Back to Compounds

Showing Compound (+)-Neomenthyl acetate (FDB006021)

Record Information
Version1.0
Creation date2010-04-08 22:06:57 UTC
Update date2025-11-18 23:00:44 UTC
Primary IDFDB006021
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(+)-Neomenthyl acetate
Description(+)-neomenthyl acetate 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 (+)-neomenthyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-neomenthyl acetate can be found in orange mint and peppermint, which makes (+)-neomenthyl acetate a potential biomarker for the consumption of these food products.
CAS Number147-85-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Neomenthyl acetic acidGenerator
(+)-Neomenthyl acetic acidGenerator
(+)-Neomenthol acetatebiospider
(+)-Neomenthyl acetatebiospider
(1R,3S,4S)-p-Menthan-3-ol acetatemanual
Menthol, acetate, (1R,3S,4S)-(+)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.54ALOGPS
logP3.11ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.6 m³·mol⁻¹ChemAxon
Polarizability23.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H22O2
IUPAC name(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl acetate
InChI IdentifierInChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12+/m1/s1
InChI KeyXHXUANMFYXWVNG-USWWRNFRSA-N
Isomeric SMILESCC(C)[C@@H]1CC[C@@H](C)C[C@@H]1OC(C)=O
Average Molecular Weight198.3019
Monoisotopic Molecular Weight198.161979948
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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-d72c827a469085629e5d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-4900000000-bf6fb3a5690a1f0320872016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9200000000-cb81ded288f2424a35562016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0900000000-3501f1a47f8406c0d6f52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-cb66f3b5eaa6461df1172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-4900000000-dcd4936d192617ff77682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9300000000-262f2d6c6ac2e61856712021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0012-9300000000-24944363b89e43dd9c2b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4f2ea1271e666be87dda2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-2900000000-6b5ecc1c9ffb6ea437372021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9500000000-d0a742a52154626c49062021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-a08bf949a70eb12bd6092021-10-21View Spectrum
NMRNot Available
ChemSpider ID68217
ChEMBL IDNot Available
KEGG Compound IDC16825
Pubchem Compound ID75699
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID(+)-NEOMENTHYL-ACETATE|NEOMENTHYL-ACETATE
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).