Disinfectants | Triclosan is an efficient broad-spectrum topical antimicrobial
disinfectant which is normally white or off-white crystalline
powder. It has a slightly phenolic odor. It is insoluble in water
but easily soluble in organic solvents and alkali. It has a
relative stable chemical property and is heating-resistant and also
resistant to acid and alkali hydrolysis without generating any
symptoms of the toxicity and environmental pollution. It is
internationally recognized as a fungicide variety with specific
efficacy. It can kill bacteria such as Staphylococcus aureus,
Escherichia coli and fungi such as Candida albicans. It also has an
inhibitory effect on the virus (e.g., hepatitis B virus, etc.)
while being able to protect the beneficial bacteria. The mechanism
of action of triclosan is as below: it is first adsorbed on the
bacterial cell wall and then further penetrates through the cell
wall and has reaction with the lipid and protein in the cytoplasm,
and thus resulting in protein denaturation which further kill the
bacteria. Currently it has been widely applied to highly-efficient
medicated soap (health soap, health lotion), removing underarm odor
(foot aerosol), hand sanitizer, wound disinfectant sprays, medical
equipment disinfectants, hygiene cleanser (cream), and air
fresheners and refrigerator deodorants and some other daily
chemicals. It is also used for the cleaning of the health fabric
and the anti-corrosion treatment of plastics. Its high purity
version can be added to the toothpaste and mouthwash for treatment
of gingivitis, periodontitis and oral ulcers. The State content
must not exceed 0.3%. |
Carcinogenicity | In 2004, a teacher (Dr. Peter Vikesland) from the Virginia Tech
University (US) had found from the experiments that the reaction
between the triclosan-containing product and the
chlorine-containing tap water containing can generate a substance
known as "chloroform aryl", that is, chloroform (chemical name:
trichloromethane) which is a colorless, volatile liquid with a
special sweetness. Upon exposure to light, it will be oxidized to
generate hydrogen chloride and phosgene. It had been once used as
an anesthetic. Animal experiments have found that this substance
will do harm to the heart and liver with mild teratogenicity and
can induce the liver cancer of mice. However, so far no studies on
the human carcinogenicity have been reported. For insurance
purposes, both the International Cancer Research Centre and the
United States have already has the chloroform be listed as
suspected carcinogens to the human body. |
Toothpaste Standard | The national standard of the toothpaste used in China is the new
national standard of toothpaste (GB8372-2008) implemented on
February 1, 2009. Compared with the 2001 version of toothpaste
standard, the new national standard has been supplemented and
adjusted in various aspects. In the new national standard of
toothpaste, the prohibited or restricted ingredients include nearly
1,500 kinds, including diethylene glycol and triclosan. The
provision of diethylene glycol is that it is not allowed to
artificially add it to the raw materials, such as being introduced
as impurities. Its content in the toothpaste should not exceed
0.1%. Triclosan were listed as being allowable preservatives but
with the usage amount not exceeding 0.3%. The new national standard
has ruled that the fluorine content of the fluoride-containing
toothpaste should be within the range of 0.04%-0.15%, and the
fluoride content should be within the range of 0.05% to 011% for
children fluoride-containing toothpaste. The above information is edited by the chemicalbook of Dai
Xiongfeng. |
Chemical Properties | It is colorless and long needle-like crystals with a melting point
being around 54-57.3 ℃ (60-61 ℃). It is slightly soluble in water
and soluble in ethanol, , ethyl r and alkali solution. It has a
chloro-phenol odor. |
Uses | 1. It can be used as antiseptic and fungicide and applied to
cosmetics, emulsions and resins; also can be used for the
manufacture of disinfection medicated soap. The LD50 of mice
subject to oral administration of this product is 4g/kg. 2. It can be used for the production of top-grade daily chemical
product, the disinfectants of medical instrument as well as diet
instrument as well as the preparation of the anti-bacterial,
deodorant finishing agent of fabric. 3. It can also be applied to biochemical studies. It is a kind of
broad-spectrum antimicrobial agents which inhibit the type II fatty
acid synthase (FAS-II) of bacteria and parasites, and also inhibits
the mammalian fatty acid synthase (FASN), and may also have
