cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5R)-rel-
Found in American pennyroyal oil (Hedeoma pulegioides), Mentha arvensis, Pelargonium tomentosum and other essential oils
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CAS Number: 1196-31-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 214-813-5
Nikkaji Web: J109.970A
Beilstein Number: 2041366
XlogP3-AA: 2.70 (est)
Molecular Weight: 154.25266000
Formula: C10 H18 O
NMR Predictor: Predict (works with chrome, Edge or firefox)
Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance: colorless clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 204.00 to  206.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.256000 mmHg @ 25.00 °C. (est)
Flash Point: 163.04 °F. TCC ( 72.80 °C. )
logP (o/w): 2.755 (est)
Soluble in:
 water, 180.5 mg/L @ 25 °C (est)
Insoluble in:
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Organoleptic Properties:
Odor Description:
Odor and/or flavor descriptions from others (if found).
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Cosmetic Information:
None found
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For experimental / research use only.
(+)-isoMenthone (GC) ≥97%
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Safety Information:
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
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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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
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 70962
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0001196312
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NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 70962
Pubchem (sid): 135026442
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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
KEGG (GenomeNet): C11952
HMDB (The Human Metabolome Database): Search
FooDB: FDB013570
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
None Found
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cornmint leaf
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 hedeoma pulegioides oil
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 pelargonium tomentosum
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 spearmint leaf
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 water mint leaf
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 cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R-cis)-
 cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5R)-
 cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5R)-rel-
p-menthan-3-one, (1R,4R)-(+)-
p-menthane-3-one, (1R,4R)-(+)-
(2R-cis)-5-methyl-2-(1-methyl ethyl) cyclohexanone
(2R,5R)-2-isopropyl-5-methyl cyclohexanone
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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.
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