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5-Isopropyl-2-methylphenol

CAS# 499-75-2

5-Isopropyl-2-methylphenol

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5-Isopropyl-2-methylphenol

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Chemical Properties of 5-Isopropyl-2-methylphenol

Cas No. 499-75-2 SDF Download SDF
PubChem ID 10364 Appearance Yellow liquid
Formula C10H14O M.Wt 150.21
Type of Compound Monoterpenoids Storage Desiccate at -20°C
Synonyms p-Cymene 2-ol; 2-Hydroxy p-cymene; Isothymol
Solubility Soluble in ethan
Chemical Name 2-methyl-5-propan-2-ylphenol
SMILES CC1=C(C=C(C=C1)C(C)C)O
Standard InChIKey RECUKUPTGUEGMW-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 5-Isopropyl-2-methylphenol

The herbs of Elsholtzia ciliata

Biological Activity of 5-Isopropyl-2-methylphenol

Description5-Isopropyl-2-methylphenol presents anxiolytic, antinociceptive, and antidepressant effects, it seems to be dependent on its interaction with the dopaminergic system, but not with the serotonergic and noradrenergic systems.
TargetsGABA Receptor
In vivo

Antinociceptive activity of carvacrol (5-isopropyl-2-methylphenol) in mice.[Pubmed: 23146035]

J Pharm Pharmacol. 2012 Dec;64(12):1722-9.

Carvacrol (5-Isopropyl-2-methylphenol) is a monoterpenic phenol which is present in the essential oil of oregano and thyme. We have investigated the behavioural effects of 5-Isopropyl-2-methylphenol in animal models of pain, such as acetic acid-induced abdominal constriction, formalin and hot-plate tests in mice. The spontaneous motor activity of animals treated with 5-Isopropyl-2-methylphenol was investigated using open-field and rotarod tests.
METHODS AND RESULTS:
5-Isopropyl-2-methylphenol was administered orally, at single doses of 50 and 100 mg/kg while indometacin (5 mg/kg), morphine (7.5 mg/kg) and diazepam (2 mg/kg) were used as standard drugs. Naloxone (1 mg/kg) and l-arginine (150 mg/kg) were used to elucidate the possible antinociceptive mechanism of 5-Isopropyl-2-methylphenol on acetic acid-induced abdominal constriction and formalin tests. The results showed that 5-Isopropyl-2-methylphenol produced significant inhibitions on nociception in the acetic acid-induced abdominal constriction, formalin and hot-plate tests. In the open-field and rotarod tests 5-Isopropyl-2-methylphenol did not significantly impair the motor performance. The effect of the highest dose of 5-Isopropyl-2-methylphenol in mice in the acetic acid-induced abdominal constriction and formalin tests were not reversed by naloxone or l-arginine.
CONCLUSIONS:
Based on these results, it has been suggested that 5-Isopropyl-2-methylphenol presents antinociceptive activity that may not act through the opioid system nor through inhibition of the nitric oxide pathway.

Carvacrol together with TRPC1 elimination improve functional recovery after traumatic brain injury in mice.[Pubmed: 22994850]

J Neurotrauma. 2012 Dec 10;29(18):2831-4.

We hypothesized that TRP channels of the TRPC subfamily may be involved in post-TBI pathophysiology and that the compound 5-Isopropyl-2-methylphenol (carvacrol), by inhibition of TRP channels, may exert neuroprotective effect after TBI.
METHODS AND RESULTS:
To test these suppositions, 5-Isopropyl-2-methylphenol was given to mice after TBI and its effect on their functional recovery was followed for several weeks. Our results show that neurological recovery after TBI was significantly enhanced by application of 5-Isopropyl-2-methylphenol. To better define the type of the specific channel involved, the effect of 5-Isopropyl-2-methylphenol on the extent and speed of recovery after TBI was compared among mice lacking TRPC1, TRPC3, or TRPC5, relative to wild type controls. We found that neurological recovery after TBI was significantly enhanced by combining 5-Isopropyl-2-methylphenol with TRPC1 elimination, but not by the absence of TRPC3 or TRPC5, showing a synergistic effect between 5-Isopropyl-2-methylphenol application and TRPC1 elimination.
CONCLUSIONS:
We conclude that TRPC1-sensitive mechanisms are involved in TBI pathology, and that inhibition of this channel by 5-Isopropyl-2-methylphenol enhances recovery and should be considered for further studies in animal models and humans.

Protocol of 5-Isopropyl-2-methylphenol

Animal Research

Anxiolytic-like effect of Carvacrol (5-isopropyl-2-methylphenol) in mice: involvement with GABAergic transmission.[Pubmed: 19909350]

Antidepressant-like effect of carvacrol (5-Isopropyl-2-methylphenol) in mice: involvement of dopaminergic system.[Pubmed: 20608992]

Fundam Clin Pharmacol. 2011 Jun;25(3):362-7.

