United States Pharmacopeia (USP) Reference Standard
Synonym: 2-Isopropyl-5-methylphenol,
5-Methyl-2-(1-methylethyl)phenol, 5-Methyl-2-isopropylphenol, IPMP
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Linear Formula 2-[(CH3)2CH]C6H3-5-(CH3)OH
·
Molecular Weight 150.22
·
Beilstein Registry
Number 1907135
Properties
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Related Categories
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grade
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USP reference standard
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vapor pressure
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1 mmHg ( 64 °C)
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InChI Key
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MGSRCZKZVOBKFT-UHFFFAOYSA-N
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bp
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232 °C(lit.)
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mp
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48-51 °C(lit.)
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density
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0.965 g/mL at
25 °C(lit.)
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Thymol (also known as 2-isopropyl-5-methylphenol,
IPMP) is a natural monoterpene phenol derivative of cymene, C10H14O, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris (common thyme) and various other kinds of plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Detailed description
Thymol
also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris.
Uses
Thymol has antimicrobial activity because of its
phenolic structure, and has shown antibacterial activity against bacterial
strains including Aeromonas
hydrophila and Staphylococcus aureus.[21] In addition, thymol
demonstrates considerable post antibacterial
effect against some microorganisms.[3] This antibacterial
activity is caused by inhibiting growth and lactate production, and by
decreasing cellular glucose uptake.[22]
Thymol has been used in alcohol solutions and in
dusting powders for the treatment of tinea or ringworm infections, and was
used in the United States to treat hookworm infections.[23] People of the Middle
East continue to use za'atar, a delicacy made with large amounts of Thyme, to
reduce and eliminate internal parasites.[24]
It is also used as a preservative in halothane, an anaesthetic, and as an antiseptic in mouthwash.
When used to reduce plaque and gingivitis, thymol has been found to be more
effective when used in combination with chlorhexidine than when used purely by itself.[25]Thymol is also the
active antiseptic ingredient in some toothpastes, such as Euthymol.
The antifungal nature of thymol is caused by
thymol's ability to alter the hyphal morphology and cause hyphal aggregates,
resulting in reduced hyphal diameters and lyses of hyphal wall.[26] Additionally, thymol
is lipophilic, enabling it to interact with the cell membrane of fungus cells,
altering cell membrane permeability permitting the loss of macromolecules.[27]
Recent medical research on rats concludes that
"Thyme extract had relaxing effects on organs possessing β2-receptors
(uterus and trachea)."[28]
In a 1994 report released by five major cigarette companies, thymol
was listed as one of 599 additives to cigarettes.[29]
Thymol has been used to successfully control varroa mites and
prevent fermentation and the growth of mold in bee
colonies, methods developed by beekeeper R.O.B. Manley.[30]
Derivatives of thymol and carvacrol with increased
antimicrobial activities have been developed.[32] The preparation of
methacrylic and p-styrenesulfonic acid esters of thymol could lead to less
toxic macromolecular biocides, which can be
attached to a polymeric backbone.[33]
A minor use of thymol is in book and paper
conservation: Paper with mold damage can be sealed in bags with
thymol crystals to kill fungal spores. However, this practice is not currently recommended due to
apparent accelerated degradation suffered by these objects.
Thymol can also be used as a medical disinfectant
and general purpose disinfectant.[34] For instance, thymol
is used as the starting material used to synthesize biclotymol. Thymol can be brominated to Bromthymol (see
[15062-34-7]), which is a recognized anthelmintic drug.
929F, the N,N-diethylaminoethoxy
ether of thymol,[35] was an antihistamine
that was studied, predating Benadryl.
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