PULEGONE (CED0006371)

Record Information
Version1.0
Creation Date2016-05-19 02:24:42 UTC
Update Date2026-04-17 19:32:44 UTC
Accession NumberCHEM007370
Identification
Common NamePULEGONE
ClassSmall Molecule
Description
Pulegone is an organic compound with the chemical formula C10H16O and an average molecular weight of 152.23 g/mol. PULEGONE belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. Industrially, the substance is utilized as a fragrance, as well as a flavouring and nutrient. The compound is found in or released from 32 recorded sources across several sectors. Within the energy, oil & gas sector, it is used in lubricants. In the healthcare, pharmaceuticals & veterinary products sector, it is associated with medical devices. Its presence in textiles, leather & furnishings includes synthetic textiles, carpets and rugs. In the food, food processing & cookware sector, pulegone is involved in food packaging, food preservation, the preparation of wort, the preparation of wine or sparkling wine, and fermentation processes for beer. Furthermore, it is recorded in household cleaning & consumer products, including perfumes within detergents and soaps, bleaching agents, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices, among five other sources. In the electrical & electronic equipment sector, it is found in batteries, capacitors, printed circuit boards, wires and cables, cell phones, and six additional sources. Two other sectors are also recorded. Exposure to pulegone may occur through oral, inhalation, or touch routes.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
(+)-(R)-PulegoneChEBI
(1R)-(+)-p-Menth-4(8)-en-3-oneChEBI
(5R)-2-Isopropylidene-5-methylcyclohexanoneChEBI
(R)-PulegoneChEBI
D-PulegoneChEBI
(+)-PulegoneKegg
Pulegone, (R)-isomerHMDB
(R)-(+)-p-Menth-4(8)-en-3-oneHMDB
(R)-p-Menth-4(8)-en-3-oneHMDB
p-Menth-4(8)-en-3-oneHMDB
(R)-5-Methyl-2-(1-methylethylidene)cyclohexanoneHMDB
(R)-(+)-PulegoneHMDB
(1R)-PulegoneHMDB
L-PulegoneHMDB
NSC 15334HMDB
PulegonHMDB
FEMA 2963HMDB
(+)-4(8)-Para-menthen-3-oneHMDB
5-Methyl-2-(1-methylethylidene)cyclohexanoneHMDB
PulegoneChEBI
(5R)-5-Methyl-2-(1-methylethylidene)cyclohexanonePhytoBank
Chemical FormulaC10H16O
Average Molecular Mass152.233 g/mol
Monoisotopic Mass152.120 g/mol
CAS Registry Number89-82-7
IUPAC Name(5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one
Traditional Name(+)-pulegone
SMILES[H][C@@]1(C)CCC(=C(C)C)C(=O)C1
InChI IdentifierInChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1
InChI KeyNZGWDASTMWDZIW-MRVPVSSYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.29 g/LALOGPS
logP2.36ALOGPS
logP2.86ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.13 m³·mol⁻¹ChemAxon
Polarizability18.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0f89-9200000000-103da19d7e73140f53a7Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0fsi-9300000000-5c40f6bc1c5dd5e64dc8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0btm-9600000000-72752a4904dbe00f2b4aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-50f4b6a38ec680e83d0cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-114i-6900000000-04a7ff4ee15b9b1c8161Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ldi-9100000000-2aee3b73ef815011023fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-cd90c558f842f253efd3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-011197e33d9b4420c257Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4u-6900000000-723bf6d0a35d2e10aafdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ik9-2900000000-7f3925a428ada570a2f6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00l6-9300000000-2fd8486379bd720b7b38Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-441dfa2e182dd78429bcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-c373c9eea3cebf186f53Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-9fc5f57a10d95a4f369bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-5900000000-7ce0df14de5e9c637a48Not AvailableView Spectrum
MSMS Spectrumsplash10-0kur-9400000000-182826a9f81c661c7496Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
998.0Log mg/kg[560:1800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
233BrushesPersonal care & cosmeticsNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSpermidine synthaseQ4CXJ6Trypanosoma cruzi (strain CL Brener)Predicted (SEA)1.01204
Click to view 3D structureSpermidine synthaseQ9NFS5Plasmodium falciparumPredicted (SEA)1.01204
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)570.323
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)77.3043
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)1273.22
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)57.1413
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)144.566
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)4003.01
Click to view 3D structureSerine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoformQ76MZ3Mus musculusPredicted (SEA)1.63483
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)3558.96
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)3756.85
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)3561.37
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)2118.59
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)7316.11
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)5817.52
Click to view 3D structureGlucose-6-phosphate 1-dehydrogenaseQ9GRG7Trypanosoma bruceiPredicted (SEA)31.1397
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)5189.74
Platelet-derived growth factor receptor alpha structureClick to view 3D structurePlatelet-derived growth factor receptor alphaP16234HumansPredicted (SEA)6766.11
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)7113.78
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)4538.53
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)1500.54
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)2851.54
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-4P28471Rattus norvegicusPredicted (SEA)13.935
Click to view 3D structureHemagglutininP03438Influenza A virus (strain A/X-31 H3N2)Predicted (SEA)9.41976
Click to view 3D structureSpermidine synthaseQ6QA75Sus scrofaPredicted (SEA)1.01204
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0035604
FooDB IDFDB030074
Phenol Explorer IDNot Available
KNApSAcK IDC00000827
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPulegone
Chemspider ID390923
ChEBI ID35596
PubChem Compound ID442495
Kegg Compound IDC09893
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Madyastha KM, Gaikwad NW: Metabolic fate of S-(-)-pulegone in rat. Xenobiotica. 1998 Aug;28(8):723-34.
2. Chen LJ, Lebetkin EH, Burka LT: Metabolism of (R)-(+)-pulegone in F344 rats. Drug Metab Dispos. 2001 Dec;29(12):1567-77.
3. Yang JP, Bao BH, Zhang L, Ding AW: [Quantitative analysis of pulegone in Herba Schizonepetae]. Zhongguo Zhong Yao Za Zhi. 2005 May;30(9):669-70.
4. Dancewicz K, Gabrys B, Dams I, Wawrzenczyk C: Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding. J Chem Ecol. 2008 Apr;34(4):530-8. doi: 10.1007/s10886-008-9448-9. Epub 2008 Mar 14.
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
10. The lipid handbook with CD-ROM
11. Wikipedia: http://en.wikipedia.org/wiki/(+)-Pulegone_reductase
12. Wikipedia: http://en.wikipedia.org/wiki/Pulegone
13. UniProt Q6WAU0 : (+)-pulegone reductase: http://www.uniprot.org/uniprot/Q6WAU0
14. Robert Carson, 'Cosmetic skin care compositions containing pulegone.' U.S. Patent US20020006423, issued January 17, 2002.: http://www.google.ca/patents/US20020006423