We have found 46587 results matching your criteria.
Please wait while we search...

General Material Information

Preferred name menthofuran
Trivial Name Menthofuran
Short Description 4,5,6,7-tetrahydro-3,6-dimethylbenzofuran
Formula C10 H14 O
CAS Number 494-90-6
Deleted CAS Number 59553-66-1
FEMA Number 3235
ECHA Number 207-795-5
FDA UNII LK024V9U3C
Beilstein Number 6053324
MDL MFCD00041851
COE Number 2265
xLogP3-AA 2.80 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 758 menthofuran
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 494-90-6 ; 4,5,6,7-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN
Synonyms
  • benzofuran, 4,5,6,7-tetrahydro-3,5-dimethyl-
  • benzofuran, 4,5,6,7-tetrahydro-3,6-dimethyl-
  • 3,5-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
  • 3,5-dimethyl-4,5,6,7-tetrahydrobenzofuran
  • 3,9-epoxy-p-mentha-3,8-diene
  • 3,9-epoxy-para-mentha-3,8-diene
  • koolada-menthofuran synthetic
  • p- mentha-3,8-diene, 3,9-epoxy-
  • menthafuran
  • mentho furan
  • menthofuran natural
  • 4,5,6,7-tetrahydro-3,6-dimethyl benzofuran
  • 4,5,6,7-tetrahydro-3,6-dimethyl coumarone
  • 4,5,6,7-tetrahydro-3,6-dimethylbenzofuran
  • 4,5,6,7-tetrahydro-3,6-dimethylcoumarone
  • tetrahydrodimethyl benzofuran
  • tetrahydrodimethylbenzofuran
  • 3,5-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
  • p-Mentha-3,8-diene, 3,9-epoxy-
  • 4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran
  • Menthofurane
  • NSC 315249
  • 3,6-Dimethyl-4,5,6,7-tetrahydrobenzofuran
  • 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran

US / EU / FDA / JECFA / FEMA / Scholar / Patents

Google Scholar Start search
Google Books Start search
Google Patents Start search
Perfumer & Flavorists Start search
EU Patents Start search
PubMeb Start search
NCBI Start search

