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(±)-menthone

Chemical Structure

General Material Information

Preferred name (±)-menthone
Trivial Name (±)-Menthone
Short Description menthone
Formula C10 H18 O
CAS Number 89-80-5
Deleted CAS Number 1074-95-9
FEMA Number 2667
Flavis Number 7.176
ECHA Number 201-941-1
FDA UNII 9NH5J4V8FN
Nikkaji Number J633E
COE Number 2035
xLogP3-AA 2.70 (est)
NMR Predictor External link
JECFA Food Flavoring 429 menthone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 89-80-5 ; MENTHONE
Synonyms
  • p- menthan-3-one racemic
  • para- menthan-3-one racemic
  • p- menthane-3-one racemic
  • para- menthane-3-one racemic
  • menthone
  • (±)- menthone
  • dextro,laevo- menthone
  • DL- menthone
  • neo menthone
  • p- menthone
  • para- menthone
  • menthone / isomenthone 70:30
  • menthone / isomenthone 80:20
  • menthone 70/30
  • menthone 80:20
  • menthone 80/20
  • menthone 90:10
  • menthone 95:5
  • menthone FCC
  • menthone pure
  • menthone, racemic
  • 5-methyl-2-(1-methyl ethyl) cyclohexanone racemic
  • 5-methyl-2-(1-methylethyl)cyclohexanone racemic
  • 5-methyl-2-propan-2-ylcyclohexan-1-one racemic
  • 2-iso propyl-5-methyl cyclohexanone racemic
  • 5-methyl-2-propan-2-ylcyclohexan-1-one
  • Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-
  • p-Menthan-3-one, trans-
  • Cyclohexanone, 5-methyl-2-(1-methylethyl)-, trans-
  • rel-(2R,5S)-5-Methyl-2-(1-methylethyl)cyclohexanone
  • Neomenthone
  • trans-p-Menthan-3-one
  • p-Menthone
  • trans-Menthan-3-one
  • trans-Menthone
  • dl-Menthone
  • trans-p-Menthone
  • Menthone G

