Record Information
Version1.0
Creation date2010-04-08 22:11:32 UTC
Update date2018-05-29 01:15:36 UTC
Primary IDFDB014912
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Isopulegol
DescriptionIsolated from Mentha pulegium (European pennyroyal) and other essential oils. (-)-Isopulegol is found in many foods, some of which are lemon balm, lemon grass, rosemary, and fats and oils.
CAS Number89-79-2
Structure
Thumb
Synonyms
SynonymSource
(-)-L-IsopulegolHMDB
(1R,3R,4S)-(-)-p-Menth-8-en-3-olHMDB
5-Methyl-2-(1-methylethenyl)-(1R,2S,5R)-cyclohexanolHMDB
L-IsopulegolHMDB
IsopulegolMeSH
(-)-Isopulegolmanual
(1R,3R,4S)-p-Menth-8-en-3-olmanual
Predicted Properties
PropertyValueSource
Water Solubility1.28 g/LALOGPS
logP2.69ALOGPS
logP2.32ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)19.47ChemAxon
pKa (Strongest Basic)-0.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.22 m³·mol⁻¹ChemAxon
Polarizability18.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H18O
IUPAC name(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
InChI IdentifierInChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
InChI KeyZYTMANIQRDEHIO-KXUCPTDWSA-N
Isomeric SMILESC[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting Point78 oC
Boiling PointBp3 65-66°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -22.5 (neat)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066u-9100000000-b05fac870c7dbc59229bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015c-9100000000-48d93dc21b89adaab452View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06di-9200000000-2ce50fb75d3deb9eb8e7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066u-9100000000-b05fac870c7dbc59229bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015c-9100000000-48d93dc21b89adaab452View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06di-9200000000-2ce50fb75d3deb9eb8e7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9400000000-488f8682a6cd647ab006View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-08mu-9620000000-8ac174806e5dc19696e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-b784ae5f8c92cdff077aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n1-8900000000-4ca9df3290f613ad8158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9000000000-f9df6d8c024d2913e865View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-13767d8f01d3cbb7cc97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-b47c5c16777566ad4c5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fs-6900000000-1d5990268c4a20c74c15View in MoNA
ChemSpider ID149356
ChEMBL IDCHEMBL237994
KEGG Compound IDNot Available
Pubchem Compound ID170833
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36078
CRC / DFC (Dictionary of Food Compounds) IDJXJ74-P:JXJ75-Q
EAFUS ID1939
Dr. Duke IDISOPULEGOL|ISOPULEGOLE
BIGG IDNot Available
KNApSAcK IDC00010938
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1014351
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 / Bioactivities
DescriptorIDDefinitionReference
anti acetylcholinesterase38462 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
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.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
minty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cooling
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  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).