(R)-(+)-pulegone

pulegone

CAS: 89-82-7 C10 H16 O MW: 152.23672000 minty minty

Identification

Name(R)-(+)-pulegone
IUPAC(5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
CAS Number89-82-7
EINECS201-943-2
FDA UNII4LF2673R3G
Molecular FormulaC10 H16 O
Molecular Weight152.23672000
MDL NumberMFCD00063000
Nikkaji NumberJ3.216F
Beilstein2040703
CoE Number2050

Regulatory

JECFA Food Flavoring753 pulegone
FEMA Number2963
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)89-82-7 ; PULEGONE
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

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, 132.00 to 133.00 °C. @ 50.00 mm Hg
Vapor Pressure 0.093000 mmHg @ 25.00 °C. (est)
Flash Point 180.00 °F. TCC ( 82.22 °C. )
logP (o/w) 3.080
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength medium
Substantivity 8 hour(s) at 100.00 %
Odor Description
at 100.00 %.
Minty, sulfuraceous, sweet with metallic buchu nuances
Odor sample from Givaudan Corporation
Taste Description at 20.00 ppm.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Human Experience10 % solution: no irritation or sensitization.
Oral/Parenteral Toxicityintravenous-dog LDLo 330 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION\nCARDIAC: CHANGE IN RATE']

Safety in Use

Categoryfragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for (R)-(+)-pulegone usage levels up to5.0000 % in the fragrance concentrate.
baked goods24.00000
beverages(nonalcoholic)5.00000
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy5.00000
fruit ices5.00000
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
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-

Berje Inc.

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Vigon International

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Manufacturer and supplier of high quality flavor and fragrance ingredients.

View All Website 570-476-6300 sales@vigon.com

Potential Uses

FR currant black currant FR grape FR herbal FR mint FR peach FL/FR pennyroyal FR peppermint FR raspberry FR strawberry FL tropical FR woody

Natural Occurrence

agathosma crenulata oil @ 53.75% Data bergamot plant wild blackberry fruit PMC blueberry plant buchu leaf oil @ 0.94% Data calamintha nepeta (l.) savi subsp. glandulosa oil greece @ 41.00% Data cayenne fruit chamomile roman chamomile cornmint oil india @ 0.13% Data cornmint plant currant black currant bud currant black currant fruit horsemint shoot lemon balm lemongrass oil morocco @ 0.90% Data mint origanum PMC pennyroyal pennyroyal oil @ 86.70% Data pennyroyal oil cuba @ 25.14% Data pennyroyal oil uruguay @ 26.8-41.10% Data pepper bell pepper fruit peppermint leaf peppermint oil america @ 1.38% Data peppermint oil CO2 extract @ 0.30% Data peppermint oil mongolia @ 0.22% Data peppermint oil russia @ 0.99% Data rosemary rue oil cuba @ 0.10% Data sage oil cuba @ 0.86% Data salvia officinalis oil cuba @ 0.86% Data satureja viminea l. oil costa rica @ 35.30% Data spearmint spearmint leaf spearmint oil tea black tea thyme oil wild or creeping pakistan @ 0.21% Data water mint leaf water mint shoot

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 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.