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HCID 442495Erstellt: 27. Oktober 2026

p-Menth-4(8)-en-3-on

PULEGONE · (R)-PULEGONE · PULEGON · (R)-(+)-PULEGONE · FEMA 2963 · D-PULEGONE · P-MENTH-4(8)-EN-3-ONE · 2-ISOPROPYLIDENE-5-METHYLCYCLOHEXANONE

https://huagongshe.com/de/chemical/442495

Molekülstruktur von p-Menth-4(8)-en-3-on

Identifikatoren & physikalische Daten

CAS No.89-82-7
SummenformelC10H16O
Durchschnittliche Molmasse152,23 g/mol
Monoisotopische Masse152,12011513 g/mol
SMILESCC(C)=C1CC[C@@H](C)CC1=O
InChIKeyNZGWDASTMWDZIW-MRVPVSSYSA-N
PubChem CID442495
ChEMBLCHEMBL2924219
ChEBICHEBI:35596
EC No.201-943-2
DTXSIDDTXSID2025975
Lokaler Namep-Menth-4(8)-en-3-on

Chemische & physikalische Eigenschaften

XLogP2,8
Polarare Oberfläche (TPSA)17,1
H-Brücken-Donoren0
H-Brücken-Akzeptoren1
Frei drehbare Bindungen0
Schwere Atome11
Formalladung0
Komplexität197
LogP (Verteilungskoeffizient)log Kow = 3.08
GeruchPleasant odor, midway between peppermint and camphor
Dichte0.9323 at 20 °C0.927-0.9390.937 g/mL at 25 °C(lit.)
Color/FormOilOily liquid
LöslichkeitPractically insoluble in waterMiscible with alcohol. ether, chloroforminsoluble in watersoluble in oilsmiscible to soluble in alcoholmiscible (in ethanol)Chloroform (Sparingly), Methanol (Slightly)
Siedepunkt224 °CBP: 151-153 °C at 100 mm Hg103 °C at 17 mm Hg84 °C at 6 mm Hg220.00 to 222.00 °C. @ 760.00 mm Hg224 °C(lit.)
DecompositionHazardous decomposition products formed under fire conditions. - Carbon oxides. /(R)-(+)-Pulegone/
Schmelzpunkt< 25 °C<=25°C
Dampfdruck138.0 [mmHg]0.123 mm Hg at 25 °C (extrapolated)138 mm Hg ( 25 °C)
Optical RotationSpecific optical rotation: +21 deg at 20 °C/D+28.2 deg at 20 °C/546 °C
BrechungsindexIndex of refraction: 1.4894 at 20 °C/D1.483-1.491n20/D 1.488
Physical DescriptionLiquid with a pleasant odor between peppermint and camphor[Merck Index] Clear light brown liquid[Sigma-Aldrich MSDS]SolidColourless to yellow liquid, herbaceous-minty, resinous odour
FEMA2963 | PULEGONE
Flammpunkt185 °F
Lagerbedingungen2-8°C
AggregatzustandLiquid
Wichte0.94
FarbeClear colorless to yellow
Geruchat 100.00 %. peppermint camphor fresh herbal buchu
Geruchsartminty
Biologische Quellesynthetic
Merck14,7937
JECFA Number753
BRN2040703
Henry-Konstante2.8×10-1 mol/(m3Pa) at 25℃, Roon et al. (2005)
Dielektrizitätskonstante9.5(20℃)
Kosmetik-Inhaltsstoffe FunktionenPERFUMING
InChI1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1
InChIKeyNZGWDASTMWDZIW-MRVPVSSYSA-N
SMILESC[C@@H]1CC\C(=C(\C)C)C(=O)C1
LogP (Verteilungskoeffizient)2.56
CAS Datenbank89-82-7(CAS DataBase Reference)
EPA chemische Informationend-Pulegone (89-82-7)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302 (96.1%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 279 reports by companies from 4 notifications to the ECHA C&L Inventory.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Regulatorische InformationenChemical: Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (R)-Hazard Traits - CarcinogenicityAuthoritative List - IARC Carcinogens - 2BProp 65Report - regardless of intended function of ingredient in the productRegulation (EC) No 178/2002 (amended)(R)-(+)-Pulegone: Does not have an individual approval but may be used under an appropriate group standard
Weitere SicherheitsinformationenIMAP assessments - Pulegone and related substances: Human health tier II assessment
GefahrenübersichtAll early deaths in 2-week oral studies of rats and mice at doses >300 mg/kg attributed to liver toxicityNon-neoplastic lesions of the liver, kidney, nose, and forestomach of rats and mice observed in 2-year oral studiesEvidence for carcinogenic activity: None in male ratssome in female ratsclear evidence (liver neoplasms) in male and female mice[NTP] Safe when used as a flavoring agent in food[JECFA] May cause irritationMay be harmful if swallowed or inhaled[Sigma-Aldrich MSDS]
FDA-AnforderungenPulegone is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Anwendungen & Verwendung

