Pulegone

CAS# 89-82-7

Pulegone

2D Structure

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Pulegone

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Chemical Properties of Pulegone

Cas No. 89-82-7 SDF Download SDF
PubChem ID 442495 Appearance Light brown liquid
Formula C10H16O M.Wt 152.2
Type of Compound Monoterpenoids Storage Desiccate at -20°C
Synonyms (+)-p-Menth 4(8)-ene 3-one
Solubility DMSO : ≥ 270 mg/mL (1773.63 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
SMILES CC1CCC(=C(C)C)C(=O)C1
Standard InChIKey NZGWDASTMWDZIW-MRVPVSSYSA-N
Standard InChI InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1
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 Pulegone

The herbs of Mentha canadensis L.

Biological Activity of Pulegone

DescriptionPulegone is a fragrance and flavour ingredient. Pulegone has cytotoxicity followed by regenerative cell proliferation is the MOA for Pulegone-induced urothelial tumors in female rats. Pulegone induces a verapamil-sensitive psychostimulant effect that appears to independ on the opening of L-type calcium channels.
TargetsGABA Receptor
In vivo

The aversive, anxiolytic-like, and verapamil-sensitive psychostimulant effects of pulegone.[Pubmed: 24790000]

Biol Pharm Bull. 2014;37(5):771-8.


METHODS AND RESULTS:
We investigated the psychostimulant, rewarding, and anxiolytic-like effects of Pulegone. Possible interactions between Pulegone and menthol concerning their psychostimulant effect were also analyzed. General mouse activity after Pulegone treatment, and the interacitons between Pulegone and menthol, were determined in the open field. The anxiolytic-like activity, motor coordination and strength force were evaluated using the elevated plus maze (EPM), rotarod test and grasping test, respectively. The motivational properties of Pulegone were evaluated by pairing the drug effects on the mice with the least preferred compartment (previously determined) of a conditioned place preference (CPP) apparatus. Pulegone increased mouse locomotor activity and immobilization time. Verapamil, but not diltiazem, haloperidol or picrotoxin, decreased the psychostimulation induced by Pulegone. Pulegone also decreased grooming and rearing behaviors and caused motor incoordination and weakness at high doses. Pulegone increased the time spent by mice in the open arms of the EPM, and flumazenil pre-treatment did not alter this effect. Pulegone either produced no CPP or induced conditioned place aversion. The changes in mouse ambulatory activity caused by the association of Pulegone with menthol were either lower than those predicted by the theoretical curve or not different from the predicted values.
CONCLUSIONS:
Therefore, Pulegone induces a verapamil-sensitive psychostimulant effect that appears to independ on the opening of L-type calcium channels. Pulegone has negative reinforcing properties and seems to possess anxiolytic-like actions unrelated to the benzodiazepine site of the γ-aminobutyric acid type A (GABAA) receptor. Finally, Pulegone might act in an addictive or synergic way with menthol.

Protocol of Pulegone

Animal Research

Mode of action of pulegone on the urinary bladder of F344 rats.[Pubmed: 22499580]

Toxicol Sci. 2012 Jul;128(1):1-8.

Essential oils from mint plants, including peppermint and pennyroyal oils, are used at low levels as flavoring agents in various foods and beverages. Pulegone is a component of these oils.
METHODS AND RESULTS:
In a 2-year bioassay, oral administration of Pulegone slightly increased the urothelial tumor incidence in female rats. We hypothesized that its mode of action (MOA) involved urothelial cytotoxicity and increased cell proliferation, ultimately leading to tumors. Pulegone was administered by gavage at 0, 75, or 150 mg/kg body weight to female rats for 4 and 6 weeks. Fresh void urine and 18-h urine were collected for crystal and metabolite analyses. Urinary bladders were evaluated by light microscopy and scanning electron microscopy (SEM) and bromodeoxyuridine (BrdU) labeling index. Pulegone and its metabolites, piperitenone, piperitone, menthofuran, and menthone, were tested for cytotoxicity in rat (MYP3) and human (1T1) urothelial cells by the 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay. No abnormal urinary crystals were observed by light microscopy. Urine samples (18-h) showed the presence of Pulegone, piperitone, piperitenone, and menthofuran in both treated groups. By SEM, bladders from treated rats showed superficial necrosis and exfoliation. There was a significant increase in the BrdU labeling index in the high-dose group. In vitro studies indicated that Pulegone and its metabolites, especially piperitenone, are excreted and concentrated in the urine at cytotoxic levels when Pulegone is administered at high doses to female rats.
CONCLUSIONS:
The present study supports the hypothesis that cytotoxicity followed by regenerative cell proliferation is the MOA for Pulegone-induced urothelial tumors in female rats.