Carvacrol (5-Isopropyl-2-methylphenol) is a monoterpenic phenol present in the essential oil of many plants. It is the major component of the essential oil fraction of oregano and thyme.
METHODS AND RESULTS:
In this study, the effect of carvacrol was investigated in two behavioral models, the forced swimming and tail suspension tests in mice, to investigate the possible antidepressant effect of this substance. Additionally, the mechanisms involved in the antidepressant-like effect of 5-Isopropyl-2-methylphenol in mice were also assessed. 5-Isopropyl-2-methylphenol (cvc) was administered orally at single doses of 12.5, 25 and 50 mg/kg. The acute treatment of cvc decreased the immobility time in the forced swimming and tail suspension tests without accompanying changes in ambulation in the open-field test. The anti-immobility effect of 5-Isopropyl-2-methylphenol (25 mg/kg) was not prevented by pretreatment of mice with p-chlorophenylalanine, prazosin and yohimbine. On the other hand, the pretreatment of mice with SCH23390 or sulpiride completely blocked the antidepressant-like effect of 5-Isopropyl-2-methylphenol (25 mg/kg) in the forced swimming test.
CONCLUSIONS:
These results show that 5-Isopropyl-2-methylphenol presents antidepressant effects in the forced swimming and tail suspension tests; this effect seems to be dependent on its interaction with the dopaminergic system, but not with the serotonergic and noradrenergic systems.

Fundam Clin Pharmacol. 2010 Aug;24(4):437-43.

Carvacrol (5-Isopropyl-2-methylphenol) is a monoterpenic phenol present in the essencial oil of many plants. It is the major component of the essential oil fraction of oregano and thyme.
METHODS AND RESULTS:
This work presents the behavioral effects of 5-Isopropyl-2-methylphenol in animal models of elevated plus maze (EPM), open field, Rotarod and barbiturate-induced sleeping time tests in mice. 5-Isopropyl-2-methylphenol (CVC) was administered orally, in male mice, at single doses of 12.5; 25 and 50 mg/kg while diazepam 1 or 2 mg/kg was used as standard drug and flumazenil (2.5 mg/kg) was used to elucidate the possible anxiolytic mechanism of 5-Isopropyl-2-methylphenol on the plus maze test. The results showed that 5-Isopropyl-2-methylphenol, at three doses, had no effect on the spontaneous motor activity in the Rotarod test nor in the number of squares crossed in the open-field test. However, 5-Isopropyl-2-methylphenol decreased the number of groomings in the open-field test. In the plus maze test, 5-Isopropyl-2-methylphenol, at three doses significantly increased all the observed parameters in the EPM test and flumazenil was able to reverse the effects of diazepam and 5-Isopropyl-2-methylphenol. Therefore, 5-Isopropyl-2-methylphenol did not alter the sleep latency and sleeping time in the barbiturate-induced sleeping time test.
CONCLUSIONS:
These results show that 5-Isopropyl-2-methylphenol presents anxiolytic effects in the plus maze test which are not influenced by the locomotor activity in the open-field test.

5-Isopropyl-2-methylphenol Dilution Calculator

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Preparing Stock Solutions of 5-Isopropyl-2-methylphenol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.6573 mL 33.2867 mL 66.5735 mL 133.1469 mL 166.4337 mL
5 mM 1.3315 mL 6.6573 mL 13.3147 mL 26.6294 mL 33.2867 mL
10 mM 0.6657 mL 3.3287 mL 6.6573 mL 13.3147 mL 16.6434 mL
50 mM 0.1331 mL 0.6657 mL 1.3315 mL 2.6629 mL 3.3287 mL
100 mM 0.0666 mL 0.3329 mL 0.6657 mL 1.3315 mL 1.6643 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 5-Isopropyl-2-methylphenol

Carvacrol together with TRPC1 elimination improve functional recovery after traumatic brain injury in mice.[Pubmed:22994850]

J Neurotrauma. 2012 Dec 10;29(18):2831-4.

Death of Central Nervous System (CNS) neurons following traumatic brain injury (TBI) is a complex process arising from a combination of factors, many of which are still unknown. It has been found that inhibition of transient receptor potential (TRP) channels constitutes an effective strategy for preventing death of CNS neurons following TBI. TRP channels are classified into seven related subfamilies, most of which are Ca(2+) permeable and involved in many cellular functions, including neuronal cell death. We hypothesized that TRP channels of the TRPC subfamily may be involved in post-TBI pathophysiology and that the compound 5-Isopropyl-2-methylphenol (carvacrol), by inhibition of TRP channels, may exert neuroprotective effect after TBI. To test these suppositions, carvacrol was given to mice after TBI and its effect on their functional recovery was followed for several weeks. Our results show that neurological recovery after TBI was significantly enhanced by application of carvacrol. To better define the type of the specific channel involved, the effect of carvacrol on the extent and speed of recovery after TBI was compared among mice lacking TRPC1, TRPC3, or TRPC5, relative to wild type controls. We found that neurological recovery after TBI was significantly enhanced by combining carvacrol with TRPC1 elimination, but not by the absence of TRPC3 or TRPC5, showing a synergistic effect between carvacrol application and TRPC1 elimination. We conclude that TRPC1-sensitive mechanisms are involved in TBI pathology, and that inhibition of this channel by carvacrol enhances recovery and should be considered for further studies in animal models and humans.

