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(−)-Menthone

Name: (−)-Menthone
Brand: ALDRICH

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

UNSPSC Code:

12352115

NACRES:

NA.22

PubChem Substance ID:

24853053

EC Number:

237-926-1

Beilstein/REAXYS Number:

2041368

MDL number:

MFCD00001634

Assay:

90%

Form:

liquid

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Properties

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.)

functional group

ketone

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

Description

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.

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pictograms

GHS07

signalword

Warning

hcodes

H315,H317

pcodes

P261 - P264 - P272 - P280 - P302 + P352 - P333 + P313

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

165.2 °F

flash_point_c

74 °C

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Chiral perrocenylalkylamines from (-)-menthone.

Siglmuller F, et al.

Tetrahedron, 42(21), 5931-5940 (1986)

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)

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)

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