AFCDB: (±)-Menthone (FDB009778)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:47 UTC

Update date

2020-09-17 15:41:34 UTC

Primary ID

FDB009778

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(±)-Menthone

Description

(-)-Menthone, also known as (1R,4S)-menthone or L-menthone, 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 lipid molecule (-)-Menthone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

CAS Number

89-80-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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	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

(2S,5R)-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/t8-,9+/m1/s1

InChI Key

NFLGAXVYCFJBMK-BDAKNGLRSA-N

Isomeric SMILES

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

Average Molecular Weight

154.253

Monoisotopic Molecular Weight

154.1357652

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

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Plant:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 77.87%; H 11.76%; O 10.37%	DFC
Melting Point	Not Available
Boiling Point	Bp10 82-83°	DFC
Experimental Water Solubility	0.688 mg/mL at 25 oC	SUZUKI,T (1991)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	n20D 1.4508	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-07bf-9300000000-03e6f833d8a9130c9648	2018-05-25	View Spectrum
GC-MS	(±)-Menthone, non-derivatized, GC-MS Spectrum	splash10-03di-7900000000-72f9ad70ae1001e21eaf	Spectrum
GC-MS	(±)-Menthone, non-derivatized, GC-MS Spectrum	splash10-004j-2900000000-9f3548951fa6e98aa410	Spectrum
GC-MS	(±)-Menthone, non-derivatized, GC-MS Spectrum	splash10-0170-4900000000-82f88e79cd91a887a98f	Spectrum
GC-MS	(±)-Menthone, non-derivatized, GC-MS Spectrum	splash10-03di-7900000000-72f9ad70ae1001e21eaf	Spectrum
GC-MS	(±)-Menthone, non-derivatized, GC-MS Spectrum	splash10-004j-2900000000-9f3548951fa6e98aa410	Spectrum
GC-MS	(±)-Menthone, non-derivatized, GC-MS Spectrum	splash10-0170-4900000000-82f88e79cd91a887a98f	Spectrum
GC-MS	(±)-Menthone, non-derivatized, GC-MS Spectrum	splash10-07bo-9300000000-3f63fc6dbb3efa362d59	Spectrum
GC-MS	(±)-Menthone, non-derivatized, GC-MS Spectrum	splash10-07bo-9300000000-3f63fc6dbb3efa362d59	Spectrum
Predicted GC-MS	(±)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052g-9300000000-f26613921d7b53d7fd71	Spectrum
Predicted GC-MS	(±)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(±)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-6701bba716a6affa8766	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0002-9000000000-b0b5dd86e6d1a6de2171	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-000t-9000000000-d18a7464317ee5b6d7cc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-244db80c070c100b12b8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-2900000000-b84cff8176943c1c01cf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-4900000000-3164f9befc45e23067a9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-7900000000-aa7dd74302c4ed215ce5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-001a-9600000000-f847c953bdb697e434a9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0012-9400000000-23a0fccfb9523e3d21ec	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000t-9200000000-54afdeb4f58eddee2447	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000t-9100000000-b0e554c807437d6fbe0a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-000t-9000000000-575fad481c43a10742f2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-00l2-9000000000-2869717ccfb0fbe67a4b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-015a-9000000000-b2a684427d58a3d1e8d8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0690-9000000000-68fcde55699d18a522f7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-0ar3-9100000000-25c9da89880a6d44b24d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-000t-9000000000-96ef6ca330f562128056	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-70388bb385562f798a7a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0a4i-1900000000-05762909cf77edb47697	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-fa99f8c083212e4f2fc3	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-9800000000-7bf975ea31bcef83aa61	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9000000000-3f8923896797c4486693	2016-08-01	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

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

36503

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JHQ37-H:LFY37-D

EAFUS ID

2145

Dr. Duke ID

MENTHONE|NEOMENTHONE

BIGG ID

Not Available

KNApSAcK ID

C00035341

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

89-80-5

GoodScent ID

rw1398981

SuperScent ID

Not Available

Wikipedia ID

Menthone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
acaricide	22153	A substance used to destroy pests of the subclass Acari (mites and ticks).	DUKE
allelopathic			DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
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
anti aggregant			DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti bacillary	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti escherichic			DUKE
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti listeria	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
cerebrotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
culicide			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
larvicide			DUKE
mutagenic			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
psychoactive	35471	A loosely defined grouping of drugs that have effects on psychological function.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
trichomonicide			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
fresh	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
green	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
minty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

(±)-Menthone (FDB009778)

Structure for FDB009778 ((±)-Menthone)