AFCDB: (+)-Neomenthol (FDB014500)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:18 UTC

Update date

2020-09-17 15:41:35 UTC

Primary ID

FDB014500

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(+)-Neomenthol

Description

(+)-Neomenthol, also known as fema 2666, 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, (+)-neomenthol is considered to be an isoprenoid lipid molecule (+)-Neomenthol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

CAS Number

2216-52-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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	19.4 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

(1S,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-UTLUCORTSA-N

Isomeric SMILES

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

Average Molecular Weight

156.2652

Monoisotopic Molecular Weight

156.151415262

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:15402 )
Menthane monoterpenoids (C00553 )
Cyclic monoterpenes (C00553 )
Menthane monoterpenoids (LMPR0102090003 )

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:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp14 83-84°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 76.86%; H 12.90%; O 10.24%	DFC
Melting Point	Mp -22°	DFC
Optical Rotation	[a]10D +18.02 (neat)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(+)-Neomenthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-9500000000-a610fe2868ba87b759ee	Spectrum
Predicted GC-MS	(+)-Neomenthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01w0-9520000000-26cc8cab97979ec9fb4d	Spectrum
Predicted GC-MS	(+)-Neomenthol, 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	splash10-052r-0900000000-fc39fb91c62eb627e3af	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-5900000000-839aa9da0c06f6d09968	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avi-9200000000-e9b33e704445c7e908ec	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3a700dc611fb070e6b45	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-5a80eb79e919e06fa63a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-7900000000-67a39bf95581e52cb931	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05mk-9800000000-bb8a9e58bdc61e2654e6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053e-9100000000-6405f7fe35f6f6bdc8c5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fee5c7d55bf523973cbf	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-f6034c6a8245c68a37ac	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-7efa42d43b7858e2c2ce	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zfr-0900000000-b6eef0a7f66ac7e97e78	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15402

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35763

CRC / DFC (Dictionary of Food Compounds) ID

JRL74-J:JRL68-K

EAFUS ID

2647

Dr. Duke ID

(+)-NEOMENTHOL|NEOMENTHOL

BIGG ID

Not Available

KNApSAcK ID

C00000825

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1060561

SuperScent ID

439263

Wikipedia ID

Not Available

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

White cabbage	Expected but not quantified	Not Available	DUKE, PATHBANK
Barley	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK
Broccoli	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK
Carrot	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK
Common pea	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK
Cucumber	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK
Dill	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK
Eggplant	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK
Garden onion	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK
Garden tomato	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis, PATHBANK

Showing 1 to 10 of 37 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Showing 1 to 2 of 2 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
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.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 4 of 4 entries

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).

(+)-Neomenthol (FDB014500)

Structure for FDB014500 ((+)-Neomenthol)