piperitenone
p-menth-1,4(8)-dien-3-one
Identification
| Name | piperitenone |
| IUPAC | 2-methyl-6-propan-2-ylidenecyclohex-2-en-1-one |
| CAS Number | 491-09-8 |
| EINECS | 207-729-5 |
| FDA UNII | IKR841W74D |
| Molecular Formula | C10 H14 O |
| Molecular Weight | 150.22078000 |
| Nikkaji Number | J2.113.085K |
| CoE Number | 11189 |
Regulatory
| JECFA Food Flavoring | 757 p-menth-1,4(8)-dien-3-one |
| DG SANTE Food Flavourings | 07.127 p-menth-1,4(8)-dien-3-one |
| FEMA Number | 3560 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 491-09-8 ; PIPERITENONE |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Appearance | yellow to amber clear liquid (est) |
| Assay | 95.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.97600 to 0.98300 @ 25.00 °C. |
| Pounds per Gallon - (est). | 8.121 to 8.180 |
| Refractive Index | 1.47200 to 1.47800 @ 20.00 °C. |
| Boiling Point | 106.00 to 107.00 °C. @ 10.00 mm Hg, 92.00 °C. @ 1.80 mm Hg |
| Vapor Pressure | 0.040000 mmHg @ 25.00 °C. (est) |
| Flash Point | 200.00 °F. TCC ( 93.33 °C. ) |
| logP (o/w) | 1.766 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Description | at 10.00 % in dipropylene glycol. |
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| 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 piperitenone usage levels up to | 0.5000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.012 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.01 (μg/capita/day) |
| Structure Class | II |
| 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 | - |
BOC Sciences
Best of Chemicals Supplier
Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...
Chemical sources Association Inc
Exchange of knowledge
Need This Item for Flavor? You can contact the Chemical Sources Association.
Potential Uses
Natural Occurrence
Synonyms
p-
menth-1,4(8)-dien-3-one
para-
menth-1,4(8)-dien-3-one
p-
mentha-1,4(8)-dien-3-one
para-
mentha-1,4(8)-dien-3-one
1,4(8)-p-
menthadien-3-one
1,4(8)-para-
menthadien-3-one
1-
methyl-4-isopropylidene-1-cyclohexen-3-one
3-
methyl-6-(1-methyl ethylidene) cyclohex-2-en-1-one
3-
methyl-6-(1-methylethylidene)cyclohex-2-en-1-one
2-
methyl-6-propan-2-ylidenecyclohex-2-en-1-one
pulespenone
PubMed:
Curcuma ecalcarata - new natural source of pinocembrin and piperitenone.
PubMed:
Comparative analysis of antioxidant activities of fourteen mentha essential oils and their components.
PubMed:
Pharmacological and therapeutic effects of Mentha Longifolia L. and its main constituent, menthol.
PubMed:
A new source of (R)-limonene and rotundifolone from leaves of Lippia pedunculosa (verbenaceae) and their trypanocidal properties.
PubMed:
Chemical composition and antimicrobial activity of the essential oil of Plectranthus mollis (Lamiaceae) from Western Ghats Region, Karnataka, India.
PubMed:
Isolation and characterization of isopiperitenol dehydrogenase from piperitenone-type Perilla.
PubMed:
Repellent Activities of Essential Oils of Some Plants Used Traditionally to Control the Brown Ear Tick, Rhipicephalus appendiculatus.
PubMed:
Discrimination of fennel chemotypes applying IR and Raman spectroscopy: discovery of a new γ-asarone chemotype.
PubMed:
In vitro inhibition of herpes simplex virus type 1 replication by Mentha suaveolens essential oil and its main component piperitenone oxide.
PubMed:
Antioxidant Activity and Volatile and Phenolic Profiles of Essential Oil and Different Extracts of Wild Mint (Mentha longifolia) from the Pakistani Flora.
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:
Essential oils of Micromeria dalmatica Benth., a Balkan endemic species of section Pseudomelissa.
PubMed:
Volatile constituents, phenolic compounds, and antioxidant activity of Calamintha glandulosa (Req.) Bentham.
PubMed:
Comparative study of the chemical composition of essential oils of five Tagetes species collected in Venezuela.
PubMed:
Biological activities of Eremostachys laevigata Bunge. grown in Iran.
PubMed:
In vitro production of M. Ã piperita not containing pulegone and menthofuran.
PubMed:
Essential-oil diversity of three Calamintha species from Greece.
PubMed:
Volatile secondary metabolites of Micromeria dalmatica Benth. (Lamiaceae): biosynthetical and chemotaxonomical aspects.
