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piperitenone

Chemical Structure

General Material Information

Preferred name piperitenone
Trivial Name Piperitenone
Short Description p-menth-1,4(8)-dien-3-one
Formula C10 H14 O
CAS Number 491-09-8
FEMA Number 3560
Flavis Number 7.127
ECHA Number 207-729-5
FDA UNII IKR841W74D
Nikkaji Number J2.113.085K
COE Number 11189
xLogP3-AA 2.70 (est)
NMR Predictor External link
JECFA Food Flavoring 757 p-menth-1,4(8)-dien-3-one
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 491-09-8 ; PIPERITENONE
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
  • 2-methyl-6-propan-2-ylidenecyclohex-2-en-1-one
  • 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)-
  • p-Mentha-1,4(8)-dien-3-one
  • 3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one
  • 3-Terpinolenone
  • NSC 667470
  • 3-Methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2-methyl-6-propan-2-ylidenecyclohex-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:491-09-8
Pubchem (cid):61128
Pubchem (sid):135017860
Pherobase:View
Publications by PubMed
Curcuma ecalcarata - new natural source of pinocembrin and piperitenone.
Comparative analysis of antioxidant activities of fourteen mentha essential oils and their components.
Pharmacological and therapeutic effects of Mentha Longifolia L. and its main constituent, menthol.
A new source of (R)-limonene and rotundifolone from leaves of Lippia pedunculosa (verbenaceae) and their trypanocidal properties.
Chemical composition and antimicrobial activity of the essential oil of Plectranthus mollis (Lamiaceae) from Western Ghats Region, Karnataka, India.
Isolation and characterization of isopiperitenol dehydrogenase from piperitenone-type Perilla.
Repellent Activities of Essential Oils of Some Plants Used Traditionally to Control the Brown Ear Tick, Rhipicephalus appendiculatus.
Discrimination of fennel chemotypes applying IR and Raman spectroscopy: discovery of a new γ-asarone chemotype.
In vitro inhibition of herpes simplex virus type 1 replication by Mentha suaveolens essential oil and its main component piperitenone oxide.
Antioxidant Activity and Volatile and Phenolic Profiles of Essential Oil and Different Extracts of Wild Mint (Mentha longifolia) from the Pakistani Flora.
Antifungal impact of volatile fractions of Peumus boldus and Lippia turbinata on Aspergillus section Flavi and residual levels of these oils in irradiated peanut.
Essential oils of Micromeria dalmatica Benth., a Balkan endemic species of section Pseudomelissa.
Volatile constituents, phenolic compounds, and antioxidant activity of Calamintha glandulosa (Req.) Bentham.
Comparative study of the chemical composition of essential oils of five Tagetes species collected in Venezuela.
Biological activities of Eremostachys laevigata Bunge. grown in Iran.
In vitro production of M. × piperita not containing pulegone and menthofuran.
Essential-oil diversity of three Calamintha species from Greece.
Volatile secondary metabolites of Micromeria dalmatica Benth. (Lamiaceae): biosynthetical and chemotaxonomical aspects.
Intraspecific variability of the essential oil of Calamintha nepeta subsp. nepeta from Southern Italy (Apulia).
Mode of action of pulegone on the urinary bladder of F344 rats.
Chemical and morphological diversity in wild populations of Mentha longifolia in Israel.
Composition of the essential oil of Origanum tyttanthum from Tajikistan.
Mentha longifolia in vitro cultures as safe source of flavouring ingredients.
HS-SPME-GC×GC-qMS volatile metabolite profiling of Chrysolina herbacea frass and Mentha spp. leaves.
Larvicidal activity of Tagetes erecta against Aedes aegypti.
Comparative study of volatile oil compositions of two Plectranthus species from northern India.
Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan.
Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae).
Antimicrobial activity and volatile constituents of the essential oil of Pulsatilla albana from Iran.
Intraspecific variability of the essential oil of Ziziphora clinopodioides ssp. rigida from Iran.
Seasonal variation in content, chemical composition and antimicrobial and cytotoxic activities of essential oils from four Mentha species.
Chemical composition and larvicidal evaluation of Mentha, Salvia, and Melissa essential oils against the West Nile virus mosquito Culex pipiens.
Composition and chemical variability of Mentha suaveolens ssp. suaveolens and M. suaveolens ssp. insularis from Corsica.
Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils.
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.
Antinociceptive effects of the essential oil of Mentha x villosa leaf and its major constituent piperitenone oxide in mice.
Influence of growth phase on the essential oil composition of Ziziphora clinopodioides Lam.
Supercritical carbon dioxide extraction of Mentha pulegium L. essential oil.
Bioactive compounds from Lippia javanica and Hoslundia opposita.
Antimicrobial activity and chemical composition of Mentha pulegium L. essential oil.
Perilla frutescens var. frutescens in northern Laos.
Highly Enantio- and s-trans C=C bond selective catalytic hydrogenation of cyclic enones: alternative synthesis of (-)-menthol.
Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris.
Antibacterial activity and composition of the essential oil of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. from Iran.
The chemical composition of essential oil and in vitro antibacterial activities of essential oil and methanol extract of Ziziphora persica Bunge.
Essential oil composition, antibacterial and antioxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran.
Transformation of a monoterpene ketone, piperitenone, and related terpenoids using Mucor piriformis.
Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L.
The composition, geographical variation and antimicrobial activity of Lippia javanica (Verbenaceae) leaf essential oils.
Piperitenone oxide as toxic, repellent, and reproduction retardant toward malarial vector Anopheles stephensi (Diptera: Anophelinae).
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.
Composition of the essential oil of Mentha microphylla from the Gennargentu Mountains (Sardinia, Italy).
Essential oil composition and antioxidant activity of endemic Ziziphora taurica subsp. cleonioides.
Antibacterial and antifungal activity of essential oils of Mentha suaveolens.
Activity of essential oils of three Micromeria species (Lamiaceae) against micromycetes and bacteria.
Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq.
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.
Phytochemical study of Mentha longifolia of Morocco.
Suppression of the furylfuramide-induced SOS response by monoterpenoids with a p-menthane skeleton using the Salmonella typhimurium TA1535/pSK1002 Umu test.
Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.
The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests.
Metabolic disposition of a monoterpene ketone, piperitenone, in rats: evidence for the formation of a known toxin, p-cresol.
Metabolic fate of S-(-)-pulegone in rat.
Effects of piperitenone oxide on the intestinal smooth muscle of the guinea pig.
Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
Devil's-claw (Proboscidea louisianica), essential oil and its components : Potential allelochemical agents on cotton and wheat.
Metabolism of monoterpenes: demonstration that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint (Mentha piperita).
Metabolism of monoterpenes: oxidation of isopiperitenol to isopiperitenone, and subsequent isomerization to piperitenone by soluble enzyme preparations from peppermint (Mentha piperita) leaves.
[Immediate toxicity of carvomenthone, carvone, piperitone and piperitenone].

