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63661

Supelco

(+)-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:
Molecular Weight:
150.22
Beilstein:
2729
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

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

SMILES string

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

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

InChI key

YGWKXXYGDYYFJU-SSDOTTSWSA-N

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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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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(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)
Council of Europe
Chemically-defined Flavouring Substances (2000)
Rahman-U-A
Studies in Natural Products Chemistry, Volume 37, 37 (2012)
Soheil S Mahmoud et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(24), 14481-14486 (2003-11-19)
(+)-Pulegone is a central intermediate in the biosynthesis of (-)-menthol, the most significant component of peppermint essential oil. Depending on environmental conditions, this branch point metabolite may be reduced to (-)-menthone en route to menthol, by pulegone reductase (PR), or
S C Khojasteh-Bakht et al.
Drug metabolism and disposition: the biological fate of chemicals, 26(7), 701-704 (1998-07-14)
(R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 (CYP or P450) 2A6. Menthofuran caused a time- and concentration-dependent loss of CYP2A6 activity. The inactivation of CYP2A6 was characterized by a Ki of 2.5 microM and a kinact

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