anticancer activity |
Production method | 1. Take 2, 4-dichloro-phenol as the raw material; use
2,4-dichloro-phenol to react with potassium hydroxide to generate
dichlorophenol potassium which further reacts with
2,5-dichloro-nitrobenzene in the catalysis of copper for generation
of 2,4,4-trichloro-2'-nitro diphenyl r. It is further reduced by
iron powder to generate 2, 4, 4-trichloro-2'-amino diphenyl r, and
then further went through diazotization hydrolysis to obtain the
product. 2. Take o-phenol as the raw material: have potassium hydroxide
powder reacted with guaiacol to generate guaiacol potassium. Apply
reaction between bromobenzene and r, togr with chlorine for
chlorination to obtain 2, 4, 4’-trichloro-2'-diphenyl r. Take AICI3
as hydrolysis catalyst to generate
2,4,4'-trichloro-2'-hydroxydiphenyl r. |
Chemical Properties | Solid |
Originator | Anti-Bac,Bentfield Europe BV,Nrlands |
Uses | Used as bacteriostat and preservative for cosmetic and detergent
compositions. Antiseptic, disinfectant. |
Uses | anticonvulsant |
Uses | Bacteriostat and preservative for cosmetic and detergent
preparations. |
Uses | triclosan is a preservative considered to have a low sensitizing
potential in leave-on preparations. |
Definition | ChEBI: An aromatic r that is phenol which is substituted at C-5 by
a chloro group and at C-2 by a 2,4-dichlorophenoxy group. It is
widely used as a preservative and antimicrobial agent in personal
care products such as soaps, skin creams, toothpaste and deodo ants
as well as in household items such as plastic chopping boards,
sports equipment and shoes. |
Indications | Triclosan is a broad-spectrum antimicrobial compound. It was
originally used in soaps, antiperspirants, and cosmetic toiletries
as a germicide. Today, triclosan is incorporated into toothpaste
because of its wide spectrum of antimicrobial activities and low
toxicity. |
Manufacturing Process | 476 g of 4-chloro-2-phenol(4-chloroguaiacol) and 578 parts of 3,4-
dichloro-1-nitrobenzene are melted in 400 ml of diethylene
glycoldimethyl r in a three necked flask fitted with a stirrer and
sloping condenser and, at about 120°C, 342 g of 49.6% potassium
hydroxide solution are added drop-wise within about 4 h. The inner
temperature is kept for 12 h at 140°- 150°C whereby water and
slight amounts of organic substances distill off, as partly occured
during the dropwise addition of the potassium hydroxide solution.
The reaction mixture is then poured into a mixture of water and
sodium hydroxide solution, the precipitate is filtered off, dried
and recrystallised from benzene. The
2--4,2'-dichloro-4'-nitrodiphenyl r obtained melts at 159°-161°C. 623 g of 2--4,2'-dichloro-4'-nitrodiphenyl r in 4000 ml of dioxan
are catalytically hydrogenated in the presence of 250 g of Raney
nickel at room temperature and under normal pressure. After the
calculated amount of hydrogen, the Raney nickel is filtered off and
the 2--4,2'-dichloro-4'- aminodiphenyl r is precipitated by the
addition of water, filtered off, washed and dried, melting point
100°-102°C. 204 g of well milled 2--4,2'-dichloro-4'-aminodiphenyl r are added
to a mixture of 254 ml of concentrated hydrochloric acid and 1600
ml of water, the addition being made at room temperature while
stirring well. The suspension formed is cooled to 0°-5°C and at
this temperature 225 g of 33% sodium nitrite solution is added
under the level of the liquid. The mixture is stirred for another
12 h at 0°-5°C. A solution of 86 g of sodium bisulphate and 60 g of
sodium hydroxide in 640 ml of water is added at 80°C to a solution
of 400 g of crystallised copper sulfate and 106 g of sodium
chloride in 1280 ml of water. The cuprous chloride formed is
allowed to settle, the water is poured off and the precipitate is
purified by decanting three times with water. The residue is dissolved in 640 ml of concentrated hydrochloric
acid, the solution is heated to 65°-70°C and the diazo suspension
produced above is added while stirring. After cooling, the aqueous
phase is poured off, the resin_x0002_like organic phase is taken up
in r, the r solution is extracted with dilute sodium hydroxide
solution, washed neutral, dried over sodium sulphate and
concentrated. The residue is distilled under water jet vacuum. The
2- -4,2',4'-trichlorodiphenyl r obtained boils at 210°-217°C. 243 g
of aluminum chloride are added to the solution of 187.5 g of 2-
-4,2',4'-trichlorodiphenyl r in 800 ml of benzene and the reaction
mixture is boiled for 30 min while stirring. After cooling, it is
poured into ice and hydrochloric acid, the benzene phase is
separated and extracted with water and sodium hydroxide solution.
