89-80-5

Basic information

• Product Name: MENTHONE
• Synonyms: P-MENTHAN-3-ONE;(±)-trans-p-menthan-3-one;Cyclohexanone, 5-methyl-2-(1-methylethyl)-, trans-;p-Menthan-3-one, trans-;p-Menthone;trans-Menthan-3-One;trans-Menthone;trans-p-Menthan-3-one
• CAS NO: 89-80-5
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 201-941-1
• Mol File: 89-80-5.mol
• Article Data: 51

Chemical Properties

• Boiling Point: 210°C
• Flash Point: 69 ºC
• Appearance: /
• Density: 0.896
• Vapor Pressure: 0.256mmHg at 25°C
• Refractive Index: 1.450
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• Water Solubility: 688mg/L at 25℃
• CAS DataBase Reference: MENTHONE(CAS DataBase Reference)
• NIST Chemistry Reference: MENTHONE(89-80-5)
• EPA Substance Registry System: MENTHONE(89-80-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43-52/53
• Safety Statements: 26-36/37-61
• Hazardous Substances Data: 89-80-5(Hazardous Substances Data)

Usage

Description

Menthone has a characteristic odor similar to menthol. May be prepared by oxidation of menthol.

Chemical Properties

Menthone has a characteristic mint-like odor.

Occurrence

Reported found in severalstereoisomersin nature; l-menthone is a constituent of the essential oils of Russian and American peppermint, geranium, Andropogon gragrans, Mentha timija and Mentha arvensis; d-menthone is present in the essential oils of Barosma pulchellum, Nepeta japonica Maxim., and others. d-Isomenthone has been reported isolated from Micromeria abis sinica Benth., Pelargonium tomentosum Jacquin and others; l-isomenthone has been identified in Réunion geranium, Pelargonium capitau and others. Also reported found in lemon peel oil, black currants, celery seed, cinnamon, peppermint, cornmint, pennyroyal and other mentha oils, nutmeg, thymus, cocoa, mushrooms, starfruit, coriander leaf, rice, tarragon, calamus, buckwheat, sweet and bitter fennel, cherimoya, buchu oil, clam and sweet grass oil.

Uses

(±)-Menthone is a Menthol derivative. A volatile flavor compound found in human milk, red and black rice bran and specialty rice types.

Preparation

By oxidation of menthol.

Aroma threshold values

Detection: 170 ppb; aroma characteristics at 1.0%: minty, cooling, sweet, refreshing, peppermint fresh, slightly dirty woody, camphoraceous with a green herbal anise nuance.

Taste threshold values

Taste characteristics at 50 ppm: cooling, peppermint, fresh green, minty, herbal, dirty mentholic with a refreshing camphoraceous nuance.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion, intravenous, and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Metabolism

H?m?l?inen (1912) claimed that menthone was probably oxidized in the rabbit to ketomenthone, since the glucuronide produced was converted by warm dilute H2SO4 to a substance which was probably △4(8 -p-menthen-3-one (pulegone). Williams (1940), however, showed that it underwent reduction in the rabbit with the production of d-neomenthol. The presence of l-menthol, the other possible reduction product, was not detected and it appeared that the biological reduction was asymmetric (Williams, 1959).

InChI:InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m0/s1

Upstream product

• 6485-40-1 (R)-Carvone 
• 89-83-8 thymol 
• 36392-06-0 3,7-dimethyl-6-octenoyl chloride 
• 109-99-9 tetrahydrofuran 
• 53282-30-7 trifluoro-methanesulfonic acid 2-methyl-propenyl ester 
• 95465-47-7 potassium menthyl oxide 
• 2216-51-5 (-)-menthol 
• 89-82-7 pulegone 
• 72311-09-2 3-Methyl-6-(1-methylethyl)-1-trimethylsilyloxy-1-cyclohexen 
• 106-95-6 allyl bromide 
• 75-36-5 acetyl chloride 
• 89-78-1 (l)-menthol 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 89-78-1 menthol 

Downstream Products

• 4884-25-7 2-cyclopentylcyclopentanol 
• 89-78-1 2-isopropyl-5-methylcyclohexan-1-ol 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 2216-51-5 (-)-menthol 
• 490-99-3 DL-neomenthol 
• 15356-70-4 menthol 
• 491-07-6 isomenthone 
• 907166-70-5 N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]pyridine-3-carbohydrazide 
• 13143-66-3 C₁₆H₂₃N₃O 
• 1299427-55-6 C₁₇H₂₃FN₂O 
• 904248-90-4 N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]benzohydrazide 
• 1299427-51-2 4-hydroxy-N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]benzohydrazide 
• 1299427-53-4 4-chloro-N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]benzohydrazide 
• 1299427-52-3 N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]-4-nitrobenzohydrazide 

Relevant articles and documents

Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide

Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.

Heterogeneous Ru(iii) oxidation catalysts: Via 'click' bidentate ligands on a periodic mesoporous organosilica support

A 100% monoallyl ring-type Periodic Mesoporous Organosilica (PMO) is prepared as a novel, versatile and exceptionally stable catalytic support with a high internal surface area and 5.0 nm pores. Thiol-ene 'click' chemistry allows straightforward attachment of bifunctional thiols (-NH2, -OH, -SH) which, exploiting the thioether functionality formed, give rise to 'solid' bidentate ligands. [Ru(acac)2(CH3CN)2]PF6 is attached and complex formation on the solid is studied via density functional theory. All resulting solid catalysts show high activity and selectivity in alcohol oxidation reactions performed in green conditions (25 °C/water). The PMO catalysts do not leach Ru during reaction and are thus easily recuperated and re-used for several runs. Furthermore, oxidation of poorly water-soluble (±)-menthol illustrates the benefits of using hydrophobic PMOs as catalytic supports.

ALPHA-HYDROGEN SUBSTITUTED NITROXYLS AND DERIVATIVES THEREOF AS CATALYSTS

The present invention relates to novel alpha-hydrogen substituted nitroxyl compounds and their corresponding oxidized (oxoammonium cations) and reduced (hydroxylamine) forms, and to the use of such compounds, inter alia, for (1) oxidation of primary and secondary alcohols to aldehydes and ketones, respectively; (2) resolution of racemic alcohols; (3) desymmetrization of meso-alcohol; (4) as radicals and spin trapping reagents; and (5) as polymerization agents. The present invention further relates to processes for preparing the novel nitroxyl/oxoammonium/ hydroxylamine compounds from the corresponding amines, and to certain novel amine derivatives and their uses. The compounds of the invention as well as the amine precursors are also useful as ligands for transition metals and as organocatalysts in e.g., aldol reactions.