(+)-menthone

General Material Information

Preferred name	(+)-menthone
Trivial Name	D-Menthone
Short Description	cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-
Formula	C10 H18 O
CAS Number	3391-87-5
ECHA Number	222-227-6
FDA UNII	15F1B5K9A5
Nikkaji Number	J205.485J
Beilstein Number	2041367
MDL	MFCD00210063
xLogP3-AA	2.70 (est)
NMR Predictor	External link
Synonyms	cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R-trans)- cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)- cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel- (1S,4R)-p- menthan-3-one (1S,4R)-para- menthan-3-one (1S,4R)-p- menthane-3-one (1S,4R)-para- menthane-3-one (2R,5S)-5-methyl-2-(propan-2-yl) cyclohexanone (2R,5S)-5-methyl-2-(propan-2-yl)cyclohexanone (2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-one (2R,5S)-2-iso propyl-5-methyl cyclohexanone (2R,5S)-2-iso propyl-5-methylcyclohexanone rel-(2R,5S)-2-iso propyl-5-methylcyclohexanone p-Menthan-3-one, (1S,4R)-(+)- (2R,5S)-5-Methyl-2-(1-methylethyl)cyclohexanone D-Menthone

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Literature & References

	(2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-one
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	443159
Pubchem (sid):	135062239

Publications by PubMed
A rationale to design longer lasting mosquito repellents.
Biocontrol potential of essential oil monoterpenes against housefly, Musca domestica (Diptera: Muscidae).
Nutritional and sensory quality during refrigerated storage of fresh-cut mints (Mentha×piperita and M. spicata).
Nematicidal activity of mint aqueous extracts against the root-knot nematode Meloidogyne incognita.
Anti-inflammatory effects of 27 selected terpenoid compounds tested through modulating Th1/Th2 cytokine secretion profiles using murine primary splenocytes.
Effect of gibberellic acid and calliterpenone on plant growth attributes, trichomes, essential oil biosynthesis and pathway gene expression in differential manner in Mentha arvensis L.
Retention of aroma compounds from Mentha piperita essential oil by cyclodextrins and crosslinked cyclodextrin polymers.
Anti-yeast activity of mentha oil and vapours through in vitro and in vivo (real fruit juices) assays.
The constituents of essential oil: antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia.
Antioxidant and antibacterial effects of Lavandula and Mentha essential oils in minced beef inoculated with E. coli O157:H7 and S. aureus during storage at abuse refrigeration temperature.
Lack of cytotoxic and genotoxic effects of Minthostachys verticillata essential oil: studies in vitro and in vivo.
Toxicity of Schizonpeta multifida essential oil and its constituent compounds towards two grain storage insects.
Composition and antimicrobial activities of Lippia multiflora Moldenke, Mentha x piperita L. and Ocimum basilicum L. essential oils and their major monoterpene alcohols alone and in combination.
Yield, content, and composition of peppermint and spearmints as a function of harvesting time and drying.
Seasonal variation in content, chemical composition and antimicrobial and cytotoxic activities of essential oils from four Mentha species.
Ultraviolet-B and photosynthetically active radiation interactively affect yield and pattern of monoterpenes in leaves of peppermint (Mentha x piperita L.).
API-IT-MS for measuring aroma release from dentifrice products using a device to simulate tooth brushing.
Supercritical fluid extraction--achiral liquid chromatography with circular dichroism detection for the determination of menthone enantiomers in natural peppermint oil samples.
Chemical composition of essential oils of Thymus and Mentha species and their antifungal activities.
Aroma permeability of hydroxypropyl maize starch films.
Antioxidant property of volatile oils determined by the ferric reducing ability.
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
Quantitative variations in the essential oil of Minthostachys mollis (Kunth.) Griseb. in response to insects with different feeding habits.
Effect of harvest time and drying method on biomass production, essential oil yield, and quality of peppermint (Mentha x piperita L.).
Biofilm in water pipelines; a potential source for off-flavours in the drinking water.
Identification of monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate in nature by high performance liquid chromatography-tandem mass spectrometry.
Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil.
Antifungal activity of peppermint and sweet basil essential oils and their major aroma constituents on some plant pathogenic fungi from the vapor phase.
Biosynthetic origin of geosmin in red beets (Beta vulgaris L.).
Simulated microgravity [bed rest] has little influence on taste, odor or trigeminal sensitivity.
Characterization of essential oils from lamiaceae species by fourier transform Raman spectroscopy.
Phytochemical induction by herbivores could affect quality of essential oils from aromatic plants.
Antimicrobial screening of Mentha piperita essential oils.
Essential oil composition of sachalinmint from Norway detected by solid-phase microextraction and gas chromatography-mass spectrometry analysis.
Genetic and biochemical characterization of a novel monoterpene epsilon-lactone hydrolase from Rhodococcus erythropolis DCL14.
Acaricidal activity of natural monoterpenes on Tyrophagus putrescentiae (Schrank), a mite of stored food.
Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways.
Monoterpene composition of essential oil from peppermint (Mentha x piperita L.) with regard to leaf position using solid-phase microextraction and gas chromatography/mass spectrometry analysis.
Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.
Biogenetic studies in Mentha x piperita. 1. deuterium-labeled monoterpene ketones: synthesis and stereoselective analysis.
Effect of sucrose on the perceived flavor intensity of chewing gum.
API-IT-MS for measuring aroma release from dentifrice products using a device to simulate tooth brushing.
Effect of harvest time and drying method on biomass production, essential oil yield, and quality of peppermint (Mentha x piperita L.).
Identification of monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate in nature by high performance liquid chromatography-tandem mass spectrometry.
Crystal structure of amylose complexes with small ligands.
Biosynthetic origin of geosmin in red beets (Beta vulgaris L.).

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEBI:	View
CHEMBL:	View
KEGG (GenomeNet):	C11390
HMDB (The Human Metabolome Database):	HMDB35783
FooDB:	FDB014530
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Suppliers

Aromatic and Allied Chemicals	Ind-Swift Laboratories
Santa Cruz Biotechnology	Sigma-Aldrich

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	154.2526550293
Boiling Point	208 to 210°C @ 760 mm Hg
Vapor Pressure	0.256 mmHg @ 25 °C
Flash Point TCC Value	71.67 °C TCC
logP (o/w)	2.625 est
Shelf life	12 months (or longer if stored properly.)
Storage notes	Refrigerate in tightly sealed containers.
Solubility
alcohol	Yes
water, 180.5 mg/L @ 25 °C (est)	Yes
water	No

Organoleptic Properties

Odor Type: Mentholic
mentholic, minty
General comment	At 10.00 % in dipropylene glycol. mentholic minty
Flavor Type: Mentholic
peppermint, mentholic
General comment	Peppermint

Occurrences

Safety Information

Safety information

European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice

Safety references

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :443159

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

(2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-one

Chemidplus:0003391875