(±)-isomenthone

DL-isomenthone

CAS: 491-07-6 C10 H18 O MW: 154.25266000 mentholic minty

Identification

Name(±)-isomenthone
IUPAC5-methyl-2-propan-2-ylcyclohexan-1-one
CAS Number491-07-6
EINECS253-295-5
FDA UNII9WZ3E2G6CL
Molecular FormulaC10 H18 O
Molecular Weight154.25266000
MDL NumberMFCD00136032
Nikkaji NumberJ633E
Beilstein3195564
CoE Number11475

Regulatory

JECFA Food Flavoring430 DL-isomenthone
DG SANTE Food Flavourings07.078 DL-isomenthone
FEMA Number3460
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)491-07-6 ; DL-ISOMENTHONE

Physical Properties

Appearance colorless clear liquid (est)
Assay 96.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 0.89600 to 0.90900 @ 25.00 °C.
Pounds per Gallon - (est). 7.456 to 7.564
Refractive Index 1.44800 to 1.45800 @ 20.00 °C.
Optical Rotation +38.00 to +69.00
Boiling Point 208.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.256000 mmHg @ 25.00 °C. (est)
Flash Point 174.00 °F. TCC ( 78.89 °C. )
logP (o/w) 2.755 (est)
Soluble in alcohol
Insoluble in water
Stability alcoholic fine fragrance, good

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength medium ,
Substantivity 4 hour(s) at 100.00 %
Odor Description
at 10.00 % in dipropylene glycol.
Mentholic, cooling, minty and camphoreous with a refreshing etherial lift
Odor sample from CA Aromatics Company Inc.
Taste Description at 30.00 ppm.

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for (±)-isomenthone usage levels up to8.0000 % in the fragrance concentrate.
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
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-

Augustus Oils Ltd

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Berje Inc.

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Global Essence Inc.

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Indukern, S.A. F&F Ingredients Division

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Lluch Essence S.L.

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M&U International LLC

Steady supply & demand

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Moellhausen S.P.A.

THE CHEMISTRY OF EMOTIONS

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Penta International Corporation

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SRS Aromatics Ltd

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Symrise AG

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Synerzine, Inc.

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R C Treatt and Co Ltd

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Ernesto Ventós S.A.

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Vigon International

Passion for Simplicity

Manufacturer and supplier of high quality flavor and fragrance ingredients.

View All Website 570-476-6300 sales@vigon.com

Potential Uses

FR carnation FL cooling FR fern FR geranium FR herbal FR lavender FR lily of the valley FR peppermint FR rose

Natural Occurrence

agathosma crenulata oil @ 3.58% Data basil oil sweet poland @ 0.32% Data bergamot mint oil @ 0.0-0.2% Data bergamot plant wild buchu leaf oil @ 19.91% Data calamintha nepeta (l.) savi subsp. glandulosa oil greece @ 4.30% Data cornmint leaf cornmint oil india @ 4.59% Data cornmint plant currant black currant bud geranium leaf oil india @ 0.58% Data geranium oil africa @ 5.38% Data geranium oil bourbon @ 6.79% Data geranium oil bourbon @ 7.20% Data geranium oil china @ 5.70% Data geranium oil egypt @ 5.39% Data geranium oil moroccan @ 5.20% Data geranium oil rwanda @ 7.49% Data geranium petiole oil india @ 0.72% Data geranium rose-scented oil (pelargonium spp.) cuba @ 0.30% Data geranium stem oil india @ 7.33% Data horsemint shoot lemongrass oil rwanda @ 0.35% Data mangrove bark red oil cuba @ trace% Data melissa oil slovak republic @ 0.42% Data pennyroyal oil @ 0.80% Data pennyroyal oil cuba @ 9.73% Data pennyroyal oil moroccan pennyroyal oil uruguay @ 35.60-40.60% Data peppermint leaf peppermint oil america @ 3.08% Data peppermint oil CO2 extract @ 7.50% Data peppermint oil mongolia @ 5.43% Data peppermint oil russia @ 23.45% Data petitgrain combava oil @ trace% Data spearmint leaf spearmint oil water mint leaf water mint shoot

