Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Appearance: | bluish clear liquid (est) |
Assay: | 95.00 to 100.00 %
|
Food Chemicals Codex Listed: | No |
Specific Gravity: | 0.96000 to 0.97000 @ 25.00 °C.
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Pounds per Gallon - (est).: | 7.988 to 8.071
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Refractive Index: | 1.48100 to 1.48600 @ 20.00 °C.
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Melting Point: | 86.00 °C. @ 760.00 mm Hg
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Boiling Point: | 80.00 to 82.00 °C. @ 13.00 mm Hg
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Vapor Pressure: | 0.275000 mmHg @ 25.00 °C. (est) |
Flash Point: | 168.00 °F. TCC ( 75.56 °C. )
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logP (o/w): | 3.562 (est) |
Soluble in: |
| alcohol | | water, 16.36 mg/L @ 25 °C (est) |
Organoleptic Properties:
|
Odor Type: musty |
|
| pungent musty nutty earthy coffee |
Odor Description: at 1.00 % in dipropylene glycol. | pungent musty nutty earthy coffee |
|
| pungent musty nutty earthy coffee |
Odor Description:
| Diffusive, pungent, musty, nutty, pyrazine like, nutty, earthy and coffee Mosciano, Gerard P&F 14, No. 6, 47, (1989) |
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Flavor Type: musty |
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| musty nutty coffee raw |
Taste Description: at 10.00 ppm. | Musty, nutty, coffee, raw and legume Mosciano, Gerard P&F 14, No. 6, 47, (1989) |
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Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Aromatic and Allied Chemicals |
Menthofuran
|
Berjé |
Mentho Furan
|
Media |
BOC Sciences |
For experimental / research use only. |
Menthofuran
|
ExtraSynthese |
For experimental / research use only. |
Menthofuran (GC) ≥90%
|
H. Interdonati, Inc. |
Menthofuran
|
Featured Products |
Indukern F&F |
MENTHOFURAN
Odor: MENTHOLATED, HERBAL, LEAF, SWEET |
Jiangyin Healthway |
Menthofuran
|
New functional food ingredients |
Lluch Essence |
MENTOFURANE
|
M&U International |
Menthofuran
|
Mentha & Allied Products |
Menthofuran
50% to 95% |
Nectar Lifesciences |
Distilled Menthofuran
|
OQEMA |
Menthofuran
|
Penta International |
MENTHOFURAN NATURAL 50%
|
Penta International |
MENTHOFURAN NATURAL 90%
|
Penta International |
MENTHOFURAN
|
R C Treatt & Co Ltd |
Menthofuran
|
Reincke & Fichtner |
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran
|
Santa Cruz Biotechnology |
For experimental / research use only. |
Menthofuran
|
Sigma-Aldrich |
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran, ≥95%
Odor: musty; minty; earthy |
Certified Food Grade Products |
Som Extracts |
MENTOFURAN
|
Synerzine |
Menthofuran
|
Safety Information:
Preferred SDS: View |
|
Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
None found. |
GHS Label elements, including precautionary statements |
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Pictogram | |
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Hazard statement(s) |
None found. |
Precautionary statement(s) |
None found. |
Oral/Parenteral Toxicity: |
Not determined
|
Dermal Toxicity: |
Not determined
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Inhalation Toxicity: |
Not determined
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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 ppm | average 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 |
References:
Other Information:
Potential Blenders and core components note
|
For Odor |
No odor group found for these |
4- | hydroxymethyl-pyridine | |
2- | methyl-3-pentyl pyrazine | |
caramellic |
| fenugreek absolute | FL/FR |
chocolate |
| cocoa hexenal | FL/FR |
2,5- | dimethyl pyrazine | FL/FR |
2,6- | dimethyl pyrazine | FL/FR |
earthy |
| geosmin | FL/FR |
| nutty pyrazine | FL/FR |
| geranium thiazole | FL/FR |
