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General Material Information

Preferred name laevo-piperitone
Trivial Name (-)-Piperitone
Short Description (R)-6-(isopropyl)-3-methylcyclohex-2-en-1-one
Formula C10 H16 O
CAS Number 4573-50-6
FEMA Number 4200
Flavis Number 7.255
ECHA Number 224-957-0
FDA UNII 8GZY0Q0N20
Nikkaji Number J297.828H
Beilstein Number 2206720
MDL MFCD00045532
xLogP3-AA 2.20 (est)
NMR Predictor External link
JECFA Food Flavoring 1856 L-piperitone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 4573-50-6 ; L-PIPERITONE
Synonyms
  • 2-cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (6R)-
  • laevo-p- menth-1-en-3-one
  • laevo-para- menth-1-en-3-one
  • (6R)-3-methyl-6-(1-methyl ethyl)-2-cyclohexen-1-one
  • (6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one
  • (6R)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
  • (6R)-3-methyl-6-isopropyl-2-cyclohexen-1-one
  • (6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
  • (-)- piperitone
  • L- piperitone
  • piperitone ex eucalyptus
  • L- piperitone natural
  • L- piperitone synthetic
  • piperitone-L nat.
  • (6R)-6-iso propyl-3-methylcyclohex-2-en-1-one
  • (R)-6-(iso propyl)-3-methylcyclohex-2-en-1-one
  • (6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
  • 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (6R)-
  • p-Menth-1-en-3-one, (R)-(-)-
  • 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (R)-
  • p-Menth-1-en-3-one, (-)-
  • (6R)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one
  • (-)-Piperitone
  • L-Piperitone
  • (R)-6-(Isopropyl)-3-methylcyclohex-2-en-1-one
  • (6R)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-one

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

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Literature & References

(6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):107561
Pubchem (sid):135062799
Publications by PubMed
Development of a Validated HPLC/Photodiode Array Method for the Determination of Isomenthone in the Aerial Parts of Ziziphora tenuior L.
Micromorphological traits and essential oil contents of Micromeria kerneri Murb. and M. juliana (L.) Benth. (Lamiaceae).
Behavioural and electroantennogram responses of the stable fly (Stomoxys calcitrans L.) to plant essential oils and their mixtures with attractants.
Evaluation of Essential Oil and its Three Main Active Ingredients of Chinese Chenopodium ambrosioides (Family: Chenopodiaceae) against Blattella germanica.
Toxicity of Zanthoxylum piperitum and Zanthoxylum armatum oil constituents and related compounds to Stomoxys calcitrans (Diptera: Muscidae).
Intraspecific variability of the essential oil of Calamintha nepeta subsp. nepeta from Southern Italy (Apulia).
Comparative study of volatile oil compositions of two Plectranthus species from northern India.
Classification of Greek Mentha pulegium L. (Pennyroyal) samples, according to geographical location by Fourier transform infrared spectroscopy.
Chemical composition and larvicidal evaluation of Mentha, Salvia, and Melissa essential oils against the West Nile virus mosquito Culex pipiens.
Variation in volatile leaf oils of 13 Eucalyptus species harvested from Souinet arboreta (Tunisia).
Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils.
Comparative analysis of some active principles of herb plants by GC/MS.
Activity of essential oils and individual components against acetyl- and butyrylcholinesterase.
Antimicrobial activity and chemical composition of Mentha pulegium L. essential oil.
Composition and antifungal activity of the essential oil of the Brazilian Chenopodium ambrosioides L.
Antimycotoxigenic characteristics of Rosmarinus officinalis and Trachyspermum copticum L. essential oils.
Bioactivity of two major constituents isolated from the essential oil of Artemisia judaica L.
Comparison of essential oils from three plants for enhancement of antimicrobial activity of nitrofurantoin against enterobacteria.
Comparative effects of Cymbopogon schoenanthus essential oil and piperitone on Callosobruchus maculatus development.
Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L.
Piperitone from Mentha longifolia var. chorodictya Rech F. reduces the nitrofurantoin resistance of strains of enterobacteriaceae.
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.
Susceptibility of the bruchid Callosobruchus maculatus (Coleoptera: Bruchidae) and its parasitoid Dinarmus basalis (Hymenoptera: Pteromalidae) to three essential oils.
Isolation and identification of house fly,Musca domestica L., repellents from pepper tree,Schinus molle L.
Floral volatiles ofTanacetum vulgare L. attractive toLobesia botrana den. et schiff. females.
Constituents of Essential Oils from Mentha X rotundifolia Growing Wild in Greece.
Constituents of Essential Oils from Mentha longifolia Growing Wild in Greece.

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
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB35737
FooDB:FDB014466
Export Tariff Code:2914.29.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Specific gravity @ 25 °C
Pounds per Gallon 7.73 to 7.78
Refractive Index 1.482 to 1.488 @ 20 °C
Vapor Pressure 0.057 mmHg @ 25 °C
Flash Point TCC Value 90.56 °C TCC
logP (o/w) 2.004 est
Solubility
alcohol Yes
water, 273.1 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Minty
pungent, minty, peppermint
Odor strength high , recommend smelling in a 1.00 % solution or less
Substantivity 87 hour(s) at 100.00 %
Luebke, William tgsc, (1986) At 1.00 % in dipropylene glycol. pungent minty peppermint
Flavor Type: Minty
minty, cooling, mentholic, peppermint, spicy, herbal
Luebke, William tgsc, (1986) Minty cooling mentholic peppermint spicy herbal

Occurrences

Safety Information

Safety information

Preferred SDS: View
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 laevo-piperitone usage levels up to:
0.2000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 12.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 320 (μg/person/day)
Threshold of Concern:540 (μg/person/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: 22
Click here to view publication 22
average usual ppmaverage maximum ppm
baked goods: 1.0000010.00000
beverages(nonalcoholic): 0.200001.00000
beverages(alcoholic): 0.200002.00000
breakfast cereal: --
cheese: --
chewing gum: 30.00000150.00000
condiments / relishes: --
confectionery froastings: 0.500005.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 0.500005.00000
fruit ices: 0.200002.00000
gelatins / puddings: 0.200002.00000
granulated sugar: --
gravies: --
hard candy: 5.0000050.00000
imitation dairy: --
instant coffee / tea: 0.200002.00000
jams / jellies: 0.200002.00000
meat products: --
milk products: 0.200005.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 5.0000040.00000
soups: --
sugar substitutes: --
sweet sauces: --
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.500005.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): --
Edible ices, including sherbet and sorbet (03.0): 0.200002.00000
Processed fruit (04.1): --
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 0.500005.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): --
Bakery wares (07.0): 1.0000010.00000
Meat and meat products, including poultry and game (08.0): --
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): --
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.200002.00000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 0.200002.00000
Ready-to-eat savouries (15.0): 5.0000050.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.200002.00000

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 212: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 212 Revision 1 (FGE.212Rev1): alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19.
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 9, Revision 4 (FGE.09Rev4): 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 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 212 Revision 3 (FGE.212Rev3): a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 9, Revision 6 (FGE.09Rev6): 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

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):4573-50-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :107561
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
Chemidplus:0004573506
RTECS:OT0257000 for cas# 4573-50-6