Category: fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Appearance: | colorless clear oily liquid (est) |
Assay: | 85.00 to 100.00 %
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Food Chemicals Codex Listed: | No |
Boiling Point: | 220.00 to 222.00 °C. @ 760.00 mm Hg
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Boiling Point: | 132.00 to 133.00 °C. @ 50.00 mm Hg
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Vapor Pressure: | 0.093000 mmHg @ 25.00 °C. (est) |
Flash Point: | 180.00 °F. TCC ( 82.22 °C. )
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logP (o/w): | 3.080 |
Soluble in: |
| alcohol | | water, 173.7 mg/L @ 25 °C (est) |
Insoluble in: |
| water |
Organoleptic Properties:
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Odor Type: minty |
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Odor Strength: | medium |
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Substantivity: | 8 hour(s) at 100.00 % |
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| peppermint camphoreous fresh herbal buchu |
Odor Description: at 100.00 %. | peppermint camphor fresh herbal buchu Luebke, William tgsc, (1985) |
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| minty sulfurous sweet metallic buchu |
Odor Description:
| Minty, sulfuraceous, sweet with metallic buchu nuances Mosciano, Gerard P&F 16, No. 1, 31, (1991) |
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Flavor Type: minty |
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| 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) |
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Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
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.
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Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
None found. |
GHS Label elements, including precautionary statements |
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Pictogram | |
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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.
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Dermal Toxicity: |
Not determined
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Inhalation Toxicity: |
Not determined
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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.
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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 ppm | average maximum ppm |
baked goods: | 24.00000 | 25.00000 |
beverages(nonalcoholic): | 5.00000 | 8.00000 |
beverages(alcoholic): | - | - |
breakfast cereal: | - | - |
cheese: | - | - |
chewing gum: | - | - |
condiments / relishes: | - | - |
confectionery froastings: | - | - |
egg products: | - | - |
fats / oils: | - | - |
fish products: | - | - |
frozen dairy: | 5.00000 | 32.00000 |
fruit ices: | 5.00000 | 32.00000 |
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:
Flavor & Extract Manufacturers Association (FEMA) reference(s): |
The FEMA GRAS assessment of alicyclic substances used as flavor ingredients. View pdf |
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 |
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 |
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 Ca²+ 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. |
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