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

(R)-(+)-pulegone
pulegone

Sponsors

Name:(5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
CAS Number: 89-82-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-943-2
FDA UNII:4LF2673R3G
Nikkaji Web:J3.216F
Beilstein Number:2040703
MDL:MFCD00063000
CoE Number:2050
XlogP3-AA:2.80 (est)
Molecular Weight:152.23672000
Formula:C10 H16 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category: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:753 pulegone
FEMA Number:2963-VOID pulegone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: PULEGONE
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 oily liquid (est)
Assay: 85.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 220.00 to 222.00 °C. @ 760.00 mm Hg
Boiling Point: 132.00 to 133.00 °C. @ 50.00 mm Hg
Vapor Pressure:0.093000 mm/Hg @ 25.00 °C. (est)
Flash Point: 180.00 °F. TCC ( 82.22 °C. )
logP (o/w): 3.080
Soluble in:
 alcohol
 water, 173.7 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:medium
Substantivity:8 hour(s) at 100.00 %
peppermint camphoreous fresh herbal buchu
Odor Description:at 100.00 %. peppermint camphor fresh herbal buchu
Luebke, William tgsc, (1985)
Odor sample from: Givaudan Corporation
minty sulfurous sweet metallic buchu
Odor Description:Minty, sulfuraceous, sweet with metallic buchu nuances
Mosciano, Gerard P&F 16, No. 1, 31, (1991)
Flavor Type: minty
minty sulfurous fruity currant black currant raspberry fresh green leafy
Taste Description: at 20.00 ppm. Minty sulfuraceous, fruity blackcurrant and raspberry, with fresh green leafy nuances
Mosciano, Gerard P&F 16, No. 1, 31, (1991)
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
Aurochemicals
PULEGONE, Natural
BOC Sciences
For experimental / research use only.
(+)-PULEGONE >95.0%(GC)
Odor: characteristic
Use: A monoterpene, commonly found in the essential oils of Nepeta cataria (Catnip).
EMD Millipore
For experimental / research use only.
(R)-(+)-Pulegone
Ernesto Ventós
PULEGONE NATURAL (EX PENNYROYAL)
Odor: MINTY, FRESH
ExtraSynthese
For experimental / research use only.
(R)-(+)-Pulegone (GC) ≥98% (sum of enantiomers)
Fleurchem
pulegone natural
Lluch Essence
PULEGONE NATURAL 95%
Odor: CAMPHORACEOUS, FRESH, MINTY
Nippon Terpene Chemicals
d-Pulegone 98% up
Parchem
(R)-(+)-pulegone
Penta International
d-PULEGONE, Kosher
Penta International
d-PULEGONE, NATURAL, Kosher
Prodasynth
PULEGONE NATURAL > 90
Odor: MINTY, FRESH
Reincke & Fichtner
D-Pulegone
Reincke & Fichtner
Pulegone natural
Santa Cruz Biotechnology
For experimental / research use only.
(+)-Pulegone
Sigma-Aldrich
(R)-(+)-Pulegone ≥90%
Certified Food Grade Products
Synerzine
Pulegone Dextro (Natural)
Synerzine
Pulegone
TCI AMERICA
For experimental / research use only.
(+)-Pulegone >95.0%(GC)
Vigon International
Pulegone Dextro Natural ex Pennyroyal Oil
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
 
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.
Human Experience:
10 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
intravenous-dog LDLo 330 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: fragrance agents
Recommendation for (R)-(+)-pulegone usage levels up to:
  5.0000 % in the fragrance concentrate.
 
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: 24.0000025.00000
beverages(nonalcoholic): 5.000008.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 5.0000032.00000
fruit ices: 5.0000032.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -17.00000
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: --
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Pulegone and Menthofuran in flavourings - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

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

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
Chemical Carcinogenesis Research Information System:Search
Env. Mutagen Info. Center:Search
EPA Substance Registry Services (TSCA):89-82-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :442495
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
Chemidplus:0000089827
RTECS:OT0261000 for cas# 89-82-7
 