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Literature & References

5-methyl-2-propan-2-ylcyclohexan-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:89-80-5
Pubchem (cid):6986
Pubchem (sid):134972993
Flavornet:89-80-5
Pherobase:View
Publications by Google Patents
Preparation of dl-menthone
Publications by PubMed
Chemical composition of essential oils of Grindelia squarrosa and G. hirsutula.
Intestinal absorptive transport of Genkwanin from Flos genkwa using a single-pass intestinal perfusion rat model.
Development of a Validated HPLC/Photodiode Array Method for the Determination of Isomenthone in the Aerial Parts of Ziziphora tenuior L.
Terpene constituents of the leaves of five Vietnamese species of Clausena (Rutaceae).
A rationale to design longer lasting mosquito repellents.
Biocontrol potential of essential oil monoterpenes against housefly, Musca domestica (Diptera: Muscidae).
Effect of different drying methods on the essential oils of mint (Mentha haplocalyx).
Nutritional and sensory quality during refrigerated storage of fresh-cut mints (Mentha×piperita and M. spicata).
Nematicidal activity of mint aqueous extracts against the root-knot nematode Meloidogyne incognita.
(3R*,6R*,4'S*,8'R*,3''R*,6''R*)-3,3''-Diisopropyl-6,6''-dimethyl-2',6'-di-phenyl-dispiro-[cyclo-hexane-1,4'-(3,7-dioxa-2,6-di-aza-bicyclo-[3.3.0]octa-ne)-8',1''-cyclo-hexa-ne]-2,2''-dione.
Olfactory responses of the antennal trichoid sensilla to chemical repellents in the mosquito, Culex quinquefasciatus.
[Study on effect and mechanism of volatile oil of schizonepetae herba and its essential components against influenza virus].
Anti-inflammatory effects of 27 selected terpenoid compounds tested through modulating Th1/Th2 cytokine secretion profiles using murine primary splenocytes.
Effect of gibberellic acid and calliterpenone on plant growth attributes, trichomes, essential oil biosynthesis and pathway gene expression in differential manner in Mentha arvensis L.
Identification of genetic markers linked to anthracnose resistance in sorghum using association analysis.
Inhibition by menthol and its related chemicals of compound action potentials in frog sciatic nerves.
Retention of aroma compounds from Mentha piperita essential oil by cyclodextrins and crosslinked cyclodextrin polymers.
Essential oils of Micromeria dalmatica Benth., a Balkan endemic species of section Pseudomelissa.
Asymmetric chiral ligand-directed alkene dioxygenation.
Anti-yeast activity of mentha oil and vapours through in vitro and in vivo (real fruit juices) assays.
The plant short-chain dehydrogenase (SDR) superfamily: genome-wide inventory and diversification patterns.
Essential oils and their compositions as spatial repellents for pestiferous social wasps.
In vitro production of M. × piperita not containing pulegone and menthofuran.
The constituents of essential oil: antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia.
Essential oil composition and antimicrobial activity of wild and cultivated mint timija (Mentha suaveolens subsp. timija (Briq.) Harley), an endemic and threatened medicinal species in Morocco.
Retro-nasal aroma release is correlated with variations in the in-mouth air cavity volume after empty deglutition.
Antioxidant and antibacterial effects of Lavandula and Mentha essential oils in minced beef inoculated with E. coli O157:H7 and S. aureus during storage at abuse refrigeration temperature.
Essential-oil diversity of three Calamintha species from Greece.
Volatile secondary metabolites of Micromeria dalmatica Benth. (Lamiaceae): biosynthetical and chemotaxonomical aspects.
Bactericidal antibiotic-phytochemical combinations against methicillin resistant Staphylococcus aureus.
Antimicrobial activity of a traditionally used complex essential oil distillate (Olbas(®) Tropfen) in comparison to its individual essential oil ingredients.
Lack of cytotoxic and genotoxic effects of Minthostachys verticillata essential oil: studies in vitro and in vivo.
Intraspecific variability of the essential oil of Calamintha nepeta subsp. nepeta from Southern Italy (Apulia).
Molecular and functional characterization of the odorant receptor2 (OR2) in the tiger mosquito Aedes albopictus.
Mode of action of pulegone on the urinary bladder of F344 rats.
Chemical and morphological diversity in wild populations of Mentha longifolia in Israel.
Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham.
Volatile organic compounds from Centaurium erythraea Rafn (Croatia) and the antimicrobial potential of its essential oil.
Quality control of modified xiaoyao san through the determination of 22 active components by ultra-performance liquid chromatography.
Blockade of TRPM8 activity reduces the invasion potential of oral squamous carcinoma cell lines.
Composition of the essential oil of Origanum tyttanthum from Tajikistan.
Simple preparative gas chromatographic method for isolation of menthol and menthone from peppermint oil, with quantitative GC-MS and (1) H NMR assay.
