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Sigma-Aldrich

(−)-Menthone

90%

Synonym(s):

(1R,4S)-p-Menthan-3-one, (2S,5R)-2-Isopropyl-5-methylcyclohexanone

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
14073-97-3
Molecular Weight:
154.25
Beilstein:
2041368
EC Number:
237-926-1
MDL number:
MFCD00001634
UNSPSC Code:
12352115
PubChem Substance ID:
24853053
NACRES:
NA.22

vapor pressure

0.5 mmHg ( 20 °C)

Quality Level

100

Assay

90%

form

liquid

optical activity

[α]20/D −20°, neat

impurities

5% isomenthone

refractive index

n20/D 1.45 (lit.)

bp

207-210 °C (lit.)

density

0.893 g/mL at 20 °C (lit.)

SMILES string

CC(C)[C@@H]1CC[C@@H](C)CC1=O

InChI

1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1

InChI key

NFLGAXVYCFJBMK-BDAKNGLRSA-N

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General description

(-)-Menthone is a monoterpenoid compound found in the essential oil extracted from the maturing peppermint (Mentha piperita L.) leaves.

(-)-Menthone can undergo hydrogenation to yield a mixture of (-)-menthol and (+)-neomenthol.

Application

(-)-Menthone may be used to synthesize chiral neomenthyl derivatives, optically pure α-ferrocenylalkylamines and optically active polyalkylcyclohexanones.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Metabolism of Monoterpenes Demonstration of (+)-Neomenthyl-?-d-Glucoside as a Major Metabolite of (-)-Menthone in Peppermint (Mentha Piperita).
Croteau R and Martinkus C.
Plant Physiology, 64(2), 169-175 (1979)
Chiral perrocenylalkylamines from (-)-menthone.
Siglmuller F, et al.
Tetrahedron, 42(21), 5931-5940 (1986)
Cerium (III) chloride promoted addition of organometallic reagents to (-)-menthone-preparation of chiral neomenthyl derivatives.
Panev S and Dimitrov V.
Tetrahedron Asymmetry, 11(7), 1517-1526 (2000)
Terpenoids. XLIX. 1 Preparation of Optically Active Polyalkylcyclohexanones from (+)-Pulegone,(-)-Menthone and (-)-Carvone2.
Djerassi C, et al.
Journal of the American Chemical Society, 83(21), 4433-4439 (1961)
Synthesis of liquid menthol by hydrogenation of dementholized peppermint oil over Ni catalysts
Manuale DL, et al.
Quimica nova, 33, 1231-1234 (2010)
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