References:
 (5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:89-82-7
Pubchem (cid):442495
Pubchem (sid):134972995
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 Everything Added to Food in the United States (EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09893
HMDB (The Human Metabolome Database):HMDB35604
FooDB:FDB014298
Export Tariff Code:2914.29.5000
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
chemical
styralyl alcohol
FL/FR
citrus
bergamot acetoacetate
FR
floral
lavender oil
FL/FR
fruity
tropical trithiane
FL/FR
green
thiogeraniol
FL/FR
herbal
buchu oxime
FR
chamomile oil morocco
FR
melaleuca quinquenervia water
FR
mentholic
cornmint oil terpeneless
FL/FR
laevo-
menthol
FL/FR
dextro,laevo-
menthol
FL/FR
peppermint cyclohexanone
FL/FR
dextro-
piperitone
FL/FR
iso
pulegyl acetate
FL/FR
minty
diosphenol
FL/FR
(-)-
menthone
FL/FR
pennyroyal oil
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
iso
pulegone
FL/FR
spicy
origanum majorana oil CO2 extract
FL/FR
sulfurous
buchu mercaptan
FL/FR
mango thiol
FL/FR
passiflora acetate
FL/FR
woody
hinoki root oil
FR
For Flavor
No flavor group found for these
diosphenol
FL/FR
iso
pulegone
FL/FR
chemical
chemical
styralyl alcohol
FL/FR
cooling
laevo-
menthol
FL/FR
dextro,laevo-
menthol
FL/FR
fruity
tropical trithiane
FL/FR
herbal
lavender oil
FL/FR
origanum majorana oil CO2 extract
FL/FR
mentholic
cornmint oil terpeneless
FL/FR
peppermint cyclohexanone
FL/FR
minty
(-)-
menthone
FL/FR
pennyroyal oil
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
dextro-
piperitone
FL/FR
thiogeraniol
FL/FR
sulfurous
buchu mercaptan
FL/FR
mango thiol
FL/FR
tropical
passiflora acetate
FL/FR
vegetable
potato butyraldehyde
FL
woody
iso
pulegyl acetate
FL/FR
 
Potential Uses:
FRcurrant black currant
FRgrape
FRherbal
FRmint
FRpeach
FL/FRpennyroyal
FRpeppermint
FRraspberry
FRstrawberry
FLtropical
FRwoody
 
Occurrence (nature, food, other):note
 agathosma crenulata oil @ 53.75%
Data GC Search Trop Picture
 bergamot plant wild
Search Trop Picture
 blackberry fruit
Search PMC Picture
 blueberry plant
Search Trop Picture
 buchu leaf oil @ 0.94%
Data GC Search Trop Picture
 calamintha nepeta (l.) savi subsp. glandulosa oil greece @ 41.00%
Data GC Search Trop Picture
 cayenne fruit
Search Trop Picture
 chamomile roman chamomile
Search Trop Picture
 cornmint oil india @ 0.13%
Data GC Search Trop Picture
 cornmint plant
Search Trop Picture
 currant black currant bud
Search Trop Picture
 currant black currant fruit
Search Trop Picture
 horsemint shoot
Search Trop Picture
 lemon balm
Search Trop Picture
 lemongrass oil morocco @ 0.90%
Data GC Search Trop Picture
 mint
Search Trop Picture
 origanum
Search PMC Picture
 pennyroyal
Search Trop Picture
 pennyroyal oil @ 86.70%
Data GC Search Trop Picture
 pennyroyal oil cuba @ 25.14%
Data GC Search Trop Picture
 pennyroyal oil uruguay @ 26.8-41.10%
Data GC Search Trop Picture
 pepper bell pepper fruit
Search Trop Picture
 peppermint leaf
Search Trop Picture
 peppermint oil america @ 1.38%
Data GC Search Trop Picture
 peppermint oil CO2 extract @ 0.30%
Data GC Search Trop Picture
 peppermint oil mongolia @ 0.22%
Data GC Search Trop Picture
 peppermint oil russia @ 0.99%
Data GC Search Trop Picture
 rosemary
Search Trop Picture
 rue oil cuba @ 0.10%
Data GC Search Trop Picture
 sage oil cuba @ 0.86%
Data GC Search Trop Picture
 salvia officinalis oil cuba @ 0.86%
Data GC Search Trop Picture
 satureja viminea l. oil costa rica @ 35.30%
Data GC Search Trop Picture
 spearmint
Search Trop Picture
 spearmint leaf
Search Trop Picture
 spearmint oil
Search Trop Picture
 tea black tea
Search Trop Picture
 thyme oil wild or creeping pakistan @ 0.21%
Data GC Search Trop Picture
 water mint leaf
Search Trop Picture
 water mint shoot
Search Trop Picture
 
Synonyms:
 cyclohexanone, 5-methyl-2- (1-methylethylidene)-, (R)-
 cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5R)-
 cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (R)-
(1R)-(+)-p-menth-4(8)-en-3-one
(1R)-(+)-para-menth-4(8)-en-3-one
(R)-(+)-p-menth-4(8)-en-3-one
(R)-(+)-para-menth-4(8)-en-3-one
(R)-p-menth-4(8)-en-3-one
(R)-para-menth-4(8)-en-3-one
R-(+)-p-menth-4(8)-en-3-one
(1R)-(+)-p-menth-4,8-en-3-one
(1R)-(+)-para-menth-4,8-en-3-one
delta-4,8-p-menthen-3-one
delta-4,8-para-menthen-3-one
(R)-5-methyl-2-(1-methyl ethylidene) cyclohexanone
(R)-5-methyl-2-(1-methylethylidene)cyclohexanone
(5R)-5-methyl-2-(2-propanyliden)cyclohexanon
(5R)-5-methyl-2-(methylethylidene)cyclohexan-1-one
(5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one
(5R)-5-methyl-2-(propan-2-ylidene)cyclohexanone
(R)-5-methyl-2-(propan-2-ylidene)cyclohexanone
(5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
(R)-1-methyl-4-isopropylidene-3-cyclohexanone
(R)-3-methyl-6-isopropylidene cyclohexanone
(R)-3-methyl-6-isopropylidenecyclohexanone
(R)-1-isopropylidene-4-methyl-2-cyclohexanone
(R)-2-isopropylidene-5-methyl-cyclohexanone
(5R)-2-isopropylidene-5-methylcyclohexanone
(R)-2-isopropylidene-5-methylcyclohexanone
 pulegone
(+)-pulegone
(+)-(R)-pulegone
(R)-pulegone
(R)-(+)-pulegone
D-pulegone
dextro-pulegone
 pulegone (ex Pennyroyal)
 pulegone dextro natural ex pennyroyal oil
D-pulegone, natural
 