Immunocytochemical localization of short-chain family reductases involved in menthol biosynthesis in peppermint.
Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)+-pulegone and menthone.
The Arabidopsis short-chain dehydrogenase/reductase 3, an abscisic acid deficient 2 homolog, is involved in plant defense responses but not in ABA biosynthesis.
In vitro activities of natural products against oral Candida isolates from denture wearers.
Quantitative comparative analysis of the bio-active and toxic constituents of leaves and spikes of Schizonepeta tenuifolia at different harvesting times.
Cremophor RH40-PEG 400 microemulsions as transdermal drug delivery carrier for ketoprofen.
Analysis of fresh Mentha haplocalyx volatile components by comprehensive two-dimensional gas chromatography and high-resolution time-of-flight mass spectrometry.
Volatile organic compounds from rhizobacteria increase biosynthesis of essential oils and growth parameters in peppermint (Mentha piperita).
Classification of Greek Mentha pulegium L. (Pennyroyal) samples, according to geographical location by Fourier transform infrared spectroscopy.
Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan.
Monoterpenes isolated from Minthostachys verticillata (Griseb.) Epling essential oil modulates immediate-type hypersensitivity responses in vitro and in vivo.
Cu(I) catalysed cyclopropanation with enantiopure scorpionate type ligands derived from (+)-camphor or (-)-menthone.
[(2R,5R,6S,9R)-6-Isopropyl-9-methyl-1,4-dioxaspiro-[4.5]decan-2-yl]methyl 4-bromo-benzoate.
Metal-free diastereoselective catalytic hydrogenations of imines using B(C6F5)3.
Fungicidal properties of the essential oil of Hesperozygis marifolia on Aspergillus flavus link.
Menthone and p-menthyl-3-carboxaldehyde as chiral auxiliaries.
Toxicity of Schizonpeta multifida essential oil and its constituent compounds towards two grain storage insects.
Peppermint oil decreases the production of virulence-associated exoproteins by Staphylococcus aureus.
Menthone aryl acid hydrazones: a new class of anticonvulsants.
Plant volatiles providing additional evidences to the occurence of a wild-growing population of Calamintha vardarensis (Greuter et Burdet) Šilić outside of its natural habitat.
Composition and antimicrobial activities of Lippia multiflora Moldenke, Mentha x piperita L. and Ocimum basilicum L. essential oils and their major monoterpene alcohols alone and in combination.
Yield, content, and composition of peppermint and spearmints as a function of harvesting time and drying.
Control of enantioselectivity with flexible biaryl axes: terpene-based alkylzinc catalysts in enantioselective dialkylzinc additions.
Potential interaction between the volatile and non-volatile fractions on the in vitro antimicrobial activity of three South African Pelargonium (Geraniaceae) species.
Pharmacological interactions of essential oil constituents on the viability of micro-organisms.
Antimicrobial activity and volatile constituents of the essential oil of Pulsatilla albana from Iran.
Topical application of TRPM8 agonists accelerates skin permeability barrier recovery and reduces epidermal proliferation induced by barrier insult: role of cold-sensitive TRP receptors in epidermal permeability barrier homoeostasis.
UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha x piperita L.).
Seasonal variation in content, chemical composition and antimicrobial and cytotoxic activities of essential oils from four Mentha species.
Fumigant toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae).
Molecular cloning and characterization of a broad substrate terpenoid oxidoreductase from Artemisia annua.
Ultraviolet-B and photosynthetically active radiation interactively affect yield and pattern of monoterpenes in leaves of peppermint (Mentha x piperita L.).
Topical toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae).
Menthone semicarbazides and thiosemicarbazides as anticonvulsant agents.
API-IT-MS for measuring aroma release from dentifrice products using a device to simulate tooth brushing.
Prolonged stimulus exposure reveals prolonged neurobehavioral response patterns.
[Study on the dynamic change of essential components in Folium Apocyni Veneti].
Stereocontrolled syntheses of (-)-cubebol and (-)-10-epicubebol involving intramolecular cyclopropanation of alpha-lithiated epoxides.
Evidence for dopamine involvement in ambulation promoted by pulegone in mice.
Insecticidal activity of essential oils from native medicinal plants of Central Argentina against the house fly, Musca domestica (L.).
Chemical composition, olfactory evaluation and antioxidant effects of essential oil from Mentha x piperita.
Chemical composition, olfactory evaluation and antioxidant effects of essential oil from Mentha canadensis.
Chemical composition and in vitro antibacterial activity of the essential oil of Minthostachys mollis (Kunth) Griseb Vaught from the Venezuelan Andes.
