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).

Contents

Onion release

The chemical is released from onions, Allium cepa, as they are sliced. The release is due to the breaking open of the onion cells, which releases enzymes called alliinases. Alliinases then break down amino acid sulfoxides, generating sulfenic acids. A specific sulfenic acid, allicin or 1-propenesulfenic acid, is rapidly rearranged by another enzyme, the lachrymatory factor synthase (LFS) to give syn-propanethial S-oxide. [3] Vapors from this volatile liquid induces tearing. [4]

A structurally related lachrymatory compound, syn-butanethial S-oxide, C4H8OS, has been found in another genus Allium plant, Allium siculum . [5]

Structure of trans-3,4-diethyl-1,2-dithietane 1,1-dioxide Trans-3,4-diethyl-1,2-dithietane 1,1-dioxide.svg
Structure of trans-3,4-diethyl-1,2-dithietane 1,1-dioxide

Propanethial S-oxide forms a stable thiosultone dimer, trans-3,4-diethyl-1,2-dithietane 1,1-dioxide. [6]

Related Research Articles

<span class="mw-page-title-main">Onion</span> Bulbous vegetable grown for food

An 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 2011. The onion's close relatives include garlic, scallion, leek, and chives.

<span class="mw-page-title-main">Allicin</span> Chemical compound

Allicin is an organosulfur compound obtained from garlic and leeks. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. Allicin is an antifeedant, i.e. the defense mechanism against attacks by pests on the garlic plant.

<span class="mw-page-title-main">Elephant garlic</span> Subspecies of flowering plant

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

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 derivatives, e.g., saccharin. Nature is abound with organosulfur compounds—sulfur is vital 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.

<span class="mw-page-title-main">Carbodiimide</span> Class of organic compounds with general structure RN=C=NR

In organic chemistry, a carbodiimide is a functional group with the formula RN=C=NR. On Earth they are exclusively synthetic, but in interstellar space the parent compound HN=C=NH has been detected by its maser emissions.

Organoselenium chemistry is the science exploring the properties and reactivity of organoselenium compounds, chemical compounds containing carbon-to-selenium chemical bonds. Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected. Organoselenium compounds are found at trace levels in ambient waters, soils and sediments.

1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula C6H4O2. It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and ethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many derivatives which are known.

Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almond odor at higher concentration. Salicylaldehyde is a precursor to coumarin and a variety of chelating agents.

Tetrahydrothiophene is an organosulfur compound with the formula (CH2)4S. The molecule consists of a five-membered saturated ring with four methylene groups and a sulfur atom. It is the saturated analog of thiophene and is therefore the sulfur analog of THF. It is a volatile, colorless liquid with an intensely unpleasant odor. It is also known as thiophane, thiolane, or THT.

<span class="mw-page-title-main">Sulfenic acid</span> Organosulfur compound of the form R–SOH

In chemistry, a sulfenic acid is an organosulfur compound and oxoacid with the general formula R−S−OH. It is the first member of the family of organosulfur oxoacids, which also include sulfinic acids and sulfonic acids, 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.

<span class="mw-page-title-main">Alliinase</span> Class of enzyme

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

<span class="mw-page-title-main">Dithietane</span> Class of chemical compounds

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:

<span class="mw-page-title-main">Thiosulfinate</span> Functional group

In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R. Thiolsulfinates are also named as alkanethiosulfinic acid esters.

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

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

<span class="mw-page-title-main">Dimethyl trisulfide</span> 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.

<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 plant in the 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.

<span class="mw-page-title-main">Sulfinyl halide</span> Class of chemical compounds

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.

<span class="mw-page-title-main">Thiosulfurous acid</span> Chemical compound

Thiosulfurous acid is a hypothetical chemical compound with the formula HS−S(=O)−OH or HO−S(=S)−OH. Attempted synthesis leads to polymers. It is a low oxidation state (+1) sulfur acid. It is the Arrhenius acid for disulfur monoxide. Salts derived from thiosulfurous acid, which are also unknown, are named "thiosulfites", "thionosulfites" or "sulfurothioites". The ion is S=SO2−
2
.

<span class="mw-page-title-main">Sulfine</span> 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.
  6. Block, E; Bazzi, AA; Revelle, LK (1980). "The chemistry of sulfines. 6. Dimer of the onion lachrymatory factor: the first stable 1,2-dithietane derivative". J. Am. Chem. Soc. 102 (7): 2490–2491. doi:10.1021/ja00527a074.