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Merck
CN

63661

(+)-Menthofuran

analytical standard

Synonym(s):

(6R)-4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran, (R)-3,6-Dimethyl-4,5,6,7-tetrahydrobenzofuran

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About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
17957-94-7
Molecular Weight:
150.22
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329759886
MDL number:
MFCD00142332
Beilstein/REAXYS Number:
2729

Key Documents

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InChI

1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3/t7-/m1/s1

SMILES string

C[C@@H]1CCc2c(C)coc2C1

InChI key

YGWKXXYGDYYFJU-SSDOTTSWSA-N

grade

analytical standard

assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D +100±2°, neat

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

refractive index

n20/D 1.484

bp

204-206 °C (lit.)

density

0.97 g/mL at 20 °C (lit.)

application(s)

food and beverages

format

neat

storage temp.

2-8°C

Quality Level

100

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General description

(+)-Menthofuran is a metabolite of pulegone, found in mint plants, which is basically produced from (+)–pulegone by menthofuran synthase enzyme, under certain conditions of stress like low sunlight, limited moisture and nutrient deficiencies.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Other Notes

This compound is commonly found in plants of the genus: mentha

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM5065
BCCK4536
BCCF4463
BCCB8760
BCBT7533

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Council of Europe
Chemically-defined Flavouring Substances (2000)
(R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6
Khojasteh - Bakht.CS
Drug Metabolism and Disposition, 26(7), 701-704 (1998)
Rahman-U-A
Studies in Natural Products Chemistry, Volume 37, 37 (2012)
S Cyrus Khojasteh et al.
Chemical research in toxicology, 23(11), 1824-1832 (2010-10-16)
Menthofuran is a monoterpene present in mint plants that is oxidized by mammalian cytochrome P450 (CYP) to hepatotoxic metabolites. Evidence has been presented that p-cresol and other unusual oxidative products are metabolites of menthofuran in rats and that p-cresol may
Maria De Lucia et al.
The Journal of organic chemistry, 72(26), 10123-10129 (2007-11-30)
The reaction chemistry of menthofuran (1), a toxic furan terpenoid from various mint oils, with nitric acid and nitrous acid has been investigated. Treatment of 1 with nitric acid afforded a 1:1 mixture of the bisfuran derivatives 5 and 6
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