Thymol
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Thymol
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CAS No:
89-83-8
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Formula:
C10H14O
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Chemical Name:
Thymol
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Synonyms:
Phenol,5-methyl-2-(1-methylethyl)-;Thymol;5-Methyl-2-(1-methylethyl)phenol;p-Cymen-3-ol;3-Hydroxy-p-cymene;1-Methyl-3-hydroxy-4-isopropylbenzene;5-Methyl-2-isopropyl-1-phenol;Thyme camphor;2-Hydroxy-1-isopropyl-4-methylbenzene;3-Methyl-6-isopropylphenol;2-Isopropyl-5-methylphenol;5-Methyl-2-isopropylphenol;m-Thymol;6-Isopropyl-3-methylphenol;6-Isopropyl-m-cresol;Thymol Chrystals;NSC 11215;NSC 47821;NSC 49142;Apiguard;T 0501;5-Methyl-2-propan-2-ylphenol
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CAS No:
Description
Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1].
PelletsLargeCrystals|Solid|White crystals, powerful, sweet-medicinal, herbaceous, warm, aromatic odour
Thymol is a phenol that is a natural monoterpene derivative of cymene. It has a role as a volatile oil component. It is a member of phenols and a monoterpenoid. It derives from a hydride of a p-cymene.|A phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. (Dorland, 28th ed)|A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.
Thymol Basic Attributes
150.22
150.22
1907135
201-944-8
3J50XA376E
49142|47821|11215
DTXSID6034972
Colorless, translucent crystals or plates from ethyl acetate, acetic acid or dimethyl carbonate
2907199090
Characteristics
20.2
3.3
White Crystals or Crystalline Powder
0.9699 g/cm3 @ Temp: 25 °C
52 °C
233 °C
216 °F
nD20 1.5227; nD25 1.5204
H2O: 0.1 g/100 mL (20 ºC);ethanol: soluble 50mg/mL
Store at RT.
1 mm Hg ( 64 °C)
LD50 orally in rats: 980 mg/kg (Jenner)
Odor of thyme
Pungent, caustic
Solution in alcohol is neutral to litmus
10.6(at 20 °C)
Henry's Law constant = 3.50X10-6 atm-cu m/mol at 25 °C (est)
10.6 (at 20 °C)|pKa = 10.62
MELTS BETWEEN 48-51 °C, BUT WHEN MELTED IT REMAINS LIQ @ CONSIDERABLY LOWER TEMP|HEAVIER THAN WATER, BUT WHEN LIQUEFIED BY FUSION IT IS LIGHTER THAN WATER|WHEN THYMOL IS TRITURATED WITH EQUAL WT OF CAMPHOR, MENTHOL, CHLORAL HYDRATE, & SOME OTHER SUBSTANCES, MIXT LIQUEFIES|Hydroxyl radical reaction rate constant = 1.1X10-10 cu cm/molecule-sec at 25 °C (est)
Safety Information
Ⅲ
8
UN 3261 8/PG 3
2
22-34-51/53
26-28-36/37/39-45-61-28A
XP2275000
C,N
Stable. Incompatible with strong oxidizing agents, organic materials, strong bases.
P273-P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338-P391
H302-H314-H411
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|Waste treatment methods. Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.
Incompatible with acetanilide.|Incompatible materials: Strong oxidizing agents, strong bases
Thymol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.|Thymol for use as a preservative only is an indirect food additive for use as a component of adhesives.|Approved as an excipient (CDER, 1996)
USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Thymol (September 1993). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of November 4, 2014: http://www.epa.gov/pesticides/reregistration/status.htm]
|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P391, P405, and P501|H302 (99.95%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 2026 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, and P501
Wear rubber gloves, face shield, and multipurpose /NIOSH approved respirator/.|Eye/face protection: Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Flammable
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.
Special hazards arising from the substance or mixture: Carbon oxides
Collect with a brush onto a paper sheet. Place in an iron pan in hood. Burn the paper.|Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Protect body from contamination. No eating in work areas.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
...thymol is corrosive to the skin and eye.|In humans, thymol on its own or as an ingredient in combination preparations, considering its wide use, has led to primary skin irritation ... .
