometimes represented by the symbol Ac (not to be confused with the element actinium).

Allicin Chemical compound

Allicin is an organosulfur compound obtained from garlic, a species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J. Cavallito and John Hays Bailey in 1944. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. The allicin generated is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. Allicin is part of a defense mechanism against attacks by pests on the garlic plant.

Elephant garlic Subspecies of flowering plant

Elephant garlic is a perennial plant belonging to the onion genus. It has a tall, solid, flowering stalk and broad, flat leaves. The flavor is milder than garlic and can be eaten raw in salads, roasted, or sauteed, but is generally not a substitute for conventional garlic in cooking. It is sometimes confused with solo garlic.

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.

In chemical nomenclature, the IUPAC nomenclature of inorganic chemistry is a systematic method of naming inorganic chemical compounds, as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in Nomenclature of Inorganic Chemistry. Ideally, every inorganic compound should have a name from which an unambiguous formula can be determined. There is also an IUPAC nomenclature of organic chemistry.

Tetrahydrothiophene is an organosulfur compound with the formula (CH2)4S. It contains a five-membered ring consisting of four carbon atoms and a sulfur atom. It is the saturated analog of thiophene. It is a volatile, colorless liquid with an intensely unpleasant odor. It is also known as thiophane, thiolane, or THT.

Monoxide Any oxide containing only one atom of oxygen.

A monoxide is any oxide containing only one atom of oxygen. A well known monoxide is carbon monoxide; see carbon monoxide poisoning.

Sulfenic acid

A sulfenic acid is an organosulfur compound and oxoacid with the general formula RSOH. It is the first member of the family of organosulfur oxoacids, which also include sulfinic acids and sulfonic acids, RSO2H and RSO3H, respectively. The base member of the sulfenic acid series with R = H is hydrogen thioperoxide.

<i>Petiveria</i> Genus of flowering plants

Petiveria is a genus of flowering plants in the pigeonberry family, Petiveriaceae. The sole species it contains, Petiveria alliacea, is native to Florida and the lower Rio Grande Valley of Texas in the United States, Mexico, Central America, the Caribbean, and tropical South America. Introduced populations occur in Benin and Nigeria. It is a deeply rooted herbaceous perennial shrub growing up to 1 m (3.3 ft) in height and has small greenish piccate flowers. The roots and leaves have a strong acrid, garlic-like odor which taints the milk and meat of animals that graze on it.

Alliinase Class of enzyme

In enzymology, an alliin lyase is an enzyme that catalyzes the chemical reaction

Dithietane

Dithietanes are saturated heterocyclic compounds that contain two divalent sulfur atoms and two sp3-hybridized carbon centers. Two isomers are possible for this class of organosulfur compounds:

In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choosing between multiple possibilities in situations where it is important to decide on a unique name. It is intended for use in legal and regulatory situations.

Thiosulfinate

In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R (R are organic substituents). Thiolsulfinates are also named as alkanethiosulfinic (or arenethiosulfinic) acid esters. They are the first member of a family of compounds containing an oxidized disulfide bond. Other members of this family include thiosulfonates (R-SO2-S-R), α-disulfoxides (R-S(O)-S(O)-R), sulfinyl sulfones (R-S(O)-SO2-R), and α-disulfones (R-SO2-SO2-R), all of which are known. The thiosulfinate group can occur in cyclic as well as acyclic structures.

<i>Allium stipitatum</i> Species of flowering plant

Allium stipitatum, Persian shallot, is an Asian species of onion native to central and southwestern Asia.

The International Union of Pure and Applied Chemistry publishes many books which contain its complete list of definitions. The definitions are divided into seven "colour books": Gold, Green, Blue, Purple, Orange, White, and Red. There is also an eighth book—the "Silver Book".

<i>Allium siculum</i> Species of flowering plant

Allium siculum, known as honey garlic, Sicilian honey lily, Sicilian honey garlic, or Mediterranean bells, is a European and Turkish species of plants genus Allium. It is native to the regions around the Mediterranean and Black Seas, and grown in other regions as an ornamental and as a culinary herb.

Sulfinyl halide

Sulfinyl halide have the general formula R−S(O)−X, where X is a halogen. They are intermediate in oxidation level between sulfenyl halides, R−S−X, and sulfonyl halides, R−SO2−X. The best known examples are sulfinyl chlorides, thermolabile, moisture-sensitive compounds, which are useful intermediates for preparation of other sufinyl derivatives such as sulfinamides, sulfinates, sulfoxides, and thiosulfinates. Unlike the sulfur atom in sulfonyl halides and sulfenyl halides, the sulfur atom in sulfinyl halides is chiral, as shown for methanesulfinyl chloride.

A descriptor is in chemical nomenclature a prefix placed before the systematic substance name, which describes the configuration or the stereochemistry of the molecule. Some listed descriptors are only of historical interest and should not be used in publications anymore as they do not correspond with the modern recommendations of the IUPAC. Stereodescriptors are often used in combination with locants to clearly identify a chemical structure unambiguously.

Sulfine Chemical compound

Sulfinylmethane or sulfine is an organic compound with molecular formula H2CSO. It is the simplest sulfine. Sulfines are chemical compounds with the general structure XY=SO. IUPAC considers the term 'sulfine' obsolete, preferring instead thiocarbonyl S-oxide, despite this the use of the term sulfine still predominates in the chemical literature.

References

  1. IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-74.2.2.1.8". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPACRSC. ISBN   978-0-85404-182-4.
  2. Zwanenburg, B. (2004). "Thioaldehyde and Thioketone S-Oxides and S-Imides (Sulfines and Derivatives)". In Padwa, A. (ed.). Heteroatom Analogues of Aldehydes and Ketones. Science of Synthesis. Vol. 27. pp. 135–176. ISBN   978-1-58890-204-7.
  3. Block, E. (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. p. 132. ISBN   978-0-85404-190-9.
  4. Scott, T. (1999-10-21). "What is the chemical process that causes my eyes to tear when I peel an onion?". Ask the Experts: Chemistry. Scientific American . Retrieved 2012-04-03.
  5. Kubec, R.; Cody, R. B.; Dane, A. J.; Musah, R. A.; Schraml, J.; Vattekkatte, A.; Block, E. (2010). "Applications of DART Mass Spectrometry in Allium Chemistry. (Z)-Butanethial S-Oxide and 1-Butenyl Thiosulfinates and their S-(E)-1-Butenylcysteine S-Oxide Precursor from Allium siculum". Journal of Agricultural and Food Chemistry. 58 (2): 1121–1128. doi:10.1021/jf903733e. PMID   20047275.