Design of improved permeation enhancers for transdermal drug delivery.
Evolution of morphine biosynthesis in opium poppy.
[Analysis on changes of chemical compounds in different samples of fried Foeniculum vulgare].
Toxicity to vapor exposure and topical application of essential oils and monoterpenes on Musca domestica (Diptera: Muscidae).
Supercritical fluid extraction--achiral liquid chromatography with circular dichroism detection for the determination of menthone enantiomers in natural peppermint oil samples.
In vitro evaluation of the permeation through reconstructed human epidermis of essentials oils from cosmetic formulations.
Headspace solid-phase microextraction-gas chromatography-mass spectrometry determination of the characteristic flavourings menthone, isomenthone, neomenthol and menthol in serum samples with and without enzymatic cleavage to validate post-offence alcohol drinking claims.
Fumigant insecticidal activity and repellent effect of five essential oils and seven monoterpenes on first-instar nymphs of Rhodnius prolixus.
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
Effects of oxygen-containing terpenes as skin permeation enhancers on the lipoidal pathways of human epidermal membrane.
Chemical composition of essential oils of Thymus and Mentha species and their antifungal activities.
Aroma permeability of hydroxypropyl maize starch films.
A 3,5-dinitro-benzoyl derivative of a stereoisomer of glycerol menthonide.
Antioxidant property of volatile oils determined by the ferric reducing ability.
Supercritical carbon dioxide extraction of Mentha pulegium L. essential oil.
Comparative analysis of some active principles of herb plants by GC/MS.
Control of asymmetric biaryl conformations with terpenol moieties: syntheses, structures and energetics of new enantiopure C2-symmetric diols.
Inhibition of lipopolysaccharide-induced interleukin-1beta and tumor necrosis factor-alpha production by menthone through nuclear factor-kappaB signaling pathway in HaCat cells.
Menthol derivative WS-12 selectively activates transient receptor potential melastatin-8 (TRPM8) ion channels.
Defense on the rocks: low monoterpenoid levels in plants on pillars without mammalian herbivores.
Enantiomeric differentiation of oxygenated p-menthane derivatives by 13C NMR using Yb(hfc)3.
Activity of essential oils and individual components against acetyl- and butyrylcholinesterase.
Evidence for dopamine involvement in ambulation promoted by menthone in mice.
Screening of chemical penetration enhancers for transdermal drug delivery using electrical resistance of skin.
[Retention of components in a mixture of volatile organic substances by maltodextrins].
Matrix-type transdermal patches of verapamil hydrochloride: in vitro permeation studies through excised rat skin and pharmacodynamic evaluation in rats.
A role for a menthone reductase in resistance against microbial pathogens in plants.
Factors influencing hydrocortisone permeation into human hair follicles: use of the skin sandwich system.
Insecticidal activity of menthol derivatives against mosquitoes.
Fumigant activity of essential oils and components of Illicium verum and Schizonepeta tenuifolia against Botrytis cinerea and Colletotrichum gloeosporioides.
Inhibitory effect of cyclic terpenes (limonene, menthol, menthone and thymol) on Fusarium verticillioides MRC 826 growth and fumonisin B1 biosynthesis.
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats.
Synthesis of +-dihydro-epi-deoxyarteannuin B.
Composition and antifungal activity of essential oils of Mentha piperita and Lavendula angustifolia on post-harvest phytopathogens.
Volatile terpenoids of endophyte-free and infected peppermint (Mentha piperita L.): chemical partitioning of a symbiosis.
A highly enantio- and diastereoselective 1,3-dimethylallylation of aldehydes.
Comparison of essential oils from three plants for enhancement of antimicrobial activity of nitrofurantoin against enterobacteria.
The effect of terpene concentrations on the skin penetration of diclofenac sodium.
Broad activation of the glomerular layer enhances subsequent olfactory responses.
Fumigant activity of plant essential oils and components from Schizonepeta tenuifolia against Lycoriella ingenua (Diptera: Sciaridae).
A review of the bioactivity and potential health benefits of peppermint tea (Mentha piperita L.).
Biotransformation of (-)-menthone by human liver microsomes.
Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).
[Comparison of supercritical fluid extraction and steam distillation methods for the extraction of essential oils from Schizonepeta tenuifolia Briq].
Metallophosphite-catalyzed asymmetric acylation of alpha,beta-unsaturated amides.
Chemical composition of the essential oil of Salvia microstegia Boiss. et Balansa growing wild in Lebanon.
Immunomodulating properties of Minthostachys verticillata on human lymphocytes and basophils.
