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isopulegone
p-menth-8-en-3-one

Sponsors

Name:5-methyl-2-prop-1-en-2-ylcyclohexan-1-one
CAS Number: 29606-79-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:249-725-6
Nikkaji Web:J2.365.190D
CoE Number:2051
XlogP3-AA:2.80 (est)
Molecular Weight:152.23672000
Formula:C10 H16 O
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Register name to be change to 2R,5S-isopulegone.
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:754 isopulegone
FLAVIS Number:07.067 (Old)
DG SANTE Food Flavourings:07.067 2R,5S-isopulegone
FEMA Number:2964 isopulegone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: ISOPULEGONE
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:colorless clear liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.92500 to 0.93200 @ 25.00 °C.
Pounds per Gallon - (est).: 7.697 to 7.755
Refractive Index:1.46500 to 1.47300 @ 20.00 °C.
Boiling Point: 101.00 to 102.00 °C. @ 17.00 mm Hg
Boiling Point: 208.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.140000 mm/Hg @ 25.00 °C. (est)
Flash Point: 175.00 °F. TCC ( 79.44 °C. )
logP (o/w): 2.408 (est)
Soluble in:
 alcohol
 water, slightly
 water, 266.2 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:medium
peppermint fresh herbal
Odor Description:at 100.00 %. peppermint fresh herbal
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
isoPulegone 95%
Penta International
isoPULEGONE, Kosher
Penta International
isoPULEGONE, NATURAL
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:
intravenous-dog LDLo 450 mg/kg
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION CARDIAC: CHANGE IN RATE
Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 236, Pg. 633, 1953.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for isopulegone usage levels up to:
  1.0000 % 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)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 2500 (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: 3
 average usual ppmaverage maximum ppm
baked goods: -16.00000
beverages(nonalcoholic): -4.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -12.00000
fruit ices: -12.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -16.00000
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: --
 
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): 6.4000011.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): --
Edible ices, including sherbet and sorbet (03.0): --
Processed fruit (04.1): --
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 9.5000012.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): --
Bakery wares (07.0): 6.100007.00000
Meat and meat products, including poultry and game (08.0): 11.0000015.00000
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): --
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): --
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): --
Ready-to-eat savouries (15.0): --
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): --
 
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 57 (FGE.57)[1]: Consideration of two structurally related pulegone metabolites and one ester thereof evaluated by JECFA (55th meeting)
View page or View pdf

Statement on List of Representative Substances for Testing. The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000).
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
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :34645
National Institute of Allergy and Infectious Diseases:Data
5-methyl-2-prop-1-en-2-ylcyclohexan-1-one
Chemidplus:0029606799
 
References:
 5-methyl-2-prop-1-en-2-ylcyclohexan-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:29606-79-9
Pubchem (cid):34645
Pubchem (sid):134996316
 
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
CHEBI:View
HMDB (The Human Metabolome Database):Search
FooDB:FDB014368
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
For Odor
camphoreous
herbal ethanone
FR
floral
menthadienyl formate
FR
fruity
3-
benzyl-4-heptanone
FL/FR
herbal
iso
dihydrolavandulol
FR
(Z)-iso
dihydrolavandulyl acetate
FR
herbal undecanol
FR
hyssop oil
FL/FR
para-
menthane-3,8-diol
FL/FR
piperitone
FL/FR
rosemary absolute
FL/FR
common
tansy flower oil
FR
common
tansy flower oil dutch
FR
mentholic
cornmint oil
FL/FR
cornmint oil india
FL/FR
cornmint oil terpeneless
FL/FR
laevo-
menthol
FL/FR
dextro,laevo-
menthol
FL/FR
(±)-iso
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
menthyl acetate racemic
FL/FR
peppermint cyclohexanone
FL/FR
dextro-
piperitone
FL/FR
iso
pulegyl acetate
FL/FR
minty
homo
menthol
FL/FR
(-)-
menthone
FL/FR
homo
menthyl acetate
FL/FR
2-
methyl cyclohexanone
FL/FR
pennyroyal oil
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
peppermint oil terpenes
FR
laevo-
piperitone
FL/FR
(-)-iso
pulegol
FL/FR
(R)-(+)-
pulegone
FR
WS-23
FL/FR
thujonic
common
tansy oil canada
FR
For Flavor
No flavor group found for these
(±)-N,N-
dimethyl menthyl succinamide
FL
para-
menthane-3,8-diol
FL/FR
3-laevo-
menthoxy-2-methyl propane-1,2-diol
FL
menthyl acetate racemic
FL/FR
2-
methyl cyclohexanone
FL/FR
piperitenone oxide
FL
menthyl methyl lactate
FL
cooling
cooling
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
homo
menthyl acetate
FL/FR
fruity
3-
benzyl-4-heptanone
FL/FR
herbal
hyssop oil
FL/FR
rosemary absolute
FL/FR
mentholic
cornmint oil
FL/FR
cornmint oil terpeneless
FL/FR
peppermint cyclohexanone
FL/FR
minty
cornmint oil india
FL/FR
homo
menthol
FL/FR
(±)-iso
menthone
FL/FR
(-)-
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
pennyroyal oil
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
dextro-
piperitone
FL/FR
laevo-
piperitone
FL/FR
piperitone
FL/FR
(-)-iso
pulegol
FL/FR
WS-23
FL/FR
woody
iso
pulegyl acetate
FL/FR
 