Thymol was identified as one of many biogenic volatile compounds emitted from dominant vegetation species tested from sites in Atlanta GA, Rhinelander WI and Hayden CO(1); The thymol emission rate from North White Cedar was 0.1 ug/hr(1). Thymol was qualitatively detected in two secondary effluents during 1980 sampling at POTWs (publicly owned treatment works) in Illinois(2).
SEDIMENT: Thymol was qualitatively detected in sediment samples collected from the Havel and Spree Rivers in Germany during 1993 and 1994 sampling(1).
Toxicity
IDENTIFICATION AND USE: Thymol forms colorless crystals, often large, or white crystalline powder. It is used as a pesticide (insecticide, fungicide, rodenticide, antimicrobial); also used in perfumery; as a mold and mildew preventive; in microscopy; as a preservative; antioxidant; flavoring; and lab reagent. Thymol is included in an FDA over-the-counter drug used as an antibacterial and antifungal agent, and approved as an excipient. HUMAN EXPOSURE AND TOXICITY: In humans, thymol on its own or as an ingredient in combination preparations, considering its wide use, has led to primary skin irritation and skin sensitisation only in rare cases. Thymol is a mild local irritant. It resembles phenol in its systemic actions but is less toxic, partly because it is less soluble. It produces gastric pain, nausea, vomiting, central hyperactivity (eg, talkativeness), occasionally convulsions, coma, cardiac and respiratory collapse. Thymol was not genotoxic in the human colon carcinoma cell line Caco-2. ANIMAL STUDIES: On acute oral administration, thymol is harmful whereas it is practically non-toxic following acute dermal application. In the rabbit, thymol is corrosive to the skin and eye. Rats subjected to subchronic administration in the feed for a period of 19 weeks tolerate thymol at 10000 ppm. Thymol did not increase the incidence of spontaneous lung tumors in mice. In embryonic chickens, thymol causes multiple malformations on injection into the air bubble or the yolk sac. In vivo, oral administration of thymol does not induce micronuclei in mice even in the toxic dose range. In the Salmonella/microsome assay, thymol exhibits no mutagenic effect; however, it has been reported to give positive results in the UDS test (liquid scintillation) and in the SCE test with embryonic cells of the Syrian hamster. The findings are statistically significant, though there is no strict dose-response relationship. The various other actions of thymol include cytotoxic, antineoplastic, antibacterial, fungicidal, anti-inflammatory, spasmolytic and other pharmacodynamic effects. ECOTOXICITY STUDIES: The effects of thymol on olfactory memory and gene expression in the brain of the honeybee were explored in bees previously exposed to thymol, and the specificity of the bee response to the conditioned stimulus was lost 24 hr after learning. The results also indicated that the genes coding for the cellular targets of thymol could be rapidly regulated after exposure to this molecule. Essential oils (including thymol) are used by beekeepers to control the Varroa mites infesting honeybee colonies.
