EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

piperitenone
p-menth-1,4(8)-dien-3-one

Supplier Sponsors

Name:2-methyl-6-propan-2-ylidenecyclohex-2-en-1-one
CAS Number: 491-09-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-729-5
FDA UNII:IKR841W74D
Nikkaji Web:J2.113.085K
CoE Number:11189
XlogP3-AA:2.70 (est)
Molecular Weight:150.22078000
Formula:C10 H14 O
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
No longer supported by industry (EFFA, 2016b)
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:757 p-menth-1,4(8)-dien-3-one
FLAVIS Number:07.127 (Old)
DG SANTE Food Flavourings:07.127 p-menth-1,4(8)-dien-3-one
FEMA Number:3560 p-menth-1,4(8)-dien-3-one
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
Subpart F--Flavoring Agents and Related Substances
Sec. 172.515 Synthetic flavoring substances and adjuvants.
 
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
Boiling Point: 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
 water, 164.7 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
sharp minty phenolic
Odor Description:at 10.00 % in dipropylene glycol. sharp minty phenolic
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
3-Methyl-6-(1-methylethylidene)cyclohex-2-en-1-one
Nippon Terpene Chemicals
Piperitenone 80% up
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
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
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
 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,-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
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
 
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
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (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
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
camphoreous
dextro-
camphor
FL/FR
mentholic
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
peppermint cyclohexanone
FL/FR
dextro-
piperitone
FL/FR
minty
laevo-
carveol
FL/FR
laevo-
carvone
FL/FR
dihydrocarveol
FL/FR
pennyroyal oil
FL/FR
peppermint oil terpeneless
FL/FR
(R)-(+)-
pulegone
FR
iso
pulegone
FL/FR
spearmint absolute
FL/FR
spearmint oil america
FL/FR
spearmint oil terpeneless
FL/FR
tetrahydrocarvone
FL/FR
For Flavor
No flavor group found for these
laevo-
carveol
FL/FR
cis+trans-para-1(7)8-
menthadien-2-yl acetate
FL
iso
pulegone
FL/FR
cooling
cooling
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
green
dihydrocarveol
FL/FR
medicinal
dextro-
camphor
FL/FR
mentholic
peppermint cyclohexanone
FL/FR
minty
laevo-
carvone
FL/FR
pennyroyal oil
FL/FR
peppermint oil terpeneless
FL/FR
dextro-
piperitone
FL/FR
spearmint absolute
FL/FR
spearmint oil america
FL/FR
spearmint oil terpeneless
FL/FR
tetrahydrocarvone
FL/FR
 
Potential Uses:
FRherbal
FRmint
FL/FRpennyroyal
 
Occurrence (nature, food, other):note
 calamintha nepeta (l.) savi subsp. glandulosa oil greece @ 7.00%
Data GC Search Trop Picture
 cornmint leaf
Search Trop Picture
 cornmint plant
Search Trop Picture
 foeniculum vulgare piperitum oil @ 0.80%
Data GC Search Trop Picture
 grapefruit juice
Search Trop Picture
 horsemint shoot
Search Trop Picture
 lemon fruit juice
Search Trop Picture
 lemon verbena oil turkey @ 0.07%
Data GC Search Trop Picture
 lippia alnifolia schau. leaf oil brazil @ 1.70%
Data GC Search Trop Picture
 mastic fruit oil @ 2.30%
Data GC Search Trop Picture
 mentha longifolia (l.) huds. oil jordan @ 0.20%
Data GC Search Trop Picture
 mint
Search Trop Picture
 orange fruit juice
Search Trop Picture
 pennyroyal
Search Trop Picture
 pennyroyal oil @ 1.80%
Data GC Search Trop Picture
 pennyroyal oil cuba @ 2.39%
Data GC Search Trop Picture
 peppermint oil
Search Trop Picture
 plectranthus glandulosus hook f. leaf oil cameroon @ 1.30%
Data GC Search Trop Picture
 rosemary leaf
Search Trop Picture
 rosemary oil egypt @ 0.27%
Data GC Search Trop Picture
 satureja viminea l. oil costa rica @ 0.70%
Data GC Search Trop Picture
 spearmint oil
Search Trop Picture
 water mint leaf
Search Trop Picture
 
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
 

Articles:

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. × 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-GC×GC-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].
 
Notes:
Flavouring agent. Present in grapefruit juice lemon juice, orange juice, spearmint oil and peppermint oil
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