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(R)-(+)-pulegone

Chemical Structure

General Material Information

Preferred name (R)-(+)-pulegone
Trivial Name (+)-Pulegone
Short Description pulegone
Formula C10 H16 O
CAS Number 89-82-7
Deleted CAS Number 90449-51-7
FEMA Number 2963
ECHA Number 201-943-2
FDA UNII 4LF2673R3G
Nikkaji Number J3.216F
Beilstein Number 2040703
MDL MFCD00063000
COE Number 2050
xLogP3-AA 2.80 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 753 pulegone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 89-82-7 ; PULEGONE
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-iso propylidene-4-methyl-2-cyclohexanone
  • (R)-2-iso propylidene-5-methyl-cyclohexanone
  • (5R)-2-iso propylidene-5-methylcyclohexanone
  • (R)-2-iso propylidene-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
  • (5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
  • p-Menth-4(8)-en-3-one, (R)-(+)-
  • (5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone
  • (+)-Pulegone
  • d-Pulegone
  • (+)-(R)-Pulegone
  • Pulegon
  • (1R)-(+)-p-Menth-4(8)-en-3-one
  • (R)-Pulegone
  • (R)-(+)-p-Menth-4(8)-en-3-one
  • (1R)-Pulegone
  • NSC 15334
  • L-Pulegone

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Literature & 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
Publications by PubMed
Divergent total synthesis of the Lycopodium alkaloids huperzine A, huperzine B, and huperzine U.
Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one.
Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one.
An efficient total synthesis of (-)-huperzine A.
R(+)-pulegone impairs Ca²+ homeostasis and causes negative inotropism in mammalian myocardium.
Pharmacological activity of (R)-(+)-pulegone, a chemical constituent of essential oils.
Fungicidal properties of the essential oil of Hesperozygis marifolia on Aspergillus flavus link.
IR-Raman-VCD study of R-(+)-pulegone: influence of the solvent.
A trapping method for semi-quantitative assessment of reactive metabolite formation using [35S]cysteine and [14C]cyanide.
Defense on the rocks: low monoterpenoid levels in plants on pillars without mammalian herbivores.
Total synthesis and structural confirmation of ent-galbanic acid and marneral.
Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding.
Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).
Dansyl glutathione as a trapping agent for the quantitative estimation and identification of reactive metabolites.
Synthesis of a highly hindered hydrindanone via alpha-carbonyl radical cyclization: enantiospecific formal syntheses of (-)-pinguisenol and (-)-alpha-pinguisene.
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.
Mitigation of pennyroyal oil hepatotoxicity in the mouse.
Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites.
Comparative disposition of (R)-(+)-pulegone in B6C3F1 mice and F344 rats.
Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization.
Revision of the absolute configuration of the tricyclic sesquiterpene (+)-kelsoene by chemical correlation and enantiospecific total synthesis of its enantiomer.
Stereoselective hydroxylation of 4-methyl-2-cyclohexenone in rats: its relevance to R-(+)-pulegone-mediated hepatotoxicity.
Metabolism of (R)-(+)-pulegone in F344 rats.
Synthesis of (+)-galiellalactone. Absolute configuration of galiellalactone.
Ambulation-promoting effect of peppermint oil and identification of its active constituents.
Chiral auxiliaries for asymmetric radical cyclization reactions: application to the enantioselective synthesis of (+)-triptocallol.
First enantioselective syntheses of (+)- and (-)-wilforonide by using chiral auxiliaries derived from the same chiral source.
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.
Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthetic approach to the key mother spiroketals.
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.
Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.
Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.
Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide.
Metabolic disposition of a monoterpene ketone, piperitenone, in rats: evidence for the formation of a known toxin, p-cresol.
Metabolic fate of S-(-)-pulegone in rat.
Hepatoprotective effect of C-phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats.
Synthesis, antiviral activity, and bioavailability studies of gamma-lactam derived HIV protease inhibitors.
Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone.
Evidence for the formation of a known toxin, p-cresol, from menthofuran.
Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity.
Metabolic activation of (R)-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins.
Metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat.
Pulegone mediated hepatotoxicity: evidence for covalent binding of R(+)-[14C]pulegone to microsomal proteins in vitro.
Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course.
Effects of drug metabolism modifiers on pulegone-induced hepatotoxicity in mice.
The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran.
Synthesis of racemate and enantiomers of 15-methyltritriacontane, sex-stimulant pheromone of stable flyStomoxys calcitrans L.

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
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

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Boiling Point 220 to 222°C @ 760 mm Hg
Boiling Point 132 to 133°C @ 50 mm Hg
Vapor Pressure 0.093 mmHg @ 25 °C
Flash Point TCC Value 82.22 °C TCC
logP (o/w) 3.08
Solubility
alcohol Yes
water, 173.7 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Minty
peppermint, camphoreous, fresh, herbal, buchu, minty, sulfurous, sweet, metallic
Odor strength medium
Substantivity 8 hour(s) at 100.00 %
Luebke, William tgsc, (1985) At 100.00 %. peppermint camphor fresh herbal buchu
Mosciano, Gerard P&F 16, No. 1, 31, (1991) Minty, sulfuraceous, sweet with metallic buchu nuances
Flavor Type: Minty
minty, sulfurous, fruity, currant black currant, raspberry, fresh, green, leafy
Mosciano, Gerard P&F 16, No. 1, 31, (1991) At 20.00 ppm. Minty sulfuraceous, fruity blackcurrant and raspberry, with fresh green leafy nuances

Occurrences

Potential Uses

Applications
Odor purposes Currant black currant, Grape, Herbal, Mint, Peach, Pennyroyal, Peppermint, Raspberry, Strawberry, Woody
Flavoring purposes Pennyroyal, Tropical
Cosmetic purposes Perfuming agents

Safety Information

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
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
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
Click here to view publication 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,ß-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
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations: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