The mimosa alkaline aqueous phase is separated, the last remains of
benzene are removed by blowing in steam, it is then filtered and
acidified with hydrochloric acid. The precipitated 2-hydroxy-
4,2',4'-tri-chlorodiphenyl r is filtered off, washed and dried.
After recrystallisation from petroleum r it melts at 60°-61°C.Model
E., Bindler J.; GB Patent No. 1,051,823; Dec. 21, 1966; Assigned:
J.R. Geigy AG, Basel |
Brand name | Stri-Dex Cleansing Bar (Sterling Health U.S.A.); Stri-Dex Face Wash
(Sterling Health U.S.A.). |
Therapeutic Function | Antiseptic |
Mechanism of action | Triclosan is active against a broad range of oral grampositive and
gram-negative bacteria.The primary target of its antibacterial
activity is the bacterial cell membrane. High concentrations cause
membrane leakage and ultimately lysis of the bacterial cell.
Effects at lower concentration are more subtle. Triclosan has been
shown to bind to cell membrane targets and inhibit enzymes
associated with the phosphotransferase and proton motive force
systems. |
Pharmacology | Triclosan is retained in dental plaque for at least 8 hours, which
in addition to its broad antibacterial property could make it
suitable for use as an antiplaque agent in oral care preparations.
However, the compound is rapidly released from oral tissues,
resulting in relatively poor antiplaque properties as assessed in
clinical studies of plaque formation.This observation is further
corroborated by a poor correlation between minimal inhibitory
concentration values generated in vitro and clinical plaque
inhibitory properties of triclosan. Improvement of substantivity
was accomplished by incorporation of triclosan in a polyvinyl
methyl r maleic acid copolymer (PVM/MA, Gantrez). With the
combination of PVM/MA copolymer and triclosan, the substantivity of
the triclosan was increased to 12 hours in the oral cavity. |
Clinical Use | Triclosan plus copolymer is available in toothpaste. Commercially
available dentifrice concentrations contain 0.3% triclosan and 2.0%
PVM/MA copolymer. |
Side effects | Triclosan is a preservative used in health care and consumer
products, including soaps, deodorants, mouthwashes, toothpastes,
cosmetics, and topical medicaments. Ozkaya et al. described a case
of suspected immune mediated Cou to triclosan. A 44-year-old female
reported experiencing an immediate localized urticarial response
after contact with numerous topical products. The use of a
toothpaste had also resulted in swelling of her lips, tongue, and
breathing difficulties. She also experienced lip swelling after
kissing her husband who had used the same product and wheals
involving her face after kissing friends on the cheek who had used
certain topical products on their faces. The suspected products all
contained triclosan 0.2%–0.5%. A severe localized urticarial
reaction occurred with open testing to 2% triclosan within 15
minutes. No tests were performed to confirm an immunological
mechanism; however, the authors suspected this to be the case
because of a positive urticarial response to triclosan within 15
minutes, a history of angioedema to the triclosan-containing
toothpaste, and because no immediate reactions were seen in five
control subjects who were open tested to 2% triclosan. |
Safety Profile | Poison by intravenous andintraperitoneal routes. Moderately toxic
by ingestion.Mildly toxic by skin contact. Mutation data reported.
Ahuman skin irritant. When heated to decomposition itemits toxic
fumes of Clí. |
Veterinary Drugs and Treatments | Found in several products, often with other active ingredients,
triclosan’s antibacterial effects may be useful in treating
superficial pyodermas. Triclosan is a bis-phenol disinfectant/antiseptic. It has a
activity against a wide range of organisms, including both
gram-positive and gram-negative bacteria and acts via inhibiting
bacterial fatty acid synthesis leading to disruption of cell
membrane integrity. Triclosan reportedly is not effective against
Pseudomonas spp. and may be less effective against staphylococci
than either chlorhexidine or ethyl lactate. |