Literature & References

Leffingwell:Chirality or Article
3,5-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:494-90-6
Pubchem (cid):62345
Pubchem (sid):135019882
Pherobase:View
Publications by PubMed
[About flavouring substances and flavouring preparations regulation in the field of manufacturing of flavourings and foodstuffs].
Chemical Composition, Antifungal and Antibiofilm Activities of the Essential Oil of Mentha piperita L.
Anti-yeast activity of mentha oil and vapours through in vitro and in vivo (real fruit juices) assays.
Chemical composition of the essential oil from Corsican Mentha aquatica--combined analysis by GC(RI), GC-MS and 13C NMR spectroscopy.
Seasonal variability of the main components in essential oil of Mentha × piperita L.
Genetic variability, character association, and path analysis for economic traits in menthofuran rich half-sib seed progeny of Mentha piperita L.
Nematicidal activity of mint aqueous extracts against the root-knot nematode Meloidogyne incognita.
Synthetic models related to methoxalen and menthofuran-cytochrome P450 (CYP) 2A6 interactions. benzofuran and coumarin derivatives as potent and selective inhibitors of CYP2A6.
Anti-yeast activity of mentha oil and vapours through in vitro and in vivo (real fruit juices) assays.
Characterization of rat liver proteins adducted by reactive metabolites of menthofuran.
In vitro production of M. × piperita not containing pulegone and menthofuran.
Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes.
Mode of action of pulegone on the urinary bladder of F344 rats.
Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol.
Chemotaxonomy of Serbian Teucrium species inferred from essential oil chemical composition: the case of Teucrium scordium L. ssp. scordioides.
Chemical composition of the essential oil from Corsican Mentha aquatica--combined analysis by GC(RI), GC-MS and 13C NMR spectroscopy.
Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)+-pulegone and menthone.
Quantitative comparative analysis of the bio-active and toxic constituents of leaves and spikes of Schizonepeta tenuifolia at different harvesting times.
Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes.
Improving peppermint essential oil yield and composition by metabolic engineering.
A solid-phase microextraction GC/MS/MS method for rapid quantitative analysis of food and beverages for the presence of legally restricted biologically active flavorings.
Volatile organic compounds from rhizobacteria increase biosynthesis of essential oils and growth parameters in peppermint (Mentha piperita).
Chrysolina herbacea modulates terpenoid biosynthesis of Mentha aquatica L.
Metabolism of (+)- and (-)-menthols by CYP2A6 in human liver microsomes.
D-Isomer of gly-tyr-pro-cys-pro-his-pro peptide: a novel and sensitive in vitro trapping agent to detect reactive metabolites by electrospray mass spectrometry.
Metabolism and toxicity of menthofuran in rat liver slices and in rats.
UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha x piperita L.).
Constituents of Calamintha ashei: effects on Florida sandhill species.
Mathematical modeling-guided evaluation of biochemical, developmental, environmental, and genotypic determinants of essential oil composition and yield in peppermint leaves.
Vapor toxicity of three prototype volatile insecticidal compounds to house fly (Diptera: Muscidae).
Synthesis and biological evaluation of new ozonides with improved plant growth regulatory activity.
Structure, function, regulation and polymorphism of human cytochrome P450 2A6.
Chemical composition and toxicity of the essential oils from Cunila species (Lamiaceae) on the cattle tick Rhipicephalus (Boophilus) microplus.
Toxicities of 31 volatile low molecular weight compounds against Aedes aegypti and Culex quinquefasciatus.
A systems biology approach identifies the biochemical mechanisms regulating monoterpenoid essential oil composition in peppermint.
Nitration versus nitrosation chemistry of menthofuran: remarkable fragmentation and dimerization pathways and expeditious entry into dehydromenthofurolactone.
Roles of human CYP2A6 and rat CYP2B1 in the oxidation of (+)-fenchol by liver microsomes.
14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats.
Metabolism of (-)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes.
Volatile terpenoids of endophyte-free and infected peppermint (Mentha piperita L.): chemical partitioning of a symbiosis.
In vitro metabolism of (-)-camphor using human liver microsomes and CYP2A6.
Metabolism of (+)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes.
Evaluation of volatile low molecular weight insecticides using Drosophila melanogaster as a model.
Quenching of singlet molecular oxygen by Commiphora myrrha extracts and menthofuran.
Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase.
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.
Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites.
Final report on the safety assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint) Leaf Water.
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.
Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase.
Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene.
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.
Metabolism of 3-methylindole by porcine liver microsomes: responsible cytochrome P450 enzymes.
Monoterpene composition of essential oil from peppermint (Mentha x piperita L.) with regard to leaf position using solid-phase microextraction and gas chromatography/mass spectrometry analysis.
Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies.
Glutathione S-transferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones.
Transformation of the limonene synthase gene into peppermint (Mentha piperita L.) and preliminary studies on the essential oil profiles of single transgenic plants.
Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide.
Metabolic fate of S-(-)-pulegone in rat.
Hepatoprotective effect of C-phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats.
(R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6.
Multiple organ failure after ingestion of pennyroyal oil from herbal tea in two infants.
Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature.
Mechanisms of the formation and disposition of reactive metabolites that can cause acute liver injury.
Allelopathic potential of menthofuran monoterpenes fromCalamintha ashei.
Effects of menthofuran, a monoterpene furan on rat liver microsomal enzymes, in vivo.
Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone.
Metabolic fate of menthofuran in rats. Novel oxidative pathways.
Reactive intermediates in the oxidation of menthofuran by cytochromes P-450.
Partial characterization of biliary metabolites of pulegone by tandem mass spectrometry. Detection of glucuronide, glutathione, and glutathionyl glucuronide conjugates.
Evidence for the formation of a known toxin, p-cresol, from menthofuran.
Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity.
Menthofuran-dependent and independent aspects of pulegone hepatotoxicity: roles of glutathione.
Metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat.
Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course.
The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran.
Chemical and Morphometrical Comparison Between two Peppermint Notomorphs.
Genetic basis for high limonene-cineole content of exceptional Mentha citrata hybrids.
Effects of light and temperature on the monoterpenes of peppermint.
ESSENTIAL OILS AND THEIR CONSTITUENTS. XX. DETECTION AND ESTIMATION OF MENTHOFURAN IN MENTHA ARVENSIS AND OTHER MINT SPECIES BY COUPLED GAS-LIQUID-THIN-LAYER CHROMATOGRAPHY.
[Physiological effect of menthofuran].
The occurrence of menthofuran in oil of peppermint.
[Determination of menthone, menthol and menthofuran in essential oil of Mentha; localization of menthofuran in the plant].
[Quantitative determination of menthofuran].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C18025
HMDB (The Human Metabolome Database):Search
FooDB:FDB014926
Export Tariff Code:2932.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 150.22077941895
Specific gravity @ 25 °C
Pounds per Gallon 7.988 to 8.071
Refractive Index 1.481 to 1.486 @ 20 °C
Boiling Point 80 to 82°C @ 13 mm Hg
Vapor Pressure 0.275 mmHg @ 25 °C
Flash Point TCC Value 75.56 °C TCC
logP (o/w) 3.562 est
Solubility
alcohol Yes
water, 16.36 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Musty
pungent, musty, nutty, earthy, coffee
General comment At 1.00 % in dipropylene glycol. pungent musty nutty earthy coffee
Mosciano, Gerard P&F 14, No. 6, 47, (1989) Diffusive, pungent, musty, nutty, pyrazine like, nutty, earthy and coffee
Flavor Type: Musty
musty, nutty, coffee, raw
Mosciano, Gerard P&F 14, No. 6, 47, (1989) At 10.00 ppm. Musty, nutty, coffee, raw and legume

Occurrences

Potential Uses

Applications
Odor purposes Coffee, Peppermint
Flavoring purposes Chocolate cocoa, Nut
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for menthofuran usage levels up to:
0.5000 % in the fragrance concentrate.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 4
Click here to view publication 4
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): -10.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -10.00000
fruit ices: -10.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -10.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Authority (EFSA) reference(s):

Pulegone and Menthofuran in flavourings - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 29 (FGE29)[1] - Substance from the priority list: Vinylbenzene from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 57 (FGE.57)[1]: Consideration of two structurally related pulegone metabolites and one ester thereof evaluated by JECFA (55th meeting)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 49, Revision 1 (FGE.49Rev1): xanthine alkaloids from the priority list
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):494-90-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :62345
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3,5-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Chemidplus:0000494906