Menthone (YMDB01741)

Identification

YMDB ID

YMDB01741

Name

Menthone

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

(-)-Menthone, also known as L-menthone or p-menthan-3-one, 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. Thus, (-)-menthone is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (-)-Menthone.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(-)-Menthone
(2R,5S)-rel-5-methyl-2-(1-methylethyl)cyclohexanone
l-Menthone
menthone
p-Menthan-3-one
rel-(1R,4S)-p-menthan-3-one
rel-(2R,5S)-2-isopropyl-5-methylcyclohexanone
trans-5-methyl-2-(1-methylethyl)cyclohexanone
trans-menthan-3-one
trans-menthone
trans-p-menthan-3-one
(1R,4S)-Menthone
(1R,4S)-p-Menthan-3-one
(2S,5R)-2-Isopropyl-5-methylcyclohexanone
(2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanone
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanone
(2S,5R)-Menthone
(-)-(1R,4S)-Menthone
(-)-(2S,5R)-Menthone
(-)-5-Methyl-2-(1-methylethyl)cyclohexanone
(1R,4S)-(-)-P-Menthan-3-one
(2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanone
(2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanone
5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanone
5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanone
(1R,4S)-p-Menth-3-one
(2S,5R)-(-)-Menthone
(2S,5R)-2-Isopropyl-5-methylcyclohexan-1-one
trans-(-)-p-Menthan-3-one

CAS number

89-80-5

Weight

Average: 154.2493
Monoisotopic: 154.135765198

InChI Key

NFLGAXVYCFJBMK-BDAKNGLRSA-N

InChI

InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1

IUPAC Name

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

Traditional IUPAC Name

(-)-menthone

Chemical Formula

C₁₀H₁₈O

SMILES

CC(C)[C@@H]1CC[C@@H](C)CC1=O

Chemical Taxonomy

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:15410 )
Menthane monoterpenoids (C00843 )
Cyclic monoterpenes (C00843 )
Menthane monoterpenoids (LMPR0102090004 )

Physical Properties

State

Liquid

Charge

Melting point

−6 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.688 mg/mL at 25 oC [SUZUKI,T (1991)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	2.65	ALOGPS
logP	3.05	ChemAxon
logS	-2.8	ALOGPS
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	19.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Fresh	FDB009778
Green	FDB009778
Minty	FDB009778

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-7900000000-72f9ad70ae1001e21eaf	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004j-2900000000-9f3548951fa6e98aa410	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0170-4900000000-82f88e79cd91a887a98f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-7900000000-72f9ad70ae1001e21eaf	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004j-2900000000-9f3548951fa6e98aa410	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0170-4900000000-82f88e79cd91a887a98f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-07bo-9300000000-3f63fc6dbb3efa362d59	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-07bo-9300000000-3f63fc6dbb3efa362d59	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052g-9300000000-f26613921d7b53d7fd71	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-6701bba716a6affa8766	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0002-9000000000-b0b5dd86e6d1a6de2171	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-000t-9000000000-d18a7464317ee5b6d7cc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-244db80c070c100b12b8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-2900000000-b84cff8176943c1c01cf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-4900000000-3164f9befc45e23067a9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-7900000000-aa7dd74302c4ed215ce5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-001a-9600000000-f847c953bdb697e434a9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0012-9400000000-23a0fccfb9523e3d21ec	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000t-9200000000-54afdeb4f58eddee2447	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000t-9100000000-b0e554c807437d6fbe0a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-000t-9000000000-575fad481c43a10742f2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-00l2-9000000000-2869717ccfb0fbe67a4b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-015a-9000000000-b2a684427d58a3d1e8d8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0690-9000000000-68fcde55699d18a522f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-0ar3-9100000000-25c9da89880a6d44b24d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-000t-9000000000-96ef6ca330f562128056	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-70388bb385562f798a7a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0a4i-1900000000-05762909cf77edb47697	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-fa99f8c083212e4f2fc3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-9800000000-7bf975ea31bcef83aa61	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9000000000-3f8923896797c4486693	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d55afdef2faae68197a6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-91ec697d11dad181a342	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01oy-9600000000-7933610ac6051fc8ef81	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-07bf-9300000000-03e6f833d8a9130c9648	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	36503
HMDB ID	HMDB0035162
Pubchem Compound ID	26447
Kegg ID	C00843
ChemSpider ID	24210726
FOODB ID	FDB009778
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xa41c3d98>