Occurrence

The l-form is found in the essential oils of Agastache formosana, Israeli orange, Barosma betulina and Barosma crenulata; the d-form is the most abundant and is found in pennyroyal oils. Also reported found in rabbiteye blueberry, black currants (buds), fresh blackberry, heated blackberry, peppermint oil, corn mint oil, spearmint oil, Scotch spearmint oil, other Mentha oils, thyme, black tea, origanum, Ocimum basilicum varieties, rosemary, lemon balm, buchu oil, anise hyssop, sweet grass oil and German chamomile oil.

Special ReportsFinal Report on the Safety Assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint)International Journal of Toxicology 20 (Suppl 3): 61-73 (2001).
Hazard Classes and CategoriesAcute Tox. 4 (96.1%)Acute toxicity (ingestion) - category 3Carcinogenicity - category 2Specific target organ toxicity (repeated exposure) - category 1
Hazardous Reactivities and IncompatibilitiesStrong oxidizing agents. /(R)-(+)-Pulegone//Conditions to avoid/ Heat, flames and sparks. /(R)-(+)-Pulegone/
BrandbekämpfungsverfahrenWear self contained breathing apparatus for fire fighting if necessary. /(R)-(+)-Pulegone/For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spraysolid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. /(R)-(+)-Pulegone/
LagerbedingungenKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. /(R)-(+)-Pulegone/
ReinigungsverfahrenContain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations (see section 13). Keep in suitable, closed containers for disposal. /(R)-(+)-Pulegone/
Preventive MeasuresUse personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. /(R)-(+)-Pulegene/
WechselwirkungenIntraperitoneal injection of R-(+)-pulegone (pulegone), the main constituent of pennyroyal oil, to ddY mice caused extensive liver injury as characterized by an increase in serum glutamic pyruvic transaminase (GPT) activity and centrilobular necrosis of hepatocytes. Treatments of mice with the cytochrome P-450 enzyme inhibitors, SKF-525A, metyrapone, piperonyl butoxide, and carbon disulfide (CS2), prevented or markedly alleviated the hepatotoxicity of pulegone. These results are compatible with the view that some metabolite of pulegone is responsible for the liver injury in mice.Pennyroyal oil ingestion has been associated with severe hepatotoxicity and death. The primary constituent, R-(+)-pulegone, is metabolized via hepatic cytochrome P450 to toxic intermediates. The purpose of this study was to assess the ability of the specific cytochrome P450 inhibitors disulfiram and cimetidine to mitigate hepatotoxicity in mice exposed to toxic levels of R-(+)-pulegone. 20-g female BALB/c mice were pretreated with either 150 mg/kg of cimetidine intraperitoneal (IP), 100 mg/kg of disulfiram IP, or both. After one hour, mice were administered 300 mg/kg of pulegone IP and were killed 24 hours later. Data were analyzed using ANOVA. Post-hoc t-tests used Bonferroni correction. There was a tendency for lower serum glutamate pyruvate transaminase in the disulfiram and cimetidine groups compared with the R-(+)-pulegone group. The differences were significant for both the cimetidine and the combined disulfram and cimetidine groups compared with the R-(+)-pulegone group. Pretreatment with the combination of disulfiram and cimetidine most effectively mitigated R-(+)-pulegone-induced hepatotoxicity. Within the limitations of a pretreatment animal model, the combination of cimetidine and disulfiram significantly mitigates the effects of pennyroyal toxicity and does so more effectively than either agent alone. These data suggest that R-(+)-pulegone metabolism through CYP1A2 appears to be more important in the development of a hepatotoxic metabolite than does metabolism via CYP2E1.Glutathione plays a role in the detoxication of pulegone. At hepatotoxic doses, pulegone depletes glutathione in the liver and the toxicity of pulegone on i.p. injection in mice is enhanced by treatment with diethyl maleate to decrease glutathione levels. No such increase in toxicity was seen with (R)-(+)-menthofuran . It was suggested that pulegone is analogous to acetaminophen in that saturation of the glutathione pathway leads to a higher proportion of the dose being metabolised to reactive metabolites (such as 8-pulegone aldehyde). However, in other studies, glutathione has been shown to react with menthofuran epoxide, the precursor to 8-pulegone aldehyde. Glutathione conjugation may play a major role in the detoxication of the reactive metabolite produced by cytochrome P450 ((R)-(+)-menthofuran or the gamma-ketoenal) as indicated by the isolation of glutathione conjugates, including a mixed glutathionyl glucuronide, from the bile of rats treated i.p. with pulegone. The evidencesuggests that the metabolic activation of pulegone occurring in animals also occurs in humans, resulting in the formation of (R)-(+)-menthofuran. At high concentrations, (R)-(+)-menthofuran is a proximate hepatoxic product but if the concentration of metabolites of pulegone is not sufficient to deplete hepatocellular concentrations of glutathione, hepatotoxicity may not be observed.The role of cytochrome P450s in metabolic activation of (R)-(+)-pulegone has been demonstrated by the observations that a variety of P450-inhibitors decreased the toxicity while pretreatment with phenobarbital enhanced the toxicity of (R)-(+)-pulegone and (R)-(+)- menthofuran. Thus, oxidation appears to enhance the toxicity of (R)-(+)-pulegone and (R)-(+)-menthofuran, which is consistent with the fact that (R)-(+)-pulegone is converted to (R)-(+)-menthofuran via 9-hydroxypulegenone, and the reactive 8-pulegone aldehyde is an ultimate toxicant. Evidence that pulegone is oxidized to 9-hydroxypulegone via a free radical mechanism is provided from the observation that treatment with the free radical scavenger C-phyocyanin decreased the hepatotoxicity of pulegone in rats.
ÖkotoxizitätswerteEC50Species: Daphnia pulex (Water Flea) age <24 hr, neonateConditions: freshwater, static, 17 °C, hard waterConcentration: 24400 ug/L for 48 hrEffect: intoxication, immobilization /> or = 96% purity/
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 670(SRC), determined from a log Kow of 3.08(2) and a regression-derived equation(3), indicates that pulegone is expected to have moderate mobility in soil(SRC). Volatilization of pulegone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.9X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Pulegone is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.12 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Biodegradation data in soil were not available(SRC, 2013).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 670(SRC), determined from a log Kow of 3.08(2) and a regression-derived equation(3), indicates that pulegone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 5.9X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 22 hours and 10 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 50(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data in water were not available(SRC, 2013).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pulegone, which has an estimated vapor pressure of 0.12 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase pulegone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 0.1 days(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Pulegone contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
LebensmitteluntersuchungswertePulegone concentrations in plants(1).Table: 3-10153 [Table#8108]Pulegone, detected, not quantified in plants(1).[Table#8109]
Unerwünschte WirkungenOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of November 21, 2013: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=89-82-7]
Soil Adsorption/MobilityThe Koc of pulegone is estimated as 670(SRC), using a log Kow of 670(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that pulegone is expected to have low mobility in soil.
