2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00156 |
| Mol. Weight | 150.221 g/mol |
| LogP | 3.13 |
| Water solubility | 0.00049 mol/L at 20 °C |
| Hydrogen Bond Donor | 0 |
| Hydrogen Bond Acceptor | 1 |
| Rotatable Bonds | 0 |
| XLogP3-AA | 3.0 |
| Identifiers | |
|---|---|
| Formula | C10H14O |
| PubChem CID | 329983 |
| FEMA | 3235 |
| Flavor Profile | Savory |
| Smiles | Cc1coc2c1CCC(C)C2 |
| InChl Key | YGWKXXYGDYYFJU-UHFFFAOYSA-N |
| InChl | InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3 |
| CAS Registry Number | 494-90-6, 17957-94-7 |
| IUPAC Systematic Name | 3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran |
Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets
Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)
| English Name | Pinyin Name (Chinese Name) | Latin Name | Properties in TCM | merdians | View Graph |
|---|---|---|---|---|---|
| NONE | NONE | NONE | NONE | NONE | View Graph |
Menthofuran is an organic compound found in a variety of essential oils including that of Pennyroyal. It is highly toxic and believed to be the primary
toxin in Pennyroyal responsible for its potentially fatal effects.After ingestion of menthofuran, it is metabolically activated to chemically reactive
intermediates that are hepatotoxic.
Methofuran is produced biosynthetically from pulegone by the enzyme menthofuran synthase.
(1)-Menthofuran is an undesirable monoterpenoid component of peppermint (Mentha 3 piperita) essential oil that is derived from the a,b-unsaturated ketone
(1)-pulegone.
Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.
1. https://en.wikipedia.org/wiki/Menthofuran
2. Thomassen D , Knebel N , Slattery J T , et al. Reactive intermediates in the oxidation of menthofuran by cytochromes P-450[J]. Chemical Research in Toxicology, 1992, 5(1):123-130.
3. Thomassen D , Knebel N , Slattery J T , et al. Reactive intermediates in the oxidation of menthofuran by cytochromes P-450[J]. Chemical Research in Toxicology, 1992, 5(1):123-130.
4. Rahimi Y, Taleei A, Ranjbar M. Changes in the expression of key genes involved in the biosynthesis of menthol and menthofuran in Mentha piperita L. under drought stress[J]. Acta Physiologiae Plantarum, 2017, 39(9): 203.
5. Bertea, C. M., Schalk, M., Karp, F., Maffei, M., Croteau, R. Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene[J]. Archives of biochemistry and biophysics, 2001, 390(2): 279-286.
6. Khojasteh-Bakht, S. C., Chen, W., Koenigs, L. L., Peter, R. M., Nelson, S. D. Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide[J]. Drug metabolism and disposition, 1999, 27(5): 574-580.
7. Picard M, de Revel G, Marchand S. First identification of three p-menthane lactones and their potential precursor, menthofuran, in red wines[J]. Food chemistry, 2017, 217: 294-302.
8. Mahmoud S S, Croteau R B. Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase[J]. Proceedings of the National Academy of Sciences, 2003, 100(24): 14481-14486.
9. Racine P, Auffray B. Quenching of singlet molecular oxygen by Commiphora myrrha extracts and menthofuran[J]. Fitoterapia, 2005, 76(3-4): 316-323.