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Showing Compound Carvone (FDB014614)

Record Information
Version1.0
Creation date2010-04-08 22:11:22 UTC
Update date2019-11-26 03:10:28 UTC
Primary IDFDB014614
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCarvone
DescriptionCarvone, also known as carvol or limonen-6-one, 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. Based on a literature review a significant number of articles have been published on Carvone.
CAS Number22327-39-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-CarvoneChEBI
2-Methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-oneChEBI
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enoneChEBI
2-Methyl-5-isopropenyl-2-cyclohexenoneChEBI
5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
CarvolChEBI
CarvonChEBI
KarvonChEBI
p-Mentha-6,8-dien-2-oneChEBI
(RS)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneHMDB
Carvone, (R)-isomerHMDB
Limonen-6-oneHMDB
2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-oneHMDB
5-Isopropyl-2-methyl-2-cyclohexen-1-oneHMDB
Carvone, (S)-isomerHMDB
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-biospider
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one, 9CIdb_source
2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-onebiospider
5-Isopropenyl-2-methyl-2-cyclohexen-1-onedb_source
5-isopropenyl-2-methylcyclohex-2-en-1-onebiospider
6,8-p-Menthadien-2-onbiospider
6,8-p-Menthadien-2-onebiospider
6,8(9)-p-Menthadien-2-onebiospider
Carvol (obsol.)db_source
Carvonebiospider
Carvone, BSIdb_source
FEMA 2249db_source
p-mentha-1(6),8-dien-2-onebiospider
p-Mentha-6, 8-dien-2-onebiospider
Talentdb_source
Predicted Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP2.77ALOGPS
logP2.55ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.17 m³·mol⁻¹ChemAxon
Polarizability17.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14O
IUPAC name2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
InChI IdentifierInChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3
InChI KeyULDHMXUKGWMISQ-UHFFFAOYSA-N
Isomeric SMILESCC(=C)C1CC=C(C)C(=O)C1
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
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
  • Cyclohexenone
  • 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 79.96%; H 9.39%; O 10.65%DFC
Melting PointNot Available
Boiling PointBoiling Pt : 231 oC
Experimental Water Solubility1.3 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0kai-9100000000-ea28fdf9d5478ea50fe22015-03-01View Spectrum
GC-MSalpha-Carvone, non-derivatized, GC-MS Spectrumsplash10-0f8c-9100000000-64d2436851c170c3898aSpectrum
GC-MSalpha-Carvone, non-derivatized, GC-MS Spectrumsplash10-0a4l-3900000000-1935fc84143fcf43b855Spectrum
GC-MSalpha-Carvone, non-derivatized, GC-MS Spectrumsplash10-0a4l-4900000000-856f6fa492156b47d6abSpectrum
GC-MSalpha-Carvone, non-derivatized, GC-MS Spectrumsplash10-0f8c-9100000000-64d2436851c170c3898aSpectrum
GC-MSalpha-Carvone, non-derivatized, GC-MS Spectrumsplash10-0a4l-3900000000-1935fc84143fcf43b855Spectrum
GC-MSalpha-Carvone, non-derivatized, GC-MS Spectrumsplash10-0a4l-4900000000-856f6fa492156b47d6abSpectrum
Predicted GC-MSalpha-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f8l-9200000000-0d07518eb09c4d6d7512Spectrum
Predicted GC-MSalpha-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-62861ac4cbf0b95e50692016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-b282dcb5d4a98c3f852f2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-0fd631d26260645c64ae2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-97d37f99bcaf0ed7d1082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-1817a8dceee7a31df4e02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-6900000000-581a45ee1ec95e2011382016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-c0270d719fd67ba328d92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-9700000000-dfa5cb40b478707933162021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-f279f95a33eb225c1b142021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07eg-9400000000-34f0a30acb50659192b62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-7b658cbdc17dd03f44ed2021-09-24View Spectrum
NMR
TypeDescriptionView
ChemSpider ID21106424
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID7439
Pubchem Substance IDNot Available
ChEBI ID38265
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35824
CRC / DFC (Dictionary of Food Compounds) IDJSX52-Q:JSX52-Q
EAFUS ID550
Dr. Duke IDCARVONE
BIGG IDNot Available
KNApSAcK IDC00035062
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID99-49-0
GoodScent IDrw1399011
SuperScent IDNot Available
Wikipedia IDCarvone
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
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.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-proliferativeAn agent that inhibits cell growth and division, particularly in cancer cells, preventing tumor expansion. It plays a biological role in regulating cell cycles and has therapeutic applications in cancer treatment, such as chemotherapy and targeted therapy, with key medical uses in managing various types of cancer and other proliferative diseases.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
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
CandidistatAn antifungal agent that inhibits the growth of Candida species, such as Candida albicans, used to treat fungal infections, particularly candidiasis.DUKE
CarminativeAn agent that prevents or relieves gas in the gastrointestinal tract, facilitating its expulsion and combating flatulence, commonly used to soothe digestive issues and alleviate symptoms of bloating and discomfort.DUKE
Central nervous system stimulant35470 An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.DUKE
Name48318 flavorDUKE
FungistatAn agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients.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
Motor depressantAn agent that reduces the normal functioning level of motor neurons, mainly in voluntary muscles, used to treat conditions such as muscle spasms, seizures, and anxiety disorders, promoting relaxation and relieving symptoms.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
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
VermicideAn agent that kills worms, playing a biological role in parasite control. Therapeutically, it is used to treat worm infestations, with key medical applications including the treatment of intestinal worms, hookworms, and other parasitic infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mint
  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
basil
  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
fennel
  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.
licorice
  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).