piperitone
2-cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-
Identification
| Name | piperitone |
| IUPAC | 3-methyl-6-propan-2-ylcyclohex-2-en-1-one |
| CAS Number | 89-81-6 |
| EINECS | 201-942-7 |
| FDA UNII | 1VZ8RG269R |
| Molecular Formula | C10 H16 O |
| Molecular Weight | 152.23672000 |
| MDL Number | MFCD00045532 |
| Nikkaji Number | J4.308G |
| Beilstein | 1907772 |
| CoE Number | 2052 |
Regulatory
| DG SANTE Food Flavourings | 07.175 p-menth-1-en-3-one |
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 94.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.92900 to 0.93400 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.730 to 7.772 |
| Refractive Index | 1.48300 to 1.48700 @ 20.00 °C. |
| Optical Rotation | -40.00 to -49.00 |
| Boiling Point | 233.00 to 235.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.057000 mmHg @ 25.00 °C. (est) |
| Flash Point | 208.00 °F. TCC ( 97.78 °C. ) |
| logP (o/w) | 2.850 |
| Soluble in | alcohol |
| Insoluble in | water |
| Stability | detergent |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Description |
at 10.00 % in dipropylene glycol. Powerful, fresh-fruity-camphoraceous
|
| Odor sample from | CA Aromatics Company Inc. |
| Taste Description | minty cooling mentholic spicy peppermint peppery |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 2450 mg/kg |
| Dermal Toxicity | subcutaneous-mouse LD50 1420 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for piperitone usage levels up to | 3.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 44.00 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 10.00 (μg/capita/day) |
| Structure Class | II |
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Potential Uses
Natural Occurrence
Synonyms
3-
carvomenthenone
2-
cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-
p-
menth-1-en-3-one
para-
menth-1-en-3-one
1-p-
menthen-3-one
1-
methyl-4-isopropyl-1-cyclohexen-3-one
3-
methyl-6-(1-methyl ethyl)-2-cyclohexen-1-one
3-
methyl-6-(1-methylethyl)-2-cyclohexen-1-one
3-
methyl-6-(propan-2-yl)cyclohex-2-en-1-one
3-
methyl-6-propan-2-ylcyclohex-2-en-1-one
piperitone 96% (natural)
4-iso
propyl-1-methyl-1-cyclohexen-3-one
6-iso
propyl-3-methyl cyclohex-2-enone
6-iso
propyl-3-methyl-2-cyclohexen-1-one
6-iso
propyl-3-methylcyclohex-2-en-1-one
PubMed:
Chemical composition and insecticidal activity of plant essential oils from Benin against Anopheles gambiae (Giles).
PubMed:
Chemical analysis and antioxidant activity of the essential oils of three Piperaceae species growing in the central region of Cuba.
PubMed:
Gas chromatographic mass analysis and further pharmacological actions of Cymbopogon proximus essential oil.
PubMed:
Biochemical Activities of Iranian Cymbopogon olivieri (Boiss) Bor. Essential Oil.
PubMed:
Comparative study of the chemical composition of essential oils of five Tagetes species collected in Venezuela.
PubMed:
Toxicity of Zanthoxylum piperitum and Zanthoxylum armatum oil constituents and related compounds to Stomoxys calcitrans (Diptera: Muscidae).
PubMed:
Comparative study of volatile oil compositions of two Plectranthus species from northern India.
PubMed:
Classification of Greek Mentha pulegium L. (Pennyroyal) samples, according to geographical location by Fourier transform infrared spectroscopy.
PubMed:
Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan.
PubMed:
Comparative analysis of some active principles of herb plants by GC/MS.
PubMed:
Composition and antifungal activity of the essential oil of the Brazilian Chenopodium ambrosioides L.
PubMed:
Bioactivity of two major constituents isolated from the essential oil of Artemisia judaica L.
PubMed:
Major constituents and anthelmintic activity of volatile oils from leaves and flowers of Cymbopogon martini Roxb.