Thymol (TOH) was investigated for its ability to protect against mercuric chloride (HgCl2 )-induced cytotoxicity and genotoxicity using human hepatocarcinoma (HepG2) cell line. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay confirmed the efficacy of TOH pretreatment in attenuating HgCl2 -induced cytotoxicity. Pretreatment with TOH inhibited HgCl2 -induced genotoxicity, depolarization of mitochondrial membrane, oxidative stress, and mitochondrial superoxide levels. Interestingly, TOH (100 uM) alone elevated the intracellular basal glutathione S-transferase (GST) levels and TOH pretreatment abrogated the decrease in glutathione, GST, superoxide dismutase, and catalase levels even after HgCl2 intoxication. Furthermore, TOH was also capable of inhibiting HgCl2 -induced apoptotic as well as necrotic cell death analyzed by flowcytometric analysis of cells dual stained with Annexin-FITC/propidium iodide. The present findings clearly indicate the cytoprotective potential of TOH against HgCl2 -induced toxicity, which may be attributed to its free radical scavenging ability which facilitated in reducing oxidative stress and mitochondrial damage thereby inhibiting cell death.|Thymol is a natural monoterpene phenol primarily found in thyme, oregano, and tangerine peel. It has been shown to possess anti-inflammatory property both in vivo and in vitro. /The present paper studied/ the anti-inflammatory effect of thymol in lipopolysaccharide (LPS)-stimulated mouse mammary epithelial cells (mMECs). The mMECs were stimulated with LPS in the presence or absence of thymol (10, 20, 40 ug/mL). The concentrations of tumor necrosis factor a (TNF-a), interleukin (IL)-6, and IL-1beta in the supernatants of culture were determined using enzyme-linked immunosorbent assay. Cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS), extracellular signal-regulated protein kinase (ERK), c-Jun N-terminal kinase (JNK), nuclear factor-kappaB (NF-kappaB), and inhibitor protein of NF-kappaB (IkappaBa) were measured using western blot. The results showed that thymol markedly inhibited the production of TNF-a and IL-6 in LPS-stimulated mMECs. The expression of iNOS and COX-2 was also suppressed by thymol in a dose-dependent manner. Furthermore, thymol blocked the phosphorylation of IkappaBa, NF-kappaB p65, ERK, JNK, and p38 mitogen-activated protein kinases (MAPKs) in LPS-stimulated mMECs. These results indicate that thymol exerted anti-inflammatory property in LPS-stimulated mMECs by interfering the activation of NF-kappaB and MAPK signaling pathways. Thereby, thymol may be a potential therapeutic agent against mastitis.
LD50 Rat oral 980 mg/kg|LD50 Mouse oral 640 mg/kg|LD50 Mouse iv 100 mg/kg|LD50 Rat dermal >2000 mg/kg
/OTHER TERRESTRIAL SPECIES/ Essential oils are used by beekeepers to control the Varroa mites that infest honeybee colonies. So, bees can be exposed to thymol formulations in the hive. The effects of the monoterpenoid thymol were explored on olfactory memory and gene expression in the brain of the honeybee. In bees previously exposed to thymol (10 or 100 ng/bee), the specificity of the response to the conditioned stimulus (CS) was lost 24 hr after learning. Besides, the octopamine receptor OA1 gene Amoa1 showed a significant decrease of expression 3 hr after exposure with 10 or 100 ng/bee of thymol. With the same doses, expression of Rdl gene, coding for a GABA receptor subunit, was not significantly modified but the trpl gene was upregulated 1 and 24 hr after exposure to thymol. These data indicated that the genes coding for the cellular targets of thymol could be rapidly regulated after exposure to this molecule.
Thymol is the main constituent of thyme and some origanum oils; it also occurs in many other essential oils(1,2).|REPORTED IN ESSENTIAL OILS OF ... SATUREIA THYMERA, ORIGANUM FLORIBUNDUM, OCIMUM VIRIDE, OCIMUM GRATISSIMUM, & PARTICULARLY IN THYME (THYMUS VULGARIS L, T CAPITATUS, T SERPILLUM L), WHERE IT IS CONTAINED UP TO 50%.|THYMOL HAS BEEN OBTAINED FROM MONARDA DIDYMA LINNE, M PUNCTATA (HORSEMINT), AMMI COPTICUM, OCIMUM BASILICUM, & PTYCHOTIS AGOWAN.
