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(+)-Pulegone

$96

  • Brand : BIOFRON

  • Catalogue Number : BD-P0957

  • Specification : 98.5%(HPLC&TLC)

  • CAS number : 89-82-7

  • Formula : C10H16O

  • Molecular Weight : 152.2

  • PUBCHEM ID : 442495

  • Volume : 0.2ml

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Catalogue Number

BD-P0957

Analysis Method

Specification

98.5%(HPLC&TLC)

Storage

-20℃

Molecular Weight

152.2

Appearance

Powder

Botanical Source

This product is isolated and purified from the herbs of Mentha canadensis L.

Structure Type

Category

SMILES

CC1CCC(=C(C)C)C(=O)C1

Synonyms

(5R)-5-methyl-2-(methylethylidene)cyclohexan-1-one/(5R)-2-Isopropylidene-5-methylcyclohexanone/(R)-Pulegone/Cyclohexanone, 5-methyl-2- (1-methylethylidene)-, (R)-/PULEGON/PULEGONE,TECH/2-isopropylidene-5-methylcyclohexan-1-one/p-Menth-4(8)-en-3-one, (R)-(+)-/(5R)-5-Methyl-2-(2-propanyliden)cyclohexanon/Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5R)-/(+)-(R)-Pulegone/D-PULEGONE/R-(+)-Pulegone/Pulegone,(d)/(1R)-(+)-pulegone/(5R)-2-Isopropylidene-5-methylcyclohexanone/(+)-Pulegone/R-(+)-p-Menth-4(8)-en-3-one/Pulegone

IUPAC Name

Applications

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.

Density

0.9±0.1 g/cm3

Solubility

Chloroform

Flash Point

82.2±0.0 °C

Boiling Point

224.0±0.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

NZGWDASTMWDZIW-MRVPVSSYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:89-82-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31134844

Abstract

Context: Pulegone, a key compound in Schizonepeta essential oil, has been identified as an anti-inflammatory. However, its underlying molecular mechanisms on NLR family pyrin domain containing 3 (NLRP3) inflammasome have not been elucidated. Objective: Here, the modulatory effects of pulegone on NLRP3 inflammasome were investigated. Materials and methods: The C57BL/6J mice were randomly divided into five groups: Normal, Lipopolysaccharides (LPS), Dexamethasone (DEX, 5 mg/kg), Pulegone (0.095 and 0.190 g/kg) groups. All mice were challenged by LPS except for the Normal group. Results: A reduced expression of Interleukin-18 (IL-18), Interleukin-1β (IL-1β), Interleukin-5 (IL-5), Tumor necrosis factor-α (TNF-α), Interferon-gamma (IFN-γ), Monocyte chemoattratctant protein-1 (MCP-1), Macrophage inflammatory protein-1β (MIP-1β), Monocyte colony stimulating factor (M-CSF) and Granulocyte-macrophage colony stimulating factor (GM-CSF) in serum were detected in the pulegone groups as compared to the LPS group. In addition, a reduced mRNA and protein expression production of ASC, NLRP3, and Caspase-1 were detected in lungs after pulegone administration. Histological analysis results indicated that the histological changes of lungs caused by LPS were ameliorated by pulegone. Immunohistochemical study showed a decreased positive cell numbers of P2X7R in Pulegone (0.095 and 0.190 g/kg) groups. Conclusion: Pulegone exerts anti-inflammatory effects on LPS-induced sepsis mice via inhibition of the NLRP3 expression.

KEYWORDS

LPS; NLRP3; Pulegone; inflammation; sepsis

Title

Pulegone inhibits inflammation via suppression of NLRP3 inflammasome and reducing cytokine production in mice.

Author

Yang Q1,2, Luo J1, Lv H1, Wen T1, Shi B1, Liu X1, Zeng N1.

Publish date

2019 Jun

PMID

31027569

Abstract

Six natural monoterpenes (1,8-cineole, (-)-citronellal, limonene, α-pinene, pulegone and 4-terpineol) showed high acaricidal activity by fumigant and contact actions against adult females of the two-spotted spider mite, Tetranychus urticae Koch. The monoterpenes exhibited varying degrees of acaricidal potency using contact toxicity test after 24 and 48 h of treatment, where the LC50 values were <160 and 45 mg/L, respectively. In fumigation test, of these six monoterpenes, pulegone exhibited the highest toxicity (LC50 = 3.81 mg/L air), while (-)-citronellal had the lowest fumigant toxicity (LC50 = 15.20 mg/L air). All compounds had high inhibitory effect on acetylcholinesterase (AChE) and gama amino butyric acid transaminase (GABA-T) activities. Pulegone was the most AChE inhibitor (IC50 = 8.79 mg/L), while 4-terpineol revealed the lowest inhibitory effect (IC50 = 32.82 mg/L). However, limonene caused the highest inhibition of GABA-T (IC50 = 11.37 mg/L). The molecular docking studies revealed that the compounds displayed different binding interactions with the amino acid residues at the catalytic sites of AChE and GABA-T enzymes. Noncovalent interactions especially van der Waals, hydrogen bonding as well as hydrophobic was found between the compounds and the enzymes. A significant relationship was found between the docking score and the biological activity of monoterpenes compared to the standard acaricide pyridaben. In silico ADMET properties were also performed and displayed potential for the development of good acaricidal candidates. Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

AChE; ADMET; Acaricidal activity; Docking; GABA-T; Monoterpenes; Tetranychus urticae

Title

Acaricidal activity, biochemical effects and molecular docking of some monoterpenes against two-spotted spider mite (Tetranychus urticae Koch).

Author

Abdelgaleil SAM1, Badawy MEI2, Mahmoud NF1, Marei AEM1.

Publish date

2019 May;

PMID

30789719

Abstract

Pycnanthemum incanum, a species of wild mountain mint endemic to North America, has a pungent mint-like odor that has not been fully characterized. Due in part to its high terpene content, P. incanum has broad potential for health-promoting, cosmetic, culinary, and food flavoring applications. Therefore, odorants of P. incanum were identified by coupling solvent assisted flavor evaporation (SAFE) and aroma extract dilution analysis (AEDA), which afforded 24 odorants including 14 odorants with flavor dilution (FD) factors ≥4. Selected odorants, including those with FD factors ≥16, were quantitated by stable isotope dilution assays (SIDAs), and odor activity values (OAVs) were determined. The odorants with the highest OAVs included β-ionone (floral, violet; OAV 300), myrcene (terpeny, OAV 120), linalool (floral, citrus; OAV 79), and pulegone (mint, medicinal; OAV 58). An odor-simulation model based on the quantitation closely matched the sensory attributes of the original P. incanum plant material. In addition, enantiomeric proportions of chiral odorants in P. incanum were determined by chiral chromatography.

KEYWORDS

Pycnanthemum incanum; aroma extract dilution analysis; chiral chromatography; solvent assisted flavor evaporation; stabile-isotope-dilution assay

Title

Characterization of Key Odorants in Hoary Mountain Mint, Pycnanthemum incanum.

Author

Dein M1, Munafo JP Jr1.

Publish date

2019 Mar 6;