Record Information
Version1.0
Creation date2010-04-08 22:11:11 UTC
Update date2019-11-26 03:09:48 UTC
Primary IDFDB014298
Secondary Accession Numbers
  • FDB014299
Chemical Information
FooDB Name(R)-p-Menth-4(8)-en-3-one
Description(R)-p-Menth-4(8)-en-3-one, also known as (+-)-pulegone or isopulegone, 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 (R)-p-Menth-4(8)-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number89-82-7
Structure
Thumb
Synonyms
SynonymSource
(+-)-PulegoneChEBI
1-Isopropylidene-4-methyl-2-cyclohexanoneChEBI
1-Methyl-4-isopropylidene-3-cyclohexanoneChEBI
4(8)-p-Menthen-3-oneChEBI
5-Methyl-2-(1-methylethylidene)cyclohexanoneChEBI
5-Methyl-2-isopropylidenecyclohexanoneChEBI
PulegoneChEBI
IsopulegoneMeSH
Pulegone, (R)-isomerMeSH
Pulegone, (S)-isomerMeSH
cis-IsopulegoneMeSH
(+)-4(8)-Para-menthen-3-oneHMDB
(+)-PulegoneHMDB
(1R)-(+)-P-Menth-4(8)-en-3-oneHMDB
(R)-PulegoneHMDB
D-PulegoneHMDB
FEMA 2963HMDB
P-Menth-4(8)-en-3-oneHMDB
(1R)-(+)-p-Menth-4(8)-en-3-onemanual
p-Menth-4(8)-en-3-onebiospider
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
Polarizability18.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name5-methyl-2-(propan-2-ylidene)cyclohexan-1-one
InChI IdentifierInChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3
InChI KeyNZGWDASTMWDZIW-UHFFFAOYSA-N
Isomeric SMILESCC1CCC(=C(C)C)C(=O)C1
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting Point< 25 oC
Boiling PointBp 224°DFC
Experimental Water SolubilityNot Available
Experimental logP3.08GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +23 (c, 5 in EtOH)DFC
Spectroscopic UV DataNot Available
Densityd204 0.94DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(R)-p-Menth-4(8)-en-3-one, non-derivatized, GC-MS Spectrumsplash10-0f89-9200000000-103da19d7e73140f53a7Spectrum
Predicted GC-MS(R)-p-Menth-4(8)-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0btm-9600000000-2638fe5c4d411ceee0dcSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-50f4b6a38ec680e83d0c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114i-6900000000-7e29b900e574c214c8cb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9100000000-cb8b1a6e7185079672ba2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cd90c558f842f253efd32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-011197e33d9b4420c2572015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-6900000000-723bf6d0a35d2e10aafd2015-05-27View Spectrum
NMRNot Available
ChemSpider ID6722
ChEMBL IDNot Available
KEGG Compound IDC09893
Pubchem Compound ID6988
Pubchem Substance IDNot Available
ChEBI ID35596
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35604
CRC / DFC (Dictionary of Food Compounds) IDJPJ96-T:JPJ72-J
EAFUS ID3254
Dr. Duke IDPULEGONE
BIGG IDNot Available
KNApSAcK IDC00000827
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1006501
SuperScent ID442495
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Acetylcholinesterase inhibitor38462 An agent that blocks the breakdown of acetylcholine, increasing its concentration and enhancing cholinergic transmission. Therapeutically, it improves cognitive function and muscle contraction, commonly used in managing Alzheimer's disease, myasthenia gravis, and glaucoma.DUKE
Anti acetylcholinesterase38462 An agent that inhibits acetylcholinesterase, increasing acetylcholine levels. It enhances cholinergic transmission, used therapeutically to treat Alzheimer's disease, myasthenia gravis, and glaucoma, improving cognitive function, muscle strength, and reducing intraocular pressure.DUKE
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti cholinesterase37733 An agent that inhibits acetylcholinesterase, increasing acetylcholine levels, and enhancing cholinergic transmission. Therapeutically, it's used to treat myasthenia gravis, glaucoma, and Alzheimer's disease, improving muscle strength, reducing eye pressure, and enhancing cognitive function.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti pyretic35493 An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.DUKE
Avifuge25944 An anthelmintic agent that expels parasitic worms, particularly tapeworms, from the body. Its therapeutic applications include treating intestinal worm infestations, with key medical uses in managing parasitic infections and promoting gastrointestinal health.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CandidicideAn agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.DUKE
Cerebrotoxic52209 A substance that is toxic to the brain, damaging or destroying brain cells and tissues. It has no therapeutic applications, but understanding its effects can inform the development of neuroprotective agents. Key medical uses include studying neurodegenerative diseases and testing brain-protective therapies.DUKE
EncephalopathicAn agent that causes or is associated with brain disease or disorder, characterized by brain dysfunction or damage, often leading to impaired cognitive, motor, or behavioral functions. Its therapeutic applications are limited, but it is used to study and understand brain disorders, with key medical uses in neurology and psychiatry for diagnostic and research purposes.DUKE
Name48318 flavorDUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
GlutathionalyticAn agent that breaks down glutathione, a key antioxidant. Its biological role involves regulating oxidative stress. Therapeutically, it has applications in cancer treatment, as it can increase the effectiveness of chemotherapy. Key medical uses include enhancing cancer therapy and managing glutathione-related disorders.DUKE
HallucinogenicAn agent that alters perception, thought, and mood, causing hallucinations and subjective changes. It has a biological role in serotonin receptor modulation. Therapeutically, it's explored for treating mental health disorders, such as depression and anxiety. Key medical uses include research in psychiatric treatment and potential applications in palliative care.DUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
Nephrotoxic50909 An agent that damages or harms the kidneys, disrupting their ability to filter waste. It has no therapeutic applications, but is often a side effect of certain medications, such as antibiotics and chemotherapy. Key medical uses involve monitoring and managing kidney damage in patients receiving nephrotoxic treatments.DUKE
Neurotoxic50910 A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Pulifuge25944 An expectorant and mucolytic agent, breaking down mucus to aid in its removal. Therapeutically, it helps relieve respiratory congestion. Key medical uses include treating coughs, colds, and chronic bronchitis, making it easier to breathe by loosening and clearing excess mucus.DUKE
Pulmonotoxic52209 An agent that damages or harms the lungs, often used to describe substances or drugs with toxic effects on pulmonary tissue, limiting its therapeutic applications but aiding in understanding lung disease mechanisms and developing protective strategies.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
lime
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
peppermint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
buchu
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.