Thymol's production and use as a starting material for racemic menthol and as an antioxidant, flavoring agent, laboratory reagent and disinfectant in oral hygiene products(1,2) may result in its release to the environment through various waste streams(SRC); its use in perfumery, as a mold and mildew preventative(1,2) and as a pesticide to control mites in beehives(3) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1500(SRC), determined from a structure estimation method(2), indicates that thymol is expected to have low mobility in soil(SRC). Volatilization of thymol from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 0.016 mm Hg(3), and water solubility, 900 mg/L(4). In an agronomic soil dissipation study using radio-labeled thymol, cumulative volatilization reached 26% of total radioactivity (thymol + degradates) after one month(5). A 0% of theoretical BOD using activated sludge in the Japanese MITI test suggests that thymol is not readily biodegradable(6). However, other studies have found thymol to be readily biodegradable(7-9). Laboratory tests using chernozem soil observed a thymol degradation of 100% in 3 days of incubation(8). A laboratory study using soil from the Iowa State University Research Farm observed a thymol dissipation half-life of 5 days, but less than 3% was mineralized over a 30-day period(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1500(SRC), determined from a structure estimation method(2), indicates that thymol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.016 mm Hg(n), and water solubility, 900 mg/L(4). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 13 and 98 days, respectively(SRC). According to a classification scheme(6), a BCF range of 7.8 to 48 measured in carp (Cyprinus carpio) over a 6-week period(7), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). A 0% of theoretical BOD using activated sludge in the Japanese MITI test suggests that thymol is not readily biodegradable(7). However, other studies have found thymol to be readily biodegradable(8,9). In aerobic degradation tests using river water from the Tamagawa River in Japan as the inoculum, thymol exhibited degradation of about 50% after 8 days of incubation(8). A laboratory study using pond water from the Iowa State University Horticultural Farm measured a thymol dissipation half-life of 16 days(10). Thymol is a phenol and phenols are susceptible to photooxidation (indirect photolysis) in natural waters exposed to sunlight with a half-life on the order of 13 days(11). Thymol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thymol, which has a vapor pressure of 0.016 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase thymol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.6 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Thymol is a phenol and phenols react readily with NO3 radicals in the atmosphere during nighttime hours(4); the half-life for the reaction of phenol in nighttime air is estimated to be about 1 hour(SRC). Based on the results of water degradation tests under light versus dark conditions(5), direct photolysis is not expected to be an important fate process(SRC).
The rate constant for the vapor-phase reaction of thymol with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Thymol is a phenol(SRC) and phenols react with NO3 radicals in the atmosphere during nighttime hours(2). The rate constant for the vapor-phase reaction of phenol with nitrate radicals is 3.64X10-12 cu cm/molecule-sec at 25 °C(3); assuming thymol has a similar rate constant, this corresponds to an atmospheric half-life of about 1 hour(SRC) at an atmospheric concentration of 2.8X10+8 nitrate radicals per cu cm(1,2). In soil and water dissipation studies, dissipation rates were effectively the same in dark versus light tests(4) suggesting direct photolysis is not an important fate process(SRC). Photooxidation (indirect photolysis) of phenols does occur in natural waters exposed to sunlight with an approximated half-life on the order of 13 days(5). Thymol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(6).
A BCF range of 7.8 to 48 was measured in fish for thymol(SRC), using carp (Cyprinus carpio) which were exposed over a 6-week period using thymol concentrations of 1-10 ug/L(1). According to a classification scheme(2), this BCF range suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of thymol can be estimated to be 1500(SRC). According to a classification scheme(2), this estimated Koc value suggests that thymol is expected to have low mobility in soil.
The Henry's Law constant for thymol is estimated as 3.5X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 0.016 mm Hg(1), and water solubility, 900 mg/L(2). This Henry's Law constant indicates that thymol is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 13 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 98 days(SRC). Thymol's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). In an agronomic soil dissipation study using radio-labeled thymol, cumulative volatilization reached 26% of total radioactivity (thymol + degradates) after one month(4). In a pond water dissipation study using radio-labeled thymol, cumulative volatilization reached 65% of total radioactivity (thymol + degradates) after one month(4).
SURFACE WATER: Thymol was detected in grab water samples collected from 37 rivers in Japan during 2004 and 2005 sampling(1); thymol concentration in estuary water from the Tamagawa River ranged from about 0.5 to 3.0 ng/L(1).
