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(+)-Menthofuran

analytical standard

Synonym: (R)-3,6-Dimethyl-4,5,6,7-tetrahydrobenzofuran

  • CAS Number 17957-94-7

  • Empirical Formula (Hill Notation) C10H14O

  • Molecular Weight 150.22

  •  Beilstein Registry Number 2729

  •  MDL number MFCD00142332

  •  PubChem Substance ID 24882793

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Properties

Related Categories Additional Standards, Alphabetical, Analytical Standards, Analytical/Chromatography, Chemical Class,
grade   analytical standard
assay   ≥99.0% (sum of enantiomers, GC)
form   neat
optical activity   [α]20/D +100±2°, neat
shelf life   limited shelf life, expiry date on the label
refractive index   n20/D 1.484
bp   204-206 °C(lit.)
density   0.97 g/mL at 20 °C(lit.)
storage temp.   2-8°C

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Safety & Documentation

Safety Information

Personal Protective Equipment 
WGK Germany 
3

Protocols & Articles

Peer-Reviewed Papers

References

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Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature. Anderson IB, Mullen WH, Meeker JE, et al. Ann. Intern. Med. 124(8), 726-34, (1996)

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Multiple organ failure after ingestion of pennyroyal oil from herbal tea in two infants. Bakerink JA, Gospe SM, Dimand RJ, et al. Pediatrics 98(5), 944-7, (1996)

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Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential. Maffei M, Camusso W, and Sacco S Phytochemistry 58(5), 703-7, (2001)

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Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. Mahmoud SS and Croteau RB Proc. Natl. Acad. Sci. U. S. A. 100(24), 14481-6, (2003)

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A systems biology approach identifies the biochemical mechanisms regulating monoterpenoid essential oil composition in peppermint. Rios-Estepa R, Turner GW, Lee JM, et al. Proc. Natl. Acad. Sci. U. S. A. 105(8), 2818-23, (2008)

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Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene. Bertea CM, Schalk M, Karp F, et al. Arch. Biochem. Biophys. 390(2), 279-86, (2001)

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In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. Taavitsainen P, Juvonen R, and Pelkonen O Drug Metab. Dispos. 29(3), 217-22, (2001)

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Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide. Khojasteh-Bakht SC, Chen W, Koenigs LL, et al. Drug Metab. Dispos. 27(5), 574-80, (1999)

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(R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Khojasteh-Bakht SC, Koenigs LL, Peter RM, et al. Drug Metab. Dispos. 26(7), 701-4, (1998)

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In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone. Engel W J. Agric. Food Chem. 51(22), 6589-97, (2003)

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Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies. Fuchs S, Zinn S, Beck T, et al. J. Agric. Food Chem. 47(10), 4100-5, (1999)

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Nitration versus nitrosation chemistry of menthofuran: remarkable fragmentation and dimerization pathways and expeditious entry into dehydromenthofurolactone. De Lucia M, Mainieri F, Verotta L, et al. J. Org. Chem. 72(26), 10123-9, (2007)

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Metabolism and toxicity of menthofuran in rat liver slices and in rats. Khojasteh SC, Oishi S, and Nelson SD Chem. Res. Toxicol. 23(11), 1824-32, (2010)

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Hepatoprotective effect of C-phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats. Vadiraja BB, Gaikwad NW, and Madyastha KM Biochem. Biophys. Res. Commun. 249(2), 428-31, (1998)

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Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. Chen LJ, Lebetkin EH, and Burka LT Drug Metab. Dispos. 31(10), 1208-13, (2003)

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Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol. Kramlinger VM, von Weymarn LB, and Murphy SE Chem. Biol. Interact. 197(2-3), 87-92, (2012)

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Characterization of rat liver proteins adducted by reactive metabolites of menthofuran. Khojasteh SC, Hartley DP, Ford KA, et al. Chem. Res. Toxicol. 25(11), 2301-9, (2012)

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Volatile organic compounds from rhizobacteria increase biosynthesis of essential oils and growth parameters in peppermint (Mentha piperita). Santoro MV, Zygadlo J, Giordano W, et al. Plant Physiol. Biochem. 49(10), 1177-82, (2011)

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Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)+-pulegone and menthone. Rossi YE, Canavoso L, and Palacios SM Fitoterapia 83(2), 336-42, (2012)

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Chemical composition and toxicity of the essential oils from Cunila species (Lamiaceae) on the cattle tick Rhipicephalus (Boophilus) microplus. Apel MA, Ribeiro VL, Bordignon SA, et al. Parasitol. Res. 105(3), 863-8, (2009)

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Vapor toxicity of three prototype volatile insecticidal compounds to house fly (Diptera: Muscidae). Chaskopoulou A, Pereira RM, Scharf ME, et al. J. Med. Entomol. 46(6), 1400-6, (2009)

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Quenching of singlet molecular oxygen by Commiphora myrrha extracts and menthofuran. Racine P and Auffray B Fitoterapia 76(3-4), 316-23, (2005)

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Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes. Stephens ES, Walsh AA, and Scott EE Drug Metab. Dispos. 40(9), 1797-802, (2012)

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14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. Ferguson LJ, Lebetkin EH, Lih FB, et al. J. Toxicol. Environ. Health A 70(17), 1416-23, (2007)

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In vitro production of M. × piperita not containing pulegone and menthofuran. Bertoli A, Leonardi M, Krzyzanowska J, et al. Acta Biochim. Pol. 59(3), 417-23, (2012)

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Beil. 17,V,1,518

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