Record Information
Version1.0
Creation date2011-05-05 18:01:57 UTC
Update date2018-05-28 20:05:15 UTC
Primary IDFDB021834
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(+)-Neoisomenthol
Description(+)-Neoisomenthol, also known as iso-neomenthol or (1R,3R,4R)-form, 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, (+)-neoisomenthol is considered to be an isoprenoid lipid molecule (+)-Neoisomenthol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number20752-34-5
Structure
Thumb
Synonyms
SynonymSource
(1alpha,2alpha,5alpha)-5-Methyl-2-(1-methylethyl)cyclohexanolChEBI
cis-1,3,cis-1,4-MentholChEBI
Iso-neomentholChEBI
(1a,2a,5a)-5-Methyl-2-(1-methylethyl)cyclohexanolGenerator
(1Α,2α,5α)-5-methyl-2-(1-methylethyl)cyclohexanolGenerator
(1R,3R,4R)-FormHMDB
p-Menthan-3-olHMDB
IsomentholMeSH
(+)-Neoisomentholdb_source
(1α,2α,5α)-5-methyl-2-(1-methylethyl)cyclohexanolGenerator
p-Menthan-3-ol; (1R,3R,4R)-formdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP2.68ALOGPS
logP2.66ChemAxon
logS-2.5ALOGPS
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
Polarizability19.45 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H20O
IUPAC name(1R,2R,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-OPRDCNLKSA-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

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionOilDFC
Mass CompositionC 76.86%; H 12.90%; O 10.24%DFC
Melting PointMp -8°DFC
Boiling PointBp 214.6°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18D +3.8 (c, 6 in EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-Neoisomenthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9500000000-a610fe2868ba87b759eeSpectrum
Predicted GC-MS(+)-Neoisomenthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01w0-9520000000-26cc8cab97979ec9fb4dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-0c54797416987a09fdc7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-6900000000-bd03de53003ab3ad94c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-cdad8953e5a863785f4cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-35bb57f3b1e1db7e0531Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-6f5b57bb56920ed10bd2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvr-5900000000-291ecb7fa19007ee756bSpectrum
NMRNot Available
ChemSpider ID18159
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID19244
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41628
CRC / DFC (Dictionary of Food Compounds) IDJRL74-J:JPV92-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference