AFCDB: (-)-Menthol (FDB014499)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:18 UTC

Update date

2019-11-26 03:10:11 UTC

Primary ID

FDB014499

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(-)-Menthol

Description

Menthol, also known as levomenthol or hexahydrothymol, 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, menthol is considered to be an isoprenoid lipid molecule. Menthol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Menthol is a potentially toxic compound.

CAS Number

2216-51-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.56 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.66	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.45 m³·mol⁻¹	ChemAxon
Polarizability	19.69 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

C10H20O

IUPAC name

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

InChI Identifier

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1

InChI Key

NOOLISFMXDJSKH-KXUCPTDWSA-N

Isomeric SMILES

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

Average Molecular Weight

156.269

Monoisotopic Molecular Weight

156.151415264

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
Cyclohexanol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

p-menthan-3-ol (CHEBI:15409 )
Menthane monoterpenoids (C00400 )
Cyclic monoterpenes (C00400 )
Menthane monoterpenoids (LMPR0102090001 )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

Ear and labyrinth disorders:

Vertigo

Gastrointestinal disorders:

Vomiting

General disorders and administration site conditions:

Pain

Ingestion

Source:

Food

Synthetic:

Personal care product

Environmental:

Tobacco smoke

Biological:

Plant:

Biological location:

Tissue and substructures:

Organ and components:

Cell and elements:

Extracellular

Cell:

Nerve cell

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp 216°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	3.40	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Experimental Water Solubility	0.49 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (1992)
Isoelectric point	Not Available
Mass Composition	C 76.86%; H 12.90%; O 10.24%	DFC
Melting Point	Mp 42.5-43°	DFC
Optical Rotation	[a]20D -50 (c, 2 in CHCl3)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00ea-9100000000-602436010653202a4da9	2014-09-20	View Spectrum
GC-MS	(-)-Menthol, 1 TMS, GC-MS Spectrum	splash10-0006-1900000000-cc06fe70d7649d059f92	Spectrum
GC-MS	(-)-Menthol, non-derivatized, GC-MS Spectrum	splash10-00ea-9100000000-0be605183591bf5f33a0	Spectrum
GC-MS	(-)-Menthol, non-derivatized, GC-MS Spectrum	splash10-00ea-9100000000-977cf0c036d597693beb	Spectrum
GC-MS	(-)-Menthol, non-derivatized, GC-MS Spectrum	splash10-0006-1900000000-cc06fe70d7649d059f92	Spectrum
GC-MS	(-)-Menthol, non-derivatized, GC-MS Spectrum	splash10-00ym-9100000000-ff2f7ebe48769147a112	Spectrum
Predicted GC-MS	(-)-Menthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4l-9600000000-fcf4b2a96455b111f889	Spectrum
Predicted GC-MS	(-)-Menthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01w0-9520000000-26cc8cab97979ec9fb4d	Spectrum
Predicted GC-MS	(-)-Menthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(-)-Menthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-053r-9300000000-d9c35833e73c8655fb23	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ldl-9000000000-abf2f837df49fbedc53c	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0007-9000000000-adee6385265c6606326d	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-00ea-9100000000-e3f1b7b69a021063fabb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , Positive	splash10-00ea-9100000000-d69777874c9615b7e751	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-39d327015211bdc2b4e8	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-6900000000-67e6c41c2a8d759d6caf	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9200000000-88888989ba15a9dc0269	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3a700dc611fb070e6b45	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-86ed17c709dc4636ad41	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-6900000000-fc116bf41f068d3f6f75	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05mk-9800000000-bb8a9e58bdc61e2654e6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053e-9100000000-6405f7fe35f6f6bdc8c5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fee5c7d55bf523973cbf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-f6034c6a8245c68a37ac	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-7efa42d43b7858e2c2ce	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zfr-0900000000-b6eef0a7f66ac7e97e78	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15409

Phenol-Explorer ID

Not Available

DrugBank ID

DB00825

HMDB ID

HMDB03352

CRC / DFC (Dictionary of Food Compounds) ID

JRL74-J:JRL66-I

EAFUS ID

2144

Dr. Duke ID

L-MENTHOL|MENTHOL|(-)-MENTHOL

BIGG ID

Not Available

KNApSAcK ID

C00000810

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

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

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	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
anesthetic			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 asthmatic	49167	A drug used to treat asthma.	DUKE
anti bacillus	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 bronchitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Showing 1 to 10 of 64 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
camphoraceous	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cooling	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mentholic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
minty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peppermint	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tobacco	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695

Showing 1 to 6 of 6 entries

Files

MSDS

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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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

(-)-Menthol (FDB014499)

Structure for FDB014499 ((-)-Menthol)