Pyrithione

Last updated
Pyrithione
Pyrithione-tautomerism-2D-skeletal.png
Interconversion of pyrithione tautomers
thione form on the left, thiol form on the right
Names
Preferred IUPAC name
1-Hydroxy-2(1H)-pyridinethione (thione)
2-Pyridinethiol 1-oxide (thiol)
Other names
Omadine
thione: 1-Hydroxypyridine-2-thione
   N-Hydroxypyridine-2-thione
thiol: 2-Mercaptopyridine monoxide
     2-Mercaptopyridine N-oxide
     2-Mercaptopyridine 1-oxide
Identifiers
3D model (JSmol)
109936
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.013.027 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-328-9
  • thione:214-329-4
913415
PubChem CID
UNII
  • thione:InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,7H
    Key: YBBJKCMMCRQZMA-UHFFFAOYSA-N
  • thiol:InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H
    Key: FGVVTMRZYROCTH-UHFFFAOYSA-N
  • thiolate salt:InChI=1S/C5H5NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4,8H;/q;+1/p-1
    Key: WNGMMIYXPIAYOB-UHFFFAOYSA-M
  • thione salt:InChI=1S/C5H4NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4H;/q-1;+1
    Key: XNRNJIIJLOFJEK-UHFFFAOYSA-N
  • thione:c1ccn(c(=S)c1)O
  • thiol:C1=CC=[N+](C(=C1)S)[O-]
  • thiolate salt:c1cc[n+](c(c1)[S-])[O-].[Na+]
  • thione salt:c1ccn(c(=S)c1)[O-].[Na+]
Properties
C5H5NOS
Molar mass 127.16 g·mol−1
AppearanceBeige crystalline powder
Melting point 70 to 73 °C (158 to 163 °F; 343 to 346 K)
2.5 g L−1 at 20 °C
Solubility Soluble: benzene, chloroform, dichloromethane, dimethylformamide, dimethylsulfoxide, ethyl acetate [1]
Slightly soluble: diethyl ether, ethanol, methyl tert-butyl ether, tetrahydrofuran [1]
Acidity (pKa)−1.95 (proton addition), 4.6 [2] [3]
Hazards
GHS labelling:
GHS-pictogram-skull.svg
Danger
H301, H315, H319, H335
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pyrithione is the common name of an organosulfur compound with molecular formula C
5H
5NOS, chosen as an abbreviation of pyridinethione, and found in the Persian shallot. [4] It exists as a pair of tautomers, the major form being the thione 1-hydroxy-2(1H)-pyridinethione and the minor form being the thiol 2-mercaptopyridine N-oxide; it crystallises in the thione form. [5] It is usually prepared from either 2-bromopyridine, [1] 2-chloropyridine, [6] [7] or 2-chloropyridine N-oxide, [8] and is commercially available as both the neutral compound and its sodium salt. [1] It is used to prepare zinc pyrithione, [9] [10] which is used primarily to treat dandruff and seborrhoeic dermatitis in medicated shampoos, [11] [12] though is also an anti-fouling agent in paints. [13]

Contents

Preparation

The preparation of pyrithione was first reported in 1950 [13] by Shaw [14] and was prepared by reaction of 2-chloropyridine N-oxide with sodium hydrosulfide followed by acidification, [8] or more recently with sodium sulfide. [15] 2-chloropyridine N-oxide itself can be prepared from 2-chloropyridine using peracetic acid. [16] Another approach involves treating the same starting N-oxide with thiourea to afford pyridyl-2-isothiouronium chloride N-oxide which undergoes base hydrolysis to pyrithione. [1] [17] 2-Bromopyridine can be oxidised to its N-oxide using a suitable peracid (as per 2-chloropyridine), both approaches being analogous to that reported in Organic Syntheses for the oxidation of pyridine to its N-oxide. [1] [18] A substitution reaction using either sodium dithionite (Na
2S
2O
4) or sodium sulfide with sodium hydroxide will allow the replacement of the bromo substituent with a thiol functional group. [1] [15]

Synth-Pyrithion.png

The alternative strategy is to form the mercaptan before introducing the N-oxide moiety. 2-Mercaptopyridine was originally synthesized in 1931 by heating 2-chloropyridine with calcium hydrosulfide, [6] an approach similar that first used to prepare pyrithione. [8] The analogous thiourea approach via a uronium salt was reported in 1958 and provides a more convenient route to 2-mercaptopyridine. [7] Oxidation to the N-oxide can then be undertaken.

