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Showing Compound (+)-Neomenthol (FDB014500)

Record Information
Version1.0
Creation date2010-04-08 22:11:18 UTC
Update date2020-09-17 15:41:35 UTC
Primary IDFDB014500
Secondary Accession NumbersNot 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 Number2216-52-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(1S,2S,5R)-(+)-NeomentholHMDB
(1S,2S,5R)-2-Isopropyl-5-methylcyclohexanolHMDB
(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexan-1-olHMDB
(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanolHMDB
D-NeomentholHMDB
FEMA 2666HMDB
(+)-Neomentholdb_source
(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-olbiospider
(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexanolbiospider
D-neomentholbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP2.68ALOGPS
logP2.66ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.45 m³·mol⁻¹ChemAxon
Polarizability19.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H20O
IUPAC name(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
InChI IdentifierInChI=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 KeyNOOLISFMXDJSKH-UTLUCORTSA-N
Isomeric SMILESCC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O
Average Molecular Weight156.2652
Monoisotopic Molecular Weight156.151415262
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane 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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 76.86%; H 12.90%; O 10.24%DFC
Melting PointMp -22°DFC
Boiling PointBp14 83-84°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]10D +18.02 (neat)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-Neomenthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9500000000-a610fe2868ba87b759eeSpectrum
Predicted GC-MS(+)-Neomenthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01w0-9520000000-26cc8cab97979ec9fb4dSpectrum
Predicted GC-MS(+)-Neomenthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-fc39fb91c62eb627e3af2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-5900000000-839aa9da0c06f6d099682015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-9200000000-e9b33e704445c7e908ec2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3a700dc611fb070e6b452015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-5a80eb79e919e06fa63a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-7900000000-67a39bf95581e52cb9312015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mk-9800000000-bb8a9e58bdc61e2654e62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053e-9100000000-6405f7fe35f6f6bdc8c52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-fee5c7d55bf523973cbf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-f6034c6a8245c68a37ac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-7efa42d43b7858e2c2ce2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-0900000000-b6eef0a7f66ac7e97e782021-09-24View Spectrum
NMRNot Available
ChemSpider ID388397
ChEMBL IDCHEMBL1907991
KEGG Compound IDC00553
Pubchem Compound ID439263
Pubchem Substance IDNot Available
ChEBI ID15402
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35763
CRC / DFC (Dictionary of Food Compounds) IDJRL74-J:JRL68-K
EAFUS ID2647
Dr. Duke ID(+)-NEOMENTHOL|NEOMENTHOL
BIGG IDNot Available
KNApSAcK IDC00000825
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1060561
SuperScent ID439263
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
camphoraceous
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
mentholic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
minty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).