Back to Compounds

Showing Compound Menthofuran (FDB014926)

Record Information
Version1.0
Creation date2010-04-08 22:11:33 UTC
Update date2019-11-26 03:10:57 UTC
Primary IDFDB014926
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMenthofuran
Description(r)-menthofuran, also known as 4,5,6,7-tetrahydro-3,6-dimethylbenzofuran or 3,9-epoxy-P-mentha-3,8-diene, is a member of the class of compounds known as aromatic monoterpenoids. Aromatic monoterpenoids are monoterpenoids containing at least one aromatic ring (r)-menthofuran is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (r)-menthofuran is a coffee, earthy, and musty tasting compound found in herbs and spices, mentha (mint), and orange mint, which makes (r)-menthofuran a potential biomarker for the consumption of these food products (r)-menthofuran can be found primarily in saliva.
CAS Number494-90-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3,9-Epoxy-p-mentha-3,8-dieneChEBI
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuranChEBI
4,5,6,7-Tetrahydro-3,6-dimethylcoumaroneChEBI
(+)-3,9-Epoxy-P-mentha-3,8-dieneHMDB
(+)-MenthofuranHMDB
(6R)-3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuranHMDB
(R)-(+)-MenthofuranHMDB
(R)-4,5,6,7-tetrahydro-3,6-DimethylbenzofuranHMDB
3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuranHMDB
3,9-Epoxy-(+)-P-mentha-3,8-dieneHMDB
4,5,6,7-tetrahydro-3,6-Dimethyl-(R)-benzofuranHMDB
4,5,6,7-tetrahydro-3,6-Dimethyl-benzofuranHMDB
MenthofuranHMDB
Menthofuran, (R)-isomerMeSH, HMDB
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran, 9CIdb_source
FEMA 3235db_source
Predicted Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP3.98ALOGPS
logP3.13ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.67 m³·mol⁻¹ChemAxon
Polarizability18.04 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14O
IUPAC name3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
InChI IdentifierInChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3
InChI KeyYGWKXXYGDYYFJU-UHFFFAOYSA-N
Isomeric SMILESCC1CCC2=C(C1)OC=C2C
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
Classification
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Menthofuran monoterpenoid
  • Bicyclic monoterpenoid
  • Aromatic monoterpenoid
  • Benzofuran
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 PointNot Available
Experimental Water SolubilityNot Available
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
GC-MSMenthofuran, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-ad7d24da86fd955477a7Spectrum
GC-MSMenthofuran, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-ad7d24da86fd955477a7Spectrum
Predicted GC-MSMenthofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pi9-1900000000-c7d34068fe20520e5e88Spectrum
Predicted GC-MSMenthofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMenthofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-295d2c3abad7c8ff4f632015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3900000000-5e060ac38ef1d423776f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-30417e50d66ad0fe9af62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-295d2c3abad7c8ff4f632015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3900000000-5e060ac38ef1d423776f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-30417e50d66ad0fe9af62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-881d258a03659e0f39302015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-01ff41b309657177e5e52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-3900000000-177076fd487978d174f12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-881d258a03659e0f39302015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-01ff41b309657177e5e52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-3900000000-177076fd487978d174f12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-a36c450a85a702daacb32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfs-9800000000-283087fbd503dd3860782021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9100000000-bb914f0c52d327a80b1b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-8ae160b4249f862d1a002021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ne-7900000000-12e4673f2e9f1e3c406d2021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJXK20-B:JXK20-B
EAFUS ID3628
Dr. Duke IDMENTHOFURAN|MEHTHOFURAN|(+)-MENTHOFURAN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
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
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
pulmonotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).