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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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Council of Europe
Chemically-defined Flavouring Substances (2000)
Rahman-U-A
Studies in Natural Products Chemistry, Volume 37, 37 (2012)
(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)
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
P Racine et al.
Fitoterapia, 76(3-4), 316-323 (2005-05-14)
The quenching activity against singlet oxygen, an actor of lipid peroxidation and DNA degradation, of the essential oil and resinoid of Commiphora myrrha from Somalia has been studied and compared to DL-alpha-tocopherol using 1,3-diphenylisobenzofuran (DPBF) as a probe. To insure

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