PubMed:
Inhibitory Effects of Chrysanthemum boreale Essential Oil on Biofilm Formation and Virulence Factor Expression of Streptococcus mutans.
PubMed:
Curcuma ecalcarata - new natural source of pinocembrin and piperitenone.
PubMed:
Antibacterial activity and mode of action of the Artemisia capillaris essential oil and its constituents against respiratory tract infection-causing pathogens.
PubMed:
Comparative analysis of antioxidant activities of fourteen mentha essential oils and their components.
PubMed:
Chemical composition and antimicrobial activity of the essential oil of Plectranthus mollis (Lamiaceae) from Western Ghats Region, Karnataka, India.
PubMed:
Microbial transformations of halolactones with p-menthane system.
PubMed:
Chemical composition and antibacterial activity of essential oil and extracts of Citharexylum spinosum flowers from Thailand.
PubMed:
Development of a Validated HPLC/Photodiode Array Method for the Determination of Isomenthone in the Aerial Parts of Ziziphora tenuior L.
PubMed:
Micromorphological traits and essential oil contents of Micromeria kerneri Murb. and M. juliana (L.) Benth. (Lamiaceae).
PubMed:
Chemical analysis and antioxidant activity of the essential oils of three Piperaceae species growing in the central region of Cuba.
PubMed:
Chemical composition, cytotoxicity and in vitro antitrypanosomal and antiplasmodial activity of the essential oils of four Cymbopogon species from Benin.
PubMed:
Antifungal impact of volatile fractions of Peumus boldus and Lippia turbinata on Aspergillus section Flavi and residual levels of these oils in irradiated peanut.
PubMed:
Structure-related antifeedant activity of halolactones with a p-menthane system against the lesser mealworm, Alphitobius diaperinus Panzer.
PubMed:
Gas chromatographic mass analysis and further pharmacological actions of Cymbopogon proximus essential oil.
PubMed:
Biochemical Activities of Iranian Cymbopogon olivieri (Boiss) Bor. Essential Oil.
PubMed:
Behavioural and electroantennogram responses of the stable fly (Stomoxys calcitrans L.) to plant essential oils and their mixtures with attractants.
PubMed:
Determination of chemical variability of phenolic and monoterpene glycosides in the seeds of Paeonia species using HPLC and profiling analysis.
PubMed:
Piperitone-derived saturated lactones: synthesis and aphid behavior-modifying activity.
PubMed:
Evaluation of Essential Oil and its Three Main Active Ingredients of Chinese Chenopodium ambrosioides (Family: Chenopodiaceae) against Blattella germanica.
PubMed:
Toxicity of Zanthoxylum piperitum and Zanthoxylum armatum oil constituents and related compounds to Stomoxys calcitrans (Diptera: Muscidae).
PubMed:
Biological activities of Eremostachys laevigata Bunge. grown in Iran.
PubMed:
The constituents of essential oil: antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia.
PubMed:
Essential-oil diversity of three Calamintha species from Greece.
PubMed:
Intraspecific variability of the essential oil of Calamintha nepeta subsp. nepeta from Southern Italy (Apulia).
PubMed:
Mode of action of pulegone on the urinary bladder of F344 rats.
PubMed:
Chemical and morphological diversity in wild populations of Mentha longifolia in Israel.
PubMed:
Investigation of the chemical composition-antibacterial activity relationship of essential oils by chemometric methods.
PubMed:
Composition of the essential oil of Origanum tyttanthum from Tajikistan.
PubMed:
Mentha longifolia in vitro cultures as safe source of flavouring ingredients.
PubMed:
Anthelmintic effect of Mentha spp. essential oils on Echinococcus granulosus protoscoleces and metacestodes.
PubMed:
Larvicidal activity of Tagetes erecta against Aedes aegypti.
PubMed:
Classification of Greek Mentha pulegium L. (Pennyroyal) samples, according to geographical location by Fourier transform infrared spectroscopy.
PubMed:
Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan.
PubMed:
Enantioselectivity of hydroxylation of racemic piperitone by fungi.