Antidepressant-like effect of carvacrol (5-Isopropyl-2-methylphenol) in mice: involvement of dopaminergic system.[Pubmed:20608992]

Fundam Clin Pharmacol. 2011 Jun;25(3):362-7.

UNLABELLED: Carvacrol (5-Isopropyl-2-methylphenol) is a monoterpenic phenol present in the essential oil of many plants. It is the major component of the essential oil fraction of oregano and thyme. In this study, the effect of carvacrol was investigated in two behavioral models, the forced swimming and tail suspension tests in mice, to investigate the possible antidepressant effect of this substance. Additionally, the mechanisms involved in the antidepressant-like effect of carvacrol in mice were also assessed. Carvacrol (cvc) was administered orally at single doses of 12.5, 25 and 50 mg/kg. The acute treatment of cvc decreased the immobility time in the forced swimming and tail suspension tests without accompanying changes in ambulation in the open-field test. The anti-immobility effect of carvacrol (25 mg/kg) was not prevented by pretreatment of mice with p-chlorophenylalanine, prazosin and yohimbine. On the other hand, the pretreatment of mice with SCH23390 or sulpiride completely blocked the antidepressant-like effect of carvacrol (25 mg/kg) in the forced swimming test. These results show that carvacrol presents antidepressant effects in the forced swimming and tail suspension tests; this effect seems to be dependent on its interaction with the dopaminergic system, but not with the serotonergic and noradrenergic systems. KEYWORDS: Carvacrol; Antidepressant; Forced swimming; Tail suspension; Dopaminergic system.

Anxiolytic-like effect of Carvacrol (5-isopropyl-2-methylphenol) in mice: involvement with GABAergic transmission.[Pubmed:19909350]

Fundam Clin Pharmacol. 2010 Aug;24(4):437-43.

Carvacrol (5-Isopropyl-2-methylphenol) is a monoterpenic phenol present in the essencial oil of many plants. It is the major component of the essential oil fraction of oregano and thyme. This work presents the behavioral effects of carvacrol in animal models of elevated plus maze (EPM), open field, Rotarod and barbiturate-induced sleeping time tests in mice. Carvacrol (CVC) was administered orally, in male mice, at single doses of 12.5; 25 and 50 mg/kg while diazepam 1 or 2 mg/kg was used as standard drug and flumazenil (2.5 mg/kg) was used to elucidate the possible anxiolytic mechanism of CVC on the plus maze test. The results showed that CVC, at three doses, had no effect on the spontaneous motor activity in the Rotarod test nor in the number of squares crossed in the open-field test. However, CVC decreased the number of groomings in the open-field test. In the plus maze test, CVC, at three doses significantly increased all the observed parameters in the EPM test and flumazenil was able to reverse the effects of diazepam and CVC. Therefore, CVC did not alter the sleep latency and sleeping time in the barbiturate-induced sleeping time test. These results show that CVC presents anxiolytic effects in the plus maze test which are not influenced by the locomotor activity in the open-field test.

Antinociceptive activity of carvacrol (5-isopropyl-2-methylphenol) in mice.[Pubmed:23146035]

J Pharm Pharmacol. 2012 Dec;64(12):1722-9.

OBJECTIVES: Carvacrol (5-Isopropyl-2-methylphenol) is a monoterpenic phenol which is present in the essential oil of oregano and thyme. We have investigated the behavioural effects of carvacrol in animal models of pain, such as acetic acid-induced abdominal constriction, formalin and hot-plate tests in mice. The spontaneous motor activity of animals treated with carvacrol was investigated using open-field and rotarod tests. METHODS: Carvacrol was administered orally, at single doses of 50 and 100 mg/kg while indometacin (5 mg/kg), morphine (7.5 mg/kg) and diazepam (2 mg/kg) were used as standard drugs. Naloxone (1 mg/kg) and l-arginine (150 mg/kg) were used to elucidate the possible antinociceptive mechanism of carvacrol on acetic acid-induced abdominal constriction and formalin tests. KEY FINDINGS: The results showed that carvacrol produced significant inhibitions on nociception in the acetic acid-induced abdominal constriction, formalin and hot-plate tests. In the open-field and rotarod tests carvacrol did not significantly impair the motor performance. The effect of the highest dose of carvacrol in mice in the acetic acid-induced abdominal constriction and formalin tests were not reversed by naloxone or l-arginine. CONCLUSIONS: Based on these results, it has been suggested that carvacrol presents antinociceptive activity that may not act through the opioid system nor through inhibition of the nitric oxide pathway.

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