Showing Compound Menthofuran (FDB014926)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:33 UTC

Update date

2025-11-19 00:50:51 UTC

Primary ID

FDB014926

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Menthofuran

Description

(r)-menthofuran, also known as 4,5,6,7-tetrahydro-3,6-dimethylbenzofuran or 3,9-epoxy-P-mentha-3,8-diene, is a member of the class of compounds known as aromatic monoterpenoids. Aromatic monoterpenoids are monoterpenoids containing at least one aromatic ring (r)-menthofuran is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (r)-menthofuran is a coffee, earthy, and musty tasting compound found in herbs and spices, mentha (mint), and orange mint, which makes (r)-menthofuran a potential biomarker for the consumption of these food products (r)-menthofuran can be found primarily in saliva.

CAS Number

494-90-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3,9-Epoxy-p-mentha-3,8-diene	ChEBI
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran	ChEBI
4,5,6,7-Tetrahydro-3,6-dimethylcoumarone	ChEBI
(+)-3,9-Epoxy-P-mentha-3,8-diene	HMDB
(+)-Menthofuran	HMDB
(6R)-3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran	HMDB
(R)-(+)-Menthofuran	HMDB
(R)-4,5,6,7-tetrahydro-3,6-Dimethylbenzofuran	HMDB
3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran	HMDB
3,9-Epoxy-(+)-P-mentha-3,8-diene	HMDB
4,5,6,7-tetrahydro-3,6-Dimethyl-(R)-benzofuran	HMDB
4,5,6,7-tetrahydro-3,6-Dimethyl-benzofuran	HMDB
Menthofuran	HMDB
Menthofuran, (R)-isomer	MeSH, HMDB
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran, 9CI	db_source
FEMA 3235	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.073 g/L	ALOGPS
logP	3.98	ALOGPS
logP	3.13	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	13.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.67 m³·mol⁻¹	ChemAxon
Polarizability	18.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H14O

IUPAC name

3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran

InChI Identifier

InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3

InChI Key

YGWKXXYGDYYFJU-UHFFFAOYSA-N

Isomeric SMILES

CC1CCC2=C(C1)OC=C2C

Average Molecular Weight

150.2176

Monoisotopic Molecular Weight

150.10446507

Classification

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Menthofuran monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Benzofuran
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzofurans (CHEBI:50542 )
monoterpenoid (CHEBI:50542 )
Menthane monoterpenoids (C09868 )
Iridoids (C09868 )
a monoterpenoid (CPD-4981 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 79.96%; H 9.39%; O 10.65%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Menthofuran, non-derivatized, GC-MS Spectrum	splash10-0a4i-4900000000-ad7d24da86fd955477a7	Spectrum
GC-MS	Menthofuran, non-derivatized, GC-MS Spectrum	splash10-0a4i-4900000000-ad7d24da86fd955477a7	Spectrum
Predicted GC-MS	Menthofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0pi9-1900000000-c7d34068fe20520e5e88	Spectrum
Predicted GC-MS	Menthofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-295d2c3abad7c8ff4f63	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-3900000000-5e060ac38ef1d423776f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-30417e50d66ad0fe9af6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-295d2c3abad7c8ff4f63	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-3900000000-5e060ac38ef1d423776f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-30417e50d66ad0fe9af6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-881d258a03659e0f3930	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-01ff41b309657177e5e5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-3900000000-177076fd487978d174f1	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-881d258a03659e0f3930	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-01ff41b309657177e5e5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-3900000000-177076fd487978d174f1	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-a36c450a85a702daacb3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfs-9800000000-283087fbd503dd386078	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9100000000-bb914f0c52d327a80b1b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-22917433edc8ad9dbc2e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-8ae160b4249f862d1a00	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05ne-7900000000-12e4673f2e9f1e3c406d	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB0036089

CRC / DFC (Dictionary of Food Compounds) ID

JXK20-B:JXK20-B

EAFUS ID

3628

Dr. Duke ID

MENTHOFURAN|MEHTHOFURAN|(+)-MENTHOFURAN

BIGG ID

Not Available

KNApSAcK ID

C00003049

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Calcium antagonist	48706	A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.	DUKE
Hepatotoxic	50908	An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.	DUKE
Nematicide	25491	An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Pulmonotoxic	52209	An agent that damages or harms the lungs, often used to describe substances or drugs with toxic effects on pulmonary tissue, limiting its therapeutic applications but aiding in understanding lung disease mechanisms and developing protective strategies.	DUKE