Record Information
Version1.0
Creation date2010-04-08 22:14:41 UTC
Update date2019-11-26 03:18:08 UTC
Primary IDFDB019941
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Isopulegol acetate
DescriptionIsopulegol acetate, also known as fema 2965, 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. Isopulegol acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number89-49-6
Structure
Thumb
Synonyms
SynonymSource
Isopulegol acetic acidGenerator
1-Methyl-4-isopropenylcyclohexan-3-yl acetateHMDB
2-Isopropenyl-5-methylcyclohexyl acetateHMDB
5-Methyl-2-(1-methylethenyl)cyclohexanol acetateHMDB
Cyclohexanol, 5-methyl-2-(1-methylethenyl), acetateHMDB
FEMA 2965HMDB
Isopropenylcyclohexan-3-ol acetateHMDB
IsopulegolacetateHMDB
Isopulegyl acetateHMDB
p-Menth-8-en-3-yl acetateHMDB
(1R,2S,5R)-5-Methyl-2-(prop-1-en-2-yl)cyclohexyl acetic acidGenerator
(-)-Isopulegol acetic acidGenerator
(-)-Isopulegol acetatemanual
(1R,3R,4S)-(-)-p-Menth-8-en-3-ol acetatemanual
Isopulegol acetatedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.49ALOGPS
logP2.76ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.37 m³·mol⁻¹ChemAxon
Polarizability22.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H20O2
IUPAC name(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate
InChI IdentifierInChI=1S/C12H20O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3/t9-,11+,12-/m1/s1
InChI KeyHLHIVJRLODSUCI-ADEWGFFLSA-N
Isomeric SMILESC[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C
Average Molecular Weight196.286
Monoisotopic Molecular Weight196.146329884
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
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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 stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.43%; H 10.27%; O 16.30%DFC
Melting PointNot Available
Boiling PointBp8 112-114°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 IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9300000000-cba940c1d1f1aaf19f8eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9700000000-2ac8659513735c5f1608JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9300000000-cba940c1d1f1aaf19f8eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9700000000-2ac8659513735c5f1608JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9400000000-782001fc756db8f2ed3eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-c310b45afbf8bebec140JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-5900000000-74e3c99e5e97bce0a7aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9100000000-7b358df4198c2d161d6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-a51ca72efa8995b84a7dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-2900000000-5a26b25a09d1449267f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m53-5900000000-6e0fbbcee54aa6be4254JSpectraViewer
ChemSpider ID85346
ChEMBL IDCHEMBL3120645
KEGG Compound IDNot Available
Pubchem Compound ID94579
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40227
CRC / DFC (Dictionary of Food Compounds) IDJXJ74-P:MGX91-C
EAFUS ID1941
Dr. Duke IDISOPULEGOL-ACETATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID89-49-6
GoodScent IDrw1014371
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
mint
  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
leaf
  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
woody
  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.
peppermint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tropical
  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).