medicinal |
| quinoline | CS |
mentholic |
| cornmint oil terpeneless | FL/FR |
laevo- | menthol | FL/FR |
dextro,laevo- | menthol | FL/FR |
| peppermint cyclohexanone | FL/FR |
dextro- | piperitone | FL/FR |
iso | pulegyl acetate | FL/FR |
minty |
(-)- | menthone | FL/FR |
| pennyroyal oil | FL/FR |
| peppermint oil idaho | FL/FR |
| peppermint oil terpeneless | FL/FR |
(R)-(+)- | pulegone | FR |
iso | pulegone | FL/FR |
musty |
2- | acetyl pyrrole | FL/FR |
3- | acetyl-2,5-dimethyl furan | FL/FR |
| hazelnut pyrazine | FL/FR |
nutty |
2- | acetyl-3-ethyl pyrazine | FL/FR |
2- | acetyl-5-methyl furan | FL/FR |
4,5- | dimethyl-2-ethyl-3-thiazoline | FL/FR |
2- | ethyl pyrazine | FL/FR |
| filbert pyrazine | FL/FR |
2,6- | lutidine | FL/FR |
5- | methyl quinoxaline | FL/FR |
2- | methyl thio-3,5 or 6-methyl pyrazine | FL/FR |
| nutty cyclohexenone | FL/FR |
| nutty quinoxaline | FL/FR |
2,3,5,6- | tetramethyl pyrazine | FL/FR |
2,3,5- | trimethyl pyrazine | FL/FR |
| vinyl sulfurol | FL/FR |
truffle |
2- | methyl acetoin | |
| mesityl oxide | FL/FR |
| tetrahydrofurfuryl alcohol | FL/FR |
waxy |
2- | tridecanone | FL/FR |
woody |
4- | hydroxybenzaldehyde | FL/FR |
|
For Flavor |
|
No flavor group found for these |
| acetyl acetaldehyde dimethyl acetal | FL |
(E)- | aconitic acid | FL |
| cyclohexyl methyl pyrazine | FL |
2,5- | diethyl thiazole | FL |
6,7- | dimethyl dihydrocyclopentapyrazine | FL |
| dimethyl dihydrocyclopentapyrazine | FL |
| geosmin | FL/FR |
2- | methyl acetoin | |
iso | pulegone | FL/FR |
caramellic |
| fenugreek absolute | FL/FR |
cocoa |
| cocoa hexenal | FL/FR |
coffee |
| difurfuryl ether | FL |
cooling |
dextro,laevo- | menthol | FL/FR |
laevo- | menthol | FL/FR |
creamy |
4- | hydroxybenzaldehyde | FL/FR |
fatty |
2- | tridecanone | FL/FR |
green |
| dihydroxyacetophenone (mixed isomers) | FL |
| geranium thiazole | FL/FR |
2- | methyl-5-isopropyl pyrazine | FL |
hazelnut |
4- | hydroxymethyl-pyridine | |
meaty |
2,6- | dimethyl pyrazine | FL/FR |
2- | methyl 3-(methyl thio) furan | FL |
mentholic |
| cornmint oil terpeneless | FL/FR |
| peppermint cyclohexanone | FL/FR |
minty |
(-)- | menthone | FL/FR |
| pennyroyal oil | FL/FR |
| peppermint oil idaho | FL/FR |
| peppermint oil terpeneless | FL/FR |
dextro- | piperitone | FL/FR |
musty |
2,5- | dimethyl pyrazine | FL/FR |
2- | ethoxythiazole | FL |
| hazelnut pyrazine | FL/FR |
2,3,5- | trimethyl pyrazine | FL/FR |
nutty |
2- | acetyl pyrrole | FL/FR |
3- | acetyl-2,5-dimethyl furan | FL/FR |
2- | acetyl-3-ethyl pyrazine | FL/FR |
2- | acetyl-5-methyl furan | FL/FR |
4,5- | dimethyl-2-ethyl-3-thiazoline | FL/FR |
2- | ethyl pyrazine | FL/FR |
| filbert pyrazine | FL/FR |
2,6- | lutidine | FL/FR |
5- | methyl quinoxaline | FL/FR |
2- | methyl thio-3,5 or 6-methyl pyrazine | FL/FR |
2- | methyl-3-pentyl pyrazine | |
| nutty cyclohexenone | FL/FR |
| nutty pyrazine | FL/FR |
| nutty quinoxaline | FL/FR |
| nutty thiazole | FL |
| peanut oxazole | FL |
| tetrahydrofurfuryl alcohol | FL/FR |
2,3,5,6- | tetramethyl pyrazine | FL/FR |
| vinyl sulfurol | FL/FR |
potato |
| mesityl oxide | FL/FR |
roasted |
| ethyl 3-(furfuryl thio) propionate | FL |
woody |
iso | pulegyl acetate | FL/FR |
|
Potential Uses:
Occurrence (nature, food, other): note
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 | | 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 |
Articles:
PubMed: | [About flavouring substances and flavouring preparations regulation in the field of manufacturing of flavourings and foodstuffs]. |
PubMed: | Chemical Composition, Antifungal and Antibiofilm Activities of the Essential Oil of Mentha piperita L. |
PubMed: | Anti-yeast activity of mentha oil and vapours through in vitro and in vivo (real fruit juices) assays. |
PubMed: | Chemical composition of the essential oil from Corsican Mentha aquatica--combined analysis by GC(RI), GC-MS and 13C NMR spectroscopy. |