Effects of mechanical wounding on essential oil composition and emission of volatiles from Minthostachys mollis.
Quantitative variations in the essential oil of Minthostachys mollis (Kunth.) Griseb. in response to insects with different feeding habits.
Effect of harvest time and drying method on biomass production, essential oil yield, and quality of peppermint (Mentha x piperita L.).
Structural investigation of amylose complexes with small ligands: helical conformation, crystalline structure and thermostability.
A chiral cyclohexanone linked to polystyrene for solid-phase synthesis of chiral alpha-carbonyls.
Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint.
Modulation of human GABAA and glycine receptor currents by menthol and related monoterpenoids.
Structural investigation of amylose complexes with small ligands: inter- or intra-helical associations?
p-Menthane-3-carboxaldehyde: a useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity.
The effect of selected monoterpenoids on the cellular slime mold, Dictyostelium discoideum NC4.
Effect of lipid bilayer alteration on transdermal delivery of a high-molecular-weight and lipophilic drug: studies with paclitaxel.
A stereodivergent approach to amino acids, amino alcohols, or oxazolidinones of high enantiomeric purity.
Release of peppermint flavour compounds from chewing gum: effect of oral functions.
The constituents of essential oil and in vitro antimicrobial activity of Micromeria cilicica from Turkey.
Biofilm in water pipelines; a potential source for off-flavours in the drinking water.
Identification of monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate in nature by high performance liquid chromatography-tandem mass spectrometry.
Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil.
Transdermal delivery of zidovudine: effect of terpenes and their mechanism of action.
Tetrahydroacridin-9-ones, 9-chlorotetrahydroacridines, 9-amino-tetrahydroacridines and 9-(pyrazol-1-yl)-tetrahydroacridines derived from chiral cyclanones.
Thiol-catalysed radical-chain redox rearrangement reactions of benzylidene acetals derived from terpenoid diols.
Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase.
Crystal structure of amylose complexes with small ligands.
Monoterpene double-bond reductases of the (-)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (-)-isopiperitenone reductase and (+)-pulegone reductase of peppermint.
Enhanced iontophoretic delivery of buspirone hydrochloride across human skin using chemical enhancers.
Antimicrobial and antioxidant activities of three Mentha species essential oils.
Antifungal activity of peppermint and sweet basil essential oils and their major aroma constituents on some plant pathogenic fungi from the vapor phase.
Transdermal delivery of insulin from poloxamer gel: ex vivo and in vivo skin permeation studies in rat using iontophoresis and chemical enhancers.
Biotransformation of aliphatic and aromatic ketones, including several monoterpenoid ketones and their derivatives by five species of marine microalgae.
Transdermal iontophoresis of insulin. V. Effect of terpenes.
Flavor release measurement by atmospheric pressure chemical ionization ion trap mass spectrometry, construction of interface and mathematical modeling of release profiles.
Biosynthetic origin of geosmin in red beets (Beta vulgaris L.).
Chiral recognition of terpenoids in some pharmaceuticals derived from natural sources.
A SPME-GC procedure for monitoring peppermint flavor in tablets.
Antibacterial and antifungal activity of essential oils of Mentha suaveolens.
The chemical constituents and biological activity of essential oil of Lavandula stoechas ssp. stoechas.
Simulated microgravity [bed rest] has little influence on taste, odor or trigeminal sensitivity.
Characterization of essential oils from lamiaceae species by fourier transform Raman spectroscopy.
Anti-HIV activity of thiosemicarbazone and semicarbazone derivatives of (+/-)-3-menthone.
Phytochemical induction by herbivores could affect quality of essential oils from aromatic plants.
Antimicrobial screening of Mentha piperita essential oils.
Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae).
Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq.
A chlorinated monoterpene ketone, acylated beta-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae).
Essential oil composition of sachalinmint from Norway detected by solid-phase microextraction and gas chromatography-mass spectrometry analysis.
Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes.
Functional MRI of congenital hyposmia: brain activation to odors and imagination of odors and tastes.
Final report on the safety assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint) Leaf Water.
Synthesis of new pryridyl alcohols and their use as catalysts in the asymmetric addition of diethylzinc to aldehydes.
Metabolism of (R)-(+)-pulegone in F344 rats.
