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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: |
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Not determined
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| Inhalation Toxicity: |
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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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