PubMed: | Seasonal variability of the main components in essential oil of Mentha × piperita L. |
PubMed: | Genetic variability, character association, and path analysis for economic traits in menthofuran rich half-sib seed progeny of Mentha piperita L. |
PubMed: | Nematicidal activity of mint aqueous extracts against the root-knot nematode Meloidogyne incognita. |
PubMed: | Synthetic models related to methoxalen and menthofuran-cytochrome P450 (CYP) 2A6 interactions. benzofuran and coumarin derivatives as potent and selective inhibitors of CYP2A6. |
PubMed: | Anti-yeast activity of mentha oil and vapours through in vitro and in vivo (real fruit juices) assays. |
PubMed: | Characterization of rat liver proteins adducted by reactive metabolites of menthofuran. |
PubMed: | In vitro production of M. × piperita not containing pulegone and menthofuran. |
PubMed: | Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes. |
PubMed: | Mode of action of pulegone on the urinary bladder of F344 rats. |
PubMed: | Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol. |
PubMed: | Chemotaxonomy of Serbian Teucrium species inferred from essential oil chemical composition: the case of Teucrium scordium L. ssp. scordioides. |
PubMed: | Chemical composition of the essential oil from Corsican Mentha aquatica--combined analysis by GC(RI), GC-MS and 13C NMR spectroscopy. |
PubMed: | Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)+-pulegone and menthone. |
PubMed: | Quantitative comparative analysis of the bio-active and toxic constituents of leaves and spikes of Schizonepeta tenuifolia at different harvesting times. |
PubMed: | Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes. |
PubMed: | Improving peppermint essential oil yield and composition by metabolic engineering. |
PubMed: | 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. |
PubMed: | Volatile organic compounds from rhizobacteria increase biosynthesis of essential oils and growth parameters in peppermint (Mentha piperita). |
PubMed: | Chrysolina herbacea modulates terpenoid biosynthesis of Mentha aquatica L. |
PubMed: | Metabolism of (+)- and (-)-menthols by CYP2A6 in human liver microsomes. |
PubMed: | 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. |
PubMed: | Metabolism and toxicity of menthofuran in rat liver slices and in rats. |
PubMed: | UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha x piperita L.). |
PubMed: | Constituents of Calamintha ashei: effects on Florida sandhill species. |
PubMed: | Mathematical modeling-guided evaluation of biochemical, developmental, environmental, and genotypic determinants of essential oil composition and yield in peppermint leaves. |
PubMed: | Vapor toxicity of three prototype volatile insecticidal compounds to house fly (Diptera: Muscidae). |
PubMed: | Synthesis and biological evaluation of new ozonides with improved plant growth regulatory activity. |
PubMed: | Structure, function, regulation and polymorphism of human cytochrome P450 2A6. |
PubMed: | Chemical composition and toxicity of the essential oils from Cunila species (Lamiaceae) on the cattle tick Rhipicephalus (Boophilus) microplus. |
PubMed: | Toxicities of 31 volatile low molecular weight compounds against Aedes aegypti and Culex quinquefasciatus. |
PubMed: | A systems biology approach identifies the biochemical mechanisms regulating monoterpenoid essential oil composition in peppermint. |
PubMed: | Nitration versus nitrosation chemistry of menthofuran: remarkable fragmentation and dimerization pathways and expeditious entry into dehydromenthofurolactone. |
PubMed: | Roles of human CYP2A6 and rat CYP2B1 in the oxidation of (+)-fenchol by liver microsomes. |
PubMed: | 14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. |
PubMed: | Metabolism of (-)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes. |