Articles:

PubMed:Divergent total synthesis of the Lycopodium alkaloids huperzine A, huperzine B, and huperzine U.
PubMed:Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one.
PubMed:Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one.
PubMed:An efficient total synthesis of (-)-huperzine A.
PubMed:R(+)-pulegone impairs Ca┬▓+ homeostasis and causes negative inotropism in mammalian myocardium.
PubMed:Pharmacological activity of (R)-(+)-pulegone, a chemical constituent of essential oils.
PubMed:Fungicidal properties of the essential oil of Hesperozygis marifolia on Aspergillus flavus link.
PubMed:IR-Raman-VCD study of R-(+)-pulegone: influence of the solvent.
PubMed:A trapping method for semi-quantitative assessment of reactive metabolite formation using [35S]cysteine and [14C]cyanide.
PubMed:Defense on the rocks: low monoterpenoid levels in plants on pillars without mammalian herbivores.
PubMed:Total synthesis and structural confirmation of ent-galbanic acid and marneral.
PubMed:Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding.
PubMed:Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).
PubMed:Dansyl glutathione as a trapping agent for the quantitative estimation and identification of reactive metabolites.
PubMed:Synthesis of a highly hindered hydrindanone via alpha-carbonyl radical cyclization: enantiospecific formal syntheses of (-)-pinguisenol and (-)-alpha-pinguisene.
PubMed:In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.
PubMed:Mitigation of pennyroyal oil hepatotoxicity in the mouse.
PubMed:Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites.
PubMed:Comparative disposition of (R)-(+)-pulegone in B6C3F1 mice and F344 rats.
PubMed:Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization.
PubMed:Revision of the absolute configuration of the tricyclic sesquiterpene (+)-kelsoene by chemical correlation and enantiospecific total synthesis of its enantiomer.
PubMed:Stereoselective hydroxylation of 4-methyl-2-cyclohexenone in rats: its relevance to R-(+)-pulegone-mediated hepatotoxicity.
PubMed:Metabolism of (R)-(+)-pulegone in F344 rats.
PubMed:Synthesis of (+)-galiellalactone. Absolute configuration of galiellalactone.
PubMed:Ambulation-promoting effect of peppermint oil and identification of its active constituents.
PubMed:Chiral auxiliaries for asymmetric radical cyclization reactions: application to the enantioselective synthesis of (+)-triptocallol.
PubMed:First enantioselective syntheses of (+)- and (-)-wilforonide by using chiral auxiliaries derived from the same chiral source.
PubMed:Effect of ring size in R-(+)-pulegone-mediated hepatotoxicity: studies on the metabolism of R-(+)-4-methyl-2-(1-methylethylidene)-cyclopentanone and DL-camphorone in rats.
PubMed:Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthetic approach to the key mother spiroketals.
PubMed:Role of C-5 chiral center in R-(+)-pulegone-mediated hepatotoxicity: metabolic disposition and toxicity of 5, 5-dimethyl-2-(1-Methylethylidene)-cyclohexanone in rats.
PubMed:Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.
PubMed:Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.
PubMed:Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide.
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:Hepatoprotective effect of C-phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats.
PubMed:Synthesis, antiviral activity, and bioavailability studies of gamma-lactam derived HIV protease inhibitors.
PubMed:Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
PubMed:Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone.
PubMed:Evidence for the formation of a known toxin, p-cresol, from menthofuran.
PubMed:Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity.
PubMed:Metabolic activation of (R)-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins.
PubMed:Metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat.
PubMed:Pulegone mediated hepatotoxicity: evidence for covalent binding of R(+)-[14C]pulegone to microsomal proteins in vitro.
PubMed:Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course.
PubMed:Effects of drug metabolism modifiers on pulegone-induced hepatotoxicity in mice.
PubMed:The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran.
PubMed:Synthesis of racemate and enantiomers of 15-methyltritriacontane, sex-stimulant pheromone of stable flyStomoxys calcitrans L.
 
Notes:
Occurs in oils of Mentha spp., Hedeoma pulegioides and many other essential oils. Fragrance and flavour ingredient
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