Record Information
Version1.0
Creation date2011-05-05 17:57:39 UTC
Update date2019-11-26 03:20:56 UTC
Primary IDFDB021833
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(±)-Neoisomenthol
Description(+)-neoisomenthol, also known as cis-1,3,cis-1,4-menthol or iso-neomenthol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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 practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Within the cell, (+)-neoisomenthol is primarily located in the membrane (predicted from logP).
CAS Number491-02-1
Structure
Thumb
Synonyms
SynonymSource
(±)-Neoisomentholdb_source
all-cis-2-Isopropyl-5-methylcyclohexanolmanual
cis-1,3,cis-1,4-mentholmanual
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1a,2a,5a)-manual
DL-Neoisomentholmanual
Isoneomentholmanual
rel-(1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-olmanual
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
Polarizability19.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H20O
IUPAC name(1S,2S,5S)-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-/m0/s1
InChI KeyNOOLISFMXDJSKH-GUBZILKMSA-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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 76.86%; H 12.90%; O 10.24%DFC
Melting PointMp 14°DFC
Boiling PointBp6 81°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn17D 1.4676DFC
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-0900000000-39d327015211bdc2b4e8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-6900000000-67e6c41c2a8d759d6cafSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9200000000-88888989ba15a9dc0269Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3a700dc611fb070e6b45Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-86ed17c709dc4636ad41Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-6900000000-fc116bf41f068d3f6f75Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID18451
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJRL74-J:JRL65-H
EAFUS IDNot Available
Dr. Duke IDNEOISOMENTHOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID491-02-1
GoodScent IDrw1374441
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
Flavours
FlavorCitations
menthol
  1. 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
  2. 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).