The disulfide dipyrithione, 2,2'-dithiobis(pyridine-N-oxide) Dipyrithione.svg
The disulfide dipyrithione, 2,2'-dithiobis(pyridine-N-oxide)

Pyrithione is found as a natural product in the Allium stipitatum plant, an Asian species of onion, also known as the Persian shallot. [4] Its presence was detected using positive ion mass spectrometry using a DART ion source [19] and the disulfide dipyrithione  [ de ] (2,2'-disulfanediylbis(pyridine)-1,1'-dioxide) has been reported from the same species. [20] Dipyrithione can be prepared in a laboratory by oxidation of pyrithione with chlorine in the presence of sodium hydroxide: [16]

2 C
5H
4NOSH  +  Cl
2  +   2 NaOH   →  ONC
5H
4–S–S–C
5H
4NO  +   2 NaCl   +   2 H
2O

Dipyrithione is used as a fungicide and bactericide, [8] and has been reported to possess novel cytotoxic activity by inducing apoptosis. [21] However, as apoptosis only occurs in higher organisms, this mechanism isn't relevant to the antifungal and bacteric idal properties of pyrithione.

Properties

Tautomerisation of the sodium salt of pyrithione (thione form on the left, thiolate form on the right) Tautomers of sodium salt of pyrithione.png
Tautomerisation of the sodium salt of pyrithione
(thione form on the left, thiolate form on the right)

Pyrithione exists as a pair of prototropes, a form of tautomerism whereby the rapid interconversion of constitutional isomers involves the shift of a single proton, in this case between the sulfur and oxygen atoms (shown in the infobox above). [3] [22] [23]

Salts of the conjugate base of pyrithione can also be considered to exhibit tautomerism by notionally associating the sodium ion with whichever heteroatom bears the negative charge of the anion (as opposed to the formal charges associated with the N-oxide); however, considering the anion alone, this could also be described as an example of resonance.

Pyrithione is a weak acid with pKa values of −1.95 and +4.6 (thiol proton), [2] [3] but is a markedly stronger acid than either of its parent compounds (pyridine-N-oxide and pyridine-2-thiol), both of which have pKa > 8. [22] It is only slightly soluble in water (2.5 g L−1) but is soluble in many organic solvents (including benzene, chloroform, dichloromethane, dimethylformamide, dimethylsulfoxide, and ethyl acetate) and slight solubility in others (diethyl ether, ethanol, methyl tert-butyl ether, and tetrahydrofuran). [1]

Pyrithione can be used as a source of hydroxyl radical in organic synthesis [24] as it photochemically decomposes to HO• and (pyridin-2-yl)sulfanyl radical. [25]

Applications

Zink-Pyrithion.svg
Zinc-pyrithione-dimer-3D-balls.png
Structures of 1:2 complexes of zinc and the conjugate base of pyrithione
Top: Structural formula of the monomer
Bottom: Ball-and-stick model of the dimer

The conjugate base of pyrithione (pyrithionate ion) is an anion containing two donor atoms, a sulfur atom and an oxygen atom each bearing a negative formal charge; the nitrogen atom remains formally positively charged. The thiolate anion can be formed by reaction with sodium carbonate, and zinc pyrithione is formed when zinc chloride is added. [10] The anion can act as either a monodentate or bidentate ligand and forms a 1:2 complex with a zinc(II) metal centre. Zinc pyrithione has been used since the 1930s though its preparation was not disclosed until a 1955 British patent [13] in which pyrithione was reacted directly with hydrated zinc sulfate in ethanol. [9] In its monomeric form, zinc pyrithione has two of the anions chelated to a zinc centre with a tetrahedral geometry. In the solid state, it forms a dimer in which each zinc centre adopts a trigonal bipyramidal geometry with two of the anions acting as bridging ligands coordinated through the oxygen atoms in the axial positions. [26] In solution, the dimers dissociate via scission of zinc-oxygen bonds to each bridging ligand. Further dissociation of the monomer into its constituents can occur and is undesirable as the complex is more potent in medical applications; for this reason, zinc carbonate can be added to formulations as it inhibits the monomer dissociation. [27]

