(R)-(+)-menthofuran
benzofuran, 4,5,6,7-tetrahydro-3,6-dimethyl-, (R)-
 
Notes:
Constit. of peppermint oil (Mentha piperita) and other Mentha spp. as minor but essential organoleptic. Used in peppermint oil formulations
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CAS Number: 17957-94-7Picture of molecule3D/inchi
FDA UNII: 9N0IS8189W
Nikkaji Web: J330.675E
Beilstein Number: 0002729
MDL: MFCD00142332
XlogP3-AA: 3.00 (est)
Molecular Weight: 150.22078000
Formula: C10 H14 O
NMR Predictor: Predict (works with chrome, Edge or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 210.70 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.300000 mmHg @ 25.00 °C. (est)
Flash Point: 168.00 °F. TCC ( 75.60 °C. ) (est)
logP (o/w): 4.020 (est)
Soluble in:
 water, 16.36 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor Type: minty
 
 minty  leafy  herbal  camphoreous  
Odor Description:
at 10.00 % in dipropylene glycol. 
mint leafy herbal camphoreous
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
(+)-Menthofuran ≥99%
Sigma-Aldrich
For experimental / research use only.
(+)-Menthofuran
analytical standard
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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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for (R)-(+)-menthofuran usage levels up to:
 not for fragrance use.
 
Recommendation for (R)-(+)-menthofuran flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 442478
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (6R)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Chemidplus: 0017957947
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References:
Leffingwell: Chirality or Article
 (6R)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 442478
Pubchem (sid): 135257956
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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
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C18025
HMDB (The Human Metabolome Database): HMDB36089
FooDB: FDB014927
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
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 mint
Search Trop  Picture
 water mint
Search Trop  Picture
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Synonyms:
 benzofuran, 4,5,6,7-tetrahydro-3,6-dimethyl-, (R)-
(6R)-(+)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
(6R)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
(+)-3,9-epoxy-p-mentha-3,8-diene
p-mentha-3,8-diene, 3,9-epoxy-, (+)-
(1R)-(+)-menthafuran
 menthofuran, (+)-
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Articles:
PubMed: N-Acetyl lysine/glutathione-derived pyrroles as potential ex vivo biomarkers of bioactivated furan-containing compounds.
PubMed: Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes.
PubMed: Structure, function, regulation and polymorphism of human cytochrome P450 2A6.
PubMed: Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites.
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: Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide.
PubMed: (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6.
PubMed: Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course.
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