Synonyms

cyclohexan-1-one, 2-isopropyl-5-methyl-, racemic cyclohexanone, 2-isopropyl-5-methyl- cyclohexanone, 5-methyl-2-(1-methylethyl)- cis-p- menthan-3-one cis-para- menthan-3-one p- menthan-3-one, DL- cis-p- menthane-3-one cis-para- menthane-3-one p- menthane-3-one, DL- dextro,laevo-iso menthone DL-iso menthone iso menthone iso menthone (d-, l-) iso menthone (ex mint) iso menthone 60 natural iso menthone DL iso menthone extra iso menthone natural iso menthone technical grade cis-5- methyl-2-(1-methyl ethyl) cyclohexanone (2R,5R)-rel-5- methyl-2-(1-methylethyl)cyclohexanone 5- methyl-2-(1-methylethyl)cyclohexanone 5- methyl-2-(isopropyl)cyclohexanone 5- methyl-2-(isopropylcyclo)hexanone 5- methyl-2-(methylethyl)cyclohexan-1-one 5- methyl-2-(propan-2-yl)cyclohexanone cis-5- methyl-2-propan-2-yl cyclohexan-1-one cis-5- methyl-2-propan-2-ylcyclohexan-1-one cis-1- methyl-4-isopropyl-3-cyclohexanone 1- methyl-4-isopropylcyclohexan-3-one 1-iso propyl-4-methyl-2-cyclohexanone cis-2-iso propyl-5-methyl cyclohexanone 2-iso propyl-5-methyl-cyclohexanone 2-iso propyl-5-methylcyclohexanone cis-2-iso propyl-5-methylcyclohexanone PubMed: Development of a Validated HPLC/Photodiode Array Method for the Determination of Isomenthone in the Aerial Parts of Ziziphora tenuior L. PubMed: Effect of different drying methods on the essential oils of mint (Mentha haplocalyx). PubMed: Nematicidal activity of mint aqueous extracts against the root-knot nematode Meloidogyne incognita. PubMed: Bioactivity-guided investigation of geranium essential oils as natural tick repellents. PubMed: [Stable life predection for Mentha haplocalyx by initial average rate stability test]. PubMed: Essential oils of Micromeria dalmatica Benth., a Balkan endemic species of section Pseudomelissa. PubMed: A somaclonal variant of rose-scented geranium (Pelargonium spp.) with moderately high content of isomenthone in its essential oil. PubMed: Antioxidant properties and essential oil composition of Calamintha grandiflora L. PubMed: 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. PubMed: Isomenthone protects human dermal fibroblasts from TNF-α-induced death possibly by preventing activation of JNK and p38 MAPK. PubMed: Essential-oil diversity of three Calamintha species from Greece. PubMed: Are the wild and laboratory insect populations different in semiochemical emission? The case of the medfly sex pheromone. PubMed: Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham. PubMed: Chemical composition and antimicrobial activities of the essential oils from Ocimum selloi and Hesperozygis myrtoides. PubMed: Classification of Greek Mentha pulegium L. (Pennyroyal) samples, according to geographical location by Fourier transform infrared spectroscopy. PubMed: Fungicidal properties of the essential oil of Hesperozygis marifolia on Aspergillus flavus link. PubMed: Toxicity of Schizonpeta multifida essential oil and its constituent compounds towards two grain storage insects. PubMed: Peppermint oil decreases the production of virulence-associated exoproteins by Staphylococcus aureus. PubMed: Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae). PubMed: Potential interaction between the volatile and non-volatile fractions on the in vitro antimicrobial activity of three South African Pelargonium (Geraniaceae) species. PubMed: Comparative study on the in vitro human skin permeation of monoterpenes and phenylpropanoids applied in rose oil and in form of neat single compounds. PubMed: Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils. PubMed: 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. PubMed: Influence of growth phase on the essential oil composition of Ziziphora clinopodioides Lam. PubMed: Acetylcholinesterase inhibitory and antioxidant properties of Cyclotrichium niveum, Thymus praecox subsp. caucasicus var. caucasicus, Echinacea purpurea and E. pallida. PubMed: Comparative analysis of some active principles of herb plants by GC/MS. PubMed: 14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. PubMed: Composition and antifungal activity of the essential oil of Mentha cervina from Portugal. PubMed: Antibacterial activity and composition of the essential oil of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. from Iran. PubMed: Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint. PubMed: Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil. PubMed: A novel enantioselective (2Z)-alk-2-enylation of aldehydes via an allyl-transfer reaction from chiral allyl donors prepared from (+)-isomenthone. PubMed: Thiol-catalysed radical-chain redox rearrangement reactions of benzylidene acetals derived from terpenoid diols. PubMed: Monoterpene double-bond reductases of the (-)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (-)-isopiperitenone reductase and (+)-pulegone reductase of peppermint. PubMed: Antimicrobial and antioxidant activities of three Mentha species essential oils. PubMed: Novel isomenthone-derived 1,3-diol ligands identified through parallel synthesis and screening catalyse an asymmetric aldol reaction. PubMed: Synthesis, stereostructure, and conformations of novel bi- and trifunctional (+)-isomenthone derivatives. PubMed: Chiral recognition of terpenoids in some pharmaceuticals derived from natural sources. PubMed: Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq. PubMed: Metabolism of (R)-(+)-pulegone in F344 rats. PubMed: The Principle of Maximum Chiral Discrimination: Chiral Recognition in Permethyl-beta-cyclodextrin. PubMed: Ambulation-promoting effect of peppermint oil and identification of its active constituents. PubMed: Hydroquinone derivatives and monoterpenoids from the Neotropical liverwort Plagiochila rutilans. PubMed: Different stereoselectivity in the reduction of pulegone by Mentha species. PubMed: 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. PubMed: Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone. PubMed: Biogenetic studies in Mentha x piperita. 1. deuterium-labeled monoterpene ketones: synthesis and stereoselective analysis. PubMed: Shade-avoidance responses in two common coastal redwood forest species, Sequoia sempervirens (Taxodiaceae) and Satureja douglasii (Lamiaceae), occurring in various light quality environments. PubMed: Chemical constituents of essential oils of muña, Bolivian plants traditionally used as pesticides, and their insecticidal properties against Chagas' disease vectors. PubMed: Essential oil analysis and field evaluation of the citrosa plant "Pelargonium citrosum" as a repellent against populations of Aedes mosquitoes. PubMed: The volatiles of two bystropogon species from the canary islands (Spain). PubMed: Chemical, physiological, and toxicological aspects of the essential oil of some species of the genus Bystropogon. PubMed: Olfactory sensitivity of two sympatric species of rice leaf folders (Lepidoptera: Pyralidae) to plant volatiles. PubMed: The Volatile Constituents of Ziziphora taurica subsp. cleonioides. PubMed: Metabolism of monoterpenes: demonstration that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint (Mentha piperita). PubMed: Biotransformation by plant cells immobilized in cross-linked polyacrylamide-hydrazide. PubMed: Biotransformation of monoterpenes by Mentha cell lines. PubMed: Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves. PubMed: Biotransformation of monoterpenes by mentha cell lines: conversion of menthone to neomenthol. PubMed: [Structure elucidation of antiasthmone (1, 1'-bisisomenthone) (author's transl)]. PubMed: Biotransformation of monoterpenes by mentha cell lines: conversion of pulegone to isomenthone. PubMed: [Microchemical analysis of isomenthone in volatile oil of "Geranium rosat"]. PubMed: 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. PubMed: Comparative analysis of three Australian finger lime (Citrus australasica) cultivars: Identification of unique citrus chemotypes and new volatile molecules. PubMed: Pharmacological and therapeutic effects of Mentha Longifolia L. and its main constituent, menthol. PubMed: Phytochemistry and bioactivity of aromatic and medicinal plants from the genus Agastache (Lamiaceae). PubMed: Cytogeography of essential oil chemotypes of Eremophila longifolia F. Muell (Scrophulariaceae).