Zinc pyrithione has a long history of use in medicated shampoos to treat dandruff and seborrhoeic dermatitis [28] [29] [30] (dandruff can be considered a mild form of seborrheic dermatitis [12] ). It exhibits both antifungal and antimicrobial properties, inhibiting the Malassezia yeasts which promote these scalp conditions. [27] The mechanisms by which this work are the subject of ongoing study. [31] [32] It can be used as an antibacterial agent against Staphylococcus and Streptococcus infections for conditions such as athlete's foot, eczema, psoriasis, and ringworm. [13] It is known to be cytotoxic against Pityrosporum ovale , especially in combination with ketoconazole, which is the preferred formulation for seborrheic dermatitis. [11] Pyrithione itself inhibits membrane transport processes in fungi. [22] [33]

Paints used in external environments sometimes include zinc pyrithione as a preventive against algae and mildew. [13] [34]

Related Research Articles

<span class="mw-page-title-main">Pyridine</span> Heterocyclic aromatic organic compound

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom (=N−). It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide.

<span class="mw-page-title-main">Dandruff</span> Skin condition of the scalp

Dandruff is a skin condition that mainly affects the scalp. Symptoms include flaking and sometimes mild itchiness. It can result in social or self-esteem problems. A more severe form of the condition, which includes inflammation of the skin, is known as seborrhoeic dermatitis.

<span class="mw-page-title-main">Seborrhoeic dermatitis</span> Skin disease

Seborrhoeic dermatitis is a long-term skin disorder. Symptoms include flaky, scaly, greasy, and occasionally itchy and inflamed skin. Areas of the skin rich in oil-producing glands are often affected including the scalp, face, and chest. It can result in social or self-esteem problems. In babies, when the scalp is primarily involved, it is called cradle cap. Seborrhoeic dermatitis of the scalp may be described in lay terms as dandruff due to the dry, flaky character of the skin. However, as dandruff may refer to any dryness or scaling of the scalp, not all dandruff is seborrhoeic dermatitis. Seborrhoeic dermatitis is sometimes inaccurately referred to as seborrhoea.

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

Zinc pyrithione is a coordination complex of zinc. It has fungistatic and bacteriostatic properties and is used in the treatment of seborrhoeic dermatitis and dandruff.

<span class="mw-page-title-main">Tautomer</span> Isomers of chemical compounds that interconvert

Tautomers are structural isomers of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life.

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

Acetylacetone is an organic compound with the chemical formula CH3−C(=O)−CH2−C(=O)−CH3. It is classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3−C(=O)−CH=C(−OH)−CH3. The mixture is a colorless liquid. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. Acetylacetone is a building block for the synthesis of many coordination complexes as well as heterocyclic compounds.

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">Cradle cap</span> Crusting or scaling of a babys scalp

Cradle cap is crusty or oily scaly patches on a baby's scalp. The condition is not painful or itchy, but it can cause thick white or yellow scales that are not easy to remove. Cradle cap most commonly begins sometime in the first three months but can occur in later years. Similar symptoms in older children are more likely to be dandruff than cradle cap. The rash is often prominent around the ear, the eyebrows or the eyelids. It may appear in other locations as well, where it is called infantile seborrhoeic dermatitis. Cradle cap is just a special—and more benign—case of this condition. The exact cause of cradle cap is not known. Cradle cap is not spread from person to person. It is also not caused by poor hygiene. It is not an allergy, and it is not dangerous. Cradle cap often lasts a few months. In some children, the condition can last until age 2 or 3.

