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Showing Compound (±)-Menthone (FDB009778)

Record Information
Version1.0
Creation date2010-04-08 22:08:47 UTC
Update date2020-09-17 15:41:34 UTC
Primary IDFDB009778
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(±)-Menthone
Description(-)-Menthone, also known as (1R,4S)-menthone or L-menthone, 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. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule (-)-Menthone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number89-80-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(1R,4S)-MenthoneChEBI
(1R,4S)-p-Menthan-3-oneChEBI
(2S,5R)-2-Isopropyl-5-methylcyclohexanoneChEBI
(2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
L-MenthoneChEBI
p-Menthan-3-oneChEBI
(2S,5R)-MenthoneChEBI, HMDB
(-)-(1R,4S)-MenthoneHMDB
(-)-(2S,5R)-MenthoneHMDB
(-)-5-Methyl-2-(1-methylethyl)cyclohexanoneHMDB
(1R,4S)-(-)-P-Menthan-3-oneHMDB
(2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanoneHMDB
(2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanoneHMDB
MenthoneMeSH, HMDB
(-)-MenthoneHMDB
(1R,4S)-p-Menth-3-oneHMDB
(2S,5R)-(-)-MenthoneHMDB
(2S,5R)-2-Isopropyl-5-methylcyclohexan-1-oneHMDB
trans-(-)-p-Menthan-3-oneHMDB
(±)-Menthonedb_source
(DL)-Menthonebiospider
Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-relmanual
DL-Menthonebiospider
DL-p-Menthan-3-onemanual
Neomenthonemanual
p-Menthonemanual
trans-Menthonemanual
trans-p-Menthonemanual
Predicted Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP2.65ALOGPS
logP3.05ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.52 m³·mol⁻¹ChemAxon
Polarizability19.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H18O
IUPAC name(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
InChI IdentifierInChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
InChI KeyNFLGAXVYCFJBMK-BDAKNGLRSA-N
Isomeric SMILESCC(C)[C@@H]1CC[C@@H](C)CC1=O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting PointNot Available
Boiling PointBp10 82-83°DFC
Experimental Water Solubility0.688 mg/mL at 25 oCSUZUKI,T (1991)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4508DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-07bf-9300000000-03e6f833d8a9130c96482018-05-25View Spectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-72f9ad70ae1001e21eafSpectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-004j-2900000000-9f3548951fa6e98aa410Spectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-0170-4900000000-82f88e79cd91a887a98fSpectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-72f9ad70ae1001e21eafSpectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-004j-2900000000-9f3548951fa6e98aa410Spectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-0170-4900000000-82f88e79cd91a887a98fSpectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-07bo-9300000000-3f63fc6dbb3efa362d59Spectrum
GC-MS(±)-Menthone, non-derivatized, GC-MS Spectrumsplash10-07bo-9300000000-3f63fc6dbb3efa362d59Spectrum
Predicted GC-MS(±)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052g-9300000000-f26613921d7b53d7fd71Spectrum
Predicted GC-MS(±)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(±)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-6701bba716a6affa87662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0002-9000000000-b0b5dd86e6d1a6de21712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-d18a7464317ee5b6d7cc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-244db80c070c100b12b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-2900000000-b84cff8176943c1c01cf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-4900000000-3164f9befc45e23067a92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-7900000000-aa7dd74302c4ed215ce52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001a-9600000000-f847c953bdb697e434a92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0012-9400000000-23a0fccfb9523e3d21ec2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9200000000-54afdeb4f58eddee24472020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9100000000-b0e554c807437d6fbe0a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000t-9000000000-575fad481c43a10742f22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00l2-9000000000-2869717ccfb0fbe67a4b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-015a-9000000000-b2a684427d58a3d1e8d82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0690-9000000000-68fcde55699d18a522f72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0ar3-9100000000-25c9da89880a6d44b24d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-96ef6ca330f5621280562020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-70388bb385562f798a7a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-1900000000-05762909cf77edb476972020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-fa99f8c083212e4f2fc32016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9800000000-7bf975ea31bcef83aa612016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9000000000-3f8923896797c44866932016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d55afdef2faae68197a62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-91ec697d11dad181a3422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-9600000000-7933610ac6051fc8ef812016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID36503
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJHQ37-H:LFY37-D
EAFUS ID2145
Dr. Duke IDMENTHONE|NEOMENTHONE
BIGG IDNot Available
KNApSAcK IDC00035341
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID89-80-5
GoodScent IDrw1398981
SuperScent IDNot Available
Wikipedia IDMenthone
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
Acaricide22153 An agent that kills mites and ticks, used to control infestations and prevent diseases like scabies and tick-borne illnesses. Therapeutically, acaricides are applied topically or systemically to treat parasitic infections, reducing discomfort and preventing disease transmission. Key medical uses include treating acariasis, demodectic mange, and tick paralysis.DUKE
AllelopathicBiochemicals that inhibit growth, survival, or reproduction in other organisms, with potential therapeutic applications in weed control, antimicrobial, and anticancer treatments, and key medical uses in developing novel pesticides, antibiotics, and chemotherapeutics.DUKE
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.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-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
Anti-bacillary33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating bacterial infections. Therapeutically, it is used to combat bacterial diseases, with key medical applications including the treatment of tuberculosis, pneumonia, and other infectious diseases.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-escherichicAn antibody binding to Escherichia-specific targets, playing a role in immune defense. Therapeutically, it is used to combat E. coli infections, with key medical applications in treating urinary tract infections, sepsis, and gastrointestinal diseases.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 listeria33282 An agent that targets and eliminates Listeria bacteria, reducing the risk of listeriosis. Its biological role is to inhibit bacterial growth, and its therapeutic applications include treating foodborne illnesses and preventing infections in immunocompromised individuals, particularly pregnant women and the elderly.DUKE
Anti-salmonella33282 An agent that targets and eliminates Salmonella bacteria, reducing the risk of food poisoning and gastrointestinal infections. Therapeutically, it is used to treat salmonellosis, a disease caused by Salmonella infection, and to prevent outbreaks in high-risk individuals, such as those with weakened immune systems.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.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
CulicideAn agent that destroys mosquitoes, playing a crucial role in preventing the spread of mosquito-borne diseases. Its therapeutic applications include vector control, and key medical uses include preventing malaria, dengue fever, and Zika virus transmission.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
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
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.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
Psychoactive35471 A substance that affects brain function, altering mood, perception, or consciousness. It plays a biological role in modifying neurotransmitter activity. Therapeutically, psychoactive substances have applications in managing mental health disorders, such as depression and anxiety. Key medical uses include treating psychiatric conditions, including attention deficit hyperactivity disorder (ADHD), and certain sleep disorders.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
TrichomonicideAn agent that kills Trichomonas organisms, used to treat Trichomonas vaginalis infections, commonly causing vaginitis, and other related genital tract infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fresh
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
green
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
minty
  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).