PubMed:
Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice.
PubMed:
Chemical composition and larvicidal evaluation of Mentha, Salvia, and Melissa essential oils against the West Nile virus mosquito Culex pipiens.
PubMed:
Variation in volatile leaf oils of 13 Eucalyptus species harvested from Souinet arboreta (Tunisia).
PubMed:
Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils.
PubMed:
Comparative analysis of some active principles of herb plants by GC/MS.
PubMed:
Activity of essential oils and individual components against acetyl- and butyrylcholinesterase.
PubMed:
Composition and antifungal activity of the essential oil of the Brazilian Chenopodium ambrosioides L.
PubMed:
Chemical composition and antispasmodic effect of Casimiroa pringlei essential oil on rat uterus.
PubMed:
Antimycotoxigenic characteristics of Rosmarinus officinalis and Trachyspermum copticum L. essential oils.
PubMed:
Major constituents and anthelmintic activity of volatile oils from leaves and flowers of Cymbopogon martini Roxb.
PubMed:
Essential oil compositions of Cymbopogon parkeri STAPF from Iran.
PubMed:
14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats.
PubMed:
Comparison of essential oils from three plants for enhancement of antimicrobial activity of nitrofurantoin against enterobacteria.
PubMed:
A TLC bioautographic assay for the detection of nitrofurantoin resistance reversal compound.
PubMed:
Comparative effects of Cymbopogon schoenanthus essential oil and piperitone on Callosobruchus maculatus development.
PubMed:
Fungicidal activity of Artemisia herba alba Asso (Asteraceae).
PubMed:
Composition and Antimicrobial Activity of Anemopsis californica leaf oil.
PubMed:
Chemical composition and antifungal activity of essential oil of Chrysactinia mexicana gray.
PubMed:
Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L.
PubMed:
Piperitone from Mentha longifolia var. chorodictya Rech F. reduces the nitrofurantoin resistance of strains of enterobacteriaceae.
PubMed:
The in vitro antioxidant and antimicrobial activities of the essential oil and methanol extracts of Achillea biebersteini Afan. (Asteraceae).
PubMed:
Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity.
PubMed:
Antimicrobial activity of essential oil and methanol extracts of Achillea sintenisii Hub. Mor. (Asteraceae).
PubMed:
In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.
PubMed:
Electroantennogram responses of Douglas-fir seed chalcids to plant volatiles.
PubMed:
Antibacterial and antifungal activity of essential oils of Mentha suaveolens.
PubMed:
Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq.
PubMed:
Susceptibility of the bruchid Callosobruchus maculatus (Coleoptera: Bruchidae) and its parasitoid Dinarmus basalis (Hymenoptera: Pteromalidae) to three essential oils.
PubMed:
Electrophysiological and behavioral responses of female Helicoverpa armigera to compounds identified in flowers of African marigold, Tagetes erecta.
PubMed:
Phytochemical study of Mentha longifolia of Morocco.
PubMed:
Metabolic fate of S-(-)-pulegone in rat.
PubMed:
Isolation and identification of house fly,Musca domestica L., repellents from pepper tree,Schinus molle L.
PubMed:
Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
PubMed:
Floral volatiles ofTanacetum vulgare L. attractive toLobesia botrana den. et schiff. females.
PubMed:
Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae).
PubMed:
Constituents of Essential Oils from Mentha X rotundifolia Growing Wild in Greece.
PubMed:
Constituents of Essential Oils from Mentha longifolia Growing Wild in Greece.
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:
Oro-facial granulomatosis: a possible allergic basis.
PubMed:
Variability in yield and composition of essential oil in Cymbopogon jawarancusa.
PubMed:
Simple analogs of the toxin callicarpone.
PubMed:
Metal substitutions incarbonic anhydrase: a halide ion probe study.
PubMed:
[Vinylogous aminomethylation of piperitone].
PubMed:
[Immediate toxicity of carvomenthone, carvone, piperitone and piperitenone].