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.
Central to Axial Transfer of Chirality in Menthone or Camphor-Derived 2,2'-Biphenols.
Effect of passive and iontophoretic skin pretreatments with terpenes on the in vitro skin transport of piroxicam.
Ambulation-promoting effect of peppermint oil and identification of its active constituents.
[Determination of the antibacterial and antiviral activity of the essential oil from Minthostachys verticillata (Griseb.) Epling].
Lateralization of brain activation to imagination and smell of odors using functional magnetic resonance imaging (fMRI): left hemispheric localization of pleasant and right hemispheric localization of unpleasant odors.
Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L).
Hydroquinone derivatives and monoterpenoids from the Neotropical liverwort Plagiochila rutilans.
Chiral auxiliary based approach toward the synthesis of C-glycosylated amino acids.
Different stereoselectivity in the reduction of pulegone by Mentha species.
Effect of menthone on the in vitro percutaneous absorption of tamoxifen and skin reversibility.
Effect of (+)-pulegone and other oil components of Mentha x Piperita on cucumber respiration.
Local anaesthetic activity of (+)- and (-)-menthol.
Genetic and biochemical characterization of a novel monoterpene epsilon-lactone hydrolase from Rhodococcus erythropolis DCL14.
Acaricidal activity of natural monoterpenes on Tyrophagus putrescentiae (Schrank), a mite of stored food.
Chiral alpha-substituted carbonyls and alcohols from the S(N)2' displacement of cuprates on chiral carbonates: An alternative to the alkylation of chiral enolates
Physiologically initiated and inhibited phantosmia: cyclic unirhinal, episodic, recurrent phantosmia revealed by brain fMRI.
Volatile constituents of Cunila polyantha (Lamiaceae) from Costa Rica. A rich source of menthone.
3-Chloropropyl and 4-chlorobutyl phenyl ethers as sources of 1, 3-dilithiopropane and 1,4-dilithiobutane: sequential reaction with carbonyl compounds
Effects of branched cyclodextrins on the solubility and stability of terpenes.
Mechanism(s) of in vitro percutaneous absorption enhancement of tamoxifen by enhancers.
Zinc modulates the electro-olfactogram of the frog.
Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways.
Taste and smell phantoms revealed by brain functional MRI (fMRI).
Developmental regulation of monoterpene biosynthesis in the glandular trichomes of peppermint.
Monoterpene composition of essential oil from peppermint (Mentha x piperita L.) with regard to leaf position using solid-phase microextraction and gas chromatography/mass spectrometry analysis.
Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.
Biogenetic studies in Mentha x piperita. 1. deuterium-labeled monoterpene ketones: synthesis and stereoselective analysis.
Effect of sucrose on the perceived flavor intensity of chewing gum.
Sex steroids and odorants modulate gonadotropin-releasing hormone secretion in primary cultures of human olfactory cells.
Enhancement of Skin Penetration of Nonsteroidal Anti-Inflammatory Drugs from Extemporaneously Compounded Topical-Gel Formulations.
In vitro percutaneous absorption enhancement of propranolol hydrochloride through porcine epidermis by terpenes/ethanol.
Influence of drug lipophilicity on terpenes as transdermal penetration enhancers.
Taste memory induces brain activation as revealed by functional MRI.
Odor memory induces brain activation as measured by functional MRI.
Transformation of the limonene synthase gene into peppermint (Mentha piperita L.) and preliminary studies on the essential oil profiles of single transgenic plants.
Antimicrobial activity of the essential oil of Calamintha nepeta and its constituent pulegone against bacteria and fungi.
Hepatic microsomal enzyme activity in the koala and tammar wallaby: high 17beta-hydroxysteroid oxidoreductase activity in koala liver microsomes.
Mechanisms of percutaneous absorption of tamoxifen by terpenes: eugenol, D-limonene and menthone.
Mapping brain activation to odorants in patients with smell loss by functional MRI.
Functional MRI of human olfaction.
Spatially organized response zones in rat olfactory epithelium.
Membrane fluidity response to odorants as seen by 2H-NMR and infrared spectroscopy.
Chemical constituents of essential oils of muña, Bolivian plants traditionally used as pesticides, and their insecticidal properties against Chagas' disease vectors.
Terpene penetration enhancers in propylene glycol/water co-solvent systems: effectiveness and mechanism of action.
Olfactory transduction is intrinsically noisy.
Aminocyclanols, I: Synthesis and analgetic activities of some aminobenzylcyclanols derived from menthone.
Effect of menthol on cytosolic Ca2+ levels in canine airway epithelium in culture.
Stimulation by menthol of Cl secretion via a Ca(2+)-dependent mechanism in canine airway epithelium.
Mechanism of stimulation of the calcium adenosinetriphosphatase by jasmone.
