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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:09:27 UTC
Update Date2021-10-13 06:53:42 UTC
HMDB IDHMDB0036089
Secondary Accession Numbers
  • HMDB36089
Metabolite Identification
Common Name(R)-Menthofuran
Description(R)-Menthofuran belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on (R)-Menthofuran.
Structure
Data?1563862819
Synonyms
ValueSource
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
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Traditional Name3,9-epoxy-p-mentha-3,8-diene
CAS Registry Number17957-94-7
SMILES
CC1CCC2=C(C1)OC=C2C
InChI Identifier
InChI=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
Chemical Taxonomy
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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point86.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point80.00 to 82.00 °C. @ 13.00 mm HgThe Good Scents Company Information System
Water Solubility16.36 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.562 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP10(3.98) g/LALOGPS
logP10(3.13) g/LChemAxon
logS10(-3.3) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.92931661259
DarkChem[M-H]-128.73231661259

Predicted Kovats Retention Indices

Not Available
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014927
KNApSAcK IDC00003049
Chemspider ID292309
KEGG Compound IDC09868
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMenthofuran
METLIN IDNot Available
PubChem Compound329983
PDB IDNot Available
ChEBI ID50542
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1019781
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Miyazawa M, Haigou R: Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes. Xenobiotica. 2011 Dec;41(12):1056-62. doi: 10.3109/00498254.2011.596230. [PubMed:22054099 ]
  2. Thomassen D, Slattery JT, Nelson SD: Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. J Pharmacol Exp Ther. 1988 Mar;244(3):825-9. [PubMed:3252034 ]
  3. Yu S, Chen Y, Zhang L, Shan M, Tang Y, Ding A: Quantitative comparative analysis of the bio-active and toxic constituents of leaves and spikes of Schizonepeta tenuifolia at different harvesting times. Int J Mol Sci. 2011;12(10):6635-44. doi: 10.3390/ijms12106635. Epub 2011 Oct 10. [PubMed:22072908 ]
  4. Chen LJ, Lebetkin EH, Burka LT: Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. Drug Metab Dispos. 2003 Oct;31(10):1208-13. [PubMed:12975329 ]
  5. Stephens ES, Walsh AA, Scott EE: Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes. Drug Metab Dispos. 2012 Sep;40(9):1797-802. doi: 10.1124/dmd.112.045161. Epub 2012 Jun 13. [PubMed:22696418 ]
  6. Miyazawa M, Marumoto S, Takahashi T, Nakahashi H, Haigou R, Nakanishi K: Metabolism of (+)- and (-)-menthols by CYP2A6 in human liver microsomes. J Oleo Sci. 2011;60(3):127-32. [PubMed:21343660 ]
  7. Khojasteh-Bakht SC, Nelson SD, Atkins WM: Glutathione S-transferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones. Arch Biochem Biophys. 1999 Oct 1;370(1):59-65. [PubMed:10496977 ]
  8. Haigou R, Miyazawa M: Metabolism of (+)-terpinen-4-ol by cytochrome P450 enzymes in human liver microsomes. J Oleo Sci. 2012;61(1):35-43. [PubMed:22188805 ]
  9. Atsbaha Zebelo S, Bertea CM, Bossi S, Occhipinti A, Gnavi G, Maffei ME: Chrysolina herbacea modulates terpenoid biosynthesis of Mentha aquatica L. PLoS One. 2011 Mar 9;6(3):e17195. doi: 10.1371/journal.pone.0017195. [PubMed:21408066 ]
  10. Lange BM, Mahmoud SS, Wildung MR, Turner GW, Davis EM, Lange I, Baker RC, Boydston RA, Croteau RB: Improving peppermint essential oil yield and composition by metabolic engineering. Proc Natl Acad Sci U S A. 2011 Oct 11;108(41):16944-9. doi: 10.1073/pnas.1111558108. Epub 2011 Sep 30. [PubMed:21963983 ]
  11. Khojasteh-Bakht SC, Koenigs LL, Peter RM, Trager WF, Nelson SD: (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Drug Metab Dispos. 1998 Jul;26(7):701-4. [PubMed:9660853 ]
  12. Khojasteh-Bakht SC, Chen W, Koenigs LL, Peter RM, Nelson SD: Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide. Drug Metab Dispos. 1999 May;27(5):574-80. [PubMed:10220485 ]
  13. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  14. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  15. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  16. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  17. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  18. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.