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Merck
CN

57594

(+)-Menthofuran

technical, ≥90% (GC)

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
PubChem Substance ID:
329758325
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
2729
MDL number:
MFCD00142332

Key Documents

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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

grade

technical

assay

≥90% (GC)

optical activity

[α]/D +97±5°, neat

bp

204-206 °C (lit.)

density

0.97 g/mL at 20 °C (lit.)

storage temp.

2-8°C

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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

ppe

Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM6615
BCCM4945
BCCF2493

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Valerie M Kramlinger et al.
Chemico-biological interactions, 197(2-3), 87-92 (2012-04-11)
Nicotine is the primary addictive agent in tobacco products and is metabolized in humans by CYP2A6. Decreased CYP2A6 activity has been associated with decreased smoking. The extrahepatic enzyme, CYP2A13 (94% identical to CYP2A6) also catalyzes the metabolism of nicotine, but
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
C M Bertea et al.
Archives of biochemistry and biophysics, 390(2), 279-286 (2001-06-09)
(+)-Menthofuran is an undesirable monoterpenoid component of peppermint (Mentha x piperita) essential oil that is derived from the alpha,beta-unsaturated ketone (+)-pulegone. Microsomal preparations, from the oil gland secretory cells of a high (+)-menthofuran-producing chemotype of Mentha pulegium, transform (+)-pulegone to
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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