Sensitivity and transduction mechanisms of responses to general odorants in turtle vomeronasal system.
Metabolism of monoterpenes in mint (mentha) species.
Chemical, physiological, and toxicological aspects of the essential oil of some species of the genus Bystropogon.
Olfactory sensitivity of two sympatric species of rice leaf folders (Lepidoptera: Pyralidae) to plant volatiles.
Percutaneous absorption enhancing effect and skin irritation of monocyclic monoterpenes.
Two-phase system membrane reactor with cofactor recycling.
Menthol blocks dihydropyridine-insensitive Ca2+ channels and induces neurite outgrowth in human neuroblastoma cells.
Metabolic activation of (R)-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins.
Hepatotoxicity of pulegone in rats: its effects on microsomal enzymes, in vivo.
Sedating and antipyretic activity of the essential oil of Calamintha sylvatica subsp. ascendens.
Chemical and Morphometrical Comparison Between two Peppermint Notomorphs.
The odorant-sensitive adenylate cyclase of olfactory receptor cells. Differential stimulation by distinct classes of odorants.
Metabolism of monoterpenes: demonstration that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint (Mentha piperita).
Short-term toxicity study in rats dosed with menthone.
Inhibitors of ex vivo aggregation of human platelets induced by decompression, during reduced barometric pressure.
Biotransformation by divison-arrested and immobilized plant cells: bioconversion of monoterpenes by gamma-irradiated suspended and entrapped cells of mentha and Nicotiana.
Determination of griseofulvin, carvone and menthone through intermediate oxime formation.
[Components of essential oils from different parts and the charcoal of Schizonepeta tenuifolia].
In vivo and in vitro destruction of rat liver cytochrome P-450 by a monoterpene ketone, pulegone.
Metabolism of Monoterpenes : Evidence for the Function of Monoterpene Catabolism in Peppermint (Mentha piperita) Rhizomes.
Metabolism of Monoterpenes : Early Steps in the Metabolism of d-Neomenthyl-beta-d-Glucoside in Peppermint (Mentha piperita) Rhizomes.
Mutagenic investigation of peppermint oil in the Salmonella/mammalian-microsome test.
Biotransformation by plant cells immobilized in cross-linked polyacrylamide-hydrazide.
Biotransformation of monoterpenes by Mentha cell lines.
Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha piperita and other Mentha species.
Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves.
Demonstration of the Intercellular Compartmentation of l-Menthone Metabolism in Peppermint (Mentha piperita) Leaves.
Biotransformation of monoterpenes by mentha cell lines: conversion of menthone to neomenthol.
Metabolism of Monoterpenes : EVIDENCE FOR COMPARTMENTATION OF l-MENTHONE METABOLISM IN PEPPERMINT (MENTHA PIPERITA) LEAVES.
Metabolism of Monoterpenes: Demonstration of (+)-Neomenthyl-beta-d-Glucoside as a Major Metabolite of (-)-Menthone in Peppermint (Mentha Piperita).
[Photochemical reaction products of L-menthone (author's transl)].
Genetic basis for high limonene-cineole content of exceptional Mentha citrata hybrids.
Effects of light and temperature on the monoterpenes of peppermint.
Some steroid hormone-like effects of menthol.
The Genetic Basis for the Conversion of Menthone to Menthol in Japanese Mint.
[Determination of menthone in mint].
The genetic basis of the ketones, carvone, and menthone in Mentha crispa L.
[Determination of menthone, menthol and menthofuran in essential oil of Mentha; localization of menthofuran in the plant].
Studies in detoxication: The biological reduction of l-menthone to d-neomenthol and of d-isomenthone to d-isomenthol in the rabbit. The conjugation of d-neomenthol with glucuronic acid.
THE INVERSION OF MENTHONE BY SODIUM, POTASSIUM AND LITHIUM ETHYLATES, AND A METHOD OF ANALYSIS FOR METHONE IN PINE OILS.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
FooDB:FDB009778
YMDB (Yeast Metabolome Database):YMDB01741
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Formulations/Preparations:
•assay: 98% dl-form; 95% optically active form •note: apinol obtained by dry distillation of wood of pinus palustris mill (p australis michx), pinaceae is chiefly l-menthoneamber-colored oil, bp about 182.2 deg c, density 0.946. apinol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 154.2526550293
Specific gravity @ 15 °C
Pounds per Gallon 7.463 to 7.513
Boiling Point 209 to 210°C @ 760 mm Hg
Boiling Point 118 to 119°C @ 50 mm Hg
Vapor Pressure 0.256 mmHg @ 25 °C
Flash Point TCC Value 85 °C TCC
logP (o/w) 2.755 est
Solubility
alcohol Yes
water, 180.5 mg/L @ 25 °C (est) Yes
water, 688 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Minty
minty
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity > 12 hour(s) at 100.00 %
General comment At 10.00 % in dipropylene glycol. minty
Flavor Type: Minty
cooling, mentholic, minty, woody
General comment Cooling mentholic minty woody

