piperitenone oxide
1-methyl-4-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-5-one
 
Notes:
Constit. of Mentha rotundifolia and other Mentha spp. Flavouring ingredient
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1-methyl-4-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-5-one (Click)
CAS Number: 35178-55-3Picture of molecule
Nikkaji Web: J373.722E
CoE Number: 10508
XlogP3-AA: 1.80 (est)
Molecular Weight: 166.21998000
Formula: C10 H14 O2
NMR Predictor: Predict (works with chrome or firefox)
Category: flavoring 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
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
JECFA Food Flavoring: 1574  piperitenone oxide
FEMA Number: 4199  piperitenone oxide
FDA Mainterm: PIPERITENONE OXIDE
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.
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Physical Properties:
Appearance: colorless solid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 25.00 °C. @ 760.00 mm Hg
Boiling Point: 255.00 to  256.00 °C. @ 760.00 mm Hg
Acid Value: 1.00 max. KOH/g
Vapor Pressure: 0.016000 mm/Hg @ 25.00 °C. (est)
Flash Point: 225.00 °F. TCC ( 107.22 °C. )
logP (o/w): 0.754 (est)
Soluble in:
 alcohol
 water
 water, 113.3 mg/L @ 25 °C (est)
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Organoleptic Properties:
Odor Type: herbal
Odor Strength: medium ,
recommend smelling in a 10.00 % solution or less
 herbal  minty  
Odor Description:
at 10.00 % in dipropylene glycol. 
herbal minty
  
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Cosmetic Information:
None found
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Suppliers:
Axsyn
For experimental / research use only.
7-Oxabicyclo[4.1.0]heptan-2-one,6-methyl-3-(1-methylethylidene)-
BOC Sciences
For experimental / research use only.
1-methyl-4-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-5-one
Parchem
piperitenone oxide
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
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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
 
Pictogram
 
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: flavoring agents
Recommendation for piperitenone oxide usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.012 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.20 (μg/capita/day)
Structure Class: III
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: 22
Click here to view publication 22
 average usual ppmaverage maximum ppm
baked goods: 3.0000015.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: 2.0000010.00000
cheese: 2.0000010.00000
chewing gum: --
condiments / relishes: 5.0000025.00000
confectionery froastings: --
egg products: 2.0000010.00000
fats / oils: 2.0000010.00000
fish products: 3.0000015.00000
frozen dairy: 5.0000025.00000
fruit ices: 1.000005.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: 3.0000015.00000
poultry: --
processed fruits: 1.000005.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 2.0000010.00000
soups: --
sugar substitutes: --
sweet sauces: --
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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
List of apha, beta-Unsaturated Aldehydes and Ketones representative of FGE.19 substances for Genotoxicity Testing [1] - Statement of the Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF)
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
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 61942
National Institute of Allergy and Infectious Diseases: Data
 1-methyl-4-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-5-one
Chemidplus: 0035178553
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References:
 1-methyl-4-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-5-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 61942
Pubchem (sid): 135018639
Pherobase: View
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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 Everything Added to Food in the United States (EAFUS): View
HMDB (The Human Metabolome Database): HMDB37044
FooDB: FDB016026
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
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Potential Blenders and core components note
 
For Odor
anisic
 estragoleFL/FR
camphoreous
 herbal ethanoneFR
floral
 menthadienyl formateFR
herbal
isodihydrolavandulolFR
(Z)-isodihydrolavandulyl acetateFR
 herbal undecanolFR
 hyssop oilFL/FR
para-menthane-3,8-diolFL/FR
 piperitoneFL/FR
 rosemary absoluteFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil indiaFL/FR
laevo-menthyl acetateFL/FR
minty
homomenthyl acetateFL/FR
 
For Flavor
 
No flavor group found for these
para-menthane-3,8-diolFL/FR
 piperitoneFL/FR
cooling
homomenthyl acetateFL/FR
herbal
 hyssop oilFL/FR
 rosemary absoluteFL/FR
licorice
 estragoleFL/FR
mentholic
 cornmint oilFL/FR
minty
 cornmint oil indiaFL/FR
laevo-menthyl acetateFL/FR
 
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Potential Uses:
 herbalFL
 mintFL
 peppermintFL
 wintergreenFL
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Occurrence (nature, food, other): note
 calamintha nepeta (l.) savi subsp. glandulosa oil greece @ 1.00%
Data  GC  Search Trop  Picture
 cornmint leaf
Search Trop  Picture
 foeniculum vulgare piperitum oil @ 14.10%
Data  GC  Search Trop  Picture
 horsemint shoot
Search Trop  Picture
 lippia alnifolia schau. leaf oil brazil @ 44.60%
Data  GC  Search Trop  Picture
 mentha longifolia (l.) huds. oil jordan @ 83.70%
Data  GC  Search Trop  Picture
 mentha rotundifolia
Search Trop  Picture
 plectranthus glandulosus hook f. leaf oil cameroon @ 10.90%
Data  GC  Search Trop  Picture
 spearmint leaf
Search Trop  Picture
 spearmint oil
Search Trop  Picture
 spearmint plant
Search Trop  Picture
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Synonyms:
7-oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethylidene)-
1,2-epoxy-p-menth-4(8)-en-3-one
1,2-epoxy-para-menth-4(8)-en-3-one
p-menth-4(8)-en-3-one, 1,2-epoxy-
6-methyl-3-(1-methyl ethylidene)-7-oxabicyclo(4.1.0)heptan-2-one
6-methyl-3-(1-methylethylidene)-7-oxabicyclo(4.1.0)heptan-2-one
1-methyl-4-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-5-one
 rotundifolone
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Articles:
Info: epoxides
PubMed: Chemical composition and antimicrobial activity of the essential oil of Plectranthus mollis (Lamiaceae) from Western Ghats Region, Karnataka, India.
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: Essential oils of Micromeria dalmatica Benth., a Balkan endemic species of section Pseudomelissa.
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: Intraspecific variability of the essential oil of Calamintha nepeta subsp. nepeta from Southern Italy (Apulia).
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: Comparative study of volatile oil compositions of two Plectranthus species from northern India.
PubMed: Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae).
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: Antinociceptive effects of the essential oil of Mentha x villosa leaf and its major constituent piperitenone oxide in mice.
PubMed: Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris.
PubMed: Piperitenone oxide as toxic, repellent, and reproduction retardant toward malarial vector Anopheles stephensi (Diptera: Anophelinae).
PubMed: Composition of the essential oil of Mentha microphylla from the Gennargentu Mountains (Sardinia, Italy).
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: 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: Effects of piperitenone oxide on the intestinal smooth muscle of the guinea pig.
PubMed: Microbial transformations of some monoterpenoids and sesquiterpenoids.
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