PubMed: | Volatile terpenoids of endophyte-free and infected peppermint (Mentha piperita L.): chemical partitioning of a symbiosis. |
PubMed: | In vitro metabolism of (-)-camphor using human liver microsomes and CYP2A6. |
PubMed: | Metabolism of (+)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes. |
PubMed: | Evaluation of volatile low molecular weight insecticides using Drosophila melanogaster as a model. |
PubMed: | Quenching of singlet molecular oxygen by Commiphora myrrha extracts and menthofuran. |
PubMed: | Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. |
PubMed: | 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. |
PubMed: | Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. |
PubMed: | 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. |
PubMed: | Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential. |
PubMed: | Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase. |
PubMed: | Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene. |
PubMed: | 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. |
PubMed: | Metabolism of 3-methylindole by porcine liver microsomes: responsible cytochrome P450 enzymes. |
PubMed: | 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. |
PubMed: | Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies. |
PubMed: | Glutathione S-transferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones. |
PubMed: | Transformation of the limonene synthase gene into peppermint (Mentha piperita L.) and preliminary studies on the essential oil profiles of single transgenic plants. |
PubMed: | Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide. |
PubMed: | Metabolic fate of S-(-)-pulegone in rat. |
PubMed: | Hepatoprotective effect of C-phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats. |
PubMed: | (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. |
PubMed: | Multiple organ failure after ingestion of pennyroyal oil from herbal tea in two infants. |
PubMed: | Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature. |
PubMed: | Mechanisms of the formation and disposition of reactive metabolites that can cause acute liver injury. |
PubMed: | Allelopathic potential of menthofuran monoterpenes fromCalamintha ashei. |
PubMed: | Effects of menthofuran, a monoterpene furan on rat liver microsomal enzymes, in vivo. |
PubMed: | Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites. |
PubMed: | Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone. |
PubMed: | Metabolic fate of menthofuran in rats. Novel oxidative pathways. |
PubMed: | Reactive intermediates in the oxidation of menthofuran by cytochromes P-450. |
PubMed: | Partial characterization of biliary metabolites of pulegone by tandem mass spectrometry. Detection of glucuronide, glutathione, and glutathionyl glucuronide conjugates. |
PubMed: | Evidence for the formation of a known toxin, p-cresol, from menthofuran. |
PubMed: | Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity. |
PubMed: | Menthofuran-dependent and independent aspects of pulegone hepatotoxicity: roles of glutathione. |
PubMed: | Metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat. |
PubMed: | Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. |
PubMed: | The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran. |
PubMed: | Chemical and Morphometrical Comparison Between two Peppermint Notomorphs. |
PubMed: | Genetic basis for high limonene-cineole content of exceptional Mentha citrata hybrids. |
PubMed: | Effects of light and temperature on the monoterpenes of peppermint. |
PubMed: | 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. |
PubMed: | [Physiological effect of menthofuran]. |
PubMed: | The occurrence of menthofuran in oil of peppermint. |
PubMed: | [Determination of menthone, menthol and menthofuran in essential oil of Mentha; localization of menthofuran in the plant]. |
PubMed: | [Quantitative determination of menthofuran]. |
|