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Pyrithione zinc is the pyrithione complexes of zinc bromide, in the early 1930s, was already synthesized and used as a topical antifungal or antibacterial agent.
At room temperature Pyrithione zinc is white to yellow crystalline powder.
Slight characteristic odor.
CAS: 13463-41-7
MF: C10H8N2O2S2Zn
MW: 317.7
EINECS: 236-671-3
Synonyms
1-HYDROXY-2-PYRIDINE THIONE, ZN SALT;1-HYDROXYPYRIDINE-2-THIONE ZINC;Pyrithione zincique;Bis[(1-oxylatopyridinium)-2-ylthio] zinc;Bis[(1-oxylatopyridinium-2-yl)thio]zinc;Bis[[(pyridine 1-oxide)-2-yl]thio] zinc salt;Bis(2-pyridylthio) Zinc 1,1'-Dioxide 1-Hydroxypyridine-2-thione Zinc Salt 2-Pyridinethiol 1-Oxide Zinc Salt Zinc Pyrithione;zincpolyanemine
Insoluble in water. Solubility: water 15mg/kg; pH = 8 Water 35mg/kg; Ethanol 100mg/kg; polyethylene glycol (PEG400) 2000mg/kg.
A pH optimum range of 4.5 to 9.5; mass fraction of 10% suspension pH3.6.
Pyrithione zinc react with cationic and non-ionic surfactants forming insoluble precipitate, unstable in the light and oxidizer, when at higher temperatures ,it is not stable to acids and bases.
Pyrithione zinc is not compatible with EDTA, non-ionic surfactants make it partially deactivated.
When with the presence of heavy metals, chelation or anti-sequestration will occur, and these chelates are insoluble in water.
EEC and GB7916-87 provide that maximum allowable concentration of mass fraction of Pyrithione zinc on cosmetics is 0.5%, only for cleaning after using products.
General concentration 250~1000mg/kg (active), Pyrithione zinc can be used in gels, creams, lotions, talcum powder and anti-dandruff shampoo, deodorant and also for disinfecting articles.
Pyrithione zinc shampoos (in concentrations between 1 to 2%) and shampoos with selenium sulide have been reported to be effective in the treatment of scalp psoriasis.
However,their efficacy has not been substantiated by controlled studies.
There is also some evidence that shampoos with antifungal agents (e.g.ketoconazole)can have a beneficial effect on scalp conditions.
Pyrithione zinc should be noted, however, that the effectiveness of these shampoos is much smaller than these containing tars, corticosteroids or keratolytics.
Pyrithione zinc is a coordination complex of zinc and pyrithione that has antimicrobial and anticancer activities.
Pyrithione zinc is active against the bacteria E. coli, S. aureus, K. pneumoniae, A. baumannii, P. aeruginosa, E. faecium, E. faecalis, and E. cloacae (MICs = 1-4 μg/ml) and the fungus P. ovale when used at concentrations ranging from 0.01 to 10 μg/ml.
Pyrithione zinc reduces tumor growth in an SCC-4 mouse xenograft model when administered at a dose of 1 mg/kg per week for six weeks.
Formulations containing Pyrithione zinc have been used in the treatment of dandruff.
Pyrithione zinc is the active ingredient in several shampoos used to control dandruff and seborrheic dermatitis and is also effective in the therapy of tinea versicolor.
Pyrithione zinc remains unclear whether the beneficial effects are caused by an antiproliferative or antimicrobial effect or both.
Pyrithione zinc is substantive to the hair, allowing continued therapeutic effect after washing.
Pyrithione zinc (or pyrithione zinc) is a coordination complex of zinc.
Pyrithione zinc has fungistatic (inhibiting the division of fungal cells) and bacteriostatic (inhibiting bacterial cell division) properties and is used in the treatment of seborrhoeic dermatitis and dandruff.
Photolysis
Pyrithione zinc is very rapidly transformed by photolysis.
Experiments conducted under sterile conditions with a light:dark cycle of 12:12 hours have shown that, under exposure to light, the concentration of [pyridine-2,6-14C]zinc pyrithione in pH 9 buffer was reduced to 33% of the radioactivity added in 15 min.
Data from this study also demonstrated that less than 5% of the 14C added occurred as Pyrithione zinc after 1 hour of exposure to light.
Similar results have been achieved when photolysis of zinc pyrithione was investigated by use of artificial seawater.
In this study, the parent compound constituted 45% of the radioactivity added after 15 min while, after 24 hours, 1.3% of the added dose occurred as Pyrithione zinc.
The estimated half-lives of the photolytic transformation of Pyrithione zinc was 13 min in pH 9 buffer and 17.5 min in artificial seawater.