Potential Uses:
FRherbal
FRmint
FRpepper
FRpeppermint
 
Occurrence (nature, food, other):note
 calamintha nepeta (l.) savi subsp. glandulosa oil greece @ 0.70%
Data GC Search Trop Picture
 cornmint leaf
Search Trop Picture
 cymbopogon laniger extract @ 0.10-0.50%
Data GC Search Trop Picture
 plectranthus glandulosus hook f. leaf oil cameroon @ 1.80%
Data GC Search Trop Picture
 satureja viminea l. oil costa rica @ 0.60%
Data GC Search Trop Picture
 tsauri grass oil @ 1.40%
Data GC Search Trop Picture
 
Synonyms:
 cyclohexanone, 2-isopropylideno-5-methyl-
 cyclohexanone, 5-methyl-2-(1-methylethenyl)-
p-menth-8-en-3-one
para-menth-8-en-3-one
delta-8,9-p-menthen-3-one
delta-8,9-para-menthen-3-one
8(9)-p-menthen-3-one, d-
trans-5-methyl-2-(1-methyl vinyl) cyclohexan-1-one
trans-5-methyl-2-(1-methylethenyl)cyclohexanone
trans-5-methyl-2-(1-methylvinyl)cyclohexan-1-one
5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one
5-methyl-2-(prop-1-en-2-yl)cyclohexanone
5-methyl-2-prop-1-en-2-ylcyclohexan-1-one
1-methyl-4-isopropenyl-3-cyclohexanone
1-isopropyl-4-methyl-2-cyclohexanone
isopulegon
(+)-cis-isopulegone
2R,5S-isopulegone
 

Articles:

PubMed:Effect of different growth stages of Ziziphora clinopodioides Lam. on its chemical composition.
PubMed:Is differential use of Juniperus monosperma by small ruminants driven by terpenoid concentration?
PubMed:Chemical composition of the essential oils of variegated pink-fleshed lemon (Citrus x limon L. Burm. f.) and their anti-inflammatory and antimicrobial activities.
PubMed:Chemical composition and biological evaluation of essential oils of Pulicaria jaubertii.
PubMed:[A new monoterpenoid glucoside from the twigs of Chamaecyparis obtusa var. breviramea f. crippsii].
PubMed:Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham.
PubMed:Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae).
PubMed:Chemical composition, antimicrobial and antioxidant activities of the essential oil of Tibetan herbal medicine Dracocephalum heterophyllum Benth.
PubMed:Genetic variability in Hesperozygis ringens Benth. (Lamiaceae), an endangered aromatic and medicinal plant of southern Brazil.
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:New monoterpenes from Mentha microphylla.
PubMed:Monoterpene double-bond reductases of the (-)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (-)-isopiperitenone reductase and (+)-pulegone reductase of peppermint.
PubMed:Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.
PubMed:Metabolic fate of S-(-)-pulegone in rat.
PubMed:Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity.
PubMed:The Essential Oil of Poliomintha incana.
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:Microbial transformations of some monoterpenoids and sesquiterpenoids.
 
Notes:
None found
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