Thymol was detected at concentrations of 1.0-6.5 ug/kg in Spanish honeydew honey(1).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of thymol is 1 to 99; the data may be greatly underestimated(1). According to the 2012 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of thymol is classified as CBI (Confidential Business Information)(2).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 21,335 workers (14,083 of these were female) were potentially exposed to thymol in the US(1). Occupational exposure to thymol may occur through inhalation and dermal contact with this compound at workplaces where thymol is produced or used. Monitoring and use data indicate that the general population may be exposed to thymol via inhalation of ambient air, ingestion of food and dermal contact with this compound or consumer products containing thymol(SRC). Thyme is used as a food seasoning ingredient and as an essential oil(2); as a result, a large numbers of humans have been and continue to be regularly exposed to the active ingredient via physical contact and in their diet(2).
Drug Information
Anti-Infective Agents; Anti-Infective Agents, Local; Antifungal Agents|EXPL THER Thymol, a naturally occurring monocyclic phenolic compound derived from Thymus vulgaris (Lamiaceae), has been reported to exhibit anti-inflammatory property in vivo and vitro. However, the mechanism of thymol is not clear. The aim of the present study was to investigate the effects of thymol on allergic inflammation in OVA-induced mice asthma and explore its mechanism. The model of mouse asthma was established by the induction of OVA. Thymol was orally administered at a dose of 4, 8, and 16 mg/kg body weight 1hr before OVA challenge. At 24h after the last challenge, mice were sacrificed, and the data were collected by various experimental methods. The results revealed that pretreatment with thymol reduced the level of OVA-specific IgE, inhibited recruitment of inflammatory cells into airway, and decreased the levels of IL-4, IL-5, and IL-13 in BALF. Moreover, the pathologic changes of lung tissues were obviously ameliorated and goblet cell hyperplasia was effectively inhibited by the pretreatment of thymol. In addition, thymol reduced the development of airway hyperresponsiveness and blocked the activation of NF-kappaB pathway. All data suggested that thymol ameliorated airway inflammation in OVA-induced mouse asthma, possibly through inhibiting NF-kappaB activation. These findings indicated that thymol may be used as an alternative agent for treating allergic asthma.|EXPL THER Obesity has become a worldwide health problem. Most of the synthetic anti-obesity drugs have failed to manage the obesity due to either ineffectiveness or adverse effect. The research of prominent chemical constituents from herbal for the management of obesity has greatly increased. The main objective of the present study was intended to examine the effects of thymol in high-fat diet (HFD)-induced obesity in murine model. Male Wistar rats were fed HFD for 6 weeks to induce obesity. Thymol (14 mg/kg) administered orally twice a day to HFD-fed rats for 4 weeks. Alteration in body weight gain, visceral fat-pads weight and serum biochemical markers were assessed. At the end of study, rats fed with HFD exhibited significantly (p< 0.001) enhanced body weight gain, visceral pad weight, lipids, alanine aminotransferase (ALT), aspartate aminotransaminase (AST), lactate dehydrogenase (LDH), blood urea nitrogen (BUN), glucose, insulin and leptin levels compared with rats fed with normal diets. Thymol treatment showed significantly (p< 0.001) decreased body weight gain, visceral fat-pad weights, lipids, ALT, AST, LDH, BUN, glucose, insulin, and leptin levels in HFD-induced obese rats. Furthermore, thymol treatment showed significantly decreased serum lipid peroxidation and increased antioxidant levels in HFD-induced obese rats. Thymol prevents HFD-induced obesity in murine model through several mechanisms including attenuation of visceral fat accumulation, lipid lowering action, improvement of insulin and leptin sensitivity and enhanced antioxidant potential.|EXPL THER Mast cells play a critical role in inflammatory skin diseases through releasing proinflammatory mediators; however, few therapies directly target these cells. In 1878, the use of topical thymol, a now recognized potent agonist for transient receptor potential channels, was first described to treat eczema and psoriasis. /The objective was/ to determine the mechanisms through which thymol can alter skin inflammation. METHODS: /This study/ examined the effect of topical thymol on IgE-dependent responses using a mast cell-dependent passive cutaneous anaphylaxis (PCA) model, as well as in vitro-cultured mast cells. Thymol dose-dependently inhibited PCA when administered topically 24 hours before antigen challenge but provoked an ear-swelling response directly on application. This direct effect was associated with local mast cell degranulation and was absent in histamine-deficient mice. However, unlike with PCA responses, there was no late-phase swelling. In vitro thymol directly triggered calcium flux in mast cells through transient receptor potential channel activation, along with degranulation and cytokine transcription. However, no cytokine protein was produced. Instead, thymol induced a significant increase in apoptotic cell death that was seen both in vitro and in vivo. /The authors/ propose that the efficacy of thymol in reducing IgE-dependent responses is through promotion of activation-induced apoptotic cell death of mast cells and that this likely explains the clinical benefits observed in early clinical reports.|For more Therapeutic Uses (Complete) data for THYMOL (8 total), please visit the HSDB record page.