Occurrences

Safety Information

Safety information

European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 [sex: M,F] 1600-1950 mg/kg
(Igimi & Ide, 1974; Levenstein, 1973c)

intravenous-dog LDLo 600 mg/kg
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION CARDIAC: CHANGE IN RATE
Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 236, Pg. 633, 1953.

oral-rat LD50 500 mg/kg
French Demande Patent Document. Vol. #2448856

Dermal Toxicity:
subcutaneous-mouse LD50 2180 mg/kg
French Demande Patent Document. Vol. #2448856

subcutaneous-mouse LD50 2180 mg/kg
BEHAVIORAL: ANTICONVULSANT BEHAVIORAL: SLEEP
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 46, Pg. 77, 1957.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for (±)-menthone usage levels up to:
4.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 890.00 (μg/capita/day)
Structure Class: II
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -52.00000
beverages(nonalcoholic): -7.70000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -8.70000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -33.00000
fruit ices: -33.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -71.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 51, (FGE.51)[1] - Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) and structurally related to alicyclic ketones, secondary alcohols and related esters evaluated by EFSA in FGE.09 (2004) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 9, Revision 1: (FGE.09 Rev1)[1] - Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical groups 8 and 30, and an ester of a phenol carboxylic acid from chemical group 25 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 9, Revision 2 (FGE.09Rev2): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
View page or View pdf

Safety and efficacy of secondary alicyclic saturated and unsaturated alcohols, ketones, ketals and esters with ketals containing alicyclic alcohols or ketones and esters containing secondary alicyclic alcohols from chemical group 8 when used as flavourings for all animal species
View page or View pdf

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EPA Substance Registry Services (TSCA):89-80-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6986
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
5-methyl-2-propan-2-ylcyclohexan-1-one
Chemidplus:0000089805