Natural Pollution SourcesPulegone is found in oils derived from plants of the Labiarae (mint) family as (+)-form(1). It is readily isolated in quantity from the pennyroyal oils from Mentha pulegium, M. Longifolia, and Hedeoma pulegioides(1,2). Pugelone is one of the components of the essential oil derived from Ziziphora clinopodioides, Blue Mint Bush or kakuti-e kuhi, (Labiarae (Lamiaceae)), which grows in Iran, Iraq, and parts of Turkey(3,4).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ A review of cases of human intoxication with pennyroyal oil (Mentha pulegium: pulegone content 62-97%) indicate that ingestion of 10 mL resulted in moderate to severe toxicity and ingestion of greater than 15 mL (ca. 250 mg/kg bw for a 60 kg woman) resulted in death. The clinical pathology is characterised by massive centrilobular necrosis, pulmonary edema and internal hemorrhage./CASE REPORTS/ A review of published reports of pennyroyal poisoning (1869 to 1996) identified 18 cases in which there was moderate to severe toxicity from ingestion of at least 10 mL (about 2 tsp.) of pennyroyal oil. The toxic symptoms included coma, seizures, and hepatic and renal effects. Ingestion of less than 10 mL was generally associated with gastritis and mild central nervous system toxicity. However, the severity of the toxic effects was not always related strictly to dose and depended on the use of emetics or other treatments. In two cases reported before 1905, coma and seizures were associated with ingestion of 5 mL pennyroyal oiltwo other cases reportedly survived after ingestion of 30 mL. Variability in the toxic effects of pennyroyal oil may be due to differing concentrations of pulegone contained in preparations from European and American pennyroyal./CASE REPORTS/ The cases of 2 infants, an 8-wk-old boy and a 6-month-old boy, who developed hepatic and neurologic injury after ingestion of mint tea that contained the toxic agent pennyroyal oil are reported. Fulminant liver failure with cerebral edema and necrosis developed in the first infant, who died. This infant was positive only for menthofuran (10 ng/mL), a metabolite of a toxic constituent (pulegone) of pennyroyal oil. In the other infant, who was positive for both pulegone (25 ng/mL) and menthofuran (41 ng/mL), hepatic dysfunction and a severe epileptic encephalopathy developed. When he was discharged 2 months after admission his hepatocellular enzyme markers remained elevated./CASE REPORTS/ Pennyroyal is a widely available herb that has long been used as an abortifacient despite its potentially lethal hepatotoxic effects. However, quantitative data for pennyroyal constituents and their metabolites in humans have not been previously reported. We report four cases of pennyroyal ingestion. One patient died, one received N-acetylcysteine, and two ingested minimally toxic amounts of pennyroyal and were not treated with N-acetylcysteine. In the fatal case, postmortem examination of a serum sample, which had been obtained 72 hours after the acute ingestion, identified 18 ng of pulegone per mL and 1 ng of menthofuran per mL. In a serum sample from the patient treated with N-acetylcysteine, which had been obtained 10 hours after ingestion, the menthofuran level was 40 ng/mL. Review of 18 previous case reports of pennyroyal ingestion documented moderate to severe toxicity in patients who had been exposed to at least 10 mL of pennyroyal oil. Pennyroyal continues to be an herbal toxin of public health importance. Data on human metabolites may provide new insights into the toxic mechanisms and treatment of pennyroyal poisoning, including the potential role of N-acetylcysteine. Better understanding of the toxicity of pennyroyal may also lead to stricter control of and more restricted access to the herb.For more Human Toxicity Excerpts (Complete) data for Pulegone (7 total), please visit the HSDB record page.
Artificial Pollution SourcesPulegone's production and use as a chemical intermediate, flavoring(1) and herbal medication(2) may result in its release to the environment through various waste streams(SRC).
Carcinogen ClassificationPulegoneGroup 2B: Possibly carcinogenic to humansVolume 108: (2016) Some Drugs and Herbal Products2013
Environmental BioconcentrationAn estimated BCF of 50 was calculated in fish for pulegone(SRC), using a log Kow of 3.08(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).
F10-23
Wassergefährdungsklasse (WGK)3
TSCA-Inventar-StatusTSCA listed
UN-Transportnummer2810
Zollcode2914 29 00
RTECS-Nr.OT0261000
R-Sätze (R)22
ToxizitätLD50 orally in Rabbit: 470 mg/kg LD50 dermal Rabbit 3090 mg/kg
GefahrensymboleXn
Sicherheitshinweise (S)23-24/25
Gefahrenklasse6.1(b)Acute Tox. 4 OralCarc. 2
VerpackungsgruppeIII
Lagerklasse10 - Combustible liquids
Gefahrstoffdaten89-82-7(Hazardous Substances Data)