Pyrithione zinc Chemical Properties
Melting point: approximate 240℃
Density: 1.782 g/cm3(Temp: 25 °C)
Vapor pressure: 0Pa at 25℃
Storage temp.: Sealed in dry,Room Temperature
Solubility: almost transparency in Pyridine
Form: Powder
Color: White to Orange to Green
Odor: Mild Characteristic
Water Solubility: Insoluble (<0.1 g/100 mL at 21 ºC)
Merck: 14,7994
InChI: InChI=1S/2C5H5NOS.Zn/c2*7-6-4-2-1-3-5(6)8;/h2*1-4,8H;/q;;+2/p-2
InChIKey: OTPSWLRZXRHDNX-UHFFFAOYSA-L
LogP: 0.9 at 25℃ and pH7.5-7.7
Surface tension: 73mN/m at 7.22mg/L and 20℃
CAS DataBase Reference: 13463-41-7(CAS DataBase Reference)
EPA Substance Registry System: Pyrithione zinc (13463-41-7)
Structure of the compound
The pyrithione ligands, which are formally monoanions, are chelated to Zn2+ via oxygen and sulfur centers.
In the crystalline state, zinc pyrithione exists as a centrosymmetric dimer (see figure), where each zinc is bonded to two sulfur and three oxygen centers.
In solution, however, the dimers dissociate via scission of one Zn-O bond.
Pyrithione zinc was first described in the 1930s.
Pyrithione zinc is the conjugate base derived from 2-mercaptopyridine-N-oxide (CAS# 1121-31-9), a derivative of pyridine-N-oxide.
Uses
Shampoo for dandruff,zinc pyrithione can inhibit Gram positive and negative bacteria and mold growth,Care hair Effectively , delay hair aging ,control white hair and hair loss generation.
Pyrithione zinc is also used as a cosmetic preservative, oil, paint biocide.
Pyrithione zinc has a strong killing power on fungi and bacteria so that it can effectively kill dandruff fungus,playing a role in dandruff.
zinc pyrithione is a preservative against bacteria, fungi, and yeast.
Pyrithione zinc is unstable in light and in the presence of oxidizing agents.
Pyrithione zinc is useful in gels, creams, heavy lotions, and talcum powder.
Reactions may lead to photosensitive eczema and actinic reticuloid syndrome.
Pyrithione zinc is used as antifungal, antibacterial and antiseborrheic agent used in many shampoos and hair creams.
Pyrithione zinc is directly cytotoxic and has antimicrobial effects.
Pyrithione zinc is found in many shampoos (DHS-Zinc, Head and Shoulders) and should be applied for 5 minutes daily for 2 weeks.
Pyrithione zinc is the active ingredient in several shampoos used to control dandruff and seborrheic dermatitis and is also effective in the therapy of tinea versicolor.
Pyrithione zinc remains unclear whether the beneficial effects are caused by an antiproliferative or antimicrobial effect or both.
Pyrithione zinc is substantive to the hair, allowing continued therapeutic effect after washing.
Pharmaceutical Applications
Pyrithione zinc is a regulator of keratinization, selenium sulfide has antimicrobial properties and ketoconazole is an antifungal agent (i.e.can provide the reduction of the lipophilic yeast Malassezia furfur).
Medicine
Pyrithione zinc can be used to treat dandruff and seborrhoeic dermatitis.
Pyrithione zinc also has antibacterial properties and is effective against many pathogens from the Streptococcus and Staphylococcus genera.
Pyrithione zinc's other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea versicolor, and vitiligo.
Paint
Because of its low solubility in water (8 ppm at neutral pH), zinc pyrithione is suitable for use in outdoor paints and other products that protect against mildew and algae.
Pyrithione zinc is an algaecide.
Pyrithione zinc is chemically incompatible with paints relying on metal carboxylate curing agents.
When Pyrithione zinc is used in latex paints with water containing much iron, a sequestering agent that preferentially binds the iron ions is needed.
Pyrithione zinc is decomposed by ultraviolet light slowly, providing years of protection in direct sunlight.
Sponges
Pyrithione zinc is an antibacterial treatment for household sponges, as used by the 3M Corporation.
Clothing
A process to apply Pyrithione zinc to cotton with washable results was patented in the United States in 1984.
Pyrithione zinc is used to prevent microbe growth in polyester.
Textiles with applied Pyrithione zinc protect against odor-causing microorganisms.
Export of antimicrobial textiles reached US$497.4 million in 2015.
Synthesis
1000 g of sodium pyrithione, 20% aqueous solution (1.34 mmol of sodium pyrithione) was added to a 2L reactor equipped with a mechanical agitator and warmed to 70 °C with stirring.
To the solution was added 190 g of 50 % zinc chloride (0.7 mmol of zinc chloride) over 10 minutes.
After the completion of the addition, the solution was stirred at 70 °C for one hour, dehydrated and then washed with 500 g of distilled water.
The solid thus obtained was dried with a heated-air drier at 70 °C to have a moisture content of less than 0.5 % and ground with a hammer mill to obtain a find powder of zinc pyrithione.
The Pyrithione zinc thus obtained was 212 g with a yield of 99.5 %.
Health effects
Pyrithione zinc is approved for over-the-counter topical use in the United States as a treatment for dandruff and is the active ingredient in several anti-dandruff shampoos and body wash gels.
In its industrial forms and strengths, Pyrithione zinc may be harmful by contact or ingestion.
Pyrithione zinc can in the laboratory setting trigger a variety of responses, such as DNA damage in skin cells.