Selenium disulfide, also known as selenium sulfide, is a chemical compound and medication used to treat seborrheic dermatitis, dandruff, and pityriasis versicolor. It is applied to the affected area as a lotion or shampoo. Symptoms frequently return if treatment is stopped.

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

Sodium dithionite is a white crystalline powder with a sulfurous odor. Although it is stable in dry air, it decomposes in hot water and in acid solutions.

Pyrylium is a cation with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.

<span class="mw-page-title-main">Dithiocarbamate</span> Chemical group (>N–C(=S)–S–)

In organic chemistry, a dithiocarbamate is a functional group with the general formula R2N−C(=S)−S−R and structure >N−C(=S)−S−. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms.

Pyridine-<i>N</i>-oxide Chemical compound

Pyridine-N-oxide is the heterocyclic compound with the formula C5H5NO. This colourless, hygroscopic solid is the product of the oxidation of pyridine. It was originally prepared using peroxyacids as the oxidising agent. The compound is used infrequently as an oxidizing reagent in organic synthesis.

Zinc compounds are chemical compounds containing the element zinc which is a member of the group 12 of the periodic table. The oxidation state of zinc in most compounds is the group oxidation state of +2. Zinc may be classified as a post-transition main group element with zinc(II). Zinc compounds are noteworthy for their nondescript appearance and behavior: they are generally colorless, do not readily engage in redox reactions, and generally adopt symmetrical structures.

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

Climbazole is a topical antifungal agent commonly used in the treatment of human fungal skin infections such as dandruff, seborrhoeic dermatitis and eczema. Climbazole has shown a high in vitro and in vivo efficacy against Malassezia spp. that appear to play an important role in the pathogenesis of dandruff. Its chemical structure and properties are similar to other azole fungicides such as ketoconazole, clotrimazole and miconazole.

<span class="mw-page-title-main">2-Mercaptopyridine</span> Chemical compound

2-Mercaptopyridine is an organosulfur compound with the formula HSC5H4N. This yellow crystalline solid is a derivative of pyridine. The compound and its derivatives serve primarily as acylating agents. A few of 2-mercaptopyridine's other uses include serving as a protecting group for amines and imides as well as forming a selective reducing agent. 2-Mercaptopyridine oxidizes to [[2,2′-dipyridyl disulfide]].

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

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

Anti-seborrheics are drugs effective in seborrheic dermatitis. Selenium sulfide, zinc pyrithione, corticosteroids, imidazole antifungals, and salicylic acid are common anti-seborrheics.

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

2-Mercaptobenzothiazole is an organosulfur compound with the formula C6H4(NH)SC=S. A white solid, it is used in the sulfur vulcanization of rubber.

<span class="mw-page-title-main">2-Bromopyridine</span> Chemical compound

2-Bromopyridine is an aryl bromide and isomer of bromopyridine with the formula BrC5H4N. It is a colorless liquid that is used as an intermediate in organic synthesis. It can be prepared from 2-aminopyridine via diazotization followed by bromination.

References

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  32. ↑ Reeder, N. L.; Xu, J.; Youngquist, R. S.; Schwartz, James R.; Rust, R. C.; Saunders, C. W. (2011). "The Antifungal Mechanism of Action of Zinc Pyrithione". Br. J. Dermatol. 165 (s2): 9–12. doi:10.1111/j.1365-2133.2011.10571.x. PMID   21919897. S2CID   31243048.
  33. ↑ Ermolayeva, Elena; Sanders, Dale (1995). "Mechanism of Pyrithione-Induced Membrane Depolarization in Neurospora crassa". Appl. Environ. Microbiol. 61 (9): 3385–3390. Bibcode:1995ApEnM..61.3385E. doi:10.1128/AEM.61.9.3385-3390.1995. PMC   167618 . PMID   7574648.
  34. ↑ USpatent 4039312,Joseph, Marcel&Patru, Gaston,"Bacteriostatic, fungistatic and algicidal compositions, particularly for submarine paints",published 1977-08-02, assigned to Joseph, Marceland Patru, Gaston
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