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:
Composition of the essential oil of Origanum tyttanthum from Tajikistan.
PubMed:
Mentha longifolia in vitro cultures as safe source of flavouring ingredients.
PubMed:
HS-SPME-GCÃGC-qMS volatile metabolite profiling of Chrysolina herbacea frass and Mentha spp. leaves.
PubMed:
Larvicidal activity of Tagetes erecta against Aedes aegypti.
PubMed:
Comparative study of volatile oil compositions of two Plectranthus species from northern India.
PubMed:
Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan.
PubMed:
Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae).
PubMed:
Antimicrobial activity and volatile constituents of the essential oil of Pulsatilla albana from Iran.
PubMed:
Intraspecific variability of the essential oil of Ziziphora clinopodioides ssp. rigida from Iran.
PubMed:
Seasonal variation in content, chemical composition and antimicrobial and cytotoxic activities of essential oils from four Mentha species.
PubMed:
Chemical composition and larvicidal evaluation of Mentha, Salvia, and Melissa essential oils against the West Nile virus mosquito Culex pipiens.
PubMed:
Composition and chemical variability of Mentha suaveolens ssp. suaveolens and M. suaveolens ssp. insularis from Corsica.
PubMed:
Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils.
PubMed:
Crude extracts of, and purified compounds from, Pterocarpus angolensis, and the essential oil of Lippia javanica: their in-vitro cytotoxicities and activities against selected bacteria and Entamoeba histolytica.
PubMed:
Antinociceptive effects of the essential oil of Mentha x villosa leaf and its major constituent piperitenone oxide in mice.
PubMed:
Influence of growth phase on the essential oil composition of Ziziphora clinopodioides Lam.
PubMed:
Supercritical carbon dioxide extraction of Mentha pulegium L. essential oil.
PubMed:
Bioactive compounds from Lippia javanica and Hoslundia opposita.
PubMed:
Antimicrobial activity and chemical composition of Mentha pulegium L. essential oil.
PubMed:
Perilla frutescens var. frutescens in northern Laos.
PubMed:
Highly Enantio- and s-trans C=C bond selective catalytic hydrogenation of cyclic enones: alternative synthesis of (-)-menthol.
PubMed:
Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris.
PubMed:
Antibacterial activity and composition of the essential oil of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. from Iran.
PubMed:
The chemical composition of essential oil and in vitro antibacterial activities of essential oil and methanol extract of Ziziphora persica Bunge.
PubMed:
Essential oil composition, antibacterial and antioxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran.
PubMed:
Transformation of a monoterpene ketone, piperitenone, and related terpenoids using Mucor piriformis.
PubMed:
Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L.
PubMed:
The composition, geographical variation and antimicrobial activity of Lippia javanica (Verbenaceae) leaf essential oils.
PubMed:
Piperitenone oxide as toxic, repellent, and reproduction retardant toward malarial vector Anopheles stephensi (Diptera: Anophelinae).
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:
Composition of the essential oil of Mentha microphylla from the Gennargentu Mountains (Sardinia, Italy).
PubMed:
Essential oil composition and antioxidant activity of endemic Ziziphora taurica subsp. cleonioides.
PubMed:
Antibacterial and antifungal activity of essential oils of Mentha suaveolens.
PubMed:
Activity of essential oils of three Micromeria species (Lamiaceae) against micromycetes and bacteria.
PubMed:
Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq.
PubMed:
Cardiovascular effects of the essential oil of Mentha x villosa and its main constituent, piperitenone oxide, in normotensive anaesthetised rats: role of the autonomic nervous system.
PubMed:
Phytochemical study of Mentha longifolia of Morocco.
PubMed:
Suppression of the furylfuramide-induced SOS response by monoterpenoids with a p-menthane skeleton using the Salmonella typhimurium TA1535/pSK1002 Umu test.
PubMed:
Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.
PubMed:
The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests.
PubMed:
Metabolic disposition of a monoterpene ketone, piperitenone, in rats: evidence for the formation of a known toxin, p-cresol.
PubMed:
Metabolic fate of S-(-)-pulegone in rat.
PubMed:
Effects of piperitenone oxide on the intestinal smooth muscle of the guinea pig.
PubMed:
Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
PubMed:
Devil's-claw (Proboscidea louisianica), essential oil and its components : Potential allelochemical agents on cotton and wheat.
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:
Metabolism of monoterpenes: oxidation of isopiperitenol to isopiperitenone, and subsequent isomerization to piperitenone by soluble enzyme preparations from peppermint (Mentha piperita) leaves.
PubMed:
[Immediate toxicity of carvomenthone, carvone, piperitone and piperitenone].