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Chemical Structure| 10458-14-7 Chemical Structure| 10458-14-7
Chemical Structure| 10458-14-7

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CAS No.: 10458-14-7

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Menthone, a natural product isolated and purified from the herbs of Mentha canadensis L., enhances the skin permeability by disordering the ordered organization of SC lipids and extracts part of SC lipids, while pulegone appears to promote drug transport across the skin only by extracting part of SC lipids.

Synonyms: p-Menthan-3-one; NSC 9280; NSC 113134

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Product Citations

Product Citations

Mei Wang ; Joseph Lee ; Jianping Zhao ; Shamba Chatterjee ; Amar G. Chittiboyina ; Zulfiqar Ali , et al.

Abstract: Peppermint essential oil (EO) has a multitude of applications, such as a fragrance in cosmetics, personal care and industrial products, or as a flavoring ingredient in food and beverages. Despite its popularity and economic significance, peppermint EO is often adulterated to reduce production costs and to increase profits. Although the ISO standard for peppermint EO exists, detecting sophisticated forms of adulteration remains challenging.The current study used conventional and chiral GC/MS analysis of volatiles compounds, and chemometric techniques to evaluate an extensive set of authentic peppermint EO (n?=?22) and commercial products (n?=?36) purported to contain peppermint EO. Specifically, thirty-six terpenoids were examined in each sample and compared with the ISO standard. Fifty-three percent of the selected commercial products did not meet the ISO specifications and the ratio between menthone/isomenthone was proven to be a good indicator for authentication and adulteration detection. Chiral GC/MS was further employed to measure eight terpenoids: α-pinene, β-pinene, limonene, menthol, menthone, isomenthone, pulegone, and menthyl acetate. The enantiomeric compositions of 27 commercial products were above or below the norm measured from authentic peppermint EOs. Of the 27 samples, eight met the ISO standard. A sample class prediction (SCP) model based on partial least squares-discriminant analysis (PLS-DA) of conventional GC/MS data was constructed using authentic peppermint EOs and cornmint EOs. The model can distinguish the most common types of peppermint EOs (US, India, and US/India blend) and cornmint EOs sold in the US market. After construction, the SCP model was then used to analyze commercial samples. One sample, which passed both ISO specification and chiral analysis, was identified as outlier by the SCP model. Overall, the applicability of combining both conventional and chiral GC/MS along with chemometric tools has been successfully demonstrated to address the overall quality of peppermint EOs in commerce and may help combat sophisticated adulteration.

Keywords: Peppermint essential oil (Mentha piperita L.) ; conventional and chiral GC/MS ; Chemometrics ; Quality evaluation ; Adulteration

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Product Details of Menthone

CAS No. :10458-14-7
Formula : C10H18O
M.W : 154.25
SMILES Code : O=C1C(C(C)C)CCC(C)C1
Synonyms :
p-Menthan-3-one; NSC 9280; NSC 113134
MDL No. :MFCD00062998

Safety of Menthone

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H302-H319-H334-H412
Precautionary Statements:P210-P261-P264-P270-P273-P280-P284-P301+P312+P330-P304+P340-P305+P351+P338-P337+P313-P342+P311-P370+P378-P403+P235-P501

Application In Synthesis of Menthone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 10458-14-7 ]

[ 10458-14-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 538-28-3 ]
  • [ 10458-14-7 ]
  • 3-Isopropyl-6-methyl-2-oxo-cyclohexanesulfonic acid; compound with 2-benzyl-isothiourea [ No CAS ]
  • 2
  • [ 98-55-5 ]
  • [ 15356-70-4 ]
  • copper catalysts [ No CAS ]
  • [ 498-81-7 ]
  • [ 10458-14-7 ]
  • 3
  • [ 98-55-5 ]
  • [ 15356-70-4 ]
  • nickel catalysts [ No CAS ]
  • [ 498-81-7 ]
  • [ 10458-14-7 ]
  • 4
  • [ 14150-94-8 ]
  • [ 110-17-8 ]
  • [ 10458-14-7 ]
  • [ 64205-92-1 ]
  • [ 214698-69-8 ]
YieldReaction ConditionsOperation in experiment
Pd-C; In methanol; methanolic ammonia; ethanol; 2-methyl-propan-1-ol; chloroform; Example 15 (5R),(8S)-2-(5,6,7,8-Tetrahydro-8-isopropyl-5-methyl-quinolin-3-yl)amino-2-imidazoline (5R), (8S)-3-Amino-5,6,7,8-tetrahydro-8-isopropyl-5-methylquinoline. (-)-Menthone (390 mg, 2.53 mm(1) was mixed with 1-methyl-3,5-dinitro-2-pyridone (500 mg, 2.51 mmol) in 1M methanolic ammonia (50 mL, 50 mmol) and heated at reflux overnight. The solvent was evaporated off and the residue was dissolved in CHCl3 and flash chromatographed over silica gel (37 g) eluding with EtOAc/hexane (1:20) to afford a colorless oil (248 mg, 1.06 mmol). It was dissolved in MeOH (5 mL), treated with 10% Pd-C (27 mg) and hydrogenated at 1 atm for 2 h. Filtration through Celite gave a pale yellow solid (207 mg). It was partitioned between CH2 Cl2 and 2N HCl. The organic layer was further extracted with 2N HCl before the aqueous layer was basined with Na2 CO3 solution and extracted with CH2 Cl2 to afford a white solid (123 mg, 24% yield). (5R), (8S)-2-(5,6,7,8-Tetrahydro-8-isopropy-5-methyl-quinolin-3-yl)amino-2-imidazoline. The above amine (119 mg, 0.58 mmol) was mixed with 2-imidazolinesulfonic acid (180 mg, 1.20 mmol) in isobutyl alcohol (5 mL) aid heated at reflux for 2 days. The solvent was evaporated off to give a residue which was dissolved in CHCl3 and flash chromatographed over silica gel (17 g) eluding with EtOAc/MeOH/Et3 N (20:3:1) to afford a white solid (129 mg, 81% yield). It was dissolved in EtOH and reated with fumaric acid (110 mg) in EtOH. Upon addition of ether and refrigeration, the solution gave white crystals (43 mg): mp 151-154 C. Anal. Calcd. for C16 H24 N4.1.6C4 H4 O4: C, 58.73; H, 6.69; N, 12.23. Found: C, 58.41; H, 7.04; N, 12.24.
 

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