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
KEGG (GenomeNet):C01951
HMDB (The Human Metabolome Database):HMDB36999
FooDB:FDB015974
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 150.22077941895
Specific gravity @ 25 °C
Pounds per Gallon 8.121 to 8.18
Refractive Index 1.472 to 1.478 @ 20 °C
Boiling Point 106 to 107°C @ 10 mm Hg
Vapor Pressure 0.04 mmHg @ 25 °C
Flash Point TCC Value 93.33 °C TCC
logP (o/w) 1.766 est
Solubility
alcohol Yes
water, 164.7 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Minty
sharp, minty, phenolic
General comment At 10.00 % in dipropylene glycol. sharp minty phenolic

Occurrences

Potential Uses

Applications
Odor purposes Herbal, Mint, Pennyroyal
Flavoring purposes Pennyroyal

Safety Information

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
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
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 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
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: 11
Click here to view publication 11
average usual ppmaverage maximum ppm
baked goods: -5.00000
beverages(nonalcoholic): -5.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -5.00000
fruit ices: --
gelatins / puddings: -5.00000
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: -5.00000
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 213: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 73, Revision 3 (FGE.73Rev3): Consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev4 (2013)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 9, Revision 5 (FGE.09Rev5): 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

Scientific Opinion on Flavouring Group Evaluation 87, Revision 2 (FGE.87Rev2): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47Rev1 (2008)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 213, Revision 2 (FGE.213Rev2): Consideration of genotoxic potential for a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 57, Revision 1 (FGE.57Rev1): consideration of isopulegone and three flavouring substances evaluated by JECFA (55th meeting)
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):491-09-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :61128
National Institute of Allergy and Infectious Diseases:Data
2-methyl-6-propan-2-ylidenecyclohex-2-en-1-one
Chemidplus:0000491098