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Showing Compound Dihydrocarveol (FDB009285)

Record Information
Version1.0
Creation date2010-04-08 22:08:30 UTC
Update date2019-11-26 03:03:26 UTC
Primary IDFDB009285
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydrocarveol
DescriptionDihydrocarveol, also known as 2-methyl-5-(1-methylethenyl)cyclohexanol or 6-methyl-3-isopropenylcyclohexanol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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. Dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Dihydrocarveol is a herbal, menthol, and minty tasting compound and can be found in a number of food items such as dill, pepper (spice), pot marjoram, and wild celery, which makes dihydrocarveol a potential biomarker for the consumption of these food products.
CAS Number619-01-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,6-DihydrocarveolChEBI
2-Methyl-5-(1-methylethenyl)cyclohexanolChEBI
2-Methyl-5-isopropenylcyclohexanolChEBI
5-Isopropenyl-2-methylcyclohexanolChEBI
6-Methyl-3-isopropenylcyclohexanolChEBI
8-p-Menthen-2-olChEBI
Menth-8-en-2-olChEBI
2-Methyl-5-(1-methylvinyl)cyclohexan-1-olMeSH
a DihydrocarveolChEBI
2-methyl-5-(1-methylvinyl)cyclohexan-1-olbiospider
2-methyl-5-(prop-1-en-2-yl)cyclohexanolbiospider
2-methyl-5-isopropenylcyclohexanolbiospider
6-Methyl-3-isopropylcyclohexanolbiospider
Carveol, dihydro-biospider
p-Menth-8-en-2-olbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.32 g/LALOGPS
logP2.7ALOGPS
logP2.32ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)18.99ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.22 m³·mol⁻¹ChemAxon
Polarizability19.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H18O
IUPAC name2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol
InChI IdentifierInChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3
InChI KeyKRCZYMFUWVJCLI-UHFFFAOYSA-N
Isomeric SMILESCC1CCC(CC1O)C(C)=C
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
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointBoiling Pt : 224.5 oC
Experimental Water SolubilityNot Available
Experimental logP3.21GRIFFIN,S ET AL. (1999)
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)splash10-05mo-9200000000-da0a49ae0820607efcab2015-03-01View Spectrum
Predicted GC-MS1-Dihydrocarveol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9300000000-c4d08d4f42ce5380cea3Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-426222b005de9ed263f72016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-7900000000-92669f5cd45165c58a8a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9100000000-a02a955b5b196ac361c32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-a7c7b44c65ac0d9983a92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-08b2ced2412775e44ff32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-8900000000-ef61141645310f0e0a802016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0532-9400000000-959ea8fcd37ca9a711e52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00l5-9100000000-66dc6c3c3f3184c185af2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-09a8ec5e3424e50d627f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-0900000000-6cb010728dc534ba406c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-318736dc4101f232fc4c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2900000000-9492df1cf757255271902021-10-21View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC18017
Pubchem Compound ID12072
Pubchem Substance IDNot Available
ChEBI ID50215
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID910
Dr. Duke IDDIHYDROCARVEOL|P-MENTH-8-EN-2-OL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID619-01-2
GoodScent IDrw1013231
SuperScent ID12072
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
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
irritantDUKE
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
spice
  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. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
menthol
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spearmint
  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.
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).