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(-)-menthone

Chemical Structure

General Material Information

Preferred name (-)-menthone
Trivial Name (-)-Menthone
Short Description L-menthone
Formula C10 H18 O
CAS Number 14073-97-3
Deleted CAS Number 21060-23-1
ECHA Number 237-926-1
FDA UNII 5F709W4OG4
Nikkaji Number J9.142A
Beilstein Number 2041368
MDL MFCD00001634
COE Number 2035
xLogP3-AA 2.70 (est)
NMR Predictor External link
Synonyms
  • cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S,5R)-
  • (1R,4S)-p- menthan-3-one
  • (1R,4S)-para- menthan-3-one
  • L- menthan-3-one
  • L-p- menthan-3-one
  • laevo- menthan-3-one
  • (1R,4S)-p- menthane-3-one
  • (1R,4S)-para- menthane-3-one
  • L- menthane-3-one
  • L-p- menthane-3-one
  • laevo- menthane-3-one
  • L- menthanone
  • laevo- menthanone
  • (-)- menthone
  • (-)-(2S,5R)- menthone
  • (2S,5R)- menthone
  • L- menthone
  • laevo- menthone
  • laevo- menthone extra FCC (-20 rotation) (natural)
  • laevo- menthone FCC (natural)
  • menthone L-23 (ex mint)
  • menthone laevogyre nat
  • L- menthone natural
  • menthone-l/isomenthone-d
  • L- menthone, natural
  • L- menthone, synthetic
  • (2S-trans)-5-methyl-2-(1-methyl ethyl) cyclohexanone
  • (2S,5R)-5-methyl-2-(1-methyl ethyl) cyclohexanone
  • (2S-trans)-5-methyl-2-(1-methylethyl)cyclohexanone
  • (2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanone
  • (2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
  • (2S,5R)-5-methyl-2-(propan-2-yl)cyclohexanone
  • (2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
  • 4-iso propyl-1-methyl cyclohexan-3-one
  • 4-iso propyl-1-methylcyclohexan-3-one
  • (2S,5R)-2-iso propyl-5-methyl-cyclohexanone
  • (2S,5R)-2-iso propyl-5-methylcyclohexanone
  • trans-2-iso propyl-5-methylcyclohexanone
  • (2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
  • p-Menthan-3-one, (1R,4S)-(-)-
  • Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-trans)-
  • (2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanone
  • L-Menthone
  • trans-(-)-p-Menthan-3-one
  • (1R,4S)-Menthone
  • (1R,4S)-p-Menthan-3-one
  • (1R,4S)-p-Menth-3-one
  • (2S,5R)-2-Isopropyl-5-methylcyclohexanone
  • (2S,5R)-(-)-Menthone
  • (2S,5R)-2-Isopropyl-5-methylcyclohexan-1-one
  • (-)-L-Menthone

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Literature & References

(2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:14073-97-3
Pubchem (cid):26447
Pubchem (sid):134989635
Publications by PubMed
Vanadium-Catalyzed C(sp(3))-H Fluorination Reactions.
Insecticidal activity of menthol derivatives against mosquitoes.
Broad activation of the glomerular layer enhances subsequent olfactory responses.
Metallophosphite-catalyzed asymmetric acylation of alpha,beta-unsaturated amides.
Percutaneous absorption enhancing effect and skin irritation of monocyclic monoterpenes.
Metabolism of Monoterpenes : Evidence for the Function of Monoterpene Catabolism in Peppermint (Mentha piperita) Rhizomes.
Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha piperita and other Mentha species.
Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves.
Demonstration of the Intercellular Compartmentation of l-Menthone Metabolism in Peppermint (Mentha piperita) Leaves.
Metabolism of Monoterpenes : EVIDENCE FOR COMPARTMENTATION OF l-MENTHONE METABOLISM IN PEPPERMINT (MENTHA PIPERITA) LEAVES.
[Photochemical reaction products of L-menthone (author's transl)].
Studies in detoxication: The biological reduction of l-menthone to d-neomenthol and of d-isomenthone to d-isomenthol in the rabbit. The conjugation of d-neomenthol with glucuronic acid.

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
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C00843
HMDB (The Human Metabolome Database):HMDB35162
FooDB:FDB013800
Export Tariff Code:2914.29.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•assay: 98% dl-form; 95% optically active form •note: apinol obtained by dry distillation of wood of pinus palustris mill (p australis michx), pinaceae is chiefly l-menthoneamber-colored oil, bp about 182.2 deg c, density 0.946. apinol

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 154.2526550293
Specific gravity @ 25 °C
Pounds per Gallon 7.389 to 7.447
Refractive Index 1.448 to 1.453 @ 20 °C
Melting Point -6 to -5°C @ 760 mm Hg
Boiling Point 207 to 210°C @ 760 mm Hg
Acid Value 1 max KOH/g
Vapor Pressure 0.256 mmHg @ 25 °C
Flash Point TCC Value 72.78 °C TCC
logP (o/w) 3.05
Solubility
alcohol Yes
fixed oils Yes
water, 180.5 mg/L @ 25 °C (est) Yes
water, 497 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Minty
mentholic, peppermint, herbal, camphoreous, minty, cooling, sweet, fresh, green, anise
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 4 hour(s) at 100.00 %
Luebke, William tgsc, (1983) At 10.00 % in dipropylene glycol. deep menthol peppermint herbal camphor
Mosciano, Gerard P&F 16, No. 4, 45, (1991) Minty, cooling, sweet, peppermint-Iike, fresh, camphoreous, herbal with a green anise nuance
Flavor Type: Minty
cooling, peppermint, fresh, green, minty, herbal
Mosciano, Gerard P&F 16, No. 4, 45, (1991) At 50.00 ppm. Cooling, peppermint, fresh green, minty with an herbal nuance
Useful in: mint. Refreshing cool, woody, slightly sweet

Occurrences

Potential Uses

Applications
Odor purposes Geranium, Guava, Herbal, Mint, Peppermint, Rose, Rose red rose, Woody
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 37/38 - Irritating to respiratory system and skin.
R 43 - May cause sensitisation by skin contact.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
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
Recommendation for (-)-menthone usage levels up to:
3.0000 % in the fragrance concentrate.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -52.00000
beverages(nonalcoholic): -7.70000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -8.70000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -33.00000
fruit ices: -33.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -71.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):14073-97-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :26447
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
Chemidplus:0014073973