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)|Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)
Aromatic herbs as feed additives in animal production are encountering growing interest, but data on the fate of the aromatic compounds from the plant in the animal body are very scarce. In the present study, thyme (Thymus vulgaris) herb consisting of leaves and flowers without stems was used as an ingredient in the diet for broilers. The herb was fed for 35 days to five groups of broilers (0, 0.1, 0.2, 0.3, and 1% w/w in the diet). Animal performance and the concentrations of the main essential oil component from thyme, thymol, were measured in gut contents, plasma and liver and muscle tissues using solid phase microextraction and gas chromatography/mass spectrometry. There were no differences between the groups in feed intake, daily weight gain, feed conversion and slaughter weight. Thymol was detected in gut contents, plasma and liver and muscle tissues. Increased intestinal thymol concentrations were found in the group with 1% thyme compared with the other groups (P<0.05). In liver and muscle tissues the thymol levels were close to the limit of quantification. The data do not indicate a positive effect of thyme on animal performance. With high dietary levels of thyme herb, thymol concentrations increased in gut contents and plasma but were very low in edible tissues such as liver and flesh.|Thymol is readily absorbed from the gastrointestinal tract following oral administration. It is essentially excreted in the urine within the first 24 hours after absorption.
Only small amounts of the absorbed substance undergo urinary excretion as hydroxylated compounds. Thymol is predominantly excreted unchanged and in the form of its glucuronide and sulfate conjugates.|Substituted monophenols, thymol ... which occur in essential oils of plants, particularly thyme, are ... conjugated with glucuronic acid & sulfate.|Thymol has known human metabolites that include Thymoquinol, p-Cymen-8-en-3-ol, p-Cymene-2,3-diol, thymol O-glucuronide, and thymol sulfate.
The potent role of thymol, a natural compound, in modulation of macrophage activity was evaluated by determining all the sequential steps involved during phagocytosis. We found a significant increase in the proliferation of splenocytes in the presence of thymol and it proved to be a good mitogen. Uptake capacity of macrophages was enhanced due to increased membrane fluidity after treatment with thymol and it also increases lysosomal activity of macrophages. Data of superoxide anion generation revealed the involvement of thymol in the generation of respiratory burst as it potentiated this property of macrophages at a concentration of 150 uM. In the case of TNF-a, IL-1beta and PGE(2) a decreased level of secretion was observed 154 pg/mL, 736.1 pg/mL, and 151 pg/mL respectively when compared with lipopolysaccharide treated cells, where the level of these cytokines was significantly high. We also determined the anti-complementary activity of thymol which showed to be more effective than rosmarinic acid. Thus, the results obtained from the study suggest the potential role of thymol as a natural immunostimulatory drug which can be used in the treatment of various immunological disorders.
Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Phenols and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Administer activated charcoal ... . Do not use emetics ... . Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's(LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is sympotomatic with severe hypoxia, cyanosis, and cardiac compromise no responding to oxygen. Direct physician order only ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/
/SIGNS AND SYMPTOMS/ In humans, thymol on its own or as an ingredient in combination preparations, considering its wide use, has led to primary skin irritation and skin sensitisation only in rare cases.|/SIGNS AND SYMPTOMS/ ... Mild local irritant. Resembles phenol in its systemic actions but less toxic, partly because it is less sol. ... Produces gastric pain, nausea, vomiting, central hyperactivity (eg, talkativeness), occasionally convulsions, coma, cardiac & respiratory collapse.|/SIGNS AND SYMPTOMS/ Believed to lie near borderline between toxicity classes 3 & 4 /moderately & very toxic/.|/GENOTOXICITY/ ...The genotoxic effects were evaluated in the human colon carcinoma cell line Caco-2, and the standard comet assay revealed that neither carvacrol (0-460 uM) nor thymol (0-250 uM) had any effects at 24 and 48 hr. The FPG-modified comet assay showed that the highest concentration of carvacrol (460 uM) caused DNA damage, indicating damage to the purine bases. These results should be used to identify the appropriate concentrations of carvacrol and thymol as additives in food packaging. Moreover, further studies are necessary to explore the safety and/or the toxicity mechanisms of these compounds.|For more Human Toxicity Excerpts (Complete) data for THYMOL (7 total), please visit the HSDB record page.
Apiguard
Thymol Use and Manufacturing
By action of potassium nitrite on thymyl amine in acetic acid solution and subsequent heating of the diazonium salt to boiling; also by boiling 1 mol of 2,4-dibromomenthone with 6 mol of quinoline.|Obtained from the essential oil of Thymus vulgaris L. and Monarda punctata L., Labiatae.|Produced synthetically from p-cymene, piperitone, or m-cresol.|From thyme oils or other oils, synthetically from m-cresol and isopropyl chloride by the Friedel-Crafts method at -10 °C.
Thymol is an antimicrobial compound which can increase the efficacy of antibiotics involving drug resistant bacteria. It inhibits growth and lactate production as well as reduces cellular glucose uptake within the bacteria.
Odor agents
Air care products
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Phenol, 5-methyl-2-(1-methylethyl)-. Aggregated National Production Volume: < 500,000 pounds.|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Phenol, 5-methyl-2-(1-methylethyl)-. National Production Volume: Withheld.
/Present in/ Listerine Antiseptic|/Present in/ bensulfoid lotion|Technical, NF, reagent|BORASOL - eucalyptol, thymol, methyl salicylate and menthol powder: Eucalyptol 0.091%; Thymol 0.063%; Methyl Salicylate 0.055%; Menthol 0.010%|For more Formulations/Preparations (Complete) data for THYMOL (20 total), please visit the HSDB record page.
Soap, cleaning compound, and toilet preparation manufacturing|Phenol, 5-methyl-2-(1-methylethyl)-: ACTIVE|REPORTED USES: NON-ALCOHOLIC BEVERAGES 2.5-11 PPM; ICE CREAM, ICES, ETC 44 PPM; CANDY 9.4 PPM; BAKED GOODS 5.0-6.5 PPM; CHEWING GUM 100 PPM|In mouthwashes and gargles (eg, Listerine) it is used in a concentration too low to be effective within any practical contact time
Food additives -> Flavoring Agents|Agrochemicals -> Fungicides|Flavoring Agents -> JECFA Flavorings Index|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]|Cosmetics -> Denaturant; Hair dyeing; Masking
Flavoring Agents
Computed Properties
Molecular Weight:150.22
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:150.104465066
Monoisotopic Mass:150.104465066
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
This product (beclomethasone dipropionate) is a potent topical glucocorticoid that can reduce and prevent tissue responses to inflammation, thereby reducing the manifestations of inflammation. Borneol has analgesic and detumescent effects; menthol, when applied topically, has the effects of promoting blood circulation, anti-inflammatory and antipruritic, and can be used for anti-inflammatory, antipruritic, analgesic, and edema reduction; methyl salicylate has a local irritant effect, can promote local blood circulation, and also has an antipruritic effect.
Registered Holders
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Fujian Zhundian New Materials Technology Co., Ltd.
Active
China
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Shanghai Yan’an Pharmaceutical (Hubei) Co., Ltd.
Active
China
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Jiangxi Alpha Hi-tech Pharmaceutical Co., Ltd.
Active
China
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