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Preparing Stock Solutions of Pulegone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.5703 mL 32.8515 mL 65.703 mL 131.406 mL 164.2576 mL
5 mM 1.3141 mL 6.5703 mL 13.1406 mL 26.2812 mL 32.8515 mL
10 mM 0.657 mL 3.2852 mL 6.5703 mL 13.1406 mL 16.4258 mL
50 mM 0.1314 mL 0.657 mL 1.3141 mL 2.6281 mL 3.2852 mL
100 mM 0.0657 mL 0.3285 mL 0.657 mL 1.3141 mL 1.6426 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 Pulegone

Mode of action of pulegone on the urinary bladder of F344 rats.[Pubmed:22499580]

Toxicol Sci. 2012 Jul;128(1):1-8.

Essential oils from mint plants, including peppermint and pennyroyal oils, are used at low levels as flavoring agents in various foods and beverages. Pulegone is a component of these oils. In a 2-year bioassay, oral administration of Pulegone slightly increased the urothelial tumor incidence in female rats. We hypothesized that its mode of action (MOA) involved urothelial cytotoxicity and increased cell proliferation, ultimately leading to tumors. Pulegone was administered by gavage at 0, 75, or 150 mg/kg body weight to female rats for 4 and 6 weeks. Fresh void urine and 18-h urine were collected for crystal and metabolite analyses. Urinary bladders were evaluated by light microscopy and scanning electron microscopy (SEM) and bromodeoxyuridine (BrdU) labeling index. Pulegone and its metabolites, piperitenone, piperitone, menthofuran, and menthone, were tested for cytotoxicity in rat (MYP3) and human (1T1) urothelial cells by the 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay. No abnormal urinary crystals were observed by light microscopy. Urine samples (18-h) showed the presence of Pulegone, piperitone, piperitenone, and menthofuran in both treated groups. By SEM, bladders from treated rats showed superficial necrosis and exfoliation. There was a significant increase in the BrdU labeling index in the high-dose group. In vitro studies indicated that Pulegone and its metabolites, especially piperitenone, are excreted and concentrated in the urine at cytotoxic levels when Pulegone is administered at high doses to female rats. The present study supports the hypothesis that cytotoxicity followed by regenerative cell proliferation is the MOA for Pulegone-induced urothelial tumors in female rats.

The aversive, anxiolytic-like, and verapamil-sensitive psychostimulant effects of pulegone.[Pubmed:24790000]

Biol Pharm Bull. 2014;37(5):771-8.

We investigated the psychostimulant, rewarding, and anxiolytic-like effects of Pulegone. Possible interactions between Pulegone and menthol concerning their psychostimulant effect were also analyzed. General mouse activity after Pulegone treatment, and the interacitons between Pulegone and menthol, were determined in the open field. The anxiolytic-like activity, motor coordination and strength force were evaluated using the elevated plus maze (EPM), rotarod test and grasping test, respectively. The motivational properties of Pulegone were evaluated by pairing the drug effects on the mice with the least preferred compartment (previously determined) of a conditioned place preference (CPP) apparatus. Pulegone increased mouse locomotor activity and immobilization time. Verapamil, but not diltiazem, haloperidol or picrotoxin, decreased the psychostimulation induced by Pulegone. Pulegone also decreased grooming and rearing behaviors and caused motor incoordination and weakness at high doses. Pulegone increased the time spent by mice in the open arms of the EPM, and flumazenil pre-treatment did not alter this effect. Pulegone either produced no CPP or induced conditioned place aversion. The changes in mouse ambulatory activity caused by the association of Pulegone with menthol were either lower than those predicted by the theoretical curve or not different from the predicted values. Therefore, Pulegone induces a verapamil-sensitive psychostimulant effect that appears to independ on the opening of L-type calcium channels. Pulegone has negative reinforcing properties and seems to possess anxiolytic-like actions unrelated to the benzodiazepine site of the gamma-aminobutyric acid type A (GABAA) receptor. Finally, Pulegone might act in an addictive or synergic way with menthol.

Description

Pulegone, the major chemical constituent of Calamintha nepeta (L.) Savi essential oil which is an aromatic herb with a mint-oregano flavor, is one of avian repellents. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations.

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