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Menthone

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Menthone Basic information

Product Name:
Menthone
Synonyms:
  • menthone,p-menthan-3-one,5-methyl-2-(1-methylethyl)cyclohexanone
  • CYCLOHEXANONE,5-METHYL-2-(1-M
  • Menthone, 90%, mixture of isomers
  • 2-(1-Methylethyl)-5-methyl-1-cyclohexanone
  • 5-Methyl-2-(1-methylethyl)cyclohexan-1-one
  • Menthone, mixed isomers, 98%
  • 5-Methyl-2-(1-methylethyl)cyclohexanone
  • Menthone, 98%, Mixture of isoMers
CAS:
10458-14-7
MF:
C10H18O
MW:
154.25
EINECS:
233-944-9
Mol File:
10458-14-7.mol
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Menthone Chemical Properties

Melting point:
-6 °C
Boiling point:
85-88 °C/12 mmHg (lit.)
Density 
0.896 g/mL at 20 °C (lit.)
refractive index 
n20/D 1.450
FEMA 
2667 | MENTHONE
Flash point:
69 °C
storage temp. 
Sealed in dry,Room Temperature
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form 
Liquid
color 
Clear colorless
Odor
minty
optical activity
[α]/D -7.0±5°, neat
Water Solubility 
Slightly soluble in water
JECFA Number
429
BRN 
774527
LogP
2.63
CAS DataBase Reference
10458-14-7(CAS DataBase Reference)
NIST Chemistry Reference
Cyclohexanone, 5-methyl-2-(1-methylethyl)-(10458-14-7)
EPA Substance Registry System
Cyclohexanone, 5-methyl-2-(1-methylethyl)- (10458-14-7)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-36-43-52/53
Safety Statements 
24/25-61-36/37-26
RIDADR 
NA 1993 / PGIII
WGK Germany 
3
RTECS 
OS9541500
HS Code 
29142990

MSDS

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Menthone Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS LIQUID

Chemical Properties

Menthone exists as two stereoisomers, trans-menthone and cis-isomenthone, each of which occurs as a pair of enantiomers, due to the two asymmetric centers present in the molecule.
Both stereoisomers occur in many essential oils, often as a single enantiomer species. A particularly high concentration (sometimes >50%) is found in oils from Mentha species.Thementhones are colorless liquids that possess a typically minty odor; the odor of isomenthone is slightly musty.They have a strong tendency to interconvert and are, therefore, difficult to obtain in high purity. Industrial products aremixtures of varying composition.
The menthones are converted into the corresponding menthols by means of hydrogenation; for example, (?)-menthone yields (+)-neomenthol and (?)-menthol.
(?)-Menthone can be obtained by distillation of dementholized cornmint oil or by oxidation of (?)-menthol (e.g., with chromic acid). Dehydrogenation of (?)- menthol (e.g., with copper chromite) yields a mixture of (?)-menthone and (+)- isomenthone.
rac-Menthone is prepared analogously to rac-menthol. However, it can also be synthesized by hydrogenation of thymol in the presence of palladium–carbon catalysts .
Menthone and isomenthone are used for synthetic peppermint oils and bases.

Uses

Menthone has been used in the following studies:

  • To prepare the model flavor mix in a study to investigate the release of various aroma compounds in xanthan-thickened food model systems having different viscosities.
  • As standard in the quantification of volatile constituents and odour-activity value (OAV) in ′Marion′ and ′Black Diamond′.
  • Modified semisolid agar antifungal susceptibility method (SAAS) to investigate the anti-fungal activities of various cyclic terpenes against Fusarium verticillioides MRC 826.

Definition

ChEBI: P-menthan-3-one is a p-menthane monoterpenoid that is p-menthane substituted by an oxo group at position 3. It has a role as a plant metabolite and a volatile oil component.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 5621, 1987 DOI: 10.1021/jo00234a021
Tetrahedron Letters, 13, p. 749, 1972

General Description

Menthone is a cyclic oxygenated terpene and its antioxidant potential has been evaluated. It is one of the key active component of Danshu capsule (DSC), a medicinal compound in traditional Chinese medicine.

Menthone Preparation Products And Raw materials

Raw materials

MenthoneSupplier

Hubei chushuo Biotechnology Co., Ltd Gold
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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Alfa Aesar
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400-6106006
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saleschina@alfa-asia.com
Adamas Reagent, Ltd.
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400-6009262 16621234537
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zhangsn@titansci.com
Shanghai Hanhong Scientific Co.,Ltd.
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021-54306202 13764082696;
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info@hanhongsci.com