AFCDB: (-)-Menthone (FDB013800)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:55 UTC

Update date

2019-11-26 03:09:05 UTC

Primary ID

FDB013800

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(-)-Menthone

Description

Occurs with menthol in many essential oils including peppermint and geranium oils. It is used in flavour compositions L-Menthone is the most abundant in nature of the four possible stereoisomers. Menthone is used in perfumery and cosmetics for its characteristic aromatic and minty odor. (-)-Menthone is found in many foods, some of which are ohelo berry, rocket salad, cauliflower, and common hazelnut.

CAS Number

14073-97-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
logP	3.05	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.52 m³·mol⁻¹	ChemAxon
Polarizability	18.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H18O

IUPAC name

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

InChI Identifier

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

InChI Key

NFLGAXVYCFJBMK-UHFFFAOYSA-N

Isomeric SMILES

CC(C)C1CCC(C)CC1=O

Average Molecular Weight

154.2493

Monoisotopic Molecular Weight

154.135765198

Classification

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

menthone (CHEBI:31 )
Menthane monoterpenoids (C11390 )
Cyclic monoterpenes (C11390 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp 207°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	3.05	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Experimental Water Solubility	0.497 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	Not Available
Mass Composition	C 77.87%; H 11.76%; O 10.37%	DFC
Melting Point	Mp -6°	DFC
Optical Rotation	[a]20D -24.8	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(+)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06r7-9300000000-1d150f2cf0a23dbfef0b	Spectrum
Predicted GC-MS	(+)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-fa99f8c083212e4f2fc3	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-9800000000-7bf975ea31bcef83aa61	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9000000000-3f8923896797c4486693	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d55afdef2faae68197a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-91ec697d11dad181a342	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01oy-9600000000-7933610ac6051fc8ef81	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-084e13e285859f435a61	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbc-9700000000-57929498deae48afce7a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bti-3900000000-5b9ac9ca9aaff729e2d1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0532-9200000000-ac0243da1ad4aa3d859e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d3a7bbb5abb9a0381a39	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15410

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35162

CRC / DFC (Dictionary of Food Compounds) ID

JHQ37-H:JHL57-O

EAFUS ID

Not Available

Dr. Duke ID

(-)-MENTHONE

BIGG ID

Not Available

KNApSAcK ID

C00000811

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1008131

SuperScent ID

26447

Wikipedia ID

Menthone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Barley	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Broccoli	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Carrot	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Common pea	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Cucumber	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Dill	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Eggplant	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Garden onion	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Garden tomato	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Garlic	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis

Showing 1 to 10 of 37 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti acetylcholinesterase	38462	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.	DUKE

Showing 1 to 1 of 1 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
camphor	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphoraceous	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
deep	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
menthol	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peppermint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
raspberry	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695

Showing 1 to 8 of 8 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

(-)-Menthone (FDB